TOP 10 Outdoor experiences in Stockbridge, Massachusetts

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.

Welcome to Stockbridge Athletic Area, your premier destination for outdoor recreation and community gatherings in the heart of Stockbridge, Massachusetts. Nestled in the picturesque Berkshires, our park offers a tranquil escape for residents and visitors alike, providing a perfect blend of natural beauty and recreational facilities. At Stockbridge Athletic Area, you'll find a variety of amenities designed to cater to all ages and interests. Our well-maintained sports fields are ideal for soccer, baseball, and other team sports, offering ample space for both casual games and organized leagues. For those looking to enjoy a leisurely day outdoors, our walking trails provide a serene setting for a peaceful stroll or invigorating jog amidst lush greenery.

Barrington Brewery & Restaurant is a popular establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This venue offers a unique combination of a brewery, bar, and restaurant, providing guests with a one-of-a-kind dining and drinking experience. The brewery produces a variety of craft beers that are served alongside delicious meals made from locally sourced ingredients. Whether you're looking to enjoy a casual drink with friends or indulge in a hearty meal, Barrington Brewery & Restaurant is the perfect destination for food and beer enthusiasts alike.

Xicohtencatl Restaurant, located at 50 Stockbridge Road in Great Barrington, Massachusetts, is a hidden gem offering authentic Mexican cuisine in the heart of the Berkshires. Known for its flavorful dishes and warm hospitality, Xicohtencatl is a must-visit for anyone craving a taste of Mexico. Chef Angel's mole, a special family recipe passed down through generations, is a standout dish that has garnered national attention, even being featured on Food Network's Emeril Live! Whether you're in the mood for something spicy or savory, Xicohtencatl's menu has something for everyone. Come experience the flavors of Mexico at Xicohtencatl Restaurant.

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.

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.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

The Cottage B and B is a charming lodging establishment located at 14 Prospect Hill Road in the picturesque town of Stockbridge, Massachusetts. This historic bed and breakfast offers cozy accommodations in a beautifully restored cottage, providing guests with a peaceful and relaxing retreat. In addition to its comfortable rooms, The Cottage B and B also features a small museum showcasing local artifacts and history, adding a unique touch to the overall guest experience. Whether you are looking for a romantic getaway or a cultural escape, The Cottage B and B is the perfect destination for your next visit to Stockbridge.

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.

Conroy's Bed & Breakfast is a charming lodging establishment located at 11 East Street in the picturesque town of Stockbridge, Massachusetts, United States. Nestled in a quaint and peaceful neighborhood, this cozy bed and breakfast offers comfortable accommodations and warm hospitality for guests looking to relax and unwind in a homely atmosphere. With its convenient location near local attractions, shops, and restaurants, Conroy's Bed & Breakfast is the perfect choice for travelers seeking a memorable stay in the heart of Stockbridge.

Jacob's Tanglewood Ranch is a charming lodging institution located at 560 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque countryside, this ranch offers a peaceful and tranquil retreat for guests looking to escape the hustle and bustle of city life. The rustic yet cozy accommodations provide a comfortable stay, while the surrounding Tanglewood forest offers plenty of opportunities for outdoor activities such as hiking, horseback riding, and birdwatching. Whether you're seeking a romantic getaway or a family vacation, Jacob's Tanglewood Ranch is the perfect destination for a relaxing and rejuvenating experience.

Flat Brook Wildlife Management Area is a beautiful park located in West Stockbridge, Massachusetts, United States. This institution is a wildlife management area that offers visitors the opportunity to explore and appreciate the natural beauty of the area. With its lush greenery, serene ponds, and diverse wildlife, visitors can enjoy hiking, bird watching, and wildlife viewing. The park is a great place for nature enthusiasts and families to spend a day outdoors and connect with the local flora and fauna. Whether you're looking for a peaceful retreat or an educational experience, Flat Brook Wildlife Management Area is the perfect destination for all nature lovers.

Solid Rock Farm is a charming institution located at 16 East Stockbridge Lee Road in Stockbridge, Massachusetts. This picturesque farm offers a serene and peaceful setting for visitors to connect with nature and experience the beauty of the surrounding landscape. With a focus on sustainable agriculture and environmental stewardship, Solid Rock Farm is committed to providing high-quality produce and products to the local community. Visitors can explore the farm, participate in educational programs, and enjoy the fresh air and natural beauty of this idyllic location. Whether you are looking to learn about sustainable farming practices or simply unwind in a tranquil setting, Solid Rock Farm is the perfect destination for nature lovers and outdoor enthusiasts alike.

Berkshire Country Day School, located at 55 Interlaken Road in Stockbridge, Massachusetts, is a vibrant educational institution dedicated to inspiring the individual promise of every student. With a comprehensive curriculum that includes project-based and experiential learning, the school leverages the talents of its engaged educators and the natural resources of its historic campus to foster independence, academic excellence, and mutual respect. The school's intentional approach of inquiry, discovery, and discussion draws on the experiences and contributions of the entire school community, creating a supportive and inclusive learning environment. Students at Berkshire Country Day School have the opportunity to learn alongside running streams, in a natural habitat with wooded trails, and on multiple fields, fostering a lifelong love of learning.

