The 30 Best Berkshires hiking trails in Massachusetts

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 Berkshire Mobile Home Park, your serene getaway nestled in the heart of the picturesque Berkshires. Conveniently located at 413 Pittsfield Road in Lenox, Massachusetts, our park offers a peaceful retreat for those seeking a unique lodging experience. Whether you're visiting for a weekend escape or an extended stay, you'll find comfort and convenience in our well-maintained facilities. Berkshire Mobile Home Park is not just an RV park; it's a community. We offer spacious lots with full hookups, ensuring you have everything you need for a comfortable stay. Our park is surrounded by the natural beauty of the Berkshires, providing a perfect backdrop for outdoor enthusiasts and nature lovers. Explore nearby hiking trails, enjoy the vibrant local culture, or simply relax and take in the tranquil surroundings.

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.

Welcome to Phelps Trail - Parking, your convenient and reliable parking solution located at 1331 Oblong Road in the picturesque town of Williamstown, Massachusetts. Nestled amidst the scenic beauty of the Berkshires, our parking facility provides easy access to the renowned Phelps Trail, a favorite among hikers and nature enthusiasts. Whether you're planning a day hike or an extended adventure, our secure and spacious parking area ensures peace of mind while you explore the stunning natural surroundings. We offer ample parking spaces suitable for both cars and larger vehicles, and our friendly staff is always ready to assist you with any questions or needs. At Phelps Trail - Parking, we are committed to providing you with a hassle-free start to your outdoor experience. Visit us today and embark on your journey with confidence.

Welcome to the Berkshire Natural Resources Council, a premier tourist attraction nestled in the heart of the Berkshires at 309 Pittsfield Road, Lenox, Massachusetts. Our mission is to preserve and protect the natural beauty and ecological integrity of the Berkshire region, offering visitors a unique opportunity to connect with nature. Explore our extensive network of scenic trails, perfect for hiking, birdwatching, and immersing yourself in the tranquility of the great outdoors. Whether you're a local resident or a visitor seeking adventure, our diverse landscapes of forests, meadows, and wetlands promise breathtaking views and unforgettable experiences.

Welcome to the Appalachian Trail at Beartown Mountain Road, a serene and picturesque park located in the charming town of Monterey, Massachusetts. Nestled within the heart of the Berkshire Hills, this section of the iconic Appalachian Trail offers nature enthusiasts, hikers, and outdoor adventurers an unforgettable experience amidst the stunning landscapes of New England. Explore miles of well-maintained trails that wind through lush forests, tranquil streams, and breathtaking vistas. Whether you are a seasoned hiker seeking a challenging trek or a family looking for a leisurely walk in nature, the diverse terrain caters to all skill levels and promises a rewarding journey for everyone.

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 the General Henry Knox Cannon Trail Marker, a historic landmark nestled in the charming town of Monterey, Massachusetts. Situated in the heart of the Berkshires, this site commemorates the remarkable journey of General Henry Knox during the American Revolutionary War. As you visit this marker, you'll step back in time to January 1776, when Knox transported 59 cannons over 300 miles from Fort Ticonderoga to Boston, a feat that played a pivotal role in the American victory at the Siege of Boston. The trail marker serves as a tribute to this extraordinary logistical achievement and offers visitors a glimpse into the challenges and triumphs of 18th-century military strategy. Surrounded by the natural beauty of Monterey, it's an ideal spot for history enthusiasts, families, and anyone interested in the rich tapestry of America's past.

Welcome to the Appalachian Trail at Housatonic St, a serene park located at 470-494 West Housatonic Street in the picturesque town of Dalton, Massachusetts. Nestled amidst the natural beauty of the Berkshires, this section of the iconic Appalachian Trail offers a peaceful retreat for nature enthusiasts, hikers, and families alike. Explore miles of well-maintained trails that wind through lush forests, open meadows, and along the tranquil Housatonic River. Whether you're embarking on a challenging hike or enjoying a leisurely stroll, the park provides breathtaking vistas and a chance to reconnect with nature. This location is perfect for spotting local wildlife, capturing stunning photographs, or simply unwinding in a serene environment.

