The Best Historic Estate & Mansion Wedding Venues in Cheshire, CT

The Best Historic Estate & Mansion Wedding Venues in Cheshire, CT

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40 Wedding Venues in Cheshire, CT

Historic estates, mansions
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Bill Miller's Castle 

5.0

Branford, CT
  • Up to 250 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $9,000

A magnificent, breathtaking landmark, Bill Miller’s Castle has served as an elegant venue for weddings, corporate events, and special occasions. Meticulous attention to detail, natural stonework, exposed reclaimed beams, an antique bronze bell weighing more than one ton, and rare antique furniture create a beautiful backdrop for any event or special occasion. Featuring five working field-stone fireplaces, three-story cathedral ceilings, ornate stained glass windows, crystal chandeliers, and a large dance floor; the grandeur of Bill Miller’s Castle will make your guests feel truly extraordinary from the moment they walk through the door.

Why you'll love this venue

  • Multiple event spaces
  • Bridal suite on site
  • Historic touches

Venue considerations

  • Not wheelchair accessible
  • No on-site guest accommodations
  • Large venue, not ideal for small guest lists
We had the most magical experience at Bill Millers Castle. They made the day everything we could have dreamed and more. Every detail was perfect, the food was phenomenal, and they scheduled everything to run smoothly without making us feel like we were stuck to a schedule. We were able to relax and enjoy the day without worry that something was not done or would not be ready. We had every one of our guests tell us it was the best wedding they have ever been too. (and as we are not a young couple most of them have been to a lot of wedding's). Not only was the experience of the day the most amazing, the planning and communication leading up to the day was phenomenal. Victoria was very easy to reach, answered all of our questions, and helped guide us through the process always having tips for us to make sure we got what we wanted. Thank you to Bill Millers Castle for the most amazing day.
Jennifer & J., 7 months ago
The Wadsworth Mansion At Long Hill Estate 

5.0

Middletown, CT
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $25,000

The Wadsworth Mansion, a nineteenth-century Beaux Art style mansion, is the quintessential country estate. Graced by expansive lawns and surrounded by 103 acres of wooded parklands the Mansion reflects an era of grandeur and elegance. There are multiple locations for outdoor ceremonies and guests can enjoy cocktails and dance on the terrace under the stars. The Mansion can accommodate two hundred guests for a seated dinner reception and larger numbers for cocktail parties. Only one event is scheduled each day and couples can select from a list of approved caterers to create the wedding of their dreams.

Why you'll love this venue

  • Has a dance floor to dance the night away
  • Versatile for various event styles
  • Private area for the wedding party

Venue considerations

  • Not wheelchair accessible
  • No built-in audiovisual options
  • No on-site guest accommodations
Weeks later, we're still absolutely gushing over the Mansion! It was the perfect venue for our wedding. They had it all, from phenomenal staff to luxurious facilities, not to mention the stunning views. We had the pleasure of working with Alexandra(Alex) we could not have asked for a better person! Alex knew all of our family members and bridal party’s names, and was extremely personable. She went above and beyond to make sure we were taken care of all night. She brought me a snack before the ceremony and continuously brought me my water all day and night (without me asking)They truly make you feel like a VIP throughout your entire day and their top notch team(along with our caterer David Alan) ensured that everything ran smoothly behind the scenes. In the early stages of planning we worked with Jessica Hess and she is extremely helpful and communicative. The mansion truly felt like home for the day. We hosted our ceremony on the vista , cocktail hour was on the terrace, and we had dinner in the East ballroom. Guests were in awe of the estate (we also lucked out with absolutely perfect weather), and how every detail was perfectly executed. Our special day was truly a dream and felt like it was out of a movie! We could not recommend the Wadsworth Mansion enough, and can't wait to return for future celebrations. It's definitely well-worth the investment and would 10/10 recommend hosting your special day here! Ps ask about the beautiful custom made bar (my stepdad built it) Our wedding Venue: The Wadsworth Mansion Photographer: Crystal Photography Second Shooter: Jenn Tee Photography Videographer: Jf3 Productions DJ: AMS - Mikey Tierney Caterer: David Alan Hospitality Group Bar: Cocktail Crusiers Gown: Grace Loves Lace Flower Girl Dress: Grace Loves Lace Tuxedo & Suits: Generation Tux Makeup: Upstyle Co. Autumn Starke Hair: The Hair Factory - Danielle Gagnon Getting Ready Suite: The Apiary Collective Cake: J Cakes MOB Dress: Camilyn Beth Bridal Bouquet & Boutonnière: Haworths Flower
Arianna C., 5 months ago
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Saint Clements Castle 

5.0

Portland, CT
  • Up to 260 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $120

Where the castle meets the river, Saint Clements Castle & Marina, is Connecticut’s premier wedding and event venue in Portland. Situated along the banks of the river, each of the three unique event spaces provide a picturesque and scenic backdrop of the riverside and lush greenery while outdoors. Inside, you will find newly renovated historical charm for a variety of special events, including weddings, showers, corporate meetings, and other celebrations. Saint Clements Castle has earned a reputation of an elevated and enchanting setting perfect for all things in life worth celebrating. Saint Clements Castle and Marina’s location, in central Connecticut, is easily accessible as a midpoint from the New York City and Boston areas.

