Top Massachusetts Proposal Venues

• Spaces for 150 Guests
• 1 Barn
• 1 Farm

Friendly Crossways is a rustic-chic destination wedding location in Massachusetts, near Boston, that offers a rustic-chic wedding experience. In the countryside, about 30 miles west of downtown Boston, we have on-site housing that is available for guests. For a complete weekend of joyful celebration on our farm, we endeavor to provide you all the flexibility and time you need to establish your own personal community. A more than 150-year-old New England barn and farmhouse that was first renovated in 1947 to serve as a summer retreat center, wedding venue, and hostel for backpackers and hostelers. From its primitive beginnings, it has evolved into a one-of-a-kind conference place and outdoor wedding venue, complete with attractive bedrooms and wonderfully planted gardens that are open all year. Among those who have benefited from our devotion to pleasant service and fair costs are family reunions, church and youth groups, health, music, and environmental organizations, as well as students from elementary school to graduate level. A staunch advocate of marriage equality, Friendly Crossways actively encourages diversity and inclusion in all parts of its business. Since it was first certified by the American Youth Hostels in 1947, Friendly Crossways (now Hostelling International USA) has established itself as the longest-running hostel in the United States, providing accommodations for independent travelers. Hiking, biking, skiing, and canoeing are all within easy reach from our serene, rural setting. Also, Friendly Crossways is a Boston wedding location with a long history of organizing outside tented weddings that dates back to the establishment of the business in 1947!

• Spaces for 250 Guests
• 1 Hotel
• 1 Ballroom

For almost 35 years, the Dennis Inn, located in the tranquil seaside community of Dennis, MA, has provided a wonderful location for weddings, receptions, family reunions, holiday parties, and many other celebratory occasions. Treats Catering, our sister company, is the sole caterer for all events held at the Dennis Inn. If you want to have an unforgettable Cape Cod celebration, come to the Dennis Inn and join us. Because the Dennis Inn only accommodates one wedding reception per day, you will have complete freedom to design your day around you, with full access to the Inn and grounds. With a large tent on our wide grounds, we can accommodate up to 250 guests for indoor gatherings and up to 100 visitors for outdoor functions. The Inn also features a wonderful suite of rooms on the second floor that can accommodate up to eight guests. Three bedrooms, two bathrooms, a kitchen and entertainment area, and a powder room make up this wedding suite. A beautiful in-ground pool and wide back yard complete out the Inn's amenities, perfect for entertaining the day before the wedding or hosting a farewell brunch the day after. Saturday receptions require a minimum of 100 guests from Memorial Day through Columbus Day. The Inn offers a discounted rate for receptions without overnight accommodations. Because we are open all year, we can also accommodate Friday, Sunday, and off-season receptions. We also provide special packages for occasions such as Valentine's Day, New Year's Eve, and Sunday Brunches. We're pleased to make recommendations for flowers, photographers, and any other vendors you might require. We'll work with them to incorporate all of the things you've envisioned so that the day is truly unique. Please contact the Dennis Inn with your wedding needs, and we will assist you in planning the wedding of your dreams.

• Spaces for 100-200 Guests
• 2 Outdoor Spaces
• 1 Barn
• 3 Total Spaces

Set on 1,200 acres of woodland, ponds, and trails in Westwood, Massachusetts, Hale Education has offered outdoor gathering spaces for more than a century. Founded in 1918 as a private nonprofit, the organization makes its natural grounds available for weddings, corporate retreats, holiday parties, and private celebrations of all kinds. Event facilities span several distinct settings. North Beach stretches 300 feet along 55-acre Noanet Pond with sunset views, a pavilion, and room for up to 200 guests. The Orchard & Barn pairs a charming barn structure with an apple orchard and butterfly garden, accommodating up to 100. Powissett Lodge brings the gathering indoors with cathedral ceilings, hardwood floors, a fireplace, a full kitchen, and a deck — all handicap-accessible — for groups of up to 100. Hale can recommend event vendors who know the property well, giving planners a head start on building a team suited to the setting.

