TOP 30 Best outdoor 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 the Appalachian Trail at Mt Wilcox Rd, a breathtaking park located in the heart of Monterey, Massachusetts. As part of the iconic Appalachian National Scenic Trail, we have been dedicated to the management and conservation of this treasured path since 1925. Our commitment to preserving the natural beauty and unique views, such as the renowned McAfee Knob, ensures that visitors can continue to experience the majesty of the Appalachian Trail for generations to come. By becoming a member, you not only support our conservation efforts but also enjoy 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®. Members also receive special volunteer opportunities and invitations to exclusive events.

Welcome to The Ledge on the Appalachian Trail Nestled within the breathtaking vistas of the Appalachian National Scenic Trail in Monterey, Massachusetts, The Ledge is more than just a park—it's a gateway to adventure, conservation, and community. Since 1925, we have been dedicated to overseeing the management and preservation of this iconic trail, ensuring its beauty and accessibility for generations to come.

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 Diane's Trail Trailhead, your gateway to the serene beauty of nature in the heart of the Berkshires. Nestled in the charming community of Monterey, Massachusetts, our park offers a tranquil escape for outdoor enthusiasts and nature lovers alike. Whether you're an avid hiker, a casual walker, or simply seeking a peaceful retreat, Diane's Trail Trailhead provides an ideal setting to explore the great outdoors. Our well-maintained trails meander through lush forests, alongside babbling brooks, and offer breathtaking views of the surrounding landscape. With trails suitable for all skill levels, everyone from beginners to seasoned hikers can find a path that suits their pace and preferences. Along the way, you'll have the opportunity to observe local wildlife and enjoy the natural beauty that defines this picturesque region.

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 Mohawk Trail Multi-Use Path - Western End, a scenic gem nestled in the charming town of Williamstown, Massachusetts. This delightful park offers a perfect escape for nature enthusiasts, fitness aficionados, and families looking for a peaceful retreat. Located in the picturesque Berkshire region, the trail provides a serene setting for walking, jogging, cycling, and more. Stretching through lush landscapes, the path invites you to explore the natural beauty of the area while enjoying the fresh air and stunning views. Whether you're seeking a leisurely stroll, an invigorating bike ride, or a quiet place to relax and unwind, the Mohawk Trail Multi-Use Path caters to all. The well-maintained path ensures a safe and enjoyable experience for visitors of all ages and abilities.

Welcome to Parking for Clark Trails, your gateway to exploring the natural beauty of Williamstown, Massachusetts. Conveniently located at the heart of the Berkshires, our parking facility offers easy access to the scenic Clark Trails, open for public enjoyment year-round. Whether you're an avid hiker, a nature enthusiast, or simply looking for a peaceful retreat, our park provides the perfect starting point for your outdoor adventures. With ample parking space and well-maintained paths, you can immerse yourself in the tranquility of lush forests, vibrant wildlife, and breathtaking vistas. Visit us at Williamstown, MA 01267 and embark on a memorable journey through nature's splendor.

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 Red Appalachian Trail Stand, your gateway to nature's serenity located in the heart of Sandisfield, Massachusetts. Nestled at 25 Jerusalem Road, our park offers a tranquil escape for outdoor enthusiasts and families alike. Immerse yourself in the breathtaking beauty of the Appalachian landscape as you explore our well-maintained trails and scenic vistas. Whether you're an avid hiker or simply looking for a peaceful spot to relax and unwind, Red Appalachian Trail Stand provides a perfect blend of adventure and tranquility. Our park is a haven for wildlife watchers, photographers, and anyone seeking a rejuvenating experience in nature. Visit us today and discover the charm of New England's great outdoors.

Welcome to Lower Linear Park Bike Trail Parking, your gateway to exploring the scenic beauty of Williamstown, Massachusetts. Nestled in the heart of the Berkshires, our park offers a convenient and accessible starting point for cyclists and outdoor enthusiasts eager to experience the stunning landscapes of the region. Whether you're a seasoned biker or a leisurely rider, our well-maintained trails promise a delightful journey through lush greenery and picturesque surroundings. Located at Williamstown, MA 01267, our park provides ample parking spaces, ensuring a hassle-free start to your adventure. The trails are designed to accommodate various skill levels, making it an ideal destination for families, groups, and solo explorers alike. In addition to biking, visitors can enjoy walking, jogging, and picnicking amidst the serene natural setting.