Why you'll love this venue

  • Bridal suite on site
  • All-inclusive venue packages
  • Provides event staff

Venue considerations

  • Best for events with big guest lists
  • No on-site guest accommodations
  • No built-in audiovisual options
Saint Clements Castle provided a beautiful venue and kind staff for our wedding day. We especially appreciated our sales coordinator, Alyssa, who was professional, fast, and clear in her communication throughout the planning process. When rain forced us to move the ceremony indoors, the team quickly adapted the art gallery for us. The servers and bridal attendants were also attentive and went above and beyond to help finish set up when our florist left early. Our guests had incredibly kind things to say about the servers, and overall we had a great experience. It was also lovely to have a place that was a one stop shop for event planning! We did lose some decor in the shuffle which was an inconvenience, and some of the instructions for set up I left were not followed (our confetti got lost, only four guests got packets, the bridal suites did not have the supplies we left for them). My husband’s family were also really upset with one of the managers on property who wouldn’t allow them to walk in a covered area and was a bit rude about it, despite an event not happening and the rain being a torrential downpour causing unsafe conditions for his elderly family to walk in. Overall we had a great experience, and would recommend the castle to anyone planning a wedding!
Elise D., 5 months ago
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Woodwinds 

4.4

Branford, CT
  • Up to 600 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $115

WoodWinds is one of the most sought after Connecticut wedding venues for wedding receptions, banquets, corporate events or any special occasion, in the Tri-State area. A wedding in our impressive European Country Manor will reflect your personal vision. Imagine a magical experience, enhanced by a unique ceremony and reception on the beautiful grounds of WoodWinds. Envision standing on a grand staircase under the twinkle of Austrian Crystal chandeliers, taking pictures in a magnificent garden and dancing the night away on a marble dance floor.

Why you'll love this venue

  • Bridal suite on site
  • Provides a dedicated team on-site
  • Provides catering services

Venue considerations

  • Does not allow pets
  • No free parking
  • Large venue, not ideal for small guest lists
The venue had a few hiccups, but overall we had a lovely reception there. The outdoor space was the highlight - truly gorgeous for photos. Communication on coordination was a bit spotty at times, but the maître d', Sergio, was a god send and stepped in to ensure things flowed smoothly. The food was phenomenal, as well! So many of our guests shared it was the best wedding food they’d ever had. We did have both our bridal attendants provided by the venue disappear on us shortly after we arrived, which was inconvenient since we would have paid for our own attendants if we knew that would be the case. While parts of the indoor space is dated, it worked out beautifully with some creative decor. When weighing everything in, the Woodwinds was a spectacular venue!
Negeena & M., 4 months ago
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The Woodwinds at The Blackstone Library 

5.0

Branford, CT
  • Up to 475 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $9,000

The James Blackstone Memorial Library, commonly known as the Blackstone Library, in Branford, Connecticut, is a historic and elegant venue perfect for weddings. Commissioned by Timothy Blackstone to honor his father, James Blackstone, the library was designed by renowned architect Solon Spencer Beman and completed in 1896. Its classic architectural features and serene ambiance make it an enchanting backdrop for wedding ceremonies and receptions. Woodwinds Catering enhances the wedding experience at the Blackstone Library with exquisite culinary offerings and impeccable service. Their attention to detail ensures that every aspect of the wedding day is flawlessly executed, from planning to the final toast. The library’s stunning exterior, with its intricate stonework and majestic columns, provides a picturesque setting for wedding photographs. Inside, the elegant interiors with high ceilings and rich woodwork create a warm and inviting atmosphere for guests.