• Spaces for 50 Guests

Harvard General Store has anchored Harvard Common since 1816, making it one of the oldest continuously operating businesses in Harvard, Massachusetts. The building has served as a community gathering place for more than two centuries, and the current iteration leans into that legacy by blending everyday retail with a full food and beverage program and flexible private event space. The store houses a grocery and gifts market, a bakery and coffee shop, a restaurant serving breakfast and lunch daily, a package store, and a pizza parlor with beer on tap. That variety of spaces and services means the venue can support events ranging from intimate showers and corporate conferences to full wedding receptions. Private rental options include the upstairs space, the patio, and a full building buyout — making Harvard General Store a fitting choice for birthdays, reunions, classes, banquets, and catered gatherings alike.

• 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 40-220 Guests
• 1 Restaurant
• 1 Meeting Space
• 1 Waterfront

Cape Ann's Marina Resort is a family-owned waterfront destination in Gloucester, Massachusetts, in continuous operation since 1972. The seven-acre property brings together a 30-room hotel with water-view balconies, a working marina with more than 275 boat slips, and Mile Marker One Restaurant & Bar — located about 45 minutes north of Boston at the start of the Intracoastal Waterway, a distinction the restaurant's name honors. Private events are hosted across multiple spaces on the property. The Compass Room, a year-round indoor venue on the second floor of Mile Marker One, seats up to 40 guests and offers panoramic views of the marina docks, salt marsh, and Annisquam River through large windows. The property also features an outdoor waterfront tent for larger celebrations. All catering is provided through Mile Marker One, and a Dock & Dine program allows guests arriving by boat to moor on-site. The resort hosts weddings, rehearsal dinners, corporate events, showers, and birthday parties, with live music available on the property seasonally from May through October.

For each family, occasion, wedding, or event, By the Sea Guests has it all. The inn has a bed and breakfast with simple guest rooms with one or two beds, apartment-styled one or two bedroom suites, and vacation houses, all of which are ideal for family reunions, special celebrations, or wedding parties. Our three inns contain a total of 46 rooms, all of which are either next door to one other or one block apart. Two of the inns are directly on the beach. One of the inns allows pets. We're off Chase Avenue in Dennis Port, Massachusetts, on Cape Cod's Mid-Cape. We can offer room blocks, though we prefer that customers book directly with us on a first-come, first-served basis. The major inn, By the Sea Guests, is where most weddings and festivities take place. It is oceanfront, with the strip's largest white sanded beach, and an enclosed veranda that overlooks and connects to the beach, as well as an outdoor grass space where a tent can be set up.

• Spaces for 60-300 Guests
• 1 Ballroom
• 2 Meeting Spaces

The Metcalf Trustee Center occupies the ninth floor of One Silber Way on the Boston University campus, offering a classically appointed ballroom and a private lounge with panoramic views of the Boston skyline. The main ballroom, adorned with crystal chandeliers and accompanied by an adjacent cocktail lounge featuring floor-to-ceiling windows, accommodates up to 300 guests for receptions or 220 for seated dinners. The space flexibly supports buffets, dance-floor receptions, lectures, and classroom-style meetings, and has served weddings, galas, corporate gatherings, and holiday parties. The adjacent Kenmore Room functions as a breakout space, bridal lounge, or green room for ballroom events. The Kenmore Room is also available as a standalone private event space for up to 65 guests, with floor-to-ceiling windows overlooking the Charles River, Fenway Park, and the Boston skyline. Audio-visual equipment and WiFi are on-site, making it well-suited for intimate dinners, corporate retreats, and small receptions.

• 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.

• Spaces for 150-250 Guests
• 1 Event Space

The Natick Lodge of Elks #1425 operates one of the largest function halls in Metrowest Massachusetts, accommodating up to 250 guests for a wide range of private events. The hall features a full bar, a full kitchen, and one of the largest dance floors in the area — complete with a stage for musicians and officiants. A sound system with projector, an outdoor BBQ area with a patio and horseshoe pits, and a generous private parking lot round out the space. The venue hosts weddings, receptions, birthday parties, holiday gatherings, banquets, class reunions, business functions, fundraisers, sports team celebrations, and community events. Renters receive two hours of setup time before each event at no additional charge.

