TOP 10 Berkshire region hiking trailhead in Massachusetts

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.

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 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 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 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 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 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 Bascom Lodge Trailhead Parking, your convenient gateway to exploring the natural beauty of Adams, Massachusetts. Located at the base of the iconic Mount Greylock, our parking facility offers easy access for hikers, nature enthusiasts, and visitors eager to immerse themselves in the stunning landscapes of the Berkshires. Whether you're planning a day hike to the summit, capturing breathtaking views, or simply enjoying a leisurely walk through the trails, Bascom Lodge Trailhead Parking provides a safe and accessible starting point for your adventure. Our well-maintained parking area is designed to accommodate vehicles of all sizes, ensuring a hassle-free experience for solo travelers, families, and groups alike.

Welcome to Dayville Trailhead, your gateway to outdoor adventure in the heart of Chester, Massachusetts. Nestled in the scenic landscapes of the Berkshires, our park offers nature enthusiasts a perfect escape into the tranquility of the great outdoors. Whether you're an avid hiker, a casual walker, or simply looking to enjoy a peaceful picnic, Dayville Trailhead provides the ideal setting for all your recreational needs. Explore our well-maintained trails that wind through lush forests, offering breathtaking views and the chance to observe local wildlife in their natural habitat. Our park is designed to cater to all skill levels, ensuring a safe and enjoyable experience for families, solo adventurers, and groups alike.

Welcome to the Chester Becket Railroad Trailhead, a captivating park located in the picturesque town of Chester, Massachusetts. Nestled in the heart of the Berkshires, this trail offers a unique journey through history and nature. Hike along the historic Chester Becket Railroad, once a bustling route where granite from the Becket Quarry was transported to meet the Boston Albany Railroad. As you traverse the trail, you'll be treated to stunning views of the old railroad from the mountain ledge visible from Route 20, especially when traveling west through Chester and Becket. For those eager to explore, start your adventure on Hampden Street in Chester, where you'll find a convenient kiosk and official parking area. This section of the trail, currently owned by the Becket Land Trust, invites visitors to step back in time and experience the rich heritage of the region. Whether you're a history enthusiast, nature lover, or avid hiker, the Chester Becket Railroad Trailhead offers an unforgettable experience.

Welcome to Negus Mountain Trailhead, your gateway to nature's beauty in Charlemont, Massachusetts. Nestled along Zoar Road, our park offers an idyllic escape for outdoor enthusiasts and nature lovers alike. Immerse yourself in the stunning landscapes of the Berkshires as you explore our well-maintained trails, perfect for hiking, birdwatching, and photography. Whether you're seeking a peaceful walk through serene woodlands or an invigorating climb to breathtaking vistas, Negus Mountain Trailhead provides a variety of paths to suit all skill levels. Enjoy the tranquility of the natural surroundings, spot local wildlife, and breathe in the fresh mountain air. Conveniently located in the heart of the region, our park is a must-visit destination for anyone looking to experience the pristine beauty of Massachusetts. Plan your visit today and discover the wonders of Negus Mountain Trailhead.

Welcome to Mitchell Woods Trailhead, a serene escape nestled in the heart of Needham, Massachusetts. Located at Needham, MA 02494, our park offers a perfect blend of natural beauty and tranquility, making it an ideal destination for nature lovers and outdoor enthusiasts. Whether you're looking for a peaceful walk, a vigorous hike, or a scenic spot to unwind, Mitchell Woods Trailhead has something for everyone. Explore our well-maintained trails that wind through lush woodlands, offering stunning views and opportunities to observe local wildlife. Perfect for families, solo adventurers, and groups, our trails cater to all skill levels. Enjoy a leisurely stroll or challenge yourself with a more intense hike, all while breathing in the fresh Massachusetts air.

Welcome to Guilder Pond Parking Area, your convenient and accessible parking solution nestled in the picturesque surroundings of Mount Washington, Massachusetts. Located at the heart of the Berkshires, our parking area serves as the perfect gateway for visitors looking to explore the natural beauty and outdoor adventures the region has to offer. Whether you're here for a day hike, a scenic picnic, or an overnight camping trip, Guilder Pond Parking Area provides a safe and affordable place to park your vehicle. Our spacious lot is designed to accommodate a range of vehicles, ensuring that you have a hassle-free start to your journey.