Why you'll love this venue

  • Has a dance floor for celebration
  • Has an intimate atmosphere
  • Full catering menu to choose from

Venue considerations

  • Best for events with big guest lists
  • No on-site guest accommodations
  • No in-house lighting and sound packages available
Worked with the woodwinds at the library and they were so helpful. They showed me ahead of time where I was setting up, on arrival they had a table waiting for me. They even made sure I ate (the food is delicious!!!) I hope I get to work with them in the future!
Jay, 4 months ago
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Riverbend 

4.2

Higganum, CT
  • Up to 300 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $25,000

Welcome to Connecticut Wedding Group's latest jewel, Riverbend—a masterpiece poised to claim its title as the state’s foremost wedding destination, with an opening scheduled for 2026! Nestled in the heart of Higganum, this venue seamlessly blends the rich tapestry of the town's industrial history with a contemporary touch, resulting in an unmatched fusion of industrial charm and modern elegance. As you step through the entrance, prepare to be enchanted by a stunning architectural marvel nestled within a lovingly restored industrial gem. Towering, exposed-beam ceilings create an expansive atmosphere, and the weathered brickwork shares the timeless tales of a bygone era. Bathed in sunlight pouring through expansive windows, every corner is adorned with a soft, natural glow, ensuring that your celebration emanates with an undeniable warmth and inherent beauty. At Riverbend, history meets modernity to create the perfect backdrop for your special day.

Why you'll love this venue

  • Has a dance floor for celebration
  • All-inclusive venue packages
  • Dressing room available

Venue considerations

  • On-site parking not available
  • Large venue, not ideal for small guest lists
  • Not wheelchair accessible
We knew from the start that to ensure the most important day of our lives went off without a hitch there was no one but CT Wedding Group we trusted. Their reviews speak for themselves but first hand we can tell you they do them little to no justice(having been guests at weddings at their venues). Imagine our surprise when we were able to see the limitless possibilities of their newest space and how it completely shattered our reality of what a wedding day could be. We are lucky enough to say we are the first wedding booked for their newest venue and the sky is the limit. The renderings they provided were unlike anything we've seen anywhere else throughout this process. The vision of what the space can and will become has us more excited by a venue than we thought imaginable. Their attention to detail, earnest care to make our day specific to us, and their overall devotion to their craft is unrivaled. There is not stress, just excitement and its all thanks to their incredible team, and astounding venue. They preach that their 9-5 is the most important day of their clients lives and they take that seriously, and boy do they practice what they preach. CAN NOT say enough about this experience thus far, and as if that wasn't enough, their planning team make the experience simply incredible (and fool proof). This is not a diamond in the rough situation. They set a standard for what the industry should be and then deliver a thousand fold. We've only before seen the end result of their reputation as guests, and now as clients can say that words just simply fall short of the reality. This. Is. What. Dreams. Are. Made. Of.
Michael, a year ago
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Glastonbury Theater 

5.0

Glastonbury, CT
  • Up to 200 guests
  • All-inclusive
  • Indoor
  • Starts at $1,300

Nestled in the heart of Glastonbury, Connecticut, the historic Glastonbury Theater has been a cornerstone of community engagement since 1929. Originally a grange hall, this venue has been transformed over the years, keeping its unique charm intact while adapting to modern necessities. Today, the theater offers a blend of timeless elegance and state-of-the-art facilities, perfect for a variety of events, from intimate gatherings to large corporate functions. We can comfortably accommodate up to 100 guests seated, and up to 200 in a theater-style arrangement. At Glastonbury Theater, we craft memorable experiences with a deep commitment to excellence, celebrating the power of community and heritage. We're excited to invite you to become part of our rich history and create your own unforgettable moments on our storied stage.

Why you'll love this venue

  • Provides catering services
  • Provides lighting and sound
  • Has a glamorous vibe

Venue considerations

  • Does not allow pets
  • No on-premises lodging options
  • Not wheelchair accessible
The event team is highly professional and goes the extra mile to ensure a successful event. Highly recommended for a unique and memorable wedding experience
Asana Crystal, 2 years ago
The Lace Factory 

5.0

Deep River, CT
  • Up to 225 guests
  • Select services
  • Indoor & outdoor

Even if one didn't put their own personal touches to this space it is still stunning. So much natural and creative lighting with a beautiful courtyard for reception or ceremony. Industrial history, attention to detail and location! Covid procedures and restriction apply.

