Top Connecticut Proposal Barns

• Spaces for 200-250 Guests
• 1 Barn
• 2 Outdoor Spaces
• 2 Total Spaces

Why You’ll Fall in Love with Falls Creek Farm Falls Creek Farm is an enchanting 300-acre destination nestled in the picturesque Connecticut countryside. With two distinct venues onsite, The Reserve and Creekside, our property offers couples the flexibility to choose a setting that reflects their vision. At The Reserve, you’ll find our timeless stone chapel, lakefront ceremony options, and the Lakefront Barn for unforgettable receptions. At Creekside, celebrate in the Orangery, followed by a reception beneath our stunning Century Tent. Whether you dream of an intimate garden ceremony or a grand celebration in a barn with chandeliers, our versatile spaces and dedicated team will bring your day to life with timeless charm and unforgettable detail.

• Spaces for 200-350 Guests
• 1 Barn
• 1 Farm

An 1843 historic Inn situated on the top of Candlewood Mountain in the Litchfield Hills of New Milford,CT. A perfect location for your tented event, a romantic getaway or your equestrian destination.

• Spaces for 200-350 Guests
• 1 Barn
• 1 Outdoor
• 1 Tent

Holiday Hill is a family-owned event venue and recreation center set on 25 acres of rural grounds in Mansfield Center, Connecticut. With over 60 years of history, the property offers two principal event spaces alongside expansive outdoor surroundings suited for weddings, reunions, performances, picnics, and private celebrations. The post-and-beam barn seats up to 200 guests beneath a cathedral-like ceiling with an open floor plan. The space is noted for its acoustics, making it well suited for ceremonies, speeches, and live or recorded music. A high-peak wedding-white tent seats up to 300 guests for dinner and can be configured with picnic tables, banquet tables, or display arrangements to fit formal or informal events alike. Beyond the two main structures, the grounds include basketball courts, volleyball and badminton courts, two 25-yard pools, miniature golf, and more — available as part of rental packages. Farmhouse lodging on-site makes Holiday Hill a practical option for multi-day or destination celebrations.

• Spaces for 70-150 Guests
• 1 Barn
• 1 Outdoor
• 2 Total Spaces

Chamard Vineyards is a working winery, farm, and bistro set on 20 acres of vines in Clinton, Connecticut, along the Connecticut Wine Trail. The property combines vineyard production with a full-service dining experience — award-winning wines poured alongside acclaimed cuisine prepared in-house, in a setting that earns the description of a destination rather than just a stop. The venue hosts private celebrations of up to 70 guests across two distinct spaces. The Barn is a lofty, rustic timber structure ideal for intimate seated dinners, rehearsal dinners, and milestone gatherings; its adjacent patio opens onto vineyard views. The Lawn, surrounded by 20 acres of vines and hand-laid stone walls, offers a naturally beautiful outdoor setting for ceremonies and al fresco receptions. Both spaces are customizable to match the event vision, with Chamard's food and wine program woven throughout.

• Spaces for 300 Guests

The Courtyard by Marriott Waterbury Downtown is an 11-story hotel in the heart of downtown Waterbury, Connecticut, roughly an hour from New York City and 30 minutes from Hartford. The property underwent a full renovation in 2014, bringing its lobby and event facilities up to the brand's modern Refreshing Business concept — open, flexible, and built for gatherings of all kinds. For events, the hotel is home to Barn on Grand, a dedicated event space on the lobby level that blends exposed brick, warm wood accents, and rustic character with contemporary elegance. The Barn accommodates up to 150 guests and is well suited for weddings, receptions, milestone celebrations, and corporate gatherings. The hotel also offers additional ballroom and meeting space, totaling over 10,000 square feet of renovated event facilities across eight rooms. Guests and attendees benefit from complimentary Wi-Fi throughout the property, full audio-visual services, in-house catering, a Starbucks, and on-site parking. The hotel's 199 guest rooms and suites — along with valet parking and a fitness center — make it a convenient all-in-one destination for multi-day events.

• Spaces for 50-350 Guests
• 1 Barn
• 1 Bar
• 8 Total Spaces

The Eugene O'Neill Theater Center is a working campus for the development of new American theater, set on a sweeping waterfront property in Waterford, Connecticut overlooking the Long Island Sound. Founded in 1964 by George C. White, the O'Neill has spent six decades as the country's preeminent organization dedicated to developing new works and new voices for the stage — earning Tony Awards in 1979 and 2010 and the National Medal of Arts in 2016. Productions first developed here include *In the Heights*, *Avenue Q*, *Fences*, and *The Piano Lesson*. The campus opens to private events from late August through spring, offering eight distinct rental spaces that range from a 300-guest outdoor garden with views of the Sound to an intimate Victorian mansion with parlor rooms and an outdoor patio. The Rose Barn Theater — original to the property — brings a rustic character to receptions and celebrations, while the Dina Merrill Theater offers the campus's largest indoor footprint with expansive windows and flexible configuration. A campus attendant is present throughout every event.

