TOP 30 Great outdoors adventure in Great Barrington, Massachusetts

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Wind in the Pines is a serene retreat nestled in the heart of Great Barrington, Massachusetts. Located at 949 South Main Street, this institution offers a tranquil and peaceful environment surrounded by the beauty of nature. Visitors can relax and rejuvenate in the midst of towering pine trees, listening to the gentle rustling of the wind. Whether seeking a quiet escape or a place for reflection and meditation, Wind in the Pines provides a welcoming sanctuary for all who enter its doors.

Barrington Outfitters, located at 289 Main Street in Great Barrington, Massachusetts, is a family-owned institution specializing in luxury outdoor patio furniture, comfortable shoes, and exceptional customer service. Since 1994, the Drucker Family has been providing the community with a wide selection of high-quality clothing, furniture, home goods, and footwear. Open seven days a week, Barrington Outfitters is conveniently situated in the heart of Great Barrington and looks forward to welcoming you with their friendly and knowledgeable staff.

Berkshire Bike and Board in Great Barrington, Massachusetts, is your go-to destination for all things cycling. Since 1995, our dedicated team has been committed to helping people of all abilities enjoy the thrill of riding bicycles. From leisurely rides around the neighborhood to intense mountain biking adventures, we have everything you need to make your ride smooth and enjoyable. Join us for group bike rides and connect with fellow cyclists while exploring the beautiful outdoors. Our professionally trained technicians are here to provide top-notch maintenance and repair services for your bike, ensuring that your ride is always in good hands.

Welcome to Great Barrington Resort House, your serene getaway nestled in the picturesque landscapes of Lenox, Massachusetts. Located at the heart of the Berkshires, our resort offers a perfect blend of luxury, comfort, and natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled vacation, our resort is the ideal destination. At Great Barrington Resort House, we pride ourselves on providing exceptional hospitality and personalized service. Our elegantly designed rooms and suites offer breathtaking views and modern amenities to ensure a relaxing stay. Enjoy gourmet dining at our on-site restaurant, unwind at our spa, or take a dip in our heated pool.

Brook Cove is a charming lodging institution located at 30 Linda Lane in the picturesque town of Great Barrington, Massachusetts. Surrounded by lush greenery and peaceful surroundings, Brook Cove offers a serene retreat for guests looking to escape the hustle and bustle of city life. The cozy accommodations and warm hospitality make it the perfect destination for a relaxing getaway. Whether you're looking to explore the beautiful Berkshires or simply unwind in nature, Brook Cove provides a tranquil and comfortable stay for all visitors.

Welcome to Berkshire Rental Properties, located at 29 Benton Avenue in Great Barrington, Massachusetts. Whether you're in search of a quaint cottage or a luxurious multifamily estate, Berkshire Rental Properties offers a wide range of options to suit your needs. Our listings are carefully selected for their desirability, location, and top-notch amenities, providing a step above the typical rental offerings. At Berkshire Rental Properties, we understand the allure of the Berkshires and aim to provide a seamless getaway experience for our guests. Whether you're seeking outdoor adventures, cultural experiences, or simply a relaxing retreat, our properties serve as the perfect gateway to all that the Berkshires have to offer.

Monument Mountain Reservation is a park and tourist attraction located in Great Barrington, Massachusetts, United States. From the 1,642-foot summit of this popular peak, visitors can gaze across the splendor of the Housatonic River Valley. The mountain has been sacred to the Mohican people and their ancestors since ancient times, with stone offerings imbued with prayers left on the mountain creating the "monument" for which it is named. The original monument was destroyed by white residents after the Mohicans were dispossessed, but was later recreated near the Mohican Monument Trail. Monument Mountain has long inspired works of art and literature, with authors such as William Cullen Bryant, Nathaniel Hawthorne, and Herman Melville finding motivation for their works on the mountain. Today, more than 20,000 hikers ascend to its summit, Peeskawso Peak, each year. Three trails offer scenic ways to explore the mountain's pale quartzite geology and views out to Mount Greylock and the Catskill Mountains.

Westerlind is a trendy clothing store located at 294 Main Street in Great Barrington, Massachusetts. Offering a curated selection of stylish and functional apparel, footwear, and accessories, Westerlind caters to the modern adventurer and outdoor enthusiast. With a focus on quality, sustainability, and timeless design, this store is a must-visit destination for those seeking high-quality, versatile pieces for their wardrobe. Whether you're exploring the great outdoors or navigating city streets, Westerlind has everything you need to stay comfortable, stylish, and ready for any adventure.