Why you'll love this venue

  • Provides a dedicated team on-site
  • Pets can join the celebration
  • Combines timeless elegance with history

Venue considerations

  • Best for events with big guest lists
  • No on-premises lodging options
I honestly forget if I already wrote a review for The Lace Factory, but recently I was reflecting on our wedding day and a few things stuck out that had me so thankful we held our reception at The Lace Factory. From the beginning of the planning process the team is extremely clear and communicative. I love a checklist and theirs is one that ensures nothing will be forgotten. Our guests are still sharing how gorgeous the venue was, how incredible the food spread was, and one detail I was surprised by, from my cousin who has been to their fair share of large celebrations. "The food was not only delicious, but they managed to serve such a large group and the food was actually hot!" This speaks to the well-oiled machine that is The Lace Factory and it must be emphasized that this machine has heart. They accomplished another feat of having my family and I not worry about the severe allergy of my dad, as they adjusted the menu accordingly, without us having to miss out on all the options. This carried over to assist some guests who also had specific dietary needs. I realize this sounds boring, but it is wonderful to know your guests are safe and fed and focus on the celebrating! The Lace Factory is a venue that can transform your wedding into something beyond your dreams while holding true to your vision.
Annie S., 4 months ago
The Spinning Wheel 

4.7

Redding, CT
  • Up to 150 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $7,000

As the embodiment of ‘Connecticut Charm’ with its 18th-century architectural design & rustic, New England inspired designs, The Spinning Wheel is the ideal destination for an intimate reception. Our venue, sitting on five acres of rolling countryside, offers both privacy and accessibility - with its picturesque location in quaint Redding, CT and its proximity to major thruways (I-95) and Manhattan (approximately an hour away). Our charmingly-appointed banquet room can accommodate weddings of up to 150 guests and features the original fireplace from 1742. The scenic garden gazebo is a favorite for nuptial exchange and the covered patio serves as a perfect setting for cocktails and outdoor receptions. Come meet our family and explore our beautiful grounds yourself – we can’t wait to meet you!

Why you'll love this venue

  • Has a dance floor for celebration
  • Multiple event spaces
  • Provides setup and cleanup

Venue considerations

  • No on-site bridal suite
  • No in-house lighting and sound packages available
  • No on-site guest accommodations
Awarded Best of Zola
The Spinning Wheel made our wedding absolutely perfect. From the beginning of the process to the wedding day, Katlyn and her Staff were so attentive, professional and friendly. They made all my dreams come true. The food was AMAZING, the wait staff efficient and attentive, the vibe was awesome. Everyone had a blast and said it was the best wedding ever. I had the best experience at The Spinning Wheel!
Melissa, 2 months ago
The Rams Head Inn 

5.0

Shelter Island Heights, NY
  • Up to 225 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $20,000

Please contact us directly to get more information, pricing and availability. Email corinna (a) the rams head inn . com, or text/call 6 3 1. 9 0 3. 2 3 5 5. Located on beautiful Shelter Island overlooking Coecles Harbor, The Ram's Head Inn has breath-taking water views. The hotel features 17 guest rooms, a private beach, hammocks and Adirondack chairs for our guests. The restaurant features the best in local fare with food coming almost exclusively from the east end of Long Island or from the Chef's garden. Website: the rams head inn .com

Why you'll love this venue

  • Historic touches
  • Caters to out-of-town guests
  • Provides catering services

Venue considerations

  • Not for you if you are looking for something nontraditional
  • Large venue, not ideal for small guest lists
  • Lighting and sound are not included
Rams Head Inn was an absolute pleasure to work with for my client's summer wedding! Their events manager was communicative and detail-oriented leading up to the wedding, and on the day of, the entire team was so on top of everything. The RHI staff is delightful and are great team players. I definitely felt like we were all working together to bring our clients' vision to life!
Leah W., 3 years ago
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Caramoor Center for Music and the Arts 

5.0

Katonah, NY
  • Up to 700 guests
  • Select services
  • Indoor & outdoor
  • Starts at $12,500

Although widely known for our weddings, many families have selected Caramoor to celebrate important milestones like special birthdays, anniversaries, family reunions, Bar and Bat Mitzvahs, and other significant life events. Caramoor’s grounds are the perfect blend of bucolic gardens and a historical mansion setting for tying the knot! Our variety of unique venues will make your wedding day a one-of-a-kind experience for you and your guests.

Why you'll love this venue

  • Wheelchair accessible
  • Exudes old-world charm
  • Private area for the wedding party

Venue considerations

  • Does not allow pets
  • No on-premises lodging options
  • Dance floor not included
Caramoor magic is real! Surrounding nature, gardens, special spaces and treasures in the Rosen House, festive tented occasions, dining, and year round concerts all happen at Caramoor. With great pleasure, and for many years, I enjoy working with this lovely, personable, dedicated Caramoor staff.
Mary Lou Pappas, 5 years ago
Curry Estate 

5.0

Hopewell Junction, NY
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

We'd love to help you if your wedding has been postponed or rescheduled. We have dates available and are ready to work with brides. Let's sit down and plan a new date for your special day! Le Chambord at Curry Estate is one of the most elegant and romantic wedding venues in the Hudson Valley. We know you have a unique vision for your wedding and this ten-acre beautifully treed and gardened property, with 1863 historic Georgian Colonial estate, ballroom, covered outdoor pavilion, four-star restaurant, conference center and overnight accomodations is the perfect setting to make that dream come true.