Welcome to the Hoosic River Nature Trail, a serene oasis nestled in the heart of Williamstown, Massachusetts. Located at the picturesque address of Williamstown, MA 01267, our park is a haven for nature enthusiasts, families, and outdoor adventurers alike. Explore the tranquil beauty of the Hoosic River as you wander along our well-maintained trails, surrounded by lush greenery and the soothing sounds of nature. Whether you're an avid hiker, a birdwatcher, or simply looking for a peaceful retreat, the Hoosic River Nature Trail offers something for everyone.

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 the Mohawk Trail Multi-use Path: Eastern Trailhead, a scenic park located in the picturesque town of Williamstown, Massachusetts. Nestled in the heart of nature, this trailhead serves as the perfect starting point for exploring the breathtaking beauty of the Mohawk Trail. Whether you're a hiker, cyclist, or a nature enthusiast, this multi-use path offers a serene escape into the great outdoors. Our trailhead provides easy access to well-maintained paths that wind through lush forests, offering stunning views of the surrounding landscape. As you journey along the trail, you'll encounter diverse wildlife, vibrant wildflowers, and the soothing sounds of nature. Perfect for families, solo adventurers, and groups, the trail is designed to accommodate varying skill levels and preferences.

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 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 the Appalachian Trail at Goose Pond Road, a serene gateway to the iconic Appalachian National Scenic Trail, located in the picturesque town of Lee, Massachusetts. Since 1925, our mission has been to oversee the management and conservation of this remarkable trail, ensuring its beauty and accessibility for generations to come. As a proud steward of the Appalachian Trail, we are committed to preserving its natural splendor and safeguarding beloved vistas, such as the renowned McAfee Knob Viewshed. Our efforts are supported by passionate members and generous donors who share our vision of protecting this national treasure.

Welcome to the Appalachian Trail at Webster Road, nestled within the picturesque Appalachian National Scenic Trail in Tyringham, Massachusetts. Since 1925, we have been dedicated to the management and conservation of this iconic trail, ensuring its natural beauty and accessibility for generations to come. Our commitment to preserving the Appalachian Trail is evident through our efforts, such as securing protection for the breathtaking McAfee Knob viewshed. As a valued member, you'll enjoy exclusive benefits including an oversized Appalachian Trail strip map, a subscription to our informative magazine, A.T. Journeys, and discounts at the Ultimate A.T. Store®. You'll also receive invitations to special events and have access to unique volunteer opportunities.

Welcome to the Appalachian Trail at MA Rt 8 North St, a serene and picturesque park located in the heart of Cheshire, Massachusetts. Nestled at 290-334 North Street, this beautiful stretch of the iconic Appalachian Trail offers nature enthusiasts, hikers, and outdoor lovers a perfect escape into the tranquility of the great outdoors. Explore miles of well-maintained trails that wind through lush forests, rolling hills, and breathtaking landscapes. Whether you're an experienced hiker seeking a challenging adventure or a family looking for a peaceful day in nature, the Appalachian Trail at MA Rt 8 North St caters to all levels of experience and interest.

Welcome to Appalachian Trail at Outlook Ave, a serene and picturesque park nestled in the charming town of Cheshire, Massachusetts. Located at the heart of the Berkshires, our park offers visitors a unique opportunity to immerse themselves in the natural beauty of the Appalachian Trail. Whether you're an avid hiker, a nature enthusiast, or simply seeking a peaceful retreat, Appalachian Trail at Outlook Ave provides a perfect escape into the great outdoors. Explore miles of scenic trails that wind through lush forests, offering breathtaking vistas and a chance to connect with nature. Our well-maintained paths are suitable for hikers of all levels, ensuring a safe and enjoyable experience for everyone. Discover the tranquility of the wilderness, observe local wildlife, and enjoy the fresh mountain air. Whether you're planning a day trip or a longer adventure, Appalachian Trail at Outlook Ave is your gateway to the stunning landscapes of the Appalachian region. Visit us and experience the natural splendor that makes this park a cherished local treasure.

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.