Top Canaan Venues

• Spaces for 20-250 Guests
• 3 Outdoor Spaces
• 1 Theater
• 7 Total Spaces

Isabella Freedman Retreat Center is a kosher, pluralistic retreat center set on 400 acres in the Connecticut Berkshires, approximately two hours from New York City and three hours from Boston. The property encompasses a 20-acre organic farm, four miles of marked hiking trails, a seasonal lake, and lodge accommodations for up to 160 overnight guests — giving groups a full-campus experience from arrival through departure. The center hosts approximately 6,000 guests each year across private events and its own programming calendar. Groups of 25 to 200 can rent the facility for weddings, b'nai mitzvot, family reunions, corporate retreats, synagogue gatherings, and community celebrations. All on-site dining is prepared under glatt kosher certification, with farm-to-table meals that draw from the property's own farm. Indoor gathering spaces include a glass-walled synagogue with lake and mountain views (up to 100 guests), a theater and recreation room (up to 140 guests), a 2,000-square-foot multi-function lounge (up to 75 guests), a lakeside dining hall with a cathedral ceiling (up to 120 guests), two 700-square-foot yurts (30 guests each), and a screened gazebo. Outdoor events accommodate up to 200 guests with tent rentals available.

• Spaces for 200-450 Guests
• 1 Outdoor
• 4 Event Spaces
• 1 Venue with Activities

Reunions. Graduations. Weddings. Corporate retreats. Sports camps. Seminars. Birthdays. Bar/Bat Mitzvahs. Whatever the occasion, it belongs at Camp Lenox. Nestled within the Berkshire Mountains, this residential summer camp sits on 170 acres of well-maintained athletic fields, pristine forests, and sparkling waters. Comfortable cabins accommodate up to 275 guests, and the dining hall overlooks the lake, offering plenty of space and rustic charm for any event. This is no one-size-fits-all event center — the camp leadership customizes a unique and memorable experience for each group, based on their needs and size. Professional chefs are available to prepare meals and satisfy any culinary preference. Staff are also on hand to run activities like the ropes course or the waterfront.

• Spaces for 200 Guests

Surrounded by hundreds of acres of open farmland and rolling hills, Lion Rock Farm provides the perfect canvas for you to bring your vision to life–with classic barns and venues on the property, we're a perfect site for a wedding or special event. Floral gardens and natural landscapes are integral to the beauty of the farm. An abundance of outdoor spaces on the property can accommodate intimate or large wedding parties of up to 200 people, with nearby graceful barns and spacious patios for tents. Every wedding is unique, and our expansive property with multiple elegant structures is a fitting landscape for weddings any time of the year.

• Spaces for 200 Guests

Blackberry River Inn is a historic 1763 colonial property set on 27 acres in Norfolk, Connecticut, in the foothills of the Southern Berkshires. The inn accommodates small intimate weddings and private gatherings with an exclusive full-property experience — the entire estate is reserved for the event group for the day and overnight, creating a genuinely private setting across the Main House, Carriage House, and a standalone Cottage. The property's event spaces include a cherry-paneled library, a music room, and extensive grounds that offer abundant opportunities for outdoor photography. A private pool with white picket fencing anchors the outdoor area, and the 27-acre setting provides room to spread out across multiple distinct areas of the property. Seventeen uniquely appointed guest rooms allow event attendees to stay on-site, and the morning after, overnight guests are treated to a made-to-order breakfast prepared with locally sourced ingredients. The inn is well suited to corporate retreats and private business meetings in addition to weddings, making it a versatile option for groups seeking a historic New England estate with full-exclusivity access.