• Spaces for 100-125 Guests
• 1 Restaurant

When you attend a private event at the Biltmore with your family, friends, or coworkers, you get to enjoy all of life's greatest hits in one wonderful evening! We can collaborate with you to design a menu based on the Biltmore's trademark appetizers, entrees, sides, and desserts. Within the renowned walls of the Biltmore, there is something very distinctive and unique. As you travel the century-old wood floors to your private Biltmore party room, you are a part of history, from the original stamped tin ceilings to the beautiful wood paneling. You can almost imagine the big parties that have taken place throughout the decades to celebrate life, love of food, and good times. With these excellent places available for your perfect celebration, this local tradition continues today. The Biltmore, which opened in 1914, has a long history as a Newton favorite. It started out selling breakfast and ale to local industrial workers staying the night, and its four-lane bowling alley was a popular hangout for decades. The Biltmore was a secret speakeasy for the upper crust during prohibition, frequently hosting private events for dignitaries, politicians, and celebrities. The Biltmore underwent a stunning refurbishment a century after it first opened, restoring the ancient building's grandeur while providing a more pleasant atmosphere. Much of the original brick façade and interior have survived the test of time, as has the original wood flooring. We maintain the Biltmore's spirit alive today with American food and a rotating variety of local beers and handcrafted cocktails. Something exciting is always happening at the Biltmore. Our events give a traditional restaurant experience a new spin. Come in for Oyster Mondays, Karaoke Fridays, and a whole lot more. We also have a private dining room available, which is ideal for any special occasion. We are excited to share history with you!

• Spaces for 125-175 Guests
• 1 Restaurant

Back Deck offers expert backyard barbecuing seven days a week in a relaxed metropolitan setting. Friends and family gather for charcoal-grilled dishes inspired by informal cookout fare, as well as porch-perfect cocktails, beer, and wine. We are committed to providing the greatest possible level of quality and consistency. Our innovative food, one-of-a-kind beverages, legendary service, and chic ambiance set us apart. We are prepared to meet your every need at the Back Deck. Back Deck is ideal for business luncheons, birthday celebrations, graduations, cocktail parties, and any other type of gathering. Our friendly staff is committed to providing service that will far exceed the expectations of your friends, family, and business associates. Back Deck offers expert backyard barbecuing seven days a week in a relaxed metropolitan setting. Friends and family gather for charcoal-grilled dishes inspired by informal cookout fare, as well as porch-perfect cocktails, beer, and wine. WE BURN HARDWOOD CHARCOAL ON THE BACK DECK. Aside from the delightful smoky flavor, charcoal produces a hotter, more intense heat. Foods sear better on charcoal, delicate foods like fish stick less, and the "grilled" flavor, which is a result of the hot grate searing the surface of the foods and the smoke produced by the fire, is improved. SHARING A MEAL AND BREAKING BREAD IS A CULTURAL EXPERIENCE BECAUSE FOOD CREATES SUCH A BOND BETWEEN PEOPLE. Our management team is dedicated to making Back Deck better for our guests by proactively influencing our path and working closely with our workforce. They are the real deal: outstanding leaders and individuals.

