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.

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., 6 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.

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., 4 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.

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., 4 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.

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., 3 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.

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, 3 months ago
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Riverbend 

4.0

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.

Riverbend is like nothing else we've experienced - the stunning buildings, winding river and peaceful sun-dappled property is just amazing. But the venue's beauty is just the beginning! The planning team at Connecticut Wedding Group is professional magic, orchestrating every detail with laser focus and contagious enthusiasm - you can't help but smile when you're with any of them. And don't even get us started on the food, it's literally the best that we've ever had. If you're dreaming of a wedding that's breathtaking, one of a kind and stress-free, you need to book Riverbend!
Daphne and Dean, 10 months 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.

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., 3 months ago
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BLDG 4 CT 

5.0

Manchester, CT
  • Up to 250 guests
  • Select services
  • Indoor & outdoor

BLDG 4 is a Connecticut historic event venue specializing in weddings, private parties and corporate functions. Our capacity for sit down is (250) and cocktail is (500)! We have ample amount of parking and we offer great amenities! We offer tables, chairs, support staff, indoor & outdoor spaces along with much more. All of our wedding packages include full access the day of and a wedding suite. You can also upgrade to our Penthouse Wedding Suite for those couples who need a bit more.

I cannot say enough wonderful things about Historic Events and Banquets! The venue itself has been so thoughtfully developed, with gorgeous details throughout and a clean, beautiful aesthetic that is perfect for weddings! But their team is...AMAZING. From the attention to detail, to the client experience they create, this is simply a wonderful experience for epic celebrations!
Teresa Johnson, 4 years ago
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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.

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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!

Awarded Best of Zola
I loved photographing Kelsey & Alex's micro wedding at The Spinning Wheel! The afternoon was so calm and easy with the Katlyn's great organization and the rest of the staff. The flowers and appeal of the venue is stunning in the spring and summer. For it being a small venue, there are still tons of different photo opportunities.
Meghan Ann Imagery LLC, 6 months ago
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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.

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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.

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.

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
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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.

We could not have been happier to have our wedding reception at Watermill! It was absolutely incredible! For our December wedding, it was so beautifully decorated for Christmas it created such an inviting and festive atmosphere. There are also so many spots to take pictures on the grounds that you don’t have to find another location between or before your ceremony and reception. In the few short weeks since our wedding, we have received so many compliments about Watermill! Our guests were blown away by the extensive cocktail hour selection and we were told “it was the best wedding food they’ve ever had.” The 9 dinner options were not only so amazing and tasty, but truly accommodated all dietary needs. The staff was AMAZING- huge shout out to Rob, Sean, Jessica and Erika! No need for a DOC here- they set up everything that we brought to Watermill without any issues. Even placing a personalized ornament at each place setting — for 280 people. Our bridal attendants and Sean kept drinks in our hand all night long and ensured that everything ran smoothly. We are hoping that someone in our lives decides to get married at Watermill in the future so we can go back and enjoy it as guests! Thank you so much Watermill for a truly unforgettable day! -Meghan & Connor 12/16/23
Meghan C., 10 months ago
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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.

Having supplied musicians and DJs at Crabtree's Kittle House for decades I am in a unique position to claim that every Kittle event is unique and handled with the highest degree of professionalism in the arts of cuisine and management. Thankfully they were available for my daughter's wedding date! There was no other choice!
Brendan O'Keefe BOK-Music, 5 years ago

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?

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