Welcome to Jacob's Ladder Scenic Byway and Appalachian Trail Parking Area, your gateway to the breathtaking beauty of the Berkshires in Lee, Massachusetts. Conveniently located at the heart of the picturesque Jacob's Ladder Scenic Byway, our parking area offers easy access to one of the most celebrated sections of the Appalachian Trail. Whether you're an avid hiker, a nature enthusiast, or simply seeking a peaceful retreat, our facility provides the perfect starting point for your outdoor adventures. Our spacious and well-maintained parking area ensures a hassle-free experience, allowing you to focus on exploring the stunning landscapes that surround you. From towering forests to serene mountain views, this region offers a unique blend of natural wonder and tranquility. Enjoy a day hike along the Appalachian Trail, immerse yourself in the vibrant fall foliage, or capture the serene beauty of a winter wonderland.

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.

Welcome to Appalachian Trail Parking, your convenient and reliable parking solution located on State Road in the picturesque town of North Adams, Massachusetts. Nestled in the heart of the Berkshires, our facility offers easy access to the renowned Appalachian Trail, making it the perfect starting point for your hiking adventure. Whether you're setting out for a day hike or embarking on a longer journey, Appalachian Trail Parking provides a safe and secure place to leave your vehicle. Our spacious parking area is designed to accommodate all types of vehicles, from compact cars to larger SUVs, ensuring peace of mind while you explore the natural beauty of the region.

Welcome to the Appalachian Trail at Fisk Street, a serene and picturesque park located in the charming town of Cheshire, Massachusetts. Nestled in the heart of the Berkshires, this section of the iconic Appalachian Trail offers visitors a unique opportunity to experience the natural beauty of the region. Whether you're an avid hiker or simply looking for a peaceful retreat, our park provides a perfect escape into nature. Explore miles of well-maintained trails that wind through lush forests, offering breathtaking views and a chance to encounter local wildlife. The park is an ideal destination for outdoor enthusiasts, families, and anyone seeking tranquility in a beautiful setting. Enjoy a leisurely walk, a challenging hike, or a relaxing picnic amidst the stunning landscapes.

Welcome to the Appalachian Trail at West Branch Road, a serene escape nestled in the heart of Washington, Massachusetts. This picturesque park offers nature enthusiasts and outdoor adventurers a unique opportunity to experience the beauty of the Appalachian Trail within the scenic landscapes of the Berkshires. Located at West Branch Road, our park serves as a perfect starting point for both short hikes and extended journeys along the famed trail. Immerse yourself in the lush greenery, diverse wildlife, and breathtaking vistas that the trail has to offer. Whether you're a seasoned hiker or a casual walker, the Appalachian Trail at West Branch Road provides an accessible and enriching outdoor experience for all. Come visit us and discover the tranquility and natural beauty that await you in this exceptional part of Massachusetts.

Welcome to the Appalachian Trail at Becket Rd, MA, a serene and picturesque park located at 64 Becket Road, Becket, Massachusetts. Nestled in the heart of the Berkshires, this section of the iconic Appalachian Trail offers nature enthusiasts and hikers a unique opportunity to explore the breathtaking landscapes and rich biodiversity of the region. Whether you are an avid hiker looking for a challenging trek or someone seeking a peaceful escape into nature, our park provides a perfect setting for outdoor adventures and relaxation. Visitors can immerse themselves in the tranquil beauty of lush forests, rolling hills, and scenic vistas that characterize this part of the Appalachian Trail. With well-maintained trails suitable for various skill levels, the park invites you to experience the natural wonders and enjoy activities such as hiking, birdwatching, and photography.