• Spaces for 10-150 Guests
• 4 Restaurants

Del Frisco's Double Eagle Steakhouse, one of the greatest restaurants in Back Bay Boston, serves hand-cut steaks and fresh seafood. Our restaurant, which is located on Boylston Street near the Mandarin Oriental Hotel, is part of Prudential Center. You'll enjoy a typical steakhouse dining experience in an elevated ambiance with elegant architecture, sophisticated décor, and big private rooms. Del Frisco's Double Eagle Steakhouse was established in 1981 with a daring goal in mind: to encapsulate the rich legacy of the classic American steakhouse. Our goal has remained the same since then. We continue this history, but with a modern, sleek twist, to provide you with an unrivaled dining experience every time you visit. Our outstanding chef-driven cuisine, comprehensive award-winning wine list, and exceptional service set us apart from any other steakhouse in the United States. On our menu, you'll find only the freshest, most delectable foods. Our sommeliers will help you navigate our comprehensive wine range. Our crew is dedicated to providing you with exceptional service in a magnificent, vibrant setting that is ideal for any event. Host your next gathering in one of our private or semi-private dining spaces to make it extra special. These rooms will enable your celebration reach its maximum potential, no matter what your needs are, with trendy decor, plenty of seats, and audio/visual capabilities. Our private and semi-private dining rooms are ideal for everything from birthday parties to board meetings. Our expert private dining organizers will design and customize your occasion to make it one to remember.

• Spaces for 25-200 Guests
• 4 Hotels
• 4 Ballrooms

The Bostonian is the ideal location for your Boston event, located just steps from Faneuil Hall, South Station, and the Financial District. Our conference and event spaces, which total 7,000 square feet, are located on separate floors, allowing for exclusivity and seclusion. Multiple conference rooms, suite-style breakout spaces, and the beautiful Seasons Ballroom provide a range of settings, natural lighting, and cutting-edge audiovisual technology. Whether you're planning a small meeting or a large conference, our Catering and Events specialists will make sure everything goes well. Consider The Bostonian for your next meeting if you want to make history. In the Seasons Ballroom, the floor-to-ceiling bay windows, glass roof, and three walk-out balconies overlooking Faneuil Hall flood this stunning space with natural light. A 750-square-foot private entryway provides a spectacular touch for displays, celebrations, or buffets. The Josiah Quincy is a small, intimate area with views of the courtyard and fountain. Meals and breakout sessions can be held in the 600-square-foot private lobby. This venue can accommodate up to 125 people. The Thomas Menino Room has a beautiful view of Faneuil Hall and is ideal for informal gatherings or events. This lobby level area is conveniently accessible and has airport-quality soundproof windows from floor to ceiling. The Thomas Menino is an amazing setting for up to 150 guests, with built-in AV, a drop-down projector and screen, and an additional 660-square-foot private room for meals and breakouts. Regardless of the nature of your business, the Faneuil Suite is ready to assist you. This is a beautiful location for up to 25 people, with natural light, a Juliet balcony with a view of Faneuil Hall, a 50" TV monitor, and an adjacent private bedroom.

Thank you for thinking of the Sagamore Inn Restaurant — All Occasion Venue for your upcoming event. An outdoor-indoor venue at the Sagamore Inn, only minutes from the Sagamore Bridge, offers the ideal experience. For all events, we offer almost two acres of beautifully manicured gardens, a tent that can accommodate 200 people, freshly prepared meals, personalized menus, and great service. Due to its vast size and excellent charm, our 46 x 86-foot tent is highly popular for wedding celebrations. It can hold up to 300 people for non-seated events like cocktail receptions or 150 people for seated events with area for dance. If you need off-site catering, we can help! Everything is available at the Sagamore Inn Restaurant! The Canalside Pavilion can host a range of wedding-related activities, including bridal showers, rehearsal dinners, wedding ceremonies, and receptions. The friendly personnel at the venue is committed to ensuring that each couple has an unforgettable celebration that runs smoothly. Couples can choose from a list of recommended vendors, but they are also free to choose their own providers to realize their wedding vision.

