TOP 30 Best Berkshires hiking and biking in Massachusetts

Berkshire East Mountain Resort is a charming lodging destination nestled in the picturesque town of Charlemont, Massachusetts. Situated at 66 Thunder Mountain Road, this resort offers guests a peaceful and serene retreat surrounded by the stunning Berkshire Mountains. With cozy accommodations, breathtaking views, and a range of outdoor activities including skiing, snowboarding, and hiking, Berkshire East Mountain Resort is the perfect destination for those seeking a relaxing getaway in the heart of nature.

Welcome to Chester Granite and Polishing Works, a historic gem nestled in the heart of Chester Factory Village at 7 Prospect Street, Chester, Massachusetts. This unique park, recently acquired by the Western Mass Hilltown Hikers, a dedicated 501(c)(3) organization, is a testament to the region's rich industrial past and natural beauty. Originally established in the early 1800s, the Granite Works played a pivotal role in the local industry, cutting and finishing granite sourced from the nearby Beckett Quarry. Visitors can marvel at the historic granite saw, once powered by steam, and the ingenious mechanisms designed to handle massive stone blocks. Thanks to the efforts of the Hilltown Hikers, this remarkable site has been preserved for future generations, preventing its loss to history.

Hoosac Range Trail is a beautiful park and popular tourist attraction located at 2441 Mohawk Trail in North Adams, Massachusetts, United States. This scenic trail offers stunning views of the surrounding mountains and valleys, making it a must-visit destination for nature lovers and outdoor enthusiasts. Whether you're looking for a leisurely hike or a challenging trek, Hoosac Range Trail has something for everyone. Come explore the natural beauty of this iconic trail and experience the tranquility of the great outdoors.

Welcome to Tyringham Cobble Park, a captivating natural retreat nestled at 20 Jerusalem Road, Tyringham, Massachusetts. As a renowned park and tourist attraction, Tyringham Cobble offers an unforgettable experience for nature enthusiasts and history buffs alike. Explore the wonders of this geologic marvel, shaped by ancient tectonic movements that left exposed bedrock atop a high ridge, offering breathtaking panoramic views of the serene Tyringham Valley. The park's rich history dates back to the late 18th century when it was part of a 2,000-acre farm owned by a Shaker community. Today, it stands as a testament to conservation efforts, protected by The Trustees since 1963.

Welcome to Appalachian Trail and Guilder Hollow Rd. Trailhead Parking, your convenient starting point for exploring the breathtaking landscapes of the Appalachian Trail in Egremont, Massachusetts. Nestled in the picturesque Berkshire region, our parking facility provides easy access to one of the most cherished hiking trails in the United States. Whether you're planning a day hike or a longer adventure, our location at Egremont, MA 01258, offers a safe and reliable parking solution for outdoor enthusiasts. Enjoy the peace of mind of knowing your vehicle is secure as you embark on your journey through the scenic beauty of the Appalachian Trail. Clean, well-maintained, and easily accessible, our parking area is designed to accommodate the needs of hikers and nature lovers alike. We look forward to serving as the starting point for your memorable outdoor experiences in this stunning natural setting.

Welcome to the Ashuwillticook Rail Trail Parking Area, conveniently located on Farnams Road in the charming town of Cheshire, Massachusetts. Nestled in the heart of the Berkshires, our parking facility serves as the perfect starting point for your outdoor adventure along the scenic Ashuwillticook Rail Trail. Whether you're planning a leisurely stroll, an invigorating bike ride, or a peaceful day of nature observation, our spacious and well-maintained parking area provides easy access to this beautiful multi-use trail. Open year-round, the Ashuwillticook Rail Trail Parking Area offers a safe and accessible spot to leave your vehicle as you explore the stunning landscapes of the Berkshires. We pride ourselves on providing a clean and secure environment for all our visitors, ensuring you have a pleasant experience from the moment you arrive. Come and discover the natural beauty that awaits you, and let the Ashuwillticook Rail Trail Parking Area be your gateway to adventure.

Welcome to Ashuwillticook Rail Trail H.Q., your gateway to outdoor adventure and natural beauty in Cheshire, Massachusetts. Nestled at 1630 Massachusetts 8, our park serves as the perfect starting point for exploring the renowned Ashuwillticook Rail Trail. This scenic trail offers a serene escape for walkers, cyclists, and nature enthusiasts alike, stretching through picturesque landscapes that showcase the best of New England's charm. At Ashuwillticook Rail Trail H.Q., we provide visitors with all the information and amenities needed for a memorable day out. Whether you're looking to embark on a leisurely stroll, a vigorous bike ride, or simply enjoy the tranquility of the surrounding environment, our park is the ideal destination. Our friendly staff is here to assist you with trail maps, local tips, and any questions you might have to ensure a delightful experience.

