TOP 10 Trails in Sheffield, Massachusetts

Welcome to the Appalachian Trail at US 7, a serene and picturesque park located in the heart of Sheffield, Massachusetts. Nestled amidst the breathtaking landscapes of the Berkshires, our park offers a perfect escape for nature enthusiasts and outdoor adventurers alike. As a part of the iconic Appalachian Trail, this section provides visitors with stunning vistas, lush forests, and a tranquil atmosphere that is ideal for hiking, bird watching, and reconnecting with nature. Whether you're an experienced hiker or a casual walker, the well-maintained trails cater to all skill levels, ensuring a memorable experience for everyone. Enjoy the beauty of the changing seasons, from vibrant spring blooms to the rich hues of autumn leaves. Our park is also a haven for wildlife, providing opportunities to observe various species in their natural habitat.

Welcome to the Appalachian Trail Access Point Trailhead Parking at Sheffield-Egremont Rd, located in the picturesque New Marlboro, Massachusetts. As a key access point to the renowned Appalachian National Scenic Trail, this park serves as a gateway to one of the most cherished hiking experiences in the United States. Since 1925, our mission has been to oversee the management and conservation of this iconic trail, ensuring its beauty and accessibility for generations to come. Our efforts have led to the protection of breathtaking viewsheds, including the popular McAfee Knob. By becoming a member, you can enjoy exclusive benefits such as an oversized Appalachian Trail strip map, a subscription to our membership magazine, A.T. Journeys, and discounts at the Ultimate A.T. Store®. Members also receive invitations to exclusive events and special volunteer opportunities.

Welcome to the Appalachian Trail Access Point in Sheffield, Massachusetts! Nestled in the picturesque landscapes of the Berkshires, our access point provides nature enthusiasts, hikers, and adventurers with a gateway to the world-famous Appalachian Trail. Located in the charming town of Sheffield, MA 01230, our park serves as an ideal starting point for your outdoor excursions. Whether you're planning a day hike, a weekend camping trip, or embarking on the journey of a lifetime along the Appalachian Trail, our access point offers convenient and easy access to one of America's most celebrated long-distance hiking trails. Surrounded by lush forests, rolling hills, and stunning vistas, this location is perfect for those seeking tranquility, natural beauty, and a connection with nature.

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 Sheffield Town Park, your serene escape nestled in the heart of Sheffield, Massachusetts. Located at 53-59 Frederic Lane, our beautiful park offers a perfect blend of natural beauty and recreational opportunities for visitors of all ages. Whether you're looking to enjoy a leisurely stroll, have a family picnic, or engage in outdoor sports, Sheffield Town Park is your ideal destination. Our park features well-maintained walking trails, lush green spaces, and picnic areas equipped with tables and grills, making it an excellent spot for gatherings and relaxation. Children can enjoy our modern playground facilities, while sports enthusiasts can take advantage of our basketball courts and open fields for soccer or frisbee.

Welcome to the Appalachian Trail and US 7 in Sheffield, Massachusetts, where nature enthusiasts and outdoor adventurers can immerse themselves in the beauty and tranquility of one of America's most treasured national scenic trails. Located at U.S. 7, Sheffield, MA 01257, our park serves as a gateway to the Appalachian National Scenic Trail, a cherished pathway that has been overseen and conserved since 1925. Our mission at the Appalachian Trail Conservancy is to protect, manage, and advocate for the trail, ensuring its preservation for future generations. We are proud to have secured protection for the stunning viewshed of the popular McAfee Knob, a testament to our commitment to conservation.

Welcome to Sheffield Town Park, your perfect escape into nature located in the heart of Sheffield, Massachusetts. Situated at 21 Depot Square, our park is a serene haven that offers an ideal setting for relaxation, recreation, and community gatherings. Whether you're looking to enjoy a peaceful stroll, host a family picnic, or engage in outdoor activities, Sheffield Town Park provides a beautiful backdrop with its lush landscapes and well-maintained facilities. Our park is designed to cater to visitors of all ages, offering playgrounds for children, walking trails for nature enthusiasts, and open spaces for various sports and events. Embrace the tranquility of this charming park and create lasting memories with family and friends. Visit Sheffield Town Park today and experience the natural beauty and welcoming atmosphere that make it a cherished local treasure.

Welcome to the Upper Sheffield Covered Bridge, a charming and historic landmark nestled in the picturesque town of Sheffield, Massachusetts. Located on Covered Bridge Lane, this iconic structure offers visitors a glimpse into the rich heritage and scenic beauty of the Berkshires. The Upper Sheffield Covered Bridge is more than just a crossing; it's a journey back in time. Originally constructed in the 19th century, this bridge is a testament to the skilled craftsmanship of the era and serves as a beloved symbol of the local community. Whether you're a history enthusiast, a nature lover, or simply seeking a peaceful retreat, the bridge provides a perfect setting for a leisurely stroll, photography, or quiet contemplation.