Why you'll love this venue

  • Provides catering services
  • Offers full-service amenities
  • Bridal suite on site

Venue considerations

  • No in-house lighting and sound packages available
  • Best for events with big guest lists
  • Not for you if you are looking for something nontraditional
I couldn't have asked for a better venue and management from Curry Estate. The sisters that own this venue truly made my husband and I feel like a part of their family. There was constant communication from booking to wedding day, with a year and a half in between. The grounds are beautiful and everyone at Curry Estate acted with intention to make our day the most amazing day that it was. We would recommend this venue to anyone a million times over. The planning, food, staff and day of coordination couldn't have been better. Our guests continue to tell us how amazing the day was and it is without a doubt a result of the wonderful team that runs and owns this venue.
Jessica B., 2 years ago
Watermill Caterers 

4.2

Smithtown, NY
  • Up to 500 guests
  • All-inclusive
  • Indoor & outdoor

One of Long Island's best-kept secrets, our sprawling estate is nestled in the heart of Suffolk County and is surrounded by manicured landscapes, winding pathways and historic architecture. With an atmosphere of rustic elegance and timeless beauty, the Watermill is the perfect marriage of old-world charm and luxurious modern comforts—perfectly providing the finest amenities and endless enchantments at every turn. For more than 25 years, the Watermill has fostered joy and thousands of lasting memories through an unyielding commitment to providing unparalleled service, award-winning cuisine, and an unforgettable experience for each and every guest who walks through our doors.

Why you'll love this venue

  • Has a chic vibe
  • Has a dance floor to dance the night away
  • Full catering menu to choose from

Venue considerations

  • Large venue, not ideal for small guest lists
  • Does not allow pets
  • Not for you if you are looking for something nontraditional
This venue was amazing from start to finish. We met with Brian during the planning process and he was extremely helpful and generous the whole time. When planning, since it was both our second weddings, I said I didn’t want a hall. We saw a few places but when we stepped into The Watermill we fell in love with it!! We loved the relaxed feeling, the amazing aromas, the gorgeous gardens, the spacious feeling, the friendly staff, the endless amount of food!!!! We still have people raving about the food! We had several add ons and even the staff commented that they never saw so much food served at a wedding! When arriving we were greeted by our Maitre’d Sean and Bridal Attendant Morgan. They never left our side all night. They helped with every little detail and made sure our drinks were always full, our napkins were on our laps, made sure our kids and family were happy and that we were having a great time!! Morgan even helped my Mom with her shoe and found tape to put on it so it would stop rubbing. They were amazing! We took pictures outside before the ceremony and they brought out a ton of food for the bridal party and family! They were all starving so this was great!! There was also food and champagne in our bridal suite! We did a run through rehearsal and Sean whisked us away so we wouldn’t be seen by anyone. We had amazing weather so were able to enjoy our beautiful ceremony and cocktail hour outside. The amount of food at cocktail hour was insane! We didn’t get to walk around much as we were greeting guests but from what I saw and pictures people took, the food just didn’t stop! It was the best mix of everything and the stations were set up in such a fun way! The guests loved it. They were all full already!! But more food was waiting!! Next came the reception in the Vanderbilt Room. We had 200 people and still had plenty of space to move around. That was important to me. The bar was never packed as they had several people working it. I didn’t eat much that night but they did pack it up for me to eat later and it was delicious. Our guests could not get over the amount of choices they had for their dinner. They’ve never seen anything like that before. Everyone said it was great. We chose the Viennese hour for dessert and wow!!!! My husband and I sat at our table and enjoyed watching everyone go around picking dessert. I can’t even explain all the amazing choices they provided! It was beyond what we could have imagined!! The whole dance floor was surrounded by tables of amazing desserts!! And let’s not forget the donut wall and hot pretzels on the way out!! I cannot rave enough about The Watermill and the staff!! If you are getting married here you are in excellent hands. They are experts at what they do. From booking, to drop off, to the day of, everything was flawless and I couldn’t have asked for anything better!! It was without a doubt the best wedding!!!
Cynthia C., a year ago
Crabtree's Kittle House Restaurant & Inn 

5.0

Chappaqua, NY
  • Up to 220 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $2,000

Nestled down a quiet, tree-lined road in Chappaqua, Crabtree’s Kittle House Restaurant & Inn is a unique estate that transports all who visit to a rich, elegant past. Join us for a taste of Old New York, where unparalleled hospitality and service meet a rich tradition of excellent food & wine. As we are committed to farm-to-table cuisine, we are continually looking for ways to improve our sustainability. We believe that these efforts go hand-in-hand — it’s a way of living we enjoy and encourage with our guests. As we support our local community farmers and producers, our footprint lessens, our local economy benefits, & the quality of our products is guaranteed much higher.