Welcome to Peck's Falls, a hidden gem nestled in the heart of Adams, Massachusetts. Located in the picturesque Berkshires, our charming establishment offers a perfect blend of natural beauty and local hospitality. Whether you're a nature enthusiast or simply seeking a tranquil escape, Peck's Falls is the ideal destination. Situated at the address Adams, Massachusetts 01220, Peck's Falls provides easy access to breathtaking waterfalls and scenic trails that capture the essence of New England's landscape. Our location is perfect for outdoor adventures, with opportunities for hiking, picnicking, and photography.

Welcome to Fork Factory Brook Reservation, a hidden gem nestled in the heart of Medfield, Massachusetts. Located on Hartford Street, this picturesque park and tourist attraction offers a serene escape into nature's embrace. Managed by The Trustees of Reservations, Fork Factory Brook Reservation is dedicated to preserving the scenic, historic, and ecological treasures of Massachusetts for all to enjoy. Explore the park's winding trails, which meander through lush woodlands and alongside the tranquil brook that gives the reservation its name. With almost 10 miles of family-friendly paths, visitors can immerse themselves in the beauty of diverse landscapes, from dense forests to open fields and charming wetlands. This idyllic setting is perfect for walking, hiking, and nature watching, offering a peaceful retreat from the hustle and bustle of everyday life.

Welcome to Taconic Trail State Park, a breathtaking natural oasis nestled in the picturesque hills of Williamstown, Massachusetts. Located at the heart of the Berkshires, our park offers an idyllic escape for nature enthusiasts, adventure seekers, and families alike. Spanning lush forests, rolling hills, and serene landscapes, Taconic Trail State Park is a haven for outdoor activities and peaceful retreats. Visitors can immerse themselves in the beauty of nature through our extensive network of hiking and biking trails, which provide stunning views and the chance to encounter local wildlife. The park is also an ideal spot for picnicking, birdwatching, and simply unwinding amidst the tranquil surroundings.

The Canalside Rail Trail is a popular park and tourist attraction located at 2 Avenue A in Montague, Massachusetts, United States. This scenic trail follows the path of an old railway line, offering visitors a unique and picturesque way to explore the surrounding area. With lush greenery, peaceful waterways, and charming bridges, the Canalside Rail Trail is the perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking for a leisurely stroll, a bike ride, or a peaceful spot to relax and enjoy the beauty of the outdoors, the Canalside Rail Trail has something for everyone.

Otis Ridge is a charming tourist attraction located at 159 Monterey Road in Otis, Massachusetts, United States. This family-friendly destination offers a variety of outdoor activities for visitors of all ages to enjoy. From skiing and snowboarding in the winter to hiking and biking in the summer, Otis Ridge is the perfect place to experience the beauty of the Berkshires. With stunning views, well-maintained trails, and a welcoming atmosphere, Otis Ridge is a must-visit destination for outdoor enthusiasts and nature lovers alike.

Shaker Trail - Trailhead is a picturesque park located in Pittsfield, Massachusetts, United States. This tranquil institution serves as the starting point for the Shaker Trail, a scenic hiking and biking trail that winds through the beautiful countryside. Visitors can enjoy the natural beauty of the area, explore the historic Shaker sites, and take in the fresh air and peaceful surroundings. Whether you're looking for a leisurely stroll or an adventurous bike ride, Shaker Trail - Trailhead is the perfect place to connect with nature and enjoy the great outdoors.

Jiminy Peak Mountain Adventure Park is a thrilling amusement park located at 37 Corey Road in Hancock, Massachusetts. Nestled in the picturesque Berkshire Mountains, this park offers a wide range of exciting activities for visitors of all ages. From zip lining and mountain coaster rides to rock climbing and aerial adventure courses, there is something for everyone to enjoy at Jiminy Peak. Whether you're seeking a heart-pounding adrenaline rush or a leisurely day in nature, this park is the perfect destination for a fun-filled day out with family and friends.

