The 30 Best Hiking trails in Massachusetts

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 Stevens Glen Trail Head, a serene and picturesque park located in the heart of the Berkshires at Lenox Road, West Stockbridge, Massachusetts. Nestled in the lush greenery of Richmond, MA, our park offers a tranquil escape for nature lovers and outdoor enthusiasts. Stevens Glen Trail Head is renowned for its breathtaking landscapes, featuring well-maintained trails that wind through dense forests, alongside babbling brooks, and past stunning waterfalls. Whether you're a seasoned hiker or just looking for a peaceful walk in nature, our trails cater to all skill levels, providing a perfect opportunity to reconnect with the great outdoors.

Welcome to Brothers Trail, your serene escape nestled in the heart of the Berkshires on Richmond Mountain Road, Lenox, Massachusetts. As a cherished local park, Brothers Trail offers visitors a peaceful retreat into nature's embrace, perfect for outdoor enthusiasts and families alike. Explore our well-maintained trails that wind through lush forests and offer stunning views of the surrounding landscapes. Whether you're hiking, birdwatching, or simply enjoying a leisurely stroll, Brothers Trail provides a rejuvenating experience for all ages. Join us year-round to witness the breathtaking beauty of each season, from vibrant fall foliage to tranquil winter snowscapes. Discover the natural charm of Brothers Trail and make unforgettable memories in this picturesque setting. Visit us today and experience the tranquility and beauty that Lenox has to offer.

Welcome to Burbank Trail Trailhead, your gateway to nature's serenity nestled in the picturesque landscapes of Richmond, Massachusetts. Located on Richmond Mountain Road, our park offers a tranquil escape for outdoor enthusiasts and families alike. Immerse yourself in the lush greenery and scenic vistas that define this beautiful region. Whether you're an avid hiker, a casual walker, or simply looking to enjoy a peaceful day in nature, Burbank Trail Trailhead provides a variety of trails suited for all skill levels. Explore winding paths through dense forests, discover hidden streams, and enjoy breathtaking views from elevated points. Our well-maintained trails ensure a safe and enjoyable experience for everyone.

Welcome to Farm & Forest Trail, a serene and picturesque park located in the heart of Hancock, Massachusetts. Nestled in the scenic landscapes of the Berkshires, our park offers a unique blend of natural beauty and outdoor adventure, perfect for visitors of all ages. Explore our well-maintained trails that wind through lush forests, open meadows, and charming farm landscapes, providing a tranquil escape from the hustle and bustle of everyday life. Whether you're an avid hiker, a nature enthusiast, or simply looking for a peaceful place to relax, Farm & Forest Trail has something for everyone. Enjoy a leisurely stroll, embark on a challenging hike, or have a picnic surrounded by the breathtaking beauty of New England's countryside. Our park is also home to diverse wildlife, making it an ideal spot for birdwatching and photography.

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 Pete's Hiking and Tea, a serene escape nestled in the heart of Lenox, Massachusetts. Located at 71 Church Street, our unique park offers a perfect blend of nature and relaxation. Whether you are a seasoned hiker or simply looking for a peaceful retreat, our scenic trails cater to all levels of adventure enthusiasts. After your invigorating hike, unwind with a soothing cup of tea in our tranquil garden setting. Our selection of teas is carefully curated to complement the serene ambiance, providing a refreshing experience for both mind and body. Visit Pete's Hiking and Tea for a rejuvenating day amidst nature's beauty, right here in Lenox.

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 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 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 Fitch Trail Parking, your gateway to the natural beauty of Williamstown, Massachusetts! Conveniently located at 261 Bee Hill Road, our parking facility offers easy access to the picturesque Fitch Trail, a perfect destination for outdoor enthusiasts and nature lovers. Whether you're planning a leisurely hike, a trail run, or simply a peaceful walk amidst the serene surroundings, Fitch Trail Parking provides a safe and accessible starting point for your adventure. Our well-maintained parking area ensures that you can focus on enjoying the stunning landscapes and diverse wildlife that the trail has to offer. Visit us today and embark on a memorable journey through the heart of nature in Williamstown.