• Spaces for 50-175 Guests
• 1 Barn
• 3 Outdoor Spaces
• 4 Total Spaces

Preston Ridge Vineyard is a working estate winery and event venue set on 60 acres in Preston, Connecticut, roughly 15 miles from Long Island Sound. Founded in 2008 by the Sawyers and Helms families and open to the public since October 2012, the property centers on a New England gambrel-style barn with a wraparound deck overlooking the vineyard rows and surrounding landscape. The venue hosts weddings, corporate functions, bridal showers, and private parties across several spaces: the barn and grounds accommodate ceremonies and receptions for up to 150 guests, while the tasting room seats up to 50 guests for intimate gatherings and expands to 100 when the deck is combined. For larger events, a seasonal tented lower green extends capacity to 175 guests. Weddings include use of the tasting room and deck for cocktail hour, a dressing suite, tables and chairs, parking attendants, and grounds access for photography and videography. The vineyard's own estate and varietal wines — reds, whites, and rosés — are available throughout, making it a natural fit for celebrations that want the feel of a working farm winery.

• Spaces for 200-300 Guests
• 1 Barn
• 1 Outdoor
• 2 Total Spaces

The Village at Boulder Ridge is a family-owned event venue set on 68 acres at the foothills of the Berkshires in Barkhamsted, Connecticut. Operating since 2003 and with more than 500 events hosted, the property combines rustic character — exposed wood, a stone fireplace, a private lake with gazebo — with full on-site catering and a range of indoor and outdoor spaces. The Main Banquet Hall accommodates up to 300 guests and features a dance floor, exposed wood beams, and a grand stone fireplace suitable for indoor ceremonies. The open-air pavilion, which overlooks the pond and pool and is strung with twinkle lights, seats up to 200 guests and opens the property's natural landscape to guests. A lakeside gazebo provides an outdoor ceremony setting. The venue hosts one event per day, giving each group exclusive use of the entire facility. The Village operates seasonally from May through mid-October.

• Spaces for 300-500 Guests
• 1 Barn
• 1 Outdoor
• 1 Park

Three Saints Park is a 25-acre private park set in Bethany, Connecticut — a small, rural town that has kept its New England character. The property spans wooded and open grounds with a pond, sports fields, and two pavilions, offering a natural backdrop for DIY celebrations of all kinds. The Large Covered Pavilion accommodates up to 300 guests and sits adjacent to a full catering kitchen, making it the centerpiece for weddings, receptions, and large gatherings. The Small Pavilion, a 1920s-era structure and the oldest on the property, overlooks the pond and provides a more intimate setting. Both spaces are available for full-day exclusive buyout — no two events share the grounds on the same day. Three Saints Park is built for couples and hosts who want creative control. Food trucks are welcome, outside vendors are encouraged, and the venue provides 12 picnic tables, a podium and stage, event lighting, parking for approximately 100 cars, and on-site restrooms.

• Spaces for 75-175 Guests
• 1 Barn
• 2 Museums
• 2 Total Spaces

This historic building makes for a great site for a wedding. The staff will help to coordinate all aspects of the wedding from entertainment to food to the ceremony. The barn is open April through November and will make for a memorable and unique day. The maximum rental time of the barn is six hours, which is a reasonable length for a wedding. It is also extremely affordable which makes it a desirable place to host a modest wedding. The seating in the barn is limited to 135 people, but you can provide additional tables and chairs if necessary to accommodate all of your guests.

• Spaces for 45-125 Guests
• 1 Barn
• 1 Restaurant
• 3 Total Spaces

Stonecroft Country Inn is a historic bed and breakfast set on 6.5 acres in Ledyard, Connecticut, minutes from Mystic. The property traces its origins to 1807, when sea captain Shubel Smith built the Georgian Colonial that still anchors the estate. Listed on the National Register of Historic Places and recognized by Select Registry Distinguished Inns of North America, the inn blends period architecture — wide-plank floors, stone walls, a working fireplace — with fully renovated accommodations across ten guest rooms. The estate offers multiple event settings for weddings, elopements, and private gatherings. The Yellow Barn accommodates ceremonies and receptions for up to 75 guests, while the intimate stone-walled dining room in the 1807 House hosts seated dinners and gatherings of up to 45. For larger celebrations, the Grand Affair tent on the manicured lawn expands capacity to 125 guests, surrounded by koi ponds, terraced gardens, and centuries-old stone walls. Exclusive buyout packages include use of the inn's guest rooms, making Stonecroft well suited for destination weddings and weekend retreats where guests stay on-site. Gourmet three-course breakfasts are included with all room stays.

• Spaces for 60-150 Guests
• 1 Barn
• 1 Outdoor
• 2 Total Spaces

Roseland Cottage is a National Historic Landmark in Woodstock, Connecticut, managed by Historic New England. Built in 1846 for New York merchant and publisher Henry Bowen, the Gothic Revival estate is instantly recognizable by its bright pink board-and-batten exterior, steep gabled rooflines, and ornamental bargeboards — considered one of the best-preserved examples of the style in the country. The grounds reflect the same Victorian ambition as the house itself. A boxwood parterre garden, designed in the 1850s, contains 21 flowerbeds with more than 4,000 annuals. The carriage barn shelters the oldest surviving indoor bowling alley in the nation, a reminder that Bowen used Roseland Cottage to entertain on a grand scale — four U.S. presidents among them. From May through October, the Carriage House and south lawn are available for private events including weddings, corporate gatherings, and celebrations. The rental includes kitchen facilities, tables and chairs, and two accessible restrooms, all set against grounds that have hosted guests since the age of Ulysses S. Grant.