TOP 30 Hiking trails in Great Barrington, Massachusetts

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 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 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 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 the Appalachian Trail at Deerwood Circle, a serene escape nestled in the heart of Great Barrington, Massachusetts. Located at Deerwood Circle, this picturesque park offers nature enthusiasts and adventurers alike a gateway to the stunning landscapes of the Appalachian Trail. Immerse yourself in the lush greenery and tranquil beauty that defines this historic trail, known for its breathtaking views and diverse wildlife. Whether you're a seasoned hiker or a casual walker, our park provides a variety of trails suitable for all skill levels. Enjoy a leisurely stroll through the gentle pathways or challenge yourself with more rugged terrain. Along the way, discover the rich flora and fauna that inhabit this unique ecosystem.

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.

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.

The Red House on Lake Buel is a charming Berkshire lakeside cottage offering a peaceful retreat for those seeking relaxation and outdoor activities. Located at 24 Downs Road in New Marlborough, Massachusetts, this vacation rental property is just a short distance from popular attractions such as Tanglewood, Jacobs Pillow, Norman Rockwell Museum, and Chesterwood. This idyllic 4 bedroom cottage is situated right on the edge of Lake Buel, providing easy access to swimming, fishing, water sports, and hiking. The house features a spacious screened-in porch with comfortable seating and a dining table for 8, perfect for enjoying meals with a view of the lake. Guests can also bring their own boat and dock it at the private dock.

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.

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.

Pfeiffer Arboretum, located at 249 Long Pond Road in Great Barrington, Massachusetts, is a stunning park and tourist attraction. Visitors can explore the beautiful grounds filled with a diverse collection of trees, shrubs, and plants from around the world. The arboretum offers a peaceful escape from the hustle and bustle of daily life, with winding paths and tranquil seating areas perfect for relaxation and contemplation. Whether you are a nature enthusiast, a photography buff, or simply looking for a peaceful retreat, Pfeiffer Arboretum is a must-visit destination in the heart of the Berkshires.

Benedict Pond Loop is a scenic park located in Great Barrington, Massachusetts, United States. This beautiful institution offers visitors the opportunity to immerse themselves in nature and enjoy the stunning views of the surrounding area. Whether you're looking to go for a leisurely stroll, have a picnic by the pond, or simply relax and take in the peaceful atmosphere, Benedict Pond Loop is the perfect destination for outdoor enthusiasts of all ages. With well-maintained trails and plenty of wildlife to observe, this park is a must-visit for anyone looking to escape the hustle and bustle of everyday life.

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 Appalachian Train at Sheffield-Egremont Rd, a serene park nestled in the picturesque landscape of Great Barrington, Massachusetts. Located at 39 Sheffield-Egremont Road, our park offers a delightful escape into nature, where visitors can immerse themselves in the tranquil beauty of the Appalachian region. Whether you're a local resident or a traveler seeking a peaceful retreat, our park provides a perfect setting for relaxation, recreation, and exploration. Discover the charm of our well-maintained trails that wind through lush greenery, offering a perfect opportunity for hiking, jogging, or a leisurely stroll. The park is ideal for nature enthusiasts, bird watchers, and families looking to enjoy a day out in the fresh air. With plenty of open spaces, it's also a great spot for picnics, outdoor games, and simply unwinding amidst nature.

Welcome to Tracey Park, a serene oasis nestled in the heart of Great Barrington, Massachusetts. Situated in the picturesque Berkshires, Tracey Park offers a perfect escape for nature lovers, families, and anyone seeking tranquility and outdoor recreation. Explore our beautifully maintained trails that wind through lush greenery, providing ideal opportunities for hiking, bird-watching, and enjoying the natural beauty of the region. Our spacious picnic areas are perfect for gatherings with family and friends, while the children's playground offers a safe and fun environment for kids to explore and play.

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 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 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 East Rock Inn, your charming getaway nestled in the heart of the Berkshires. Located at 304 State Road, Great Barrington, Massachusetts, our inn offers a perfect blend of comfort and tranquility, making it an ideal destination for both relaxation and adventure. At East Rock Inn, we pride ourselves on providing a warm and inviting atmosphere where guests can unwind and enjoy the natural beauty of the surrounding area. Our elegantly appointed rooms are designed to offer a cozy retreat, complete with modern amenities to ensure a comfortable stay. Whether you're here for a romantic escape, a family vacation, or a solo journey, you'll find the perfect accommodation to suit your needs.