TOP 30 Best Family friendly in Stockbridge, Massachusetts

The Stockbridge Country Inn is a charming bed and breakfast located at 26 Glendale Road in Stockbridge, Massachusetts. Nestled in the heart of the picturesque Berkshires, this cozy inn offers beautifully appointed guest accommodations, each with its own unique character and style. Guests can enjoy a peaceful and relaxing atmosphere, surrounded by stunning gardens and a cozy fireplace room. Conveniently located just 1 mile away from the Norman Rockwell Museum and Chesterwood, The Stockbridge Country Inn is the #1 closest Berkshires Bed and Breakfast to these popular attractions. This makes it an ideal choice for visitors looking to explore the museum while enjoying the serene surroundings of the Berkshires.

Stockbridge Playground is a vibrant and family-friendly recreational institution located at 52 Main Street in the charming town of Stockbridge, Massachusetts, United States. This playground offers a variety of activities and amenities for children of all ages, including swings, slides, climbing structures, and open green spaces for running and playing. With its convenient location in the heart of Stockbridge, families can easily spend a fun-filled day enjoying the great outdoors and making lasting memories together. Whether you're a local resident or just passing through, Stockbridge Playground is the perfect destination for a day of laughter, play, and relaxation.

Stockbridge General Store is a charming and historic institution located in the heart of Stockbridge, Massachusetts. Situated at 40 Main Street, this beloved local spot offers a wide range of food, groceries, and household essentials. From fresh produce and baked goods to pantry staples and unique artisanal products, Stockbridge General Store has everything you need for your everyday shopping needs. Whether you're a resident stocking up on necessities or a visitor looking for a taste of local flavor, this quaint store is a must-visit destination in Stockbridge. With its friendly staff, cozy atmosphere, and convenient location, Stockbridge General Store is a true gem in the community.

Located in the charming town of West Stockbridge, Massachusetts, the Pleasant Valley Motel offers comfortable and affordable lodging for those looking to explore the beautiful Berkshires region. Situated at 42 West Stockbridge Road, this cozy motel provides a peaceful retreat for visitors seeking a relaxing getaway. With its convenient location and friendly staff, Pleasant Valley Motel is the perfect choice for travelers looking for a comfortable stay in West Stockbridge.

Welcome to Stockbridge Skate Park, the premier destination for skateboarding enthusiasts in the heart of Stockbridge, Massachusetts! Nestled amid the picturesque landscapes of the Berkshires, our skate park offers a vibrant and welcoming community space for skaters of all ages and skill levels. Conveniently located in Stockbridge, MA 01262, we provide a safe and dynamic environment where skaters can hone their skills, make new friends, and enjoy the thrill of the ride. Our park features a variety of ramps, rails, and bowls designed to challenge and inspire, whether you're a beginner or a seasoned pro. At Stockbridge Skate Park, we prioritize safety and fun, ensuring that our facilities are well-maintained and up to industry standards. The park is open year-round, weather permitting, so you can enjoy skateboarding in every season.

Welcome to West Stockbridge Town Park, a serene and picturesque haven nestled in the charming town of West Stockbridge, Massachusetts. Located in the heart of the Berkshires, our park offers a perfect escape for nature enthusiasts, families, and anyone seeking tranquility amidst beautiful surroundings. Explore our well-maintained walking trails that meander through lush greenery, providing a peaceful setting for a leisurely stroll or an invigorating jog. The park's open spaces are ideal for picnics, casual gatherings, and outdoor activities, offering a refreshing break from the hustle and bustle of everyday life.

The Backstage Grille is a cozy restaurant located at 109 Stockbridge Road in Great Barrington, Massachusetts. Offering delicious food options for dine-in or carry-out, with the convenience of curbside pickup available. The restaurant's regular hours are Monday-Thursday from 5pm-10pm, Friday from 4pm-midnight, Saturday from noon-midnight, and Sunday from noon-10pm. Situated inside Cove Lanes, The Backstage Grille is the perfect spot to enjoy a meal with friends and family. Contact them at 413-717-8804 for more information.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

Franklin Dining Commons is a popular dining establishment located at 260 Stockbridge Road in Amherst, Massachusetts. This bustling restaurant offers a wide variety of delicious and freshly prepared dishes for breakfast, lunch, and dinner. With a welcoming atmosphere and friendly staff, Franklin Dining Commons is the perfect place to enjoy a satisfying meal with friends or family. Whether you're craving a hearty breakfast, a light salad, or a comforting dinner entree, this institution has something for everyone. Come experience the culinary delights of Franklin Dining Commons today!

Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.