Welcome to the Appalachian Trail at Boardman St, a serene and picturesque section of the renowned Appalachian National Scenic Trail, located in Sheffield, Massachusetts. Since 1925, we have been dedicated to the management and conservation of this iconic trail, ensuring its beauty and accessibility for generations to come. Our efforts have secured protection for popular viewsheds, including the breathtaking McAfee Knob. As a member of our community, you can enjoy numerous benefits, such as an oversized Appalachian Trail strip map, a subscription to our exclusive membership magazine, A.T. Journeys, and discounts at the Ultimate A.T. Store®. Additionally, you'll receive invitations to special events and unique volunteer opportunities.

Welcome to the Appalachian Trail at Kellogg Rd Trailhead Parking, your convenient gateway to exploring the stunning natural beauty of the Appalachian Trail in Sheffield, Massachusetts. Nestled in the heart of the Berkshires, our parking facility offers easy access to one of the most picturesque sections of the trail. Whether you're a seasoned hiker or a first-time adventurer, our location provides the perfect starting point for your outdoor journey. Located at Kellogg Rd, Sheffield, MA 01257, our trailhead parking is designed to accommodate day hikers and long-distance backpackers alike. With ample parking spaces, you can rest assured that your vehicle will be safe while you immerse yourself in the serene landscapes and rich biodiversity the Appalachian Trail has to offer.

Birch Hill Bed & Breakfast is a charming lodging located at 254 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshires region, this cozy B&B offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations, delicious homemade breakfasts, and warm hospitality, Birch Hill Bed & Breakfast is the perfect place to relax and unwind during your stay in the Berkshires.

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

Dolomite Ledges Wildlife Management Area is a stunning park located in Sheffield, Massachusetts, United States. This beautiful institution is home to a diverse range of wildlife, offering visitors the opportunity to observe and learn about various species in their natural habitat. The park features lush greenery, rocky ledges, and serene walking trails, providing a peaceful escape from the hustle and bustle of everyday life. Whether you're a nature enthusiast, wildlife lover, or simply looking for a relaxing day out, Dolomite Ledges Wildlife Management Area is the perfect destination to connect with nature and enjoy the great outdoors.

Hubbard Brook Wildlife Management Area is a stunning park and zoo located in Sheffield, Massachusetts, United States. This institution offers visitors the opportunity to explore and observe a variety of wildlife in their natural habitat. With its lush forests, meandering streams, and diverse range of animal species, Hubbard Brook Wildlife Management Area is a perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking to hike through the beautiful landscape or simply relax and enjoy the sights and sounds of the wilderness, this institution provides a unique and unforgettable experience for all who visit.

Bartholomew's Cobble Reservation is a scenic and historic destination located at 105 Weatogue Road in Sheffield, Massachusetts, United States. This institution serves as a museum, park, and tourist attraction all in one, offering visitors a unique and immersive experience in the beautiful Berkshire region. The reservation is home to stunning natural landscapes, including a variety of plant and animal species, as well as geological formations that date back millions of years. Visitors can explore the well-maintained trails, take guided tours, and learn about the area's rich history and conservation efforts. Bartholomew's Cobble Reservation is a must-visit destination for nature lovers, history buffs, and anyone looking to enjoy the great outdoors in a serene and educational setting.

Race Brook Falls Trailhead & Parking is a convenient and easily accessible parking facility located at 716-732 South Undermountain Road in Sheffield, Massachusetts. This parking area serves as the starting point for the popular Race Brook Falls Trail, a picturesque hiking trail that winds through the beautiful Berkshire Mountains. Visitors can park their vehicles here and begin their outdoor adventure, exploring the lush forests, babbling brooks, and stunning waterfalls along the trail. Whether you're a seasoned hiker or just looking for a peaceful nature walk, Race Brook Falls Trailhead & Parking provides a perfect starting point for your outdoor exploration in this scenic area of the United States.

Perlman Pond is a tranquil park located at 689 Home Road in Sheffield, Massachusetts, United States. This picturesque pond offers a peaceful escape from the hustle and bustle of everyday life, with lush greenery and serene waters perfect for relaxing or enjoying a leisurely stroll. Visitors can take in the natural beauty of the surroundings, go for a swim, or simply unwind by the water's edge. Perlman Pond is a hidden gem waiting to be discovered by nature lovers and outdoor enthusiasts alike.

Welcome to Dolomite Ledges Wildlife Management Area Parking, your convenient starting point for exploring the natural beauty of Sheffield, Massachusetts. Situated in the heart of the Berkshires, our parking area provides easy access to the stunning Dolomite Ledges Wildlife Management Area, renowned for its diverse ecosystems and picturesque landscapes. Whether you're here for a day of hiking, birdwatching, or simply to enjoy the serenity of nature, our well-maintained parking facilities offer a hassle-free experience for visitors. Located in Sheffield, MA 01257, we are committed to providing a safe and accessible parking solution for outdoor enthusiasts and nature lovers alike. Visit us today and embark on your adventure in this beautiful corner of Massachusetts.

