The 30 Best Berkshires hiking trails in Massachusetts

Welcome to Berkshire Hathaway HomeServices Verani Realty, your premier real estate agency located at 290 Merrimack Street, Lawrence, Massachusetts. Since 1967, Verani Realty has been a trusted partner in the real estate industry, offering a full spectrum of services to both buyers and sellers. Our legacy of excellence is built on decades of experience, ensuring that every client's real estate journey is successful and satisfying. Our dedicated team of seasoned professionals provides expert guidance for buyers searching for their dream home and sellers looking to make strategic moves. We understand the unique demands of the real estate market and pride ourselves on our commitment to integrity, professionalism, and innovation in every transaction.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 1 Main Street, Andover, Massachusetts. As a premier real estate agency, we offer a comprehensive range of services tailored to meet the needs of both buyers and sellers. With a legacy of excellence dating back to 1967, Verani Realty brings decades of experience and a commitment to integrity, professionalism, and innovation to every transaction. Our team of seasoned professionals is dedicated to guiding you through your real estate journey, whether you're in search of your dream home or planning to make a strategic sale. Locally known, nationally recognized, and globally respected, Verani Realty is proud to be an affiliate of Berkshire Hathaway HomeServices, a global network of over 50,000 real estate professionals.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 297 South Main Street, Haverhill, Massachusetts. Since 1967, we have been dedicated to providing exceptional real estate services to both buyers and sellers, ensuring a successful and satisfying experience for all our clients. Our team of seasoned professionals is committed to guiding you every step of the way, whether you're in search of your dream home or looking to make a strategic sale. We pride ourselves on our integrity, professionalism, and innovative approach, which is evident in every transaction we handle.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 61 State Street, Newburyport, Massachusetts. With a rich legacy of excellence dating back to 1967, Verani Realty is dedicated to providing a comprehensive range of services for both buyers and sellers. Our seasoned professionals are committed to ensuring your real estate journey is successful and satisfying, whether you're searching for your dream home or making a strategic move. As a proud affiliate of the globally respected Berkshire Hathaway HomeServices network, Verani Realty benefits from a vast network of over 50,000 real estate professionals across 1,500 offices worldwide. Our sterling reputation, built locally, is recognized nationally and respected globally. We believe in fostering meaningful relationships in every transaction, prioritizing collaboration over competition, and supporting the growth of successful real estate businesses.

Bartholomew's Cobble Reservation is a scenic and historic destination located at 105 Weatogue Road in Sheffield, Massachusetts, United States. This institution serves as a museum, park, and tourist attraction all in one, offering visitors a unique and immersive experience in the beautiful Berkshire region. The reservation is home to stunning natural landscapes, including a variety of plant and animal species, as well as geological formations that date back millions of years. Visitors can explore the well-maintained trails, take guided tours, and learn about the area's rich history and conservation efforts. Bartholomew's Cobble Reservation is a must-visit destination for nature lovers, history buffs, and anyone looking to enjoy the great outdoors in a serene and educational setting.

Housatonic Flats Reserve is a beautiful park located at 439 Stockbridge Road in Great Barrington, Massachusetts, United States. This serene reserve offers visitors a peaceful escape into nature, with lush greenery, meandering trails, and stunning views of the Housatonic River. Perfect for a leisurely stroll, birdwatching, or simply relaxing in the great outdoors, Housatonic Flats Reserve is a hidden gem waiting to be explored. Whether you're looking for a quiet retreat or a place to reconnect with nature, this park is the perfect destination for nature lovers of all ages.