Welcome to Titus Mansion Ruins, a captivating destination nestled in the heart of the Tyringham Valley at 264 Main Road, Tyringham, Massachusetts. This enchanting locale invites you to explore the harmonious blend of history, art, and nature that defines Ashintully Gardens. Originally established in the early 20th century by Robb and Grace de Peyster Tytus, the estate once featured the magnificent Marble Palace, a Georgian-style mansion renowned for its reflective stucco exterior. Today, visitors can wander through the evocative ruins of the Marble Palace, where the enduring Doric columns stand as solemn sentinels of its storied past. The gardens, sculpted over three decades by contemporary classical composer John McLennan, offer a serene escape with their intricate mix of formal and informal designs. McLennan's dedication to creating this verdant masterpiece was recognized with the prestigious Hunnewell Medal from the Massachusetts Horticultural Society in 1997.

Welcome to Fork Factory Brook Reservation, a hidden gem nestled in the heart of Medfield, Massachusetts. Located on Hartford Street, this picturesque park and tourist attraction offers a serene escape into nature's embrace. Managed by The Trustees of Reservations, Fork Factory Brook Reservation is dedicated to preserving the scenic, historic, and ecological treasures of Massachusetts for all to enjoy. Explore the park's winding trails, which meander through lush woodlands and alongside the tranquil brook that gives the reservation its name. With almost 10 miles of family-friendly paths, visitors can immerse themselves in the beauty of diverse landscapes, from dense forests to open fields and charming wetlands. This idyllic setting is perfect for walking, hiking, and nature watching, offering a peaceful retreat from the hustle and bustle of everyday life.

Located in the charming town of West Stockbridge, Massachusetts, the Shaker Mill Inn offers a cozy and comfortable lodging experience. Situated at 2 Oak Street, this historic inn provides a peaceful retreat for guests looking to relax and unwind. The beautifully decorated rooms and friendly staff make for a memorable stay. With its convenient location and warm hospitality, the Shaker Mill Inn is the perfect choice for travelers visiting the Berkshires region.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

The Constance is a charming lodging located at 11 Old Stockbridge Road in Lenox, Massachusetts. This historic institution offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway in the heart of the Berkshires. Guests can enjoy comfortable rooms, beautiful gardens, and personalized service during their stay. Whether you're looking for a weekend retreat or a longer vacation, The Constance is the perfect choice for a memorable experience in this idyllic New England town.

Welcome to Naumkeag, a stunning museum, park, and tourist attraction nestled in the heart of Stockbridge, Massachusetts. Located at 5 Prospect Hill Road, this exquisite 48-acre estate offers a glimpse into the grandeur of the Gilded Age, featuring breathtaking gardens and a rare Berkshire "cottage" that was once the summer retreat of the Choate family. Designed in 1884 by the renowned architectural firm McKim, Mead & White, Naumkeag is a remarkable example of shingle-style architecture with 44 rooms that served as a family home for several generations. Visitors can explore the meticulously maintained landscapes, including 8 acres of formal gardens, meadows, and farmland, which provide a serene escape and a chance to step back in time. Please note that due to the estate's age and terrain, it is not wheelchair- or stroller-accessible.

Papa Gino's is a popular pizza and Italian cuisine restaurant located at 370 Stockbridge Road in Lee, Massachusetts. Known for their delicious pizzas, pastas, and sandwiches, Papa Gino's offers a cozy and welcoming atmosphere for diners to enjoy a casual meal with family and friends. With a wide variety of menu options and friendly service, Papa Gino's is a favorite dining destination for locals and visitors alike.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

The Public Market is a bustling food and grocery store located at 8 Main Street in West Stockbridge, Massachusetts. This local institution offers a wide variety of fresh produce, meats, dairy products, and pantry staples. Customers can also find specialty items, baked goods, and ready-to-eat meals made with locally sourced ingredients. With its convenient location and friendly staff, the Public Market is a go-to destination for all your shopping needs in the West Stockbridge area.

Williams & Sons Country Store is a charming and quaint establishment located in the heart of Stockbridge, Massachusetts. Situated at 38 Main Street, this family-owned store offers a wide variety of goods ranging from locally sourced produce to handmade crafts and gifts. Step inside and you'll be greeted by friendly faces and a warm atmosphere that embodies the spirit of a traditional country store. Whether you're looking for fresh groceries, unique souvenirs, or simply a taste of small-town charm, Williams & Sons Country Store has something for everyone. Come visit us and experience the charm of this beloved institution in the heart of New England.

Welcome to Monument Mountain Motel, a budget-friendly lodging option in the heart of Great Barrington, Massachusetts. Located in the beautiful Berkshire Mountains, our motel offers comfortable rooms and family-style amenities. Whether you're in town for business or pleasure, our convenient location puts you near iconic attractions such as Tanglewood Music Festival, Ski Butternut Resort, and the Norman Rockwell Museum. At Monument Mountain Motel, we strive to provide a pleasant and affordable experience for all our guests. Enjoy free wifi, in-room microwaves and fridges, and a spacious patio with barbecue facilities. Family travelers will appreciate our family-friendly amenities, while business travelers will find our simplicity and affordability to be just what they need.