Welcome to Cascade Trail - Trailhead, your gateway to nature's splendor nestled in the heart of North Adams, Massachusetts. Located at 180 Marion Avenue, our serene park offers a perfect escape for outdoor enthusiasts and families alike. Immerse yourself in the picturesque landscapes as you explore well-maintained trails that wind through lush forests, alongside tranquil streams, and lead to breathtaking views. Whether you're looking for a leisurely stroll or an invigorating hike, Cascade Trail provides an ideal setting for all skill levels. Our park is open year-round, inviting you to witness the changing seasons and the unique beauty each brings. Discover a haven of peace and adventure at Cascade Trail - Trailhead, where nature meets community in the picturesque Berkshires.

Welcome to Ashuwillticook Trail Actual Endpoint, a serene and picturesque park located at 65 Print Works Drive in Adams, Massachusetts. Nestled in the heart of the Berkshires, our park serves as the official endpoint of the renowned Ashuwillticook Rail Trail. This beautiful destination offers visitors a peaceful retreat surrounded by nature's splendor. Whether you're an avid cyclist, a leisurely walker, or a nature enthusiast, our well-maintained trails and lush landscapes provide the perfect setting for outdoor activities and relaxation. Enjoy a day of exploration, take in the stunning views, and discover the natural beauty of this charming region. Visit us today and experience the tranquility and charm of Ashuwillticook Trail Actual Endpoint, where your outdoor adventure begins.

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 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.

Welcome to Berkshire Lake Camp, your serene getaway nestled in the heart of the Berkshires at 822 Peru Road, Hinsdale, Massachusetts. Our picturesque camp offers a tranquil escape from the hustle and bustle of everyday life, perfect for families, friends, and solo adventurers seeking a connection with nature. At Berkshire Lake Camp, you'll find a harmonious blend of rustic charm and modern amenities. Our spacious grounds provide ample opportunities for outdoor activities, including hiking, fishing, and kayaking, ensuring there's something for everyone. Enjoy a peaceful afternoon by the lake or explore the nearby trails that showcase the stunning beauty of the Berkshires.

Welcome to Esau's Heel Trail, a serene and picturesque park nestled in the heart of Becket, Massachusetts. Located at 3 Jacobs Ladder Road, our park offers a tranquil escape from the hustle and bustle of everyday life. Surrounded by the natural beauty of the Berkshires, Esau's Heel Trail invites visitors to explore its lush landscapes and scenic trails. Whether you're an avid hiker, a nature enthusiast, or simply looking for a peaceful retreat, Esau's Heel Trail has something for everyone. Our well-maintained paths meander through diverse ecosystems, offering breathtaking views and the chance to encounter local wildlife. Perfect for a family outing, a solo adventure, or a leisurely walk with friends, the park provides an ideal setting for relaxation and rejuvenation.

Welcome to Appalachian Trail Jerusalem Rd Trailhead Parking, conveniently located in the picturesque town of Lee, Massachusetts. Nestled in the heart of the Berkshires, our parking facility offers easy access to one of the most scenic sections of the renowned Appalachian Trail. Whether you're embarking on a day hike or a longer trek, our parking area provides a safe and reliable spot to leave your vehicle while you explore the natural beauty of the region. Open year-round, our facility is designed to accommodate hikers and outdoor enthusiasts looking to experience the tranquility and adventure of the trail. Enjoy the peace of mind knowing your vehicle is securely parked as you immerse yourself in the breathtaking landscapes and diverse wildlife of the Appalachian Trail. Visit us at Jerusalem Rd Trailhead Parking and start your journey into the great outdoors today!

Welcome to Appalachian Trail - Goose Pond Road Trailhead Parking, conveniently located in the scenic town of Lee, Massachusetts. Nestled in the heart of the Berkshires, our parking facility serves as the perfect starting point for your Appalachian Trail adventures. Whether you're a seasoned hiker or a nature enthusiast seeking a tranquil escape, our trailhead parking provides easy access to one of the most beautiful and renowned hiking trails in the United States. Our facility is designed to accommodate both short-term and long-term parking needs, ensuring that your vehicle is safely parked while you explore the breathtaking landscapes and diverse wildlife of the Appalachian Trail. With ample space and a well-maintained lot, you can embark on your journey with peace of mind.