Field Farm Reservation is a park and tourist attraction located at 554 Sloan Road, Williamstown, Massachusetts, United States. It is known as Williamstown’s favorite authentic mid-century modern B&B and has been rated #1 Bed & Breakfast in Williamstown, MA by Tripadvisor. The institution offers a unique experience with two Modernist homes, including a bed & breakfast, and over 300 acres of open fields, woods, and wetlands with four miles of footpaths. Guests can enjoy a peaceful getaway vacation in the Berkshires or explore beautiful sculptures and architecture at Field Farm. The Guest House at Field Farm is an architectural gem offering authentic mid-century-modern accommodations with stunning views of Mt. Greylock. The property also features period artwork and thirteen sculptures in the surrounding gardens. Visitors can explore the property or stay in The Folly, a three-bedroom guest cottage designed by modernist architect Ulrich Franzen in 1965. Field Farm offers special winter discounts for guests staying between November 20, 2023, and March 11, 2024. The institution provides opportunities for outdoor activities such as walking, snowshoeing, and cross-country skiing on its 320-acre property. Guests can also enjoy hiking on more than four miles of trails with scenic views of Mount Greylock. The property is home to a variety of wildlife, including white-tail deer, coyotes, bobcats, beavers, turtles, and various bird species. The Guest House at Field Farm offers six spacious and finely appointed rooms with mountain views, although the facility is not wheelchair accessible. Visitors can use the electric car charger for overnight guests staying at the Field Farm Inn. The property also hosts private events and groups, and guests are encouraged to take a photo of the map or download a trail map before heading out. Field Farm is part of The Trustees, an organization dedicated to preserving and protecting Massachusetts’ special places. The institution offers a unique blend of history, architecture, design, and natural beauty, making it a must-visit destination for a weekend trip or a cozy inn stay.

Olivia's Overlook is a stunning tourist attraction located in the beautiful town of West Stockbridge, Massachusetts, United States. Situated along the scenic Hiking Trails, this overlook offers breathtaking views of the surrounding landscape, making it a perfect spot for nature lovers and outdoor enthusiasts. Visitors can enjoy a peaceful hike to the overlook and take in the picturesque vistas, making it a great destination for those looking to escape the hustle and bustle of city life. Whether you're looking for a relaxing day in nature or a challenging hike, Olivia's Overlook is sure to provide a memorable experience for all who visit.

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

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

Welcome to Money Brook Falls Trailhead, a serene escape nestled in the heart of the Berkshires on Notch Road, Williamstown, Massachusetts. Managed by the Massachusetts Department of Conservation and Recreation as part of the Mt. Greylock State Reservation, this picturesque park offers a rejuvenating experience for nature enthusiasts and hikers alike. Embark on a journey through lush valleys and experience the awe-inspiring beauty of cascading waterfalls. Our trails offer various levels of adventure, from a gentle 2.7-mile (4.3 km) hike with an elevation gain of 894 feet (272.42 meters) to more challenging routes that stretch up to 6.6 miles (10.7 km) with an ascent of 2,251 feet (686.23 meters). Whether you're seeking a tranquil walk in the shadow of the falls or a vigorous hike through the valley, Money Brook Falls Trailhead provides an unforgettable outdoor experience.

Welcome to Bob's Way, a serene haven nestled in the heart of Monterey, Massachusetts. As a premier park destination in the picturesque Berkshires, Bob's Way offers an idyllic escape for nature lovers and outdoor enthusiasts alike. Immerse yourself in the tranquility of lush landscapes, winding trails, and breathtaking vistas that define our unique park. Whether you're seeking a peaceful stroll, a challenging hike, or a perfect picnic spot, Bob's Way caters to all. Our well-maintained paths invite you to explore the natural beauty of the region, while our scenic overlooks provide stunning views that capture the essence of New England's charm. Families, friends, and solo adventurers will find plenty of spaces to relax, play, and connect with nature.

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.

Birch Hill Bed & Breakfast is a charming lodging located at 254 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshires region, this cozy B&B offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations, delicious homemade breakfasts, and warm hospitality, Birch Hill Bed & Breakfast is the perfect place to relax and unwind during your stay in the Berkshires.