Why you'll love this venue

  • Flexible event spaces
  • All-inclusive venue packages
  • Space for a large guest list

Venue considerations

  • On-site parking not available
  • Large venue, not ideal for small guest lists
  • Not for you if you prefer a more modern aesthetic
(Long review but worth it... trust me) Not sure if a wedding could ever be called "stress-free" but I'm tempted to say.... it basically was. I would never be able to say that if it weren't for everyone at Crabtree's: Kim, Leo, the Barbaras, everyone. Kim was there for us during the planning every step of the way. From the beginning, she was easy to reach and never more than an email away to answer my millions of questions. Furthermore, her expertise was extremely helpful in helping us to complete our vision. We were planning this wedding based off of the little we've seen at other weddings and a lot of Pinterest, but Kim has been doing this for years and knows exactly how to make a vision into a reality. Leo, our maitre'd was phenomenal as well. He was there every step of the day, making sure it went smoothly. He was even there to help our toddler flower girls get down the aisle when they were, well.... being toddlers lol. If we needed something, I'd turn around and he was there. Even when we didn't know we needed something, he took the initiative to make sure we were comfortable. Like when he realized we didn't get back to our dinner right away he brought them back to make sure it didn't get cold. Or when he realized we barely ate our dinner, he made sure we had some food to eat when everything was over. He is incredible thoughtful and amazing at what he does. We didn't need for anything because we had Leo by our side. The food.... Let's be real, a lot of wedding food/catering hall's food is... meh. Not at Crabtree's! If you read a little about them, you'll see that they take pride in their food. Unlike a lot of venues, where the food at the tasting is delicious but then the day of is lacking (in both taste and presentation), that was not the case. The food was JUST as delicious and well-presented as it was at the tasting. Our guests were very pleased with the food, even the biggest food snobs in attendance. I have friends still (we got married 7 months ago) telling me how they wish they could go back to our cocktail hour for some snacks! The space.... Not much to say other than GORGEOUS! Minimal decor is necessary because the outdoor and indoor space are beautiful as is. If you're fortunate to have good weather like we did, the garden is beautiful, especially with the changing leaves in autumn. So many guests have told me how this was one of the most beautiful weddings they've been too. The value... Weddings are rarely cheap, especially if you have a specific vision of that day. What I've learned is that if you're looking within a certain price range, and something is a little bit above, take a look at what they're offering in that price. See if there are ways to shave off a few dollars per person. Initially, we thought Crabtree's would be above our budget but when we looked at what they were offering and some of the options they offered to save some money, we were getting far more than other venues we had looked at. Do yourself a favor, take a visit to Crabtree's, sit down with Kim, and you'll see the value in what they are offering. We are not rich by any means but this was worth every one of our hard-earned pennies. Crabtree's and the people there will forever have a special place in our hearts. I cannot recommend them enough!
Laila & J., 5 years ago
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The Estate 
New Haven, CT
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $4,500

NOTE: For additional information about The Estate, please email us directly via our website. The Estate is a countryside wedding venue located in New Haven, Connecticut. Nestled near the flowing waters of the coastline, this historic property is located on 12 acres and provides a refined setting for couples wanting to celebrate their special day in style. To begin your day on the right note, you can use the wedding suites for pre-ceremony preparations. Receptions are held outside in our elegant sailcloth tent while the mansion is a wonderful choice for hosting the cocktail reception. For your big day, The Estate is exclusively yours, giving you and your loved ones the time to create unforgettable memories together. When selecting The Estate as your wedding venue, the in-house event coordinator will work with you to ensure that your dream celebrations become a reality. Contact us today to learn more!

Why you'll love this venue

  • Both indoor and outdoor options
  • Provides lighting and sound
  • Surrounded by beautiful vineyards

Venue considerations

  • Does not provide event staff
  • Does not have a dance floor
  • No on-site guest accommodations
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19Main 
New Milford, CT
  • Up to 130 guests
  • Raw space
  • Indoor
  • Starts at $6,000

Constructed soon after the Great Fire of 1902, The United Bank Building was built to house two banks whose previous buildings had been destroyed, New Milford Savings Bank and the New Milford First National Bank. The two banks immediately organized to rebuild, quickly agreeing in principal to build a joint facility on the site of the New England House, a locally well known tavern and inn located at the corner of Bank and Main Street. For most of its life, the building had been used in some form of a bank, but had been largely under-used in recent decades, and had fallen into disrepair. The building was listed on the National Register of Historic Places in 1982 and taken over by Village Green Investments in 2015. After 9 months of renovations, the building became 19Main. Throughout renovations, we strived for modern amenities with historic elegance; three vaults remain from the building’s former bank days.

