The Best Small Wedding Venues in Cheshire, CT

The Best Small Wedding Venues in Cheshire, CT

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39 Wedding Venues in Cheshire, CT

Farms, barns, ranches
Up to 50 guests
Nathan Hale Homestead 
Coventry, CT
  • Up to 250 guests
  • Raw space
  • Outdoor
  • Starts at $500

Built in 1776, the Nathan Hale Homestead is a National Historic Landmark and the birthplace of Connecticut’s State Hero, Nathan Hale. The property features an 18th-century English Barn with rare gunstock timber framing, a charming 19th-century Dairy Barn, and open pastures surrounded by stone walls and forest. This beautiful home offers a quintessentially New England backdrop for your wedding day or other event.

Why you'll love this venue

  • Provides event staff
  • Offers full flexibility in setup and decor
  • Rustic-chic setting

Venue considerations

  • Not wheelchair accessible
  • No venue-provided food services
  • No dedicated areas for getting ready
Akindale Farm 
Pawling, NY
  • Up to 200 guests
  • Raw space
  • Indoor & outdoor

Akindale Farm is one of a kind. Situated on 310 picturesque acres on Quaker Hill in the center of the Hudson Valley, Akindale offers a backdrop of rolling hills, herds of stunning racehorses, incredible vistas, and a wealth of different locations on the property to suit your special event. Akindale is not a typical wedding venue; but it is an exceptional place for your wedding. Our core mission is to rescue and care for retired Thoroughbred racehorses and we have over 120 on site. We are working farm, not a manufactured showplace. Therein lies our natural beauty. We welcome all types of ceremonies, and respect individual creativity. As a nonprofit, we are able to fund our work with the horses through offering our spaces and as such, your location fee will be completely tax-deductible. We hope you consider our space and invite you to come visit!

Why you'll love this venue

  • Rustic charm with elegance
  • Flexible event spaces
  • Offers full flexibility in setup and decor

Venue considerations

  • Does not have a dance floor
  • Does not provide event staff
  • Couple must handle cleanup and setup
Lucky Orphans Horse Rescue 
Dover Plains, NY
  • Up to 300 guests
  • Select services
  • Indoor & outdoor
  • Starts at $7,500

Have your wedding at a scenic barn in the rolling hills of Dover Plains. Enjoy your wedding outside in a paddock with a picturesque backdrop of beautiful trees and horses, and/ or inside our 11,000 square foot arena, or the main barn! Our mission of People Helping Horses Heal People is rooted in the care we provide for all of our rescued horses, including retired Thoroughbred racehorses. We give back to our community through our developmental, youth, and therapy programs. We encourage individual expressiveness, and embrace all ceremony types at our location. We are a horse sanctuary and a working farm, not just an event venue. By having your wedding here, you are funding a nonprofit, benefiting both our horses and community. We invite you to come visit the farm any day from 9-3!

Why you'll love this venue

  • Flexible event spaces
  • Space for a large guest list
  • Has a relaxed and casual vibe

Venue considerations

  • No on-site bridal suite
  • No free parking
  • No on-premises lodging options
Greer Southern Table 
Norwalk, CT
  • Up to 80 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $2,500

We call ourselves a southern table; a place to enjoy casual yet refined low & high country cuisine- where you're treated like family and can seek respite from the world in a relaxed, fun, and comfortable atmosphere. "The Table" is where so much occurs, from celebrations to business deals. We eat, drink, and break bread at the table. We share stories of laughter and tears. We toast to yesterday, today, and to the future - all at the table. A place where we come together after a long day or week and spend time with each other to connect.

Why you'll love this venue

  • Has a luxe vibe
  • Full catering menu to choose from
  • Rustic-chic setting

Venue considerations

  • Not for you if you're looking for a sleek and contemporary space
  • Not wheelchair accessible
  • Does not allow pets
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
Race Brook Lodge 
Sheffield, MA
  • Up to 200 guests
  • Select services
  • Indoor & outdoor

Welcome to Race Brook Lodge, gateway to the Berkshires! Nestled at the foot of Mount Race in Sheffield MA, Race Brook Lodge welcomes you to a place of peaceful respite and outstanding hospitality in alignment with local sustainability and inner harmony right here in the Berkshires. When you step outside your room, you’ll be greeted with breathtaking hiking trails that will lead you to the must-see views from the top of Race Brook Falls. We host couples seeking a tranquil, romantic Berkshires getaway for anniversaries, weddings, or just because. We also host wellness and yoga retreats, corporate events, and family gatherings. Regardless of your needs, we are here to provide you with an unforgettable, easeful experience that will leave you feeling rejuvenated, refreshed, and more connected to yourself, nature, and any new friends you made along the way.