Marketplace Kitchen Table is a cozy cafe and restaurant located at 240 Stockbridge Road in Great Barrington, Massachusetts. They offer a variety of delicious dishes that are prepared and ready to be reheated and served. On Carvery Night, they serve up a mouthwatering Roast Rib of Beef with all the fixings. You can order individual dinners or dinners for four at their Specialty Shop. In addition to their food offerings, Marketplace Kitchen Table also has a selection of specialty wines available for purchase. They offer a range of sparkling, rose, white, and red wines that pair perfectly with their menu items.

Cafe Adam, Bar and Restaurant is a charming establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This versatile venue offers a cozy and inviting atmosphere perfect for enjoying a delicious meal, grabbing a drink at the bar, or even staying overnight in their comfortable lodging accommodations. The restaurant serves up a diverse menu featuring a range of culinary delights, from classic American dishes to international cuisine. Whether you're looking for a casual meal with friends or a romantic dinner for two, Cafe Adam has something for everyone. Come and experience exceptional hospitality and delectable fare at this hidden gem in the heart of the Berkshires.

Once Upon a Table is a charming restaurant located at 36 Main Street in Stockbridge, Massachusetts. This cozy establishment offers a delightful dining experience with a menu filled with delicious dishes made from locally sourced ingredients. The warm and inviting atmosphere of Once Upon a Table makes it the perfect spot for a romantic dinner or a casual meal with friends. Whether you're craving a hearty burger or a gourmet salad, this restaurant has something for everyone. Come and enjoy a memorable dining experience at Once Upon a Table.

Main Street Cafe is a charming eatery located at 40 Main Street in the picturesque town of Stockbridge, Massachusetts. This cozy restaurant offers a warm and inviting atmosphere where guests can enjoy delicious food and drinks. The menu features a variety of classic American dishes made with fresh, locally sourced ingredients. Whether you're looking for a hearty breakfast, a leisurely lunch, or a satisfying dinner, Main Street Cafe has something for everyone. Stop by and experience the friendly service and mouthwatering meals that have made this cafe a beloved dining destination in Stockbridge.

Laurel Hill, located at 50 Main Street in Stockbridge, Massachusetts, is a picturesque park and popular tourist attraction. Visitors can enjoy the natural beauty of the area while exploring the various trails and properties that are open to the public. In light of the COVID-19 pandemic, Laurel Hill has implemented safety guidelines to ensure the well-being of all visitors. Unvaccinated individuals are expected to wear a face covering or mask when unable to maintain a distance of 6 feet from others. By following these guidelines, visitors can help create a safe environment for everyone to enjoy. Come visit Laurel Hill and experience the beauty of nature in a safe and responsible way.

Agaves Mexican Grill is a vibrant and authentic Mexican restaurant located at 389 Stockbridge Road in Great Barrington, Massachusetts. Known for its delicious and flavorful dishes, Agaves offers a wide variety of traditional Mexican cuisine, including tacos, burritos, enchiladas, and more. The restaurant's vibrant atmosphere and friendly staff create a welcoming environment for guests to enjoy a memorable dining experience. Whether you're looking for a casual meal with friends or a special evening out, Agaves Mexican Grill is the perfect destination for a taste of Mexico in the heart of Massachusetts.

AMICI is a charming Italian restaurant located at 5 Albany Road in West Stockbridge, Massachusetts. Known for its warm and inviting atmosphere, AMICI offers a wide range of delicious Italian dishes made with fresh, locally sourced ingredients. From homemade pastas to wood-fired pizzas, there is something for everyone to enjoy at this cozy eatery. Whether you're looking for a casual dinner with friends or a romantic date night, AMICI is the perfect spot to indulge in authentic Italian cuisine. Come visit us and experience the true taste of Italy in the heart of West Stockbridge.

Rio Cafe is a charming cafe and restaurant located at 403 Stockbridge Road in Great Barrington, Massachusetts. This cozy establishment offers a variety of delicious food options, including freshly brewed coffee, hearty breakfast dishes, scrumptious sandwiches, and delectable desserts. With a warm and inviting atmosphere, Rio Cafe is the perfect spot to relax and enjoy a meal with friends or family. Whether you're looking for a quick bite to eat or a leisurely dining experience, Rio Cafe has something for everyone to enjoy. Come visit us and experience the delicious flavors and friendly service that make Rio Cafe a beloved local favorite.

Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.