Welcome to The Boulders Reserve - Dalton Ave Trailhead, a serene and picturesque park located in the heart of Pittsfield, Massachusetts. Nestled on Dalton Avenue, this natural haven offers an escape into the great outdoors, perfect for nature enthusiasts and adventure seekers alike. Explore our extensive network of trails that meander through lush forests and rocky landscapes, providing an ideal setting for hiking, biking, and bird watching. Whether you're looking for a leisurely stroll or a challenging trek, our trails cater to all levels of outdoor enthusiasts.

Jiminy Peak Mountain Resort is a premier destination located at 37 Corey Road in Hancock, Massachusetts, United States. This institution offers a wide range of activities for visitors, including skiing and snowboarding in the winter, as well as hiking, biking, and zip-lining in the summer. With on-site lodging options, dining establishments, and a variety of recreational amenities, Jiminy Peak Mountain Resort is the perfect destination for a family vacation or weekend getaway. Experience the beauty of the Berkshire Mountains while enjoying all that this top-rated tourist attraction has to offer.

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 Kennedy Park, a serene natural retreat located at 18 Evergreen Trail in the picturesque town of Lenox, Massachusetts. Spanning over 500 acres, Kennedy Park offers a perfect escape for nature lovers, outdoor enthusiasts, and families alike. Immerse yourself in the beauty of New England's landscapes as you explore our extensive network of trails, ideal for hiking, mountain biking, and cross-country skiing in the winter months. The park is home to diverse flora and fauna, providing a peaceful sanctuary for wildlife observation and photography. With its well-maintained paths and scenic vistas, Kennedy Park is a favorite destination for both locals and visitors seeking tranquility and adventure in the heart of the Berkshires.

Welcome to North Mount Wilcox Shelter, your premier destination for outdoor adventure and relaxation in the heart of Monterey, Massachusetts. Nestled amidst the picturesque landscapes of the Berkshires, our campground and lodging facilities offer a unique blend of natural beauty and modern comfort. At North Mount Wilcox Shelter, we are dedicated to nurturing a passion for the outdoors through a variety of recreational experiences. Our commitment to safeguarding critical landscapes and supporting sustainable land use ensures that you can enjoy the great outdoors responsibly. We pride ourselves on creating a welcoming environment that expands opportunities for all. Whether you're a seasoned camper or a first-time visitor, our park provides the perfect setting for your outdoor journey. With summer in full swing, take advantage of the warm weather and explore our destinations stretching from Maine to New Jersey.

Welcome to Thunderbolt Lodge Trailhead Parking, your convenient starting point for outdoor adventures in the scenic town of Adams, Massachusetts. Located at the heart of the Berkshires, our parking facility offers easy access to the renowned Thunderbolt Trail and other beautiful hiking routes in the area. Whether you're planning a day hike, a trail run, or a leisurely walk through nature, our spacious and secure parking area ensures a hassle-free experience. With our prime location, you can immerse yourself in the stunning landscapes and rich history of the region. Open year-round, Thunderbolt Lodge Trailhead Parking is the ideal spot for nature enthusiasts and adventurers looking to explore the natural beauty of Adams, MA. We look forward to welcoming you!

Welcome to Hot Point Scenic Overlook, a stunning natural park located in the heart of Clarksburg, Massachusetts. Nestled in the picturesque landscapes of the Berkshires, Hot Point offers visitors breathtaking panoramic views and a serene escape from the hustle and bustle of everyday life. Whether you're a nature enthusiast, an avid hiker, or simply seeking a peaceful retreat, our park provides the perfect backdrop for relaxation and adventure. At Hot Point Scenic Overlook, you'll find well-maintained trails suitable for all skill levels, allowing you to explore the area's rich flora and fauna. Capture the beauty of the changing seasons, enjoy a leisurely picnic with family and friends, or simply unwind as you take in the stunning vistas. Our park is an ideal destination for photography, bird watching, and connecting with nature.

Welcome to Hanging Mountain Parking Lot, your convenient and secure parking solution in Sandisfield, Massachusetts. Nestled in the picturesque surroundings of Berkshire County, our parking facility offers easy access to the beautiful Hanging Mountain area, making it the perfect starting point for outdoor enthusiasts and nature lovers. Located at Sandisfield, MA 01255, Hanging Mountain Parking Lot provides ample parking spaces for vehicles of all sizes, ensuring a hassle-free experience for visitors. Whether you're here for a day of hiking, rock climbing, or simply exploring the natural beauty of the region, our parking lot offers a safe and accessible place to leave your vehicle.