Why you'll love this venue

  • Multiple event spaces
  • Allows pets
  • Handles all cleanup logistics

Venue considerations

  • Not for you if you prefer a more modern aesthetic
  • Large venue, not ideal for small guest lists
  • Not wheelchair accessible
Quick responder
Bush Meadow Farm, LLC 
Union, CT
  • Up to 400 guests
  • Raw space
  • Indoor & outdoor

At Bush Meadow Farm, we don't host wedding days. We host wedding experiences so you can celebrate your love, your way. Located in the Quiet Corner of Connecticut, our beautiful farm property features multiple reception and ceremony locations for you to dream up the most unique, true to your love, family and friend filled, wedding. Our goal is to create a relationship with our couples, and we will look out for them. We have an open communication style. Our Brides and Grooms feel relaxed and settle into this amazing space with their family and friends.

Why you'll love this venue

  • Offers full flexibility in setup and decor
  • Both indoor and outdoor options
  • Space for a large guest list

Venue considerations

  • Limited cleanup and setup services
  • Lighting and sound are not included
  • Best for events with big guest lists
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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

Connecticut creates a magical backdrop for weddings with its diverse landscape ranging from historic mansions to renovated barns, waterfront properties and lush gardens. You'll find venues that perfectly blend traditional New England charm with modern amenities while showcasing the state's distinct seasonal beauty - exactly what you need to create those perfect wedding memories.

What Makes Connecticut Wedding Venues Distinctive?

Architectural diversity really sets Connecticut wedding venues apart. Eolia Mansion features an incredible amphitheater ceremony space and lovingly preserved period details that transport you back in time. The Barns at Wesleyan Hills stands out with its Edison Light Wall that creates absolutely magical evening ambiance you and your guests will remember forever. Fall weddings between September and October deliver spectacular foliage colors for ceremonies while July offers perfect conditions for waterfront celebrations along the Connecticut shoreline with comfortable temperatures and stunning water views.

How Much Do Connecticut Wedding Venues Cost?

Wedding venue costs in Connecticut typically range from $8,300 to $10,200 and represent about 17% of your total wedding budget. This aligns nicely with the national average of $6,500-$12,000 or 25% of total wedding costs, so you're getting good value in Connecticut.

For different guest counts, your approximate total wedding budgets will look like:

  • 50 guests: $24,172
  • 100 guests: $39,982
  • 150 guests: $54,842
  • 200 guests: $68,120
  • 250 guests: $81,398
  • 300 guests: $94,676

Where Can You Find Accessible Wedding Venues in Connecticut?

The Riverview in Weatogue accommodates up to 500 seated guests with complete accessibility features and packages starting at $10,000. You'll find The Waterview in Monroe offers beautiful lakeside event spaces for up to 300 guests with handicap-accessible indoor and outdoor areas that make movement easy for all your guests.

Eolia Mansion at Harkness Memorial State Park gives you accessible ceremony locations for up to 150 guests with pricing starting at $5,000, while The Glastonbury Boathouse welcomes 150 guests with wheelchair accessibility throughout its indoor and outdoor spaces so everyone can enjoy your special day without limitations.

Which Connecticut Venues Offer Outstanding Culinary Experiences?

The Omni New Haven Hotel at Yale showcases local ingredients through their upscale in-house catering that will impress even your foodie guests. Delamar West Hartford features the award-winning Artisan Restaurant offering refined cuisine in an upscale setting that perfectly complements your celebration.

The Pond House Cafe in West Hartford has earned serious praise for unique food options and stunning presentation that elevates your reception experience. Winvian in Morris delivers true 5-star farm-to-table dining with ingredients harvested from their on-site gardens; you'll taste the difference in every bite and your guests will be talking about the meal for years.

How Can Connecticut Venues Accommodate Remote Wedding Guests?

The Waterview offers cutting-edge virtual reality applications allowing your remote guests to explore venue grounds and interact with on-site attendees almost like they're physically there. Anthony's Ocean View provides dedicated event concierges who help integrate technology for seamless remote participation so no one feels left out.

Innovative venues now incorporate interactive video conferencing virtual reality experiences and personalized virtual engagement platforms that go far beyond simple streaming. These technologies create truly inclusive experiences for remote guests who can't make it in person but still want to share in your special day.

When Should You Book Your Connecticut Wedding Venue?

Connecticut venues typically need booking 16 months in advance with September generating the highest volume of venue inquiries. The peak wedding season spans September-October when fall foliage creates stunning natural decor driving serious competition for prime weekend dates at barn and outdoor venues. You'll want to secure your date early especially if you're dreaming of that perfect autumn wedding.

What Wedding Costs Should You Expect in Connecticut?

Key wedding expenses for a 150-guest wedding include:

  • Venue: $9,243 (17%)
  • Catering: $7,395 (13%)
  • Florists: $6,399 (12%)
  • Bar Services: $5,916 (11%)
  • Planners: $5,119 (9%)
  • Photographers: $4,977 (9%)

What types of wedding venues are in Cheshire, CT?

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