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 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 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 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 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 the Farmington River Wildlife Management Area Parking, conveniently located in the scenic town of Otis, Massachusetts. Nestled in the heart of the Berkshires, our parking area offers easy access to the stunning natural beauty of the Farmington River Wildlife Management Area. Whether you're here for a day of hiking, fishing, birdwatching, or simply enjoying the great outdoors, our facility provides a safe and accessible place to start your adventure. Designed to accommodate visitors year-round, our parking area is well-maintained and spacious, ensuring a hassle-free experience for both locals and travelers. With clear signage and close proximity to trails and key access points, you can seamlessly embark on your exploration of the diverse wildlife and picturesque landscapes that the area has to offer.

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 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 the Farmington River Wildlife Management Area Parking, your convenient and accessible gateway to the natural beauty of Otis, Massachusetts. Located in the heart of the stunning Berkshires, our parking facility provides easy access to the expansive Farmington River Wildlife Management Area, a haven for outdoor enthusiasts and nature lovers alike. Whether you're planning a day of hiking, birdwatching, fishing, or simply enjoying the serene landscape, our parking area offers a safe and secure spot to leave your vehicle as you embark on your adventure. We are committed to maintaining a clean and organized facility to ensure a hassle-free experience for all visitors.

Welcome to Shales Brook Wildlife Management Area Parking, your convenient gateway to exploring the natural beauty of Lee, Massachusetts. Nestled in the heart of the Berkshires, our parking facility offers easy access to the stunning landscapes and diverse wildlife of the Shales Brook Wildlife Management Area. Whether you're planning a day of hiking, birdwatching, or simply enjoying the serenity of nature, our well-maintained parking area provides a safe and accessible starting point for your adventure. Located in Lee, MA 01238, our facility is designed to accommodate visitors year-round, with ample space and clear signage to ensure a hassle-free experience. Discover the tranquility of the outdoors and connect with nature at Shales Brook, where your journey begins.

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 Day Mountain Wildlife Management Area Parking, your convenient gateway to exploring the natural beauty of Dalton, Massachusetts. Nestled in the heart of the scenic Berkshires, our parking facility provides easy access to the Day Mountain Wildlife Management Area, a haven for outdoor enthusiasts and nature lovers alike. Our parking area is designed to accommodate visitors looking to immerse themselves in the stunning landscapes and diverse wildlife of this pristine region. Whether you're planning a day of hiking, bird-watching, or simply enjoying a peaceful picnic in the great outdoors, Day Mountain Wildlife Management Area Parking offers a safe and accessible starting point for your adventure.

Welcome to the Tracy Pond Wildlife Management Area Parking, conveniently located in the serene town of Peru, Massachusetts. Nestled in the heart of the Berkshires, our parking facility provides easy access to the beautiful and expansive Tracy Pond Wildlife Management Area, a haven for nature enthusiasts and outdoor adventurers. Our parking area is designed to accommodate visitors looking to explore the stunning landscapes and diverse wildlife of the region. Whether you're here for hiking, bird watching, or simply to enjoy the tranquility of nature, our location offers the ideal starting point for your adventure.

Welcome to Farmington River Wildlife Management Area Parking, conveniently located in the scenic town of Otis, Massachusetts. Nestled in the heart of the beautiful Berkshires, our facility provides easy and accessible parking for visitors eager to explore the natural wonders of the Farmington River Wildlife Management Area. Whether you're planning a day of hiking, birdwatching, or simply enjoying the serene environment, our parking area is the perfect starting point for your outdoor adventures. We offer ample space to accommodate vehicles of various sizes, ensuring a hassle-free experience as you embark on your journey into nature. Visit us at Otis, MA 01253, and take the first step towards discovering the breathtaking landscapes and diverse wildlife of this cherished region. Your adventure awaits!

Welcome to the Eugene D. Moran Wildlife Management Area Parking, conveniently located in the serene town of Windsor, Massachusetts. Nestled in the heart of the Berkshires, our parking facility provides easy access to the breathtaking natural beauty and diverse wildlife of the Eugene D. Moran Wildlife Management Area. Whether you’re an avid hiker, birdwatcher, or simply looking to immerse yourself in nature, our parking area serves as the perfect starting point for your outdoor adventures. Our well-maintained parking lot offers ample space for vehicles, ensuring a hassle-free experience for visitors. Enjoy the peace of mind that comes with knowing your vehicle is securely parked while you explore the trails, scenic vistas, and rich biodiversity that this stunning area has to offer.