TOP 30 Hiking destination in Great Barrington, Massachusetts

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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.

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.

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.

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.

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 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.