Butternut Ski Area and Tubing Center is a popular tourist attraction located at 380 State Road in Great Barrington, Massachusetts. This institution offers a wide range of winter activities for visitors to enjoy, including skiing, snowboarding, and tubing. The ski area features well-maintained slopes for all skill levels, while the tubing center provides a thrilling experience for all ages. With stunning views of the surrounding area and top-notch facilities, Butternut Ski Area and Tubing Center is the perfect destination for outdoor enthusiasts looking for a fun and exciting winter adventure.

Mansfield Pond is a picturesque park and popular tourist attraction located on Lake Mansfield Road in Great Barrington, Massachusetts, United States. This serene destination offers visitors a tranquil escape surrounded by lush greenery and the calming waters of Mansfield Pond. Perfect for picnics, leisurely walks, or simply enjoying the beauty of nature, Mansfield Pond is a must-visit for anyone looking to relax and unwind in a peaceful setting. With its scenic views and peaceful ambiance, Mansfield Pond is sure to captivate visitors of all ages.

Fountain Pond State Park is a picturesque park located in Great Barrington, Massachusetts, United States. Situated along U.S. 7, this park is a popular tourist attraction known for its serene atmosphere and beautiful natural surroundings. Visitors can enjoy hiking trails, fishing in the pond, picnicking, and birdwatching. The park is a perfect spot for a relaxing day outdoors with family and friends. Whether you're looking to unwind in nature or explore the local wildlife, Fountain Pond State Park offers something for everyone to enjoy.

Old Maid's Park is a charming and tranquil green space located at 30 Wyantenuck Street in Great Barrington, Massachusetts. This historic park offers a peaceful retreat for visitors to enjoy nature, relax, and unwind. With its lush greenery, scenic walking paths, and picnic areas, Old Maid's Park is the perfect spot for a leisurely afternoon or a family outing. Whether you're looking to read a book under a shady tree, take a leisurely stroll, or simply soak in the beauty of the surroundings, this park provides a serene escape from the hustle and bustle of everyday life. Plan a visit to Old Maid's Park and experience the beauty and tranquility of this hidden gem in Great Barrington.

Housatonic Flats Reserve is a beautiful park located at 439 Stockbridge Road in Great Barrington, Massachusetts, United States. This serene reserve offers visitors a peaceful escape into nature, with lush greenery, meandering trails, and stunning views of the Housatonic River. Perfect for a leisurely stroll, birdwatching, or simply relaxing in the great outdoors, Housatonic Flats Reserve is a hidden gem waiting to be explored. Whether you're looking for a quiet retreat or a place to reconnect with nature, this park is the perfect destination for nature lovers of all ages.

Monument Mountain Reservation Parking is a convenient parking area located at 546 Stockbridge Road in Great Barrington, Massachusetts. This parking facility serves visitors to Monument Mountain Reservation, a beautiful park known for its stunning views and hiking trails. Whether you're looking to explore the natural beauty of the Berkshires or simply need a place to park while enjoying the outdoors, Monument Mountain Reservation Parking provides easy access to this popular destination. With ample parking spaces and a convenient location, this institution is the perfect starting point for your outdoor adventure.

East Mountain State Forest is a picturesque park and popular tourist attraction located in Great Barrington, Massachusetts, United States. This beautiful forest offers visitors a serene escape into nature, with hiking trails, stunning views, and an abundance of wildlife to discover. Whether you're looking for a peaceful stroll through the woods or a challenging hike to the summit, East Mountain State Forest has something for everyone to enjoy. Come explore this hidden gem in the heart of the Berkshires and experience the natural beauty of Massachusetts at its finest.

Welcome to Barrett East Woods, a serene and picturesque park nestled in the heart of Great Barrington, Massachusetts. Located at 68 Seekonk Cross Road, our park offers a tranquil escape from the hustle and bustle of everyday life, providing visitors with a perfect setting for relaxation and outdoor adventures. Barrett East Woods is renowned for its lush landscapes, winding trails, and diverse wildlife, making it an ideal destination for nature lovers and outdoor enthusiasts. Whether you're looking to enjoy a peaceful walk, a challenging hike, or a scenic picnic, our park caters to all ages and interests.

