The Best Vineyard & Winery Wedding Venues in Chester, MA

The Best Vineyard & Winery Wedding Venues in Chester, MA

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4 Wedding Venues in Chester, MA

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Stablegate Farm & Vineyard 

5.0

Castleton On Hudson, NY
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $14,500

From the minute you arrive at Upstate New York’s finest farm and vineyard venue, you will be enamored by the historic charm and rustic elegance that defines Stablegate Farm and Vineyard. Fall in love with the 19th-century Stablegate Barn filled with charming antique decor and ambient market-street lighting. For more intimate gatherings, our Stablegate Lodge provides guests with a warm, inviting atmosphere to celebrate. Choose from a private vineyard, a hilltop view of the Catskill mountains, a 200-year-old Dutch barn door, or a fossil stone fireplace for your Upstate New York ceremony.

I don’t even know where to begin. At the beginning of our wedding journey, finding a venue was the hardest thing we could’ve done. My husband and I had a specific vision in mind and had an incredibly difficult time finding a place that we loved that was also within our budget. We’re from the LI area but knew we wished to get married upstate. We must have visited at least 10 venues. Then on our way home from one, my husband found Stablegate on a whim. We looked everything over and it had the barn that I wanted, and the catering included that my husband wanted and I said “if we visit and we like it, I’m putting a deposit down the next day.” And that’s exactly what we did. Birch Hill is an incredible family owned company with so many aspects attached to it, it was hard not to fall in the second we saw it. Over 2.5 years, I never once regretted that decision and once the wedding day came and went I knew it was the right choice for us. The food is amazing and a ton of different options (including catering to my vegan guests), the staff are incredible, and the vibes are immaculate. Our wedding coordinator Jared was really the star of the show. He was super accommodating to all of our needs, organized, and just all in all a ridiculously sweet and funny guy. When our wedding day ended up getting rained out, he came up with backup plans right on the spot that honestly fit our vibe so much more than our original plan and I really truly have Jared to thank for that. Jared treated us like we were old friends that he was just helping throughout the day. He is someone I will truly forever be the most grateful for to have on my wedding day. I have heard so many horror stories about venues, and I can honestly say this is not one of them. Stablegate Barn and the Birch Hill Catering Company have my highest recommendation. And if you need a coordinator, ask for Jared. Really truly from the bottom of my heart, thank you for an amazing wedding day.
Ariella P., a month ago
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Birch Hill Catering & Estate 

5.0

Castleton On Hudson, NY
  • Up to 400 guests
  • All-inclusive
  • Indoor & outdoor

With over 80 years of experience, Birch Hill Catering continues to be one of Upstate New York’s most memorable wedding destinations. From a formal sit-down dinner in a ballroom setting to casual outdoor BBQ style wedding or even a rustic barn wedding; any one of the venues at Birch Hill Estate or Stablegate Farm is sure to capture your imagination.

My wedding experience at Birch Hill was incredible, and I owe so much of that to Serena and her amazing team! We started the booking process in early March, hoping for a September/October wedding date, and thankfully found one that worked. Serena was an absolute goddess from start to finish—she gave us a thorough tour of all the location options, answered every question, and made the entire process feel effortless. We knew almost immediately that no other venue would compare! Since we were on a tight timeline, I reached out to Serena frequently with questions, and she always responded promptly and thoroughly. By our 90-day planning meeting, we were already so comfortable with everything, and Serena guided us seamlessly through food choices (of which there were so many!) and other details. Her expertise really shone through when I wasn’t sure about certain things; she made it all so simple and stress-free. On the big day, I felt so confident in Serena and her team—it was like everything was taken care of before I could even think about it. I truly felt like I had nothing to worry about and could be fully present in every moment, which made the day even more magical. They thought of every detail, big and small, allowing me to simply enjoy and soak it all in. Speaking of the food—it was hands down the best meal I’ve ever had! We chose the Cocktail Style package and went with a wide range of options, including crispy calamari with lemon-garlic aioli, French onion soup, cider bacon-wrapped chicken, pulled pork wonton bites, and mini grilled cheeses with tomato soup shooters, among others. Every single bite was phenomenal! The prime rib was cooked to perfection, and the mashed potato bar and pasta station were crowd favorites. Our guests raved about the gourmet French fry station that we had later in the night. While we handpicked the items, I genuinely believe that anything else on their menu would have been just as amazing—the quality and flavors were out of this world. At the end of the night, everything was packed up perfectly and already in my car before I even stopped partying! If I had to give any constructive feedback, it would be about the bridal suite. It was a very warm day for late September, and the air conditioning hadn’t been turned on before we arrived, so the suite was quite hot initially. Other than that, our ceremony by the pond was absolutely beautiful. While the mosquitos and some goose droppings were a minor annoyance, the setting was otherwise perfect and so romantic. All in all, I couldn’t have asked for a better experience. Serena’s commitment and attention to detail made our wedding truly unforgettable!
Macy H., 11 days ago

Location flexible? Discover venues near Chester, MA

About wedding venues in Chester, MA

How much do wedding venues typically cost in Chester, MA?

The cost of a wedding venue varies widely by location, number of guests, and many other details of the wedding package. Chester, MA offers a range of options that can fit most budgets. All-inclusive packages start at $500 and average $6,600.

What types of venues can I find in Chester, MA?

Chester 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 Chester, MA?

Some of the most popular venues in this area include Quonquont Farm, The Boylston Rooms and The Log Cabin. 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 Chester, MA?

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 (80% in Chester do) or whether the venue provides an event coordinator (75% in Chester 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 Chester, MA accommodate both small and large weddings?

Of course! Small wedding venues in Chester, MA can host intimate parties while large venues can accommodate up to 500. The average venue in Chester can seat 150 guests.

What amenities do the reception venues in Chester, MA offer?

The venues in Chester, MA are known for the exceptional suite of services and amenities offered to couples and their wedding parties. The most common services provided are Wheelchair accessible, Wi-Fi and Bar services. Some venues even offer Transportation!

What types of wedding venues are in Chester, MA?

What other Chester vendors will I need?

What other wedding venues are nearby?

What other wedding services are nearby?