Race Brook Lodge, which is located in Sheffield, Massachusetts, is tucked away at the base of Mount Race, and it extends to you a warm invitation to a place of tranquil respite and exceptional hospitality that is in harmony with both the local environment and your own inner harmony. Visit us for a variety of experiences, including lodging, dining, hiking, weddings, retreats, and live music. When you leave your room, you will be greeted by breathtaking hiking trails that will lead you to the must-see views from the top of Race Brook Falls. These views are not to be missed. From there, you can gain immediate access to The Appalachian Trail, and just on the other side of the brook, you'll find our farm garden, where we grow the majority of the produce that we use in our restaurant. The foundation of our family-run establishment is a profound dedication to catering to the specific requirements of each of our visitors. We welcome married couples who are looking for a peaceful and romantic getaway in the Berkshires to celebrate anniversaries, weddings, or just because. In addition, we are a venue for corporate events, family get-togethers, and yoga and wellness retreats. We are here to provide you with a once-in-a-lifetime, stress-free experience that will leave you feeling rejuvenated, refreshed, and more connected to yourself, nature, and any new friends you made along the way. Regardless of what your needs are, we are here to meet them. Our historic lodge, which is run by our family and is situated in the heart of the beautiful Berkshires, has 31 guest rooms, as well as walking trails, waterfalls, a variety of gathering spaces, and a serene atmosphere, making it the ideal location for a truly enchanted vacation. We provide a variety of wedding packages that are designed to bring each couple's vision to life. One of these packages includes the one-of-a-kind opportunity to gather for the entire weekend, during which time close friends and family can spend extended periods of quality time together. Your group can choose from a wide variety of activities both on and off the premises, and we will be happy to provide any catering services or other amenities you require. Our multiethnic team creates an environment that is warm and inviting for everyone, and we are fully dedicated to assisting you in planning the wedding of your dreams.

• Spaces for 96-450 Guests
• 1 Outdoor
• 1 Event Space
• 2 Total Spaces

Established in 1901 and set on 560 acres of woodland in Colebrook, Connecticut, Camp Jewell YMCA is a year-round retreat and event destination operated by the YMCA of Greater Hartford. The property spans two distinct campuses — Main Camp and the secluded Hide-A-Way Ranch — separated by Triangle Lake, offering groups a range of settings from large-scale gatherings to smaller, more intimate retreats. The Main Camp dining hall accommodates more than 450 guests and serves homemade meals with options for gluten-free, vegetarian, and vegan diets. The Hide-A-Way Ranch, tucked away across the lake, hosts groups of 30 to 96 in its Longhouse and Bunkhouse cabins, each with private restrooms, furnished common rooms, and covered decks. Its dining hall seats up to 100 and features a fireplace room with views overlooking the chapel and Triangle Lake. Beyond accommodations, the property offers a 40-acre private lake, high ropes courses, horseback riding, rock climbing, archery, kayaking, and miles of hiking trails — making it a distinctive setting for retreats, conferences, team-building events, weddings, school programs, and family gatherings throughout the year.

• Spaces for 250 Guests
• 1 Barn
• 1 Farm

Since its inception 30 years ago, Gedney Farm has established itself as one of the most sought-after wedding and event venues in the New England region. Our pastoral setting serves as much more than just a picturesque backdrop for our events. Every aspect of your day is influenced by it. Our dedicated and experienced staff is on hand to take care of the details, allowing you to relax and take pleasure in the peace and tranquility of your surroundings. Our team works tirelessly to ensure that your wedding is everything you dreamed it would be when you first started planning your special day. We understand that, despite the fact that arrangements have been made, you still have a lot on your mind. By doing everything we can, we are removing time concerns and worries from the equation. You and your guests will be welcomed into a truly tranquil environment that will honor the significance of the moment and inspire you for a lifetime. Gedney Farm earned its stellar reputation the right way: by demanding the highest possible standards from its employees and in every endeavor it undertakes. We have identified and formed partnerships with the best food growers and suppliers in the area, ensuring that you have the opportunity to sample the best that the Berkshires has to offer. The smallest details, such as seating your guests in a way that keeps the sun out of their eyes or ensuring that every place setting looks exactly the way you had imagined, are given careful consideration by our team. Whether it's an executive chef with years of experience in some of New York City's most prestigious kitchens or our owner/sommelier, who can collaborate with you on the perfect wine and cocktail program, we've put together a team of experts to ensure that your weekend is one to remember. Our event manager will work directly with you from the time of the property tour until the last of your guests has left the property to ensure that you have the wedding you have always dreamed of having. No matter what time of year it is, our Event Barn is a beautiful setting for a reception. Featuring a rustic feel while still providing the comforts of heat and air conditioning, the space is handicap accessible and adaptable to your specific requirements.