Welcome to the Appalachian Trail at W Road, a serene and picturesque park located at 600-736 West Road, Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this scenic destination offers nature enthusiasts and outdoor adventurers an opportunity to explore one of the most iconic hiking trails in the United States. Whether you're a seasoned hiker or simply looking for a peaceful escape, our park provides a variety of trails that cater to all skill levels, each offering breathtaking views of the surrounding landscapes. Immerse yourself in the natural beauty of the Appalachian Trail as you traverse through lush forests, rolling hills, and tranquil streams. Our well-maintained paths ensure a safe and enjoyable experience for all visitors. Keep an eye out for local wildlife and enjoy the diverse flora that changes with the seasons, offering something new to discover year-round.

Welcome to Riverfront Trail (North), a serene escape nestled in the heart of Great Barrington, Massachusetts. Located at 81 Bridge Street, our picturesque park offers a perfect blend of natural beauty and tranquility. Ideal for outdoor enthusiasts and families alike, Riverfront Trail (North) features well-maintained walking paths that meander along the scenic river, providing breathtaking views and a peaceful atmosphere. Whether you're looking for a leisurely stroll, a place to enjoy a picnic, or an opportunity to connect with nature, our park is the perfect destination. Discover local wildlife, enjoy the vibrant seasonal foliage, and experience the calming sounds of the river as you explore. Riverfront Trail (North) is a cherished community space where visitors can relax, unwind, and recharge. We invite you to visit and enjoy all that our beautiful park has to offer.

Welcome to Lake Mansfield Beach Parking Area, your gateway to a serene and scenic retreat in the heart of Great Barrington, Massachusetts. Nestled at 45 Lake Mansfield Road, our park offers a tranquil escape where nature's beauty meets community recreation. Surrounded by lush greenery and the sparkling waters of Lake Mansfield, this idyllic spot is perfect for families, friends, and solo adventurers seeking relaxation and outdoor fun. Enjoy a day of swimming, picnicking, or simply lounging by the beach. With well-maintained facilities and ample parking, Lake Mansfield Beach Parking Area ensures a convenient and enjoyable experience for all visitors.

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

Welcome to Thomas and Palmer Brook Reserve, a serene natural oasis nestled in the heart of Great Barrington, Massachusetts. Located at 305 State Road, our beautiful park offers a peaceful escape for nature enthusiasts, families, and anyone seeking to enjoy the great outdoors. Explore the lush landscapes and tranquil trails that wind through our reserve, offering stunning views and the chance to observe local wildlife in their natural habitat. Whether you're interested in a leisurely stroll, a vigorous hike, or simply a quiet spot for reflection, Thomas and Palmer Brook Reserve provides the perfect setting.

Welcome to Lookout Trail, your premier destination for outdoor adventure and natural beauty in Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape from the hustle and bustle of everyday life. Whether you're an avid hiker, a nature enthusiast, or simply seeking a peaceful retreat, Lookout Trail provides an ideal setting for all. Explore our well-maintained trails that wind through lush forests and open meadows, offering breathtaking views of the surrounding landscape. Perfect for both beginners and experienced hikers, our paths promise a memorable journey through nature's splendor.

Welcome to the Appalachian Trail at Lake Buel Rd, a stunning natural haven nestled in the heart of Great Barrington, Massachusetts. As part of the renowned Appalachian National Scenic Trail, this picturesque park offers outdoor enthusiasts a unique opportunity to explore one of the most beautiful sections of the trail. Located at Great Barrington, MA 01230, our park provides visitors with breathtaking vistas, lush forests, and serene landscapes that are perfect for hiking, bird watching, and photography. Whether you're a seasoned hiker or a casual nature lover, the Appalachian Trail at Lake Buel Rd promises an unforgettable experience.

Welcome to Beartown Site 7, your ultimate destination for an unforgettable outdoor experience in Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, our campground offers a serene escape for nature enthusiasts, adventure seekers, and families alike. Whether you're looking to pitch a tent under a canopy of stars or enjoy the comfort of our well-appointed lodging facilities, Beartown Site 7 provides the perfect setting for relaxation and recreation. Our park is surrounded by breathtaking natural beauty, offering a wide range of activities to suit all interests. Explore scenic hiking trails, enjoy fishing in nearby lakes, or simply unwind by a campfire and savor the tranquility of the great outdoors. With modern amenities and a friendly atmosphere, Beartown Site 7 ensures a comfortable and enjoyable stay for all our guests.