• Spaces for 200 Guests

Eddie V's Prime Seafood restaurant in Boston, near the Prudential Center, Hynes Convention Center, and Copley Place, offers a stylish fine dining experience. To accompany great steaks hand-cut in house and exquisite seafood flown in fresh daily, we offer an extensive range of fine wines and hand-crafted cocktails. At our restaurant, we try to make each guest's visit unforgettable and to provide a world-class dining experience to downtown Boston. Sip on inventive hand-crafted cocktails with attitude while eating signature tapas in The V Lounge. Join us tonight for an amazing dinner. We're located close to the Belvidere St public parking garage at 122 Belvidere St. Whether you're commemorating a personal achievement or hoping for a successful meeting, working with us is for individuals who value meticulous planning. Book a private or semi-private room here, and our Private Dining Managers will expertly guide you through every detail to ensure that your celebration is really memorable. WHAT WE HAVE TO OFFER - A personal event planner - Personalized menus tailored to your tastes and preferences - Wine pairing suggestions - Valet parking - Webcasting and other cutting-edge media technology - A sophisticated private dining experience for both lunch and dinner We have the technology you need to make your presentations stunning, whatever your meeting requirements are. The majority of our rooms have high-definition plasma TV screens with cable, huge projection screens with LCD projectors, laser pointers, and other amenities. If you need equipment that we don't have on-site, we can usually get it for you. Reach out today! We can’t wait to host your next event.

• Spaces for 175 Guests
• 1 Hotel
• 1 Ballroom

A hidden gem nestled between the towns of Lee and Lenox, Massachusetts, in the Berkshire Mountains. This tiny four-season boutique hotel is noted for its warm, friendly hospitality as well as its great position in the heart of downtown. Tanglewood, Kripalu, Jacobs Pillow, Barrington Stage, The Mount, and Monument Mountain Reservation are all excellent places to spend your time during your visit. The LakeHouse is one of the most popular wedding venues in the Berkshires, as well as a popular corporate retreat and relaxation destination. Pull into our driveway, take a look around, and you'll quickly realize that you've discovered a hidden gem in the Berkshire Mountains. Take advantage of the LakeHouse sunset views across Laurel Lake by sitting on the back cliff with a glass of wine at the start of your stay. Save some time to explore the lake, whether it's with a kayak or a paddle board, which are both available to our guests at no extra price. Our goal is for you to feel completely at ease while on your Berkshire getaway with us. The Lakehouse Inn, which is centrally placed, offers a variety of lake activities as well as a tranquil atmosphere that is known to relax the mind. Away from the site, the Berkshires are home to some of the best food and culture in the region. “There aren’t enough superlatives to describe this gorgeous Inn! Fully renovated to such elegant beauty. The rooms are beautiful, comfortable with the best views of Laurel lake… Every detail of this Inn is so well and lovingly thought out.” - Yuki C.

The breathtaking view from the historic Edwin Vanderhoop Homestead property encompasses the whole southwest coast of Martha's Vineyard, including Gay Head Cliffs and the Atlantic Ocean. Both the beach and the Gay Head Lighthouse are within easy walking distance. Ideal for your wedding, rehearsal dinner, or any other event you're planning. Up to 250 persons can be accommodated at one time. Send an email or give us a call for further information. Location is very key to the success of this property! The historically significant Vanderhoop Homestead, which dates back to as early as 1850 and can be seen inside the Aquinnah Circle, is also the location of the Aquinnah Cultural Center. The grounds and the stone terrace are accessible for use for events, however the Cultural Center and the building themselves are not. The Cultural Center and its grounds, like the Lighthouse, look out over the stunning clay cliffs and are conveniently located within walking distance of a number of restaurants, stores, and Moshup Beach (public beach). The grounds are large enough to host a tent measuring up to 100 feet by 60 feet. There is access to water, power, and parking at this location. Please contact Gabriella Camilleri at 508-645-2304 or send her an email at townclerk@aquinnah-ma.gov if you would like further information regarding the rental of this facility.

• Spaces for 350 Guests

The Country Club of Halifax is an 18-hole championship golf and events venue in Halifax, Massachusetts. Designed by architect Phil Wogan and established in 1966, the course stretches 6,738 yards from the back tees at par 72, with four tee options that make it accessible for players of all skill levels. The club hosts weddings, corporate outings, charity tournaments, and private gatherings for groups ranging from 20 to over 140 guests. A dedicated events team supports hosts through every stage of planning — from program formats and tournament structures to day-of coordination. On-site amenities include a pro shop, driving range, and practice putting green.