Gould Meadows is a charming park and tourist attraction located at 110B Interlaken Road in Stockbridge, Massachusetts, United States. This picturesque destination offers visitors a tranquil escape into nature, with lush greenery, serene walking paths, and stunning views of the surrounding landscape. Whether you're looking to relax and unwind or explore the great outdoors, Gould Meadows is the perfect place to visit. Come and experience the beauty and serenity of this hidden gem in the heart of Massachusetts.

Eden Hill Summer Day Camp at Berkshire Country Day School offers a fun and enriching summer experience for children in Stockbridge, Massachusetts. Located at 55 Interlaken Road, our camp provides a safe and welcoming environment where kids can explore, learn, and make lasting memories. With a focus on outdoor activities, sports, arts and crafts, and team-building exercises, our campers are sure to have a summer they'll never forget. Join us for a summer of adventure and growth at Eden Hill Summer Day Camp!

Ice Glen Trail is a unique park located in Stockbridge, Massachusetts, United States. Visitors can enjoy a challenging hike through a glacial ravine, navigating giant boulders while surrounded by old pine and hemlock trees. The rocks in the glen are said to retain ice and snow well into the summer months. At the north end of the trail, visitors can see an inscription from the donor, David Dudley Field, on a flat rock face. At the south end of the trail, there is reportedly the tallest pine tree in Massachusetts. To reach the trail, visitors must cross the Goodrich Memorial footbridge and continue up the path. The trail is difficult, with some sections requiring climbing and careful navigation. It offers a unique and adventurous outdoor experience for nature lovers and hikers.

Olivia's Overlook is a stunning tourist attraction located in the beautiful town of West Stockbridge, Massachusetts, United States. Situated along the scenic Hiking Trails, this overlook offers breathtaking views of the surrounding landscape, making it a perfect spot for nature lovers and outdoor enthusiasts. Visitors can enjoy a peaceful hike to the overlook and take in the picturesque vistas, making it a great destination for those looking to escape the hustle and bustle of city life. Whether you're looking for a relaxing day in nature or a challenging hike, Olivia's Overlook is sure to provide a memorable experience for all who visit.

Welcome to Turn Park Art Sculptures, a unique art gallery nestled in the scenic heart of the Berkshires at 2 Moscow Road, West Stockbridge, Massachusetts. Once a historic marble quarry, this enchanting space has been transformed into a captivating sculpture park that invites visitors to explore its winding paths and discover a world of fantastical art. With its whimsical atmosphere, many liken the experience to stepping into an "Alice in Wonderland" adventure, where creativity and nature harmoniously blend. As a 501C3 tax-exempt nonprofit organization, TurnPark Art Space is dedicated to enriching the community through art and culture. We rely on the generous support of patrons and art enthusiasts like you to continue our mission. Whether you're an art lover, a curious explorer, or a supporter of the arts, your visit and contributions help sustain this magical destination. Come and immerse yourself in the beauty and wonder of Turn Park Art Sculptures. We look forward to welcoming you!

Welcome to Partridge Hollow Campground, your serene getaway nestled in the beautiful landscape of West Stockbridge, Massachusetts. Located at 5 Albany Road, our campground offers a perfect blend of nature and comfort, making it an ideal destination for families, couples, and outdoor enthusiasts seeking a memorable retreat. At Partridge Hollow Campground, we pride ourselves on providing a welcoming and relaxing environment for all our guests. Our spacious campsites are designed to accommodate tents, RVs, and trailers, ensuring that everyone can enjoy the great outdoors in their preferred style. Each site is equipped with essential amenities to make your stay as comfortable as possible.

Welcome to Foundry Green, a serene oasis nestled in the heart of West Stockbridge, Massachusetts. Located on Harris Street, this picturesque park offers a perfect escape for nature lovers, families, and anyone seeking a peaceful retreat. Foundry Green boasts beautifully landscaped grounds, lush greenery, and scenic walking paths that invite you to unwind and explore the great outdoors. Visitors can enjoy a leisurely stroll, a relaxing picnic, or simply bask in the tranquility of the surroundings. The park features well-maintained facilities, including benches and shaded areas, ensuring a comfortable experience for all guests. Whether you're looking to enjoy a quiet moment alone or spend quality time with loved ones, Foundry Green provides the ideal setting.

Welcome to Ashley House, a captivating museum and tourist attraction located at 117 Cooper Hill Road, Sheffield, Massachusetts. Nestled in the picturesque Berkshires, this historic site offers a profound journey through time, exploring the narratives of two influential figures who fought for freedom and liberty, forever altering the course of our region’s history. The Colonel John Ashley House, a cornerstone of the Upper Housatonic Valley African American Heritage Trail, stands as one of the earliest European-style dwellings in the Berkshires. Built in 1735, this remarkable Colonial-era house was once the epicenter of white political and social life in colonial Sheffield. Colonel John Ashley, a prominent and wealthy figure, owned vast lands and businesses, prospering significantly from the institution of slavery.