Why you'll love this venue

  • Dressing room available
  • Raw space for complete customization
  • Classic seating dinner

Venue considerations

  • Dance floor not included
  • Couple must handle cleanup and setup
  • Additional event staff required
Quick responder
The Garden House at Keeler Tavern Museum 
Ridgefield, CT
  • Up to 80 guests
  • Select services
  • Indoor & outdoor
  • Starts at $6,000

Designed for entertaining by renowned architect, Cass Gilbert, The Garden House at Keeler Tavern Museum in Ridgefield, Connecticut charms in a manner that is once lavish, classically beautiful, and intimate. Step into a world of gorgeous gardens, lush landscapes, and intimate reception surroundings. Experience the distinction and elegance your special event deserves. The Garden House offers indoor and outdoor spaces, making your event as inspired and memorable as you imagine it to be. It is exclusively yours on your wedding day.

Why you'll love this venue

  • Has a dance floor for celebration
  • Classic elegance
  • Pets can join the celebration

Venue considerations

  • No on-site guest accommodations
  • Limited cleanup and setup services
  • No free parking
1920 Bar and Bistro 
Norwalk, CT
  • Up to 250 guests
  • Select services
  • Indoor
  • Starts at $2,250

Discover a one-of-a-kind event space nestled within the historic walls of a former Hat Factory in Old Norwalk. Immerse yourself in the allure of a bygone era and celebrate special moments at a venue that holds a piece of Norwalk's captivating history as the 'hat capital of the world.' Whether it's a grand wedding, or an intimate affair, our venue offers a unique backdrop that pays homage to Norwalk's illustrious past. Our versatile space can accommodate up to 250 guests, providing a sit-down setting that begins with private dining for 12 guests and extends to a grand affair, accommodating up to 150 guests for dinner. Our venue seamlessly blends the charm of history with the sophistication required for your special day. The space features a DJ or live music stage, pre-function areas, and an adjoining stylish bar available for private event rentals. Step into a space that not only hosts events but also weaves the narrative of Norwalk's rich heritage into every celebration.

Why you'll love this venue

  • Provides lighting and sound
  • Provides catering services
  • Pets can join the celebration

Venue considerations

  • No on-site guest accommodations
  • Large venue, not ideal for small guest lists
  • Not wheelchair accessible
Quick responder
Pinstripes Norwalk 
Norwalk, CT
  • Up to 1200 guests
  • All-inclusive
  • Indoor & outdoor

Are you looking for a private event venue to host your next corporate event, wedding reception, Holiday party, or birthday party? Pinstripes provides the perfect event space to meet whatever your party or group event needs! We offer a variety of flexible room sizes, awesome menu options, and fun group activities including bowling and bocce ball. Our Norwalk, Connecticut location offers a unique variety of entertainment and events every day of the week. Enjoy our made-from-scratch Italian-American cuisine during Sunday Brunch with the family, happy hour after work, or a night of bowling and bocce.

Why you'll love this venue

  • Private area for the wedding party
  • Offers full-service amenities
  • Feels like a getaway

Venue considerations

  • No free parking
  • Not for you if you are looking for something nontraditional
  • Does not allow pets
Quick responder
Breezehill Farm 
Peconic, NY
  • Select services
  • Outdoor
  • Starts at $25,000

Nestled into over 72 acres of sprawling apple orchards and a private hunting preserve on the North Fork of Long Island rests an exquisitely constructed farmhouse and charming Farm Stand featuring fresh-picked fruits and veggies along with sweet treats like our famous apple cider donuts and fresh-baked pies. One visit to Breeze Hill Farm and Preserve and you’ll quickly realize why it’s one of Long Island’s local gems and most treasured destination.

Why you'll love this venue

  • Venue is completely outdoors
  • Exudes old-world charm
  • Has a sophisticated vibe

Venue considerations

  • Couple must handle cleanup and setup
  • Not wheelchair accessible
  • No in-house lighting and sound packages available
Quick responder
The Waveny House 
New Canaan, CT
  • Up to 160 guests
  • Raw space
  • Indoor & outdoor
  • Starts at $3,600
  • Offer

Established in 1912 for the Lewis Lapham family. Waveny House, a historic Tudor style mansion sits majestically overlooking 300 hundred acres of countryside in picturesque New Canaan, Connecticut. Accommodating up to 160 guests Waveny House is a fairytale setting for weddings and receptions. Take a tour down the flagstone walkways through the gardens and fish pond to discover the beautiful Walled Garden, a special nook for a small ceremony. The bride and groom truly have an opportunity to create that special wedding at Waveny House.