Welcome to the Roger and Virginia Drury Preserve, a captivating natural sanctuary nestled in the heart of Sheffield, Massachusetts. As the first Nature Conservancy preserve in the southern Berkshires, this cherished site was established in 1997 in honor of Roger and Virginia Drury's generous donation of 65 acres in 1984. Today, it stands as part of the expansive Schenob Brook wetland complex, a vital area renowned for its calcareous wetlands and diverse ecosystems. Visitors to the Drury Preserve can explore a lightly marked, approximately 3-mile trail that meanders through a stunning array of lowland forests and plant communities. The trail, which gently slopes through a variety of wet and dry environments, offers a unique opportunity to immerse oneself in nature's beauty. Along the way, you'll encounter a rich understory of northern hardwoods, vibrant spring ephemeral wildflowers, and fall-blooming asters. The path also winds around distinctive cobbles typical of the southern Berkshires, adding to the scenic charm.

Welcome to Kellogg Rd Trailhead, nestled in the picturesque town of Sheffield, Massachusetts. As a key access point to the Appalachian National Scenic Trail, our park offers nature enthusiasts and hikers an opportunity to explore one of America's most iconic trails. Since 1925, we have been committed to the management and conservation of this breathtaking natural wonder. At Kellogg Rd Trailhead, you'll find yourself immersed in the beauty of the Appalachian Trail, with views that include the stunning McAfee Knob. Our dedication to preserving these vistas ensures that visitors can enjoy the pristine landscape for generations to come.

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.

Welcome to Ledges Trailhead, a picturesque park nestled in the charming town of Sheffield, Massachusetts. Located at the heart of the Berkshires, our park offers a serene escape into nature, where visitors can explore a variety of scenic trails that wind through lush forests and offer breathtaking views of the surrounding landscape. Whether you're an avid hiker, a nature enthusiast, or simply looking for a peaceful retreat, Ledges Trailhead is the perfect destination. Our well-maintained trails cater to all levels of hikers, from beginners to seasoned adventurers, ensuring an enjoyable experience for everyone. As you wander through the park, you'll encounter diverse wildlife, tranquil streams, and striking rock formations that make for perfect photo opportunities.

Welcome to Tractor Path Trailhead, a serene park nestled in the heart of Sheffield, Massachusetts. Located at Sheffield, MA 01257, our trailhead offers a perfect escape into the natural beauty of the Berkshire region. Whether you're an avid hiker, a nature enthusiast, or simply seeking a peaceful retreat, Tractor Path Trailhead provides an ideal setting for outdoor exploration and relaxation. Our well-maintained trails wind through lush forests, open meadows, and along picturesque streams, offering a variety of routes suitable for all skill levels. As you traverse the paths, keep an eye out for local wildlife and the diverse flora that make this area their home. Tractor Path Trailhead is a haven for birdwatchers, photographers, and anyone looking to reconnect with nature.

Welcome to Cmelak Field-MA18, your gateway to aviation excellence in the heart of the Berkshires. Nestled at 418 Galvin Farm Trail in the picturesque town of Sheffield, Massachusetts, our private airport offers a unique and intimate experience for aviation enthusiasts and pilots alike. At Cmelak Field-MA18, we pride ourselves on providing exceptional service and a welcoming atmosphere, ensuring a seamless and enjoyable visit for all our guests. Whether you're flying in for business, leisure, or to explore the stunning natural beauty of the surrounding area, Cmelak Field-MA18 is your ideal landing spot. Our well-maintained facilities and dedicated staff are here to meet your needs, offering a range of services to enhance your flying experience. From fueling and maintenance assistance to detailed local information and support, we are committed to making your time with us as pleasant and efficient as possible.

Welcome to Dolomite Ledges Wildlife Management Area Parking, your convenient and accessible gateway to exploring the natural beauty of Sheffield, Massachusetts. Located in the heart of the picturesque Berkshires, our parking facility offers a safe and well-maintained space for visitors to begin their outdoor adventures. Whether you're here for hiking, bird watching, or simply to enjoy the tranquil surroundings, our parking area provides easy access to the stunning landscapes and diverse wildlife of the Dolomite Ledges Wildlife Management Area. Designed with nature enthusiasts in mind, our parking area is conveniently situated to accommodate vehicles of various sizes, ensuring a hassle-free experience. We are committed to maintaining a clean and organized environment, allowing you to focus on enjoying the natural wonders that await. Open year-round, Dolomite Ledges Wildlife Management Area Parking serves as the perfect starting point for your exploration of this beautiful region.

Welcome to Wilder House Berkshires, your serene escape nestled in the heart of the picturesque Berkshires. Located at 48 South Main Street, Sheffield, Massachusetts, our charming lodging offers a perfect blend of comfort, tranquility, and rustic elegance. Whether you're seeking a peaceful retreat or an adventurous getaway, Wilder House provides the ideal base for exploring the natural beauty and cultural richness of the area. Our accommodations are thoughtfully designed to provide a cozy and inviting atmosphere, ensuring a restful stay for all our guests. Each room is equipped with modern amenities while retaining the charm and warmth of a classic Berkshire residence. Wake up to the stunning views of the surrounding landscapes and enjoy a delicious breakfast to start your day.