Welcome to Beartown State Forest Site 11, your premier destination for a serene and memorable outdoor experience in Great Barrington, Massachusetts. Nestled in the heart of the picturesque Berkshires, our campground offers a perfect blend of natural beauty and modern convenience, making it an ideal getaway for nature enthusiasts, families, and adventure seekers alike. At Beartown State Forest Site 11, you'll find a variety of lodging options to suit your needs, whether you're looking to pitch a tent under the stars or park your RV amidst lush greenery. Our well-maintained facilities ensure a comfortable stay, complete with amenities that cater to both relaxation and recreation.

Welcome to Beartown State Forest Site 12, your gateway to the natural beauty and tranquility of Great Barrington, Massachusetts. Nestled in the heart of Beartown State Forest, our site offers a unique blend of campground, lodging, and park experiences, perfect for nature enthusiasts and adventure seekers alike. At Beartown State Forest Site 12, you can immerse yourself in the serene surroundings of lush forests, scenic trails, and sparkling water bodies. Whether you're planning a weekend getaway, a family camping trip, or a solo retreat, our site provides the ideal setting to unwind and reconnect with nature.

Welcome to Benedict Pond Trail Head and Canoe Launch, your gateway to nature's tranquility in the heart of Great Barrington, Massachusetts. Nestled in the lush landscapes of the Berkshires, our park offers a serene escape for outdoor enthusiasts and families alike. Whether you're looking to embark on a scenic hike, enjoy a peaceful paddle, or simply relax amidst the beauty of nature, Benedict Pond has something for everyone. Our well-maintained trails provide an ideal setting for hiking and exploring the diverse flora and fauna of the region. For those who love water activities, the canoe launch offers easy access to the pristine waters of Benedict Pond, perfect for canoeing, kayaking, and fishing. With picturesque views and a calm atmosphere, it's a perfect spot for both adventure and relaxation.

Welcome to Beartown State Forest Site 10, your perfect getaway nestled in the heart of the Berkshires in Great Barrington, Massachusetts. Our scenic campground offers a serene escape for nature lovers, adventure seekers, and those looking to unwind in a tranquil setting. Located at the picturesque address of Great Barrington, MA 01230, Beartown State Forest Site 10 provides an ideal backdrop for camping, hiking, and exploring the great outdoors. Our site is part of the expansive Beartown State Forest, which boasts lush forests, sparkling streams, and a variety of wildlife. Whether you're pitching a tent or parking your RV, our well-equipped facilities ensure a comfortable stay for all guests.

Welcome to the Appalachian Trail at Blue Hill Rd, a serene and picturesque park located at 116 Blue Hill Road in the charming town of Great Barrington, Massachusetts. Nestled within the stunning landscapes of the Berkshires, this section of the iconic Appalachian Trail offers nature enthusiasts and adventure seekers an unparalleled experience of the great outdoors. Whether you are an avid hiker, a casual walker, or simply someone looking to escape the hustle and bustle of everyday life, our park provides a perfect retreat. Explore miles of well-maintained trails that wind through lush forests, over rolling hills, and alongside tranquil streams. The park is an ideal spot for observing local wildlife, enjoying a peaceful picnic, or capturing the breathtaking beauty of New England's natural scenery through photography. With its easy accessibility and welcoming atmosphere, Appalachian Trail at Blue Hill Rd is perfect for individuals, families, and groups seeking a day of adventure and relaxation.

Welcome to Appalachian Trail Parking, your convenient and reliable parking solution located at 102-110 Lake Buel Road in picturesque Great Barrington, Massachusetts. Situated in the heart of the stunning Berkshires, our parking facility provides easy access to the renowned Appalachian Trail, making it the perfect starting point for your hiking adventure. At Appalachian Trail Parking, we understand the needs of outdoor enthusiasts and offer a safe and secure area to park your vehicle while you explore the natural beauty of the region. Our spacious lot is designed to accommodate both short-term and long-term parking, ensuring that you have the flexibility you need for day hikes or extended treks.