Why you'll love this venue

  • Allows pets
  • Private area for the wedding party
  • Wheelchair accessible

Venue considerations

  • Limited cleanup and setup services
  • Requires outside catering services
  • No on-site guest accommodations
Quick responder
DCA Meadowlands 
Darien, CT
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $6,000

Fall in love with our beautiful mansion and create the wedding of your dreams. Whatever season, whatever style, this historic home opens its doors and becomes yours for the day. Dress in our romantic bridal suite. Get married in our historic formal garden – it makes a magnificent stage for your outdoor ceremony. Commemorate your special day with photos in our manicured gardens or on the sweeping front lawn. And finally, celebrate with a reception in our spacious Garden Wing and other unique, historic rooms. If your dream is to have your reception under a tent, the DCA Meadowlands can accommodate up to five tent weddings per year.

Why you'll love this venue

  • Has a dance floor for celebration
  • Has an intimate atmosphere
  • Bridal suite on site

Venue considerations

  • No in-house catering options
  • No on-site guest accommodations
  • Large venue, not ideal for small guest lists
Quick responder
Heavitree of Griswold Bed and Breakfast 
Griswold, CT
  • Up to 100 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $2,500

Our ancestors settled here in 1635 from Heavitree, England, hence the name. We are one of the few longest-living farms to continue in the founder’s name “Geer.” The Heavitree is an original 18th-century building saved and moved to its current location, a 140+ acre farm started by our ancestors in 1700. The original structure was a tavern in Rhode Island, saved from destruction by Charlotte Geer to complement her family’s historic farmland. With twelve rooms, including four sleeping chambers, modern amenities, and unique 18th-century rooms, the 4,780 sq. ft. farmhouse offers a historic experience. Enjoy the vast lawns, fields, gardens, and beautiful private vistas.

Why you'll love this venue

  • Exudes old-world charm
  • Full catering menu to choose from
  • Caters to out-of-town guests

Venue considerations

  • Not for you if you're looking for a sleek and contemporary space
  • Couple must handle cleanup and setup
  • No built-in audiovisual options

Location flexible? Discover venues near Cheshire, CT

About wedding venues in Cheshire, CT

How much do wedding venues typically cost in Cheshire, CT?

The cost of a wedding venue varies widely by location, number of guests, and many other details of the wedding package. Cheshire, CT offers a range of options that can fit most budgets. Raw venue space rentals (which only include the space itself) start at $1,200 and average $1,200. All-inclusive packages start at $115 and average $9,000.

What types of venues can I find in Cheshire, CT?

Cheshire offers a wide range of venues, including Ballroom, Historic estate and Barn and ranch.

What are some of the best wedding and reception venues available in Cheshire, CT?

Some of the most popular venues in this area include The Lake House, Bill Miller's Castle and Woodwinds. But just like finding "the one," finding the perfect wedding venue takes time and a little bit of magic. Start by envisioning your dream wedding - the ambiance, style, and location. Then, explore our extensive collection of carefully curated wedding venues. Our marketplace provides detailed information, stunning photos, and real couples' reviews to help you make an informed decision. Trust your instincts, and when you find that venue that gives you butterflies, you'll know it's the one.

What questions should I ask when booking a venue in Cheshire, CT?

It all depends on what you're looking for, but you may want to consider things like whether the venue has an on-site bridal suite (87% in Cheshire do) or whether the venue provides an event coordinator (78% in Cheshire do!).

Additionally, some venues work with certain caterers and require a minimum food and beverage spend in addition to the space rentals. Others might have a recommended list of preferred caterers that they'd like you to work with.

Can the venues in Cheshire, CT accommodate both small and large weddings?

Of course! Small wedding venues in Cheshire, CT can host intimate parties while large venues can accommodate up to 600. The average venue in Cheshire can seat 150 guests.

What amenities do the reception venues in Cheshire, CT offer?

The venues in Cheshire, CT are known for the exceptional suite of services and amenities offered to couples and their wedding parties. The most common services provided are Wi-Fi, Dressing room / Bridal Suite and Wheelchair accessible. Some venues even offer Transportation!

What types of wedding venues are in Cheshire, CT?

What other Cheshire vendors will I need?

What other wedding venues are nearby?

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