• Spaces for 150-400 Guests
• 2 Hotels
• 1 Ballroom
• 1 Event Space

Set in the rolling hills of Litchfield, Connecticut, The Litchfield Inn is a family-operated colonial boutique hotel that has been welcoming guests for more than 40 years. The property spans 10.5 acres adjacent to over 100 acres of conservation land, offering a secluded countryside setting just two hours from New York City and Boston and less than two miles from downtown Litchfield's shops and restaurants. The inn accommodates events of varying scales across its indoor and outdoor spaces. The Ballroom provides a spacious, high-ceilinged setting for weddings, receptions, and corporate galas, while the Gathering Room suits more intimate occasions — baby showers, small parties, and meetings. The grounds extend the venue outdoors, with formal gardens and open lawns available for ceremonies and tented receptions. With 32 guestrooms on-site, wedding parties and their guests can stay for the full weekend, and the inn's event team works with each group to tailor catering and logistics throughout the planning process.

• Spaces for 200-300 Guests
• 1 Outdoor
• 1 Barn
• 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 Guests
• 1 Event Space

Barrington Hall is a 4,500-square-foot event venue in Great Barrington, Massachusetts, situated in the heart of the Berkshires. The space accommodates 10 to 300 guests across a flexible combination of an indoor banquet hall, a 30-by-60-foot outdoor lawn, a covered patio, and an A-frame ceremony area suitable for year-round use. Founded by two longtime friends and neighbors with a shared passion for live music and community gathering, the venue hosts weddings, private celebrations, corporate retreats, and live performances. Each booking receives exclusive use of the full grounds, along with tables, chairs, glassware, linens, professional setup and breakdown, and in-house bartending staff. An on-site commercial kitchen is available for outside caterers.

The spirit of Winbrooke is tangible. It has a warm and welcoming presence that you feel immediately upon entering the property. We knew we wanted to share this special place with as many people as possible. Three and a half years ago, we began an extensive restoration that brought life back to the property and restored its original beauty. We decided to combine our love for the property, appreciation for world-class service, and attention to detail. With that, we created an intimate Berkshire, Massachusetts wedding venue that is unlike any other. Nick and I have an extensive background in production and event planning and, together, are able to provide next-level service that assures you feel as though Winbrooke is your own private estate while celebrating your special day. We are Berkshire natives and hold the Berkshires near to our hearts. With that comes an inspired passion to make your time with us remarkable. We work closely with you every step of the way to create the Berkshire wedding of your dreams. It's a pleasure to open our property to you and create an unforgettable experience on your wedding day! Sincerely, Amy & Nick

• Spaces for 8-100 Guests
• 1 Restaurant
• 7 Hotels
• 7 Total Spaces

The Red Lion Inn has stood at the corner of Main Street in Stockbridge, Massachusetts since 1773, making it one of New England's longest-continuously operating inns. The property occupies the heart of the village immortalized in Norman Rockwell's painting "Stockbridge Main Street at Christmas" and is managed by Mainstream Hospitality Group. For private events, the inn offers a range of dedicated gathering spaces suited to meetings, dinners, and celebrations of varying scale. The Hitchcock Room, the largest of the private meeting spaces, accommodates up to 96 seated dinner guests and includes an entrance foyer for registration. Smaller rooms — including the Townsend Room, the intimate Plumb Room overlooking the Courtyard, the historically appointed Treadway Room, and the Side Parlor just off the lobby — serve groups from 8 to 48 guests. The flower-filled Courtyard opens seasonally from June through October for outdoor receptions and dining, and the Side Piazza provides a charming porch setting for cocktail receptions. All on-site events are served by the inn's in-house culinary team, whose farm-to-table menus emphasize local Berkshires ingredients. A dedicated Director of Sales guides event planning from first inquiry through the day itself.

• Spaces for 220 Guests

• Spaces for 300 Guests

Club Getaway is a 300-acre lakeside resort nestled in the Berkshire Mountains of Connecticut, roughly 90 minutes from New York City. The property offers a full weekend wedding experience — rather than a single-day venue rental, couples and their guests arrive together, stay in rustic chic country cabins, and share meals and activities across an entire weekend in the mountains. The resort's wedding program includes a dedicated wedding coordinator, on-site catering by in-house chefs, and a range of accommodations featuring memory foam mattresses, private bathrooms, heating and air conditioning, and daily housekeeping. Guests enjoy an array of recreational activities throughout the weekend, from ziplines and aerial adventure courses to paddle boarding and waterfront water parks. Wedding packages encompass lodging, gourmet dining — breakfast buffets, international lunch selections, and dinner — along with themed parties and live entertainment, making Club Getaway a self-contained destination for couples looking to celebrate with their full group over a long weekend.