Welcome to the Ashuwillticook Rail Trail Parking Area, conveniently located at 850 Crane Avenue in Pittsfield, Massachusetts. This well-maintained parking facility provides easy access to the picturesque Ashuwillticook Rail Trail, a popular destination for outdoor enthusiasts. Whether you're planning a leisurely walk, a scenic bike ride, or a peaceful jog, our parking area offers a safe and accessible starting point for your adventure. Situated in a serene setting, it is the perfect spot to begin your exploration of the trail's beautiful landscapes. Ample parking spaces are available to accommodate both local visitors and those traveling from afar. Visit us today and enjoy the natural beauty of the Berkshires right from your doorstep.

Welcome to Thunderbolt Lodge, a serene and picturesque park nestled in the heart of Adams, Massachusetts. Located in the scenic Berkshires, Thunderbolt Lodge offers a perfect blend of natural beauty and outdoor adventure for visitors of all ages. Whether you're seeking a peaceful retreat or an exciting day out, our park provides a variety of activities to suit your interests. Explore our well-maintained trails for hiking, biking, and nature walks, where you can immerse yourself in the stunning landscapes and diverse wildlife of the region. For those looking to unwind, enjoy a leisurely picnic in our designated areas, surrounded by the tranquility of nature.

Welcome to the Ashuwillticook Rail Trail Parking Area, your convenient starting point for exploring the scenic Ashuwillticook Rail Trail. Located at the intersection of US 7 and Route 8 Connector Road in Lanesborough, Massachusetts, our parking facility offers easy access to one of the region's most popular recreational trails. Whether you're planning a leisurely walk, a bike ride, or a day of outdoor adventure, our spacious parking area provides a hassle-free experience for all visitors. Enjoy the natural beauty of the Berkshires as you embark on your journey from this well-maintained and strategically located parking spot. Open daily, we look forward to serving as your gateway to the picturesque landscapes and serene environments of the Ashuwillticook Rail Trail.

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 Mount Hope Park, a serene oasis nestled in the heart of Williamstown, Massachusetts. Located at [address], this picturesque park offers a perfect retreat for nature lovers and families alike. Spanning lush green landscapes, Mount Hope Park is an ideal destination for outdoor enthusiasts seeking tranquility and adventure. Explore scenic walking trails that weave through vibrant flora and provide breathtaking views of the surrounding countryside. Whether you're planning a leisurely stroll or an invigorating hike, our well-maintained paths cater to all fitness levels. The park also features picnic areas, perfect for enjoying a meal amidst nature's beauty, and open spaces where children can play freely.

Welcome to Rounds Rock Trailhead, your gateway to nature’s beauty in the heart of Cheshire, Massachusetts. Located at 14-18 Rockwell Road, our park offers a serene escape from the hustle and bustle of everyday life. Nestled amidst the picturesque landscapes of the Berkshires, Rounds Rock Trailhead provides a perfect setting for outdoor enthusiasts and families alike. Explore our well-maintained trails that wind through lush forests and offer breathtaking views of the surrounding hills. Whether you're an avid hiker, a casual walker, or simply looking to enjoy a peaceful picnic, our park caters to all. Discover native wildlife, vibrant flora, and the tranquil sounds of nature as you journey through our scenic paths.

Welcome to Pittsfield State Forest, a breathtaking natural haven located at 123-221 Potter Mountain Road, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and adventure seekers alike. Spanning over 11,000 acres, Pittsfield State Forest is home to lush woodlands, sparkling streams, and stunning vistas that promise to captivate visitors of all ages. Explore a myriad of recreational activities, including hiking, mountain biking, and horseback riding along our extensive trail network. During the warmer months, enjoy picnicking, camping, and fishing in the tranquil setting of Berry Pond, the highest natural body of water in the state. In the winter, embrace the snowy landscape with opportunities for cross-country skiing and snowmobiling.

Welcome to Long Trail Southern Terminus, a picturesque park located at the Appalachian National Scenic Trail in Clarksburg, Massachusetts. Nestled in the heart of nature, our park serves as the gateway to the renowned Long Trail, offering breathtaking views and a serene environment for outdoor enthusiasts. Whether you're an avid hiker ready to embark on a long-distance trek or someone seeking a peaceful day in nature, our park provides the perfect starting point. Enjoy well-maintained trails, diverse wildlife, and the tranquility of the great outdoors. Visit us to experience the beauty of New England's natural landscapes and create unforgettable memories.