Located in the picturesque town of Sandisfield, Massachusetts, Hillside Garden Inn offers a charming and relaxing Bed and Breakfast experience. Housed in the historic Elijah Twining House, dating back to 1785, guests can enjoy immaculate accommodations and gracious hospitality. The inn boasts a spacious wrap-around porch overlooking the Farmington River, as well as a screened-in patio and hilltop gazebo with stunning panoramic views of the distant hills. Sandisfield, with its beautiful landscapes and thriving arts scene, is the perfect destination for outdoor enthusiasts and culture lovers alike. The Berkshires region offers plenty of activities year-round, from skiing and hiking to water sports and cultural events. For those who enjoy shopping, Prime Outlets are just a short drive away.

Laurel Ridge Campground is a family-friendly destination located in the picturesque Berkshire mountains of Otis, Massachusetts. Whether you're camping solo or with a group, our campground offers a variety of sites to suit your needs. From grassy safari field sites to gravel or grass inner loop sites, there's something for everyone. Our campground features a range of amenities, including a new playscape for kids, a basketball court, horseshoes, a swimming pool, and even bingo nights. If you're looking for a peaceful retreat, you'll find plenty of relaxation here too. Enjoy the fresh mountain air, good company, and a full schedule of activities to keep you entertained.

TOURISTS is a unique lodging institution located at 915 State Road in North Adams, Massachusetts. Situated in the scenic Berkshires region of the United States, TOURISTS offers a one-of-a-kind experience for travelers looking to immerse themselves in nature and art. The institution provides a range of accommodations, from cozy cabins to stylish rooms, all designed with a modern and minimalist aesthetic. Guests can enjoy amenities such as a communal kitchen, outdoor fire pits, and access to hiking trails. Whether you're seeking a peaceful retreat or a cultural adventure, TOURISTS is the perfect destination for your next getaway.

The Red House on Lake Buel is a charming Berkshire lakeside cottage offering a peaceful retreat for those seeking relaxation and outdoor activities. Located at 24 Downs Road in New Marlborough, Massachusetts, this vacation rental property is just a short distance from popular attractions such as Tanglewood, Jacobs Pillow, Norman Rockwell Museum, and Chesterwood. This idyllic 4 bedroom cottage is situated right on the edge of Lake Buel, providing easy access to swimming, fishing, water sports, and hiking. The house features a spacious screened-in porch with comfortable seating and a dining table for 8, perfect for enjoying meals with a view of the lake. Guests can also bring their own boat and dock it at the private dock.

Mount Everett State Reservation is a picturesque park and tourist attraction located at 143 East Street in Mount Washington, Massachusetts, United States. This stunning natural oasis offers visitors the opportunity to explore lush forests, scenic hiking trails, and breathtaking mountain views. Whether you're looking for a peaceful escape into nature or an exciting outdoor adventure, Mount Everett State Reservation has something for everyone to enjoy. Come and experience the beauty of this hidden gem in the heart of the Berkshires.

Bash Bish Falls State Park is a picturesque park and popular tourist attraction located on Falls Road in Mount Washington, Massachusetts, United States. The park is home to the stunning Bash Bish Falls, a cascading waterfall that drops over 60 feet into a sparkling pool below. Visitors can enjoy hiking trails, picnicking areas, and breathtaking views of the surrounding Berkshire Mountains. With its natural beauty and tranquil atmosphere, Bash Bish Falls State Park is the perfect destination for nature lovers and outdoor enthusiasts alike.

Beartown State Forest is a picturesque park and popular tourist attraction located at 69 Blue Hill Road in Monterey, Massachusetts, United States. This stunning forest offers visitors a peaceful escape into nature with its lush greenery, scenic hiking trails, and tranquil ponds. Whether you're looking to enjoy a leisurely walk, go for a swim, or simply relax and take in the beauty of the surroundings, Beartown State Forest is the perfect destination for outdoor enthusiasts of all ages. Don't miss the opportunity to explore this hidden gem in the heart of the Berkshires.