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 Appalachian Trail at Jerusalem Rd, a treasured segment of the iconic Appalachian National Scenic Trail, located in the picturesque town of Lee, Massachusetts. Since 1925, we have been dedicated to the management and conservation of this historic trail, ensuring its beauty and accessibility for generations to come. As a valued visitor or member, you play a crucial role in our mission to protect and preserve the trail. By joining our community, you gain access to exclusive benefits, including an oversized Appalachian Trail strip map, a subscription to our engaging membership magazine, A.T. Journeys, and discounts at the Ultimate A.T. Store®. Additionally, members receive invitations to special events and unique volunteer opportunities, allowing you to connect with fellow trail enthusiasts and contribute to the trail's upkeep.

Welcome to the Appalachian Trail at Tyringham Cobble Path, a picturesque park nestled in the heart of Lee, Massachusetts. Located at Tyringham Cobble Path, this serene destination offers visitors a unique opportunity to immerse themselves in the natural beauty of the Appalachian Trail. Whether you're an avid hiker or simply looking for a peaceful retreat, our park provides a stunning backdrop of rolling hills, diverse wildlife, and breathtaking vistas. Explore miles of well-maintained trails that cater to all skill levels, from leisurely walks to more challenging hikes. The Tyringham Cobble, a prominent geological feature, offers a spectacular vantage point to view the surrounding landscape. Along the way, enjoy the tranquility of lush forests, open meadows, and babbling brooks.

Welcome to the Appalachian Trail at Jerusalem Rd, nestled in the picturesque town of Tyringham, Massachusetts. As a vital part of the Appalachian National Scenic Trail, we have been dedicated to the management and conservation of this iconic trail since 1925. Our mission is to protect, manage, and advocate for the Appalachian Trail, ensuring its beauty and accessibility for generations to come. Visitors can enjoy the breathtaking views from the popular McAfee Knob, a highlight of our protected viewshed. As a member, you’ll receive an oversized Appalachian Trail strip map, a subscription to our membership magazine, A.T. Journeys, exclusive discounts at the Ultimate A.T. Store®, and invitations to special events.

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 National Scenic Trail Trailhead Parking in Williamstown, Massachusetts. Conveniently located at the gateway to the Appalachian National Scenic Trail, our parking facility offers easy access for hikers and nature enthusiasts eager to explore the stunning landscapes of the Appalachian region. Since 1925, we have been dedicated to overseeing the management and conservation of this iconic trail. Our mission, led by the Appalachian Trail Conservancy, is to protect, manage, and advocate for the trail, ensuring its beauty and accessibility for generations to come. Our efforts have secured protection for popular viewsheds, including the renowned McAfee Knob.

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 Upper Goose Pond Trail/AT Parking, a serene gateway to the majestic Appalachian National Scenic Trail, located at 2120 Cape Street, Lee, Massachusetts. Established in 1925, our park is dedicated to the management and conservation of this iconic trail, ensuring its beauty and accessibility for generations to come. Visitors to Upper Goose Pond Trail can enjoy breathtaking views and explore the natural wonders of the trail, including the protected viewshed of the renowned McAfee Knob. As a member, you'll receive exclusive benefits, such as an oversized Appalachian Trail strip map, a subscription to our insightful membership magazine, A.T. Journeys, and discounts at the Ultimate A.T. Store®. Members are also invited to participate in special volunteer opportunities and exclusive events that celebrate our shared love for the trail.

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 the Appalachian Trail at the MA/VT State Line, a scenic park nestled in the heart of Clarksburg, Massachusetts. This picturesque location offers outdoor enthusiasts a perfect gateway to explore the natural beauty of the Appalachian Trail. Whether you're an avid hiker or a nature lover seeking tranquility, this park provides a serene escape with its lush landscapes and breathtaking vistas. Located at the Massachusetts-Vermont border, visitors can enjoy a unique experience as they traverse the diverse terrains of two states. The park is ideal for day hikes, picnics, and wildlife observation, offering a refreshing retreat for individuals and families alike. Come and discover the enchanting allure of the Appalachian Trail at this iconic state line crossing, where adventure and nature unite.

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.

Appalachian Trail Parking at Blotz Rd. - Washington, MA Welcome to the Appalachian Trail Parking at Blotz Road, conveniently located at 57-1 Blotz Road, Washington, Massachusetts 01223. Our parking facility serves as a gateway to the majestic Appalachian National Scenic Trail, a cherished natural treasure overseen by the Appalachian Trail Conservancy since 1925.

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.