Welcome to Appalachian Trail-Webster Road Trailhead Parking, your convenient and reliable parking solution located in the scenic town of Tyringham, Massachusetts. Nestled in the heart of the beautiful Berkshires, our parking facility offers easy access to the renowned Appalachian Trail, making it the perfect starting point for hikers, nature enthusiasts, and outdoor adventurers. Our well-maintained parking area provides ample space for vehicles, ensuring a hassle-free experience as you embark on your journey through some of the most picturesque landscapes in the United States. Whether you're planning a day hike or a longer trek along the trail, our location offers the ideal base for your adventures.

Welcome to the Ashuwillticook Rail Trail Parking Area, conveniently located on Railroad Street in the charming town of Cheshire, Massachusetts. Our parking facility offers easy access to the picturesque Ashuwillticook Rail Trail, a popular destination for outdoor enthusiasts seeking a scenic and serene escape. Whether you're planning a leisurely walk, a refreshing bike ride, or a peaceful afternoon surrounded by nature, our parking area provides a safe and accessible starting point for your adventure. We pride ourselves on maintaining a clean and secure environment for all visitors. Open year-round, our parking area is the perfect gateway to exploring the beauty of the Berkshires. We invite you to park with us and embark on a memorable journey along this beloved rail trail.

Welcome to Mohawk Trail Sightseeing Parking, your gateway to the breathtaking beauty of the Mohawk Trail in Savoy, Massachusetts. Nestled in the heart of the Berkshires, our convenient parking facility offers easy access to one of the most scenic drives in New England. Whether you're here to explore the vibrant fall foliage, take in the panoramic mountain vistas, or discover the rich history of the area, our location provides the perfect starting point for your adventure. Our spacious and secure parking lot is designed to accommodate vehicles of all sizes, ensuring a hassle-free experience for both locals and visitors. From here, you can embark on a variety of outdoor activities, including hiking, photography, and picnicking, or simply enjoy a leisurely drive along the trail. We are committed to making your visit enjoyable and memorable, providing helpful information and tips to enhance your experience.

Welcome to H. Newman Marsh Trail, a serene and picturesque park located on Sanderson Brook Road in Blandford, Massachusetts. Nestled in the heart of the scenic Berkshires, our park offers a tranquil escape into nature, perfect for outdoor enthusiasts and families alike. Explore well-maintained trails that wind through lush woodlands and alongside bubbling brooks, providing an ideal setting for hiking, bird watching, and photography. With its rich diversity of flora and fauna, H. Newman Marsh Trail invites visitors to reconnect with nature and enjoy the peaceful beauty of the outdoors. Whether you're seeking a leisurely walk or an adventurous trek, our park is a haven for relaxation and exploration. Visit us today and experience the natural charm of Blandford.

Welcome to New Eatonville Berkshire Spa and Resort, your serene escape nestled in the picturesque town of Lanesborough, Massachusetts. Located at A Street, our resort offers a perfect blend of luxury and tranquility, making it an ideal destination for relaxation and rejuvenation. At New Eatonville Berkshire Spa and Resort, we pride ourselves on providing exceptional lodging experiences that cater to your every need. Our elegantly designed rooms and suites offer breathtaking views of the stunning Berkshire landscape, ensuring a peaceful retreat from the hustle and bustle of everyday life.

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.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 251 Broadway, Methuen, Massachusetts. As a premier real estate agency, we offer a comprehensive range of services tailored to both buyers and sellers. With a legacy of excellence since 1967, our decades of experience ensure a successful and satisfying real estate journey for every client. Our team of seasoned professionals is committed to providing expert guidance, whether you're searching for your dream home or planning a strategic sale. We understand the unique demands of the real estate market and are dedicated to integrity, professionalism, and innovation in every transaction.