Pfeiffer Arboretum, located at 249 Long Pond Road in Great Barrington, Massachusetts, is a stunning park and tourist attraction. Visitors can explore the beautiful grounds filled with a diverse collection of trees, shrubs, and plants from around the world. The arboretum offers a peaceful escape from the hustle and bustle of daily life, with winding paths and tranquil seating areas perfect for relaxation and contemplation. Whether you are a nature enthusiast, a photography buff, or simply looking for a peaceful retreat, Pfeiffer Arboretum is a must-visit destination in the heart of the Berkshires.

Becket Quarry is a picturesque park and tourist attraction located at 456 Quarry Road in Becket, Massachusetts, United States. This historic site offers visitors the opportunity to explore the remnants of an old quarry, with stunning rock formations and crystal-clear water. Perfect for hiking, picnicking, and photography, Becket Quarry is a must-visit destination for nature lovers and history enthusiasts alike. Immerse yourself in the natural beauty and unique charm of this hidden gem in the heart of the Berkshires.

Monument Mountain Reservation Parking is a convenient parking area located at 546 Stockbridge Road in Great Barrington, Massachusetts. This parking facility serves visitors to Monument Mountain Reservation, a beautiful park known for its stunning views and hiking trails. Whether you're looking to explore the natural beauty of the Berkshires or simply need a place to park while enjoying the outdoors, Monument Mountain Reservation Parking provides easy access to this popular destination. With ample parking spaces and a convenient location, this institution is the perfect starting point for your outdoor adventure.

East Mountain State Forest is a picturesque park and popular tourist attraction located in Great Barrington, Massachusetts, United States. This beautiful forest offers visitors a serene escape into nature, with hiking trails, stunning views, and an abundance of wildlife to discover. Whether you're looking for a peaceful stroll through the woods or a challenging hike to the summit, East Mountain State Forest has something for everyone to enjoy. Come explore this hidden gem in the heart of the Berkshires and experience the natural beauty of Massachusetts at its finest.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Club Wyndham Bentley Brook is a premier lodging destination nestled in the picturesque town of Hancock, Massachusetts. As a part of the renowned Wyndham vacation ownership network, this institution offers luxurious accommodations, top-notch amenities, and exceptional service. Whether you're looking for a relaxing getaway or an adventurous vacation, Club Wyndham Bentley Brook has something for everyone. With its prime location near ski slopes, hiking trails, and other outdoor activities, guests can enjoy a truly unforgettable experience. Plan your next vacation with Club Wyndham Bentley Brook and create lasting memories in the beautiful Berkshires region of Massachusetts.

Mt. Greylock Campsite Park is a picturesque campground and park located at 15 Scott Road in Lanesborough, Massachusetts. Surrounded by the natural beauty of the Berkshires, this RV park offers a tranquil setting for outdoor enthusiasts to relax and unwind. The park features spacious campsites for tents and RVs, as well as cozy lodging options for those looking for a comfortable stay. Guests can enjoy hiking trails, fishing spots, and breathtaking views of Mt. Greylock, the highest peak in Massachusetts. Whether you're looking for a peaceful retreat or a fun-filled outdoor adventure, Mt. Greylock Campsite Park has something for everyone.

Bascom Lodge is a charming lodging institution nestled in the picturesque surroundings of Adams, Massachusetts. Located at 3 Summit Road, this historic lodge offers guests a unique and tranquil retreat in the heart of the Berkshires. With cozy accommodations and stunning views of the surrounding mountains, Bascom Lodge is the perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking to relax and unwind or explore the nearby hiking trails and attractions, Bascom Lodge provides a comfortable and welcoming atmosphere for all guests. Experience the beauty and serenity of the Berkshires at Bascom Lodge.

26 Church Street is a charming lodging institution located in the heart of Lenox, Massachusetts. Situated at the address 26 Church Street, this cozy establishment offers a warm and inviting atmosphere for guests looking to experience the beauty of the Berkshires. With comfortable accommodations and a convenient location near local attractions, 26 Church Street is the perfect choice for a relaxing getaway in this picturesque New England town. Whether you're exploring the nearby shops and restaurants or simply unwinding in your well-appointed room, you'll feel right at home at this lovely inn.