Monument Mountain Reservation/Flag Rock Trailhead Location: Great Barrington, Massachusetts 01230, United States Type: Park

Welcome to Stevens Glen Trail Head, a serene and picturesque park located in the heart of the Berkshires at Lenox Road, West Stockbridge, Massachusetts. Nestled in the lush greenery of Richmond, MA, our park offers a tranquil escape for nature lovers and outdoor enthusiasts. Stevens Glen Trail Head is renowned for its breathtaking landscapes, featuring well-maintained trails that wind through dense forests, alongside babbling brooks, and past stunning waterfalls. Whether you're a seasoned hiker or just looking for a peaceful walk in nature, our trails cater to all skill levels, providing a perfect opportunity to reconnect with the great outdoors.

Welcome to Lower Bowker's Woods, a serene park located at 16-18 Glendale Middle Road, Stockbridge, Massachusetts. Nestled in the heart of the Berkshires, our park offers a tranquil escape for nature lovers and outdoor enthusiasts. Explore our well-maintained trails and immerse yourself in the natural beauty of the area. At Lower Bowker's Woods, we are committed to ensuring the safety and well-being of all our visitors. In accordance with COVID-19 safety guidelines, all trails and properties are open to the public. We kindly ask that unvaccinated visitors adhere to state guidelines by wearing a face covering or mask when unable to maintain a distance of 6 feet from others. Your cooperation helps us maintain a safe environment for everyone and allows us to keep our trails accessible for all to enjoy.

Welcome to Charcoal Trail Trailhead, a serene escape nestled in the picturesque landscape of West Stockbridge, Massachusetts. Located at Michael H. Walsh Trail, our park offers a perfect starting point for nature enthusiasts and adventure seekers alike. Immerse yourself in the tranquility of lush forests, winding trails, and breathtaking vistas that showcase the natural beauty of the Berkshires. Whether you're an avid hiker, a casual walker, or simply looking for a peaceful spot to connect with nature, Charcoal Trail Trailhead provides a variety of trails suitable for all skill levels. Explore the rich biodiversity, discover local wildlife, and enjoy the fresh air as you journey through this charming outdoor haven.

Welcome to The Trustees of Reservations, a haven for nature lovers and history enthusiasts alike, located at 1 Sergeant Street, Stockbridge, Massachusetts. As a distinguished museum and tourist attraction, we are dedicated to preserving the exceptional scenic, historic, and ecological treasures of Massachusetts. Our mission is to protect the places you love for their trails, history, gardens, and beaches, recognizing that nature and culture enrich our lives and soothe the soul. Explore the beauty of Massachusetts through our diverse offerings, from historic estates to breathtaking natural landscapes. Immerse yourself in our scenic trails, picturesque gardens, and serene beaches that promise a rejuvenating experience. For those interested in history, delve into the rich past of the region with guided tours and educational programs.

Welcome to Kwuniikwat Island, a serene and picturesque park located in Stockbridge, Massachusetts. Managed by the Stockbridge Bowl Association (SBA), Kwuniikwat Island is a testament to our commitment to preserving the natural beauty and ecological integrity of the Stockbridge Bowl area. Since our founding in 1946, the SBA has been dedicated to protecting and enhancing the environmental, recreational, and aesthetic values of this cherished region. Kwuniikwat Island, along with Bullard Woods, is open to the public and offers a tranquil escape into nature. Visitors can explore well-maintained trails, enjoy scenic picnic areas, and take in the beauty of the surrounding landscapes. Our efforts include regular maintenance, improved signage, and the addition of amenities like benches and docks to make your visit more enjoyable.

Welcome to Beachwood Beach, a serene and picturesque park nestled in the heart of Stockbridge, Massachusetts. Located in the charming Berkshires region, our park offers a perfect escape for nature lovers and outdoor enthusiasts. With its pristine sandy shores and sparkling waters, Beachwood Beach is the ideal destination for a relaxing day by the water. Visitors can enjoy a variety of activities, from swimming and sunbathing to picnicking and leisurely strolls along the shoreline. The park is equipped with well-maintained facilities, including picnic tables, restrooms, and ample parking, ensuring a comfortable and convenient experience for all guests.

Welcome to Carriage House, a charming haven nestled in the picturesque town of Stockbridge, Massachusetts. Located in the heart of the Berkshires at 01240, our establishment offers a unique blend of historic charm and modern comfort, making it the perfect destination for both locals and visitors alike. At Carriage House, we pride ourselves on providing an exceptional experience that caters to a variety of needs. Whether you're seeking a cozy retreat, a venue for special occasions, or a delightful spot to unwind, our welcoming atmosphere and attentive service ensure a memorable visit. Our beautifully appointed spaces reflect the rich history of Stockbridge while offering all the contemporary amenities you desire.