City Hiking Guides

Best Hikes in Massachusetts: A Journey Through New England’s Stunning Landscapes

POSTED ON May 8, 2024 BY Ralph S.


Massachusetts, nestled in the heart of New England, is a treasure trove of natural beauty and hiking adventures waiting to be discovered. But what are best hikes in Massachusetts?

Whether you’re an avid hiker looking for your next challenge or a family in search of easy hikes that offer accessibility and breathtaking views, the best hikes in Massachusetts have something for everyone. From the lush, rolling hills of Western Massachusetts to the scenic coastal paths that trace the Atlantic, this state is a microcosm of North America and the United States’ diverse landscapes.

Thanks to our guide, planning your next hike in Massachusetts is easier than ever. Whether you’re comparing trails in the serene Berkshires or considering a more ambitious expedition near the New Hampshire border, information and directions are just a few clicks away.

For those eager to start exploring the rugged beauty of Massachusetts, you’ll find that these trails encapsulate the essence of New England hikes, offering both serenity and adventure.

In this blog post, we’re shedding light on the best hikes Massachusetts has to offer, taking you from the heights of Mount Greylock to the seashores of the Cape Cod National Seashore.

Appalachian Trail

On the AT in Massachusetts. Section: Mass 23 to Tyringham.

  • Location: Western Massachusetts
  • Distance: 90 miles/145 km (within Massachusetts)
  • Hiking Duration: Varies
  • Difficulty: Easy to Challenging
  • Trail Type: Point-to-Point

The Appalachian Trail cuts a scenic path through western Massachusetts, making it an easy access point for hikers exploring a section of this iconic trail in New England. Covering approximately 90 miles (145 km) within the state, the trail offers a variety of experiences, from gentle strolls to more rigorous hikes.

One notable starting point for day hikers is the Mount Everett State Reservation (location), acknowledged for its expansive views across southern Massachusetts.

Massachusetts’s stretch of the Appalachian Trail is prized for landmarks like Mount Greylock and the serene beauty of areas leading to the “three-state view” from Mount Race. This unique vantage point borders Connecticut and New York, offering hikers breathtaking views that encapsulate the region’s natural diversity.

Robert Frost Trail

Robert Frost trail Massachusetts

  • Location: Sunderland, MA
  • Distance: 47 miles (76 km)
  • Hiking Duration: Varies
  • Difficulty: Moderate
  • Trail Type: Point-to-Point

The Robert Frost Trail (RFT) is a mesmerizing footpath that weaves through the eastern Connecticut River Valley, in Massachusetts. This moderate trail, beginning at the Connecticut River in South Hadley and stretching to Ruggles Pond in Wendell State Forest, traverses the scenic counties of Hampshire and Franklin. It’s known for connecting several of the region’s most remarkable natural landmarks, including the Holyoke Range, Mount Orient, and Mount Toby, offering hikers numerous environments to explore.

Among the trail’s highlights, Puffer’s Pond stands out as a serene stop for relaxation or picnicking, while the trek across the Holyoke Range presents panoramic views that are particularly striking during the autumn months.

Whether you’re looking for a peaceful hike through dense forestation or an opportunity to observe the area’s unique geological formations, the Robert Frost Trail delivers an enriching outdoor experience. Hikers can find more information and maps in the official trail guide.

Great Island Trail

Great Island Trail, Cape Cod National Seashore, near Wellfleet, Massachusetts.

  • Location: Wellfleet, MA
  • Distance: 3.9 miles/6.3 km (Tavern Loop) to 8.8 miles/14 km (to Jeremy Point Overlook, including Tavern Loop)
  • Hiking Duration: Varies
  • Difficulty: Moderate to Challenging
  • Trail Type: Loop/Out and Back

The Great Island Trail in Cape Cod National Seashore, located in Wellfleet, MA, presents a unique hiking experience combining scenic views, historical sites, and varied natural landscapes. This trail offers two main outings: a 3.9-mile round trip on the Tavern Loop for those looking for a manageable hike with impressive views of Wellfleet Harbor, and an 8.8-mile (14 km) extended trek to Jeremy Point Overlook, which includes the Tavern Loop for more adventurous hikers. The trail passes through diverse settings, from sandy beaches and marshlands to thick forests, providing a rich tapestry of Cape Cod’s environment.

For those desiring a longer walk, the South Esker Loop extends just over 2 miles (3.2 km) and showcases the area’s distinct topography and ecosystems. Meanwhile, a more relaxed path can be found on the scenic Money Brook Trail, which offers peaceful surroundings, cascading waterfalls, and serene pond views. Both routes provide unique perspectives on Cape Cod’s natural beauty and are worth exploring for different reasons.

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Purgatory Chasm Loop Trail

Purgatory Chasm

The Chasm Loop Trail is a captivating moderate loop trail in the heart of Purgatory Chasm State Reservation in Sutton. This signature hike unveils the raw beauty of natural rock formations and the chasm’s fascinating geological history. Along the route, hikers can take side trails towards awe-inspiring sights such as the Devil’s Corncrib and Fat Man’s Misery, emblematic of the area’s unique landscape.

Continuing the adventure, the trail meanders back through the center of the chasm, where explorers are greeted by the impressive Devil’s Pulpit and Lover’s Leap. These natural sculptures not only offer a visual feast but tell tales of the chasm’s storied past.

Mount Greylock Trek

Mount Greylock State Park

  • Location: Mount Greylock State Park, Massachusetts
  • Distance: 6.5-mile (10 km)
  • Hiking Duration: 3 hours, 50 minutes
  • Difficulty: Moderate
  • Trail Type: Out and Back Loop

Mount Greylock State Park, the pinnacle of Massachusetts at 3,491 feet (1,064 meters), is not just the state’s highest point, but a sanctuary for hikers, bird watchers, and nature enthusiasts. One of the most celebrated routes is a 6.5-mile (10 km) loop trail to the summit, connecting the Gould and Thunderbolt trails, which takes approximately 3 hours and 50 minutes to complete. This challenging hike rewards adventurers with sightings of wildlife such as river otters and red foxes amidst a forested backdrop.

The historical Thunderbolt Trail, known for its non-lift-served backcountry ski route, transforms into a demanding trek for experienced hikers during the off-season. At its zenith, Mount Greylock opens up to unveil the stunning biodiversity of Massachusetts and illuminate the natural beauty that inspired icons like Herman Melville and Henry David Thoreau.

Middlesex Fells Reservation

Middlesex Fells Reservation

  • Location: Stoneham, Massachusetts
  • Size: 2,575 acres (4.02 sq. mi.)
  • Number of Hiking Trails: 5+
  • Total Length of Hiking Trails: Over 100 miles (160 km)
  • Download the trail map

The Middlesex Fells Reservation is a natural haven in Stoneham, renowned for its extensive network of over 100 miles (160 km) of mixed-use trails. This expansive area offers a varied landscape that includes, but is not limited to, hiking trails that wander around picturesque ponds, extensive areas designated for dog walking, and dedicated paths for biking enthusiasts. It serves as a vital green space for residents and visitors seeking an escape into nature without leaving the urban vicinity.

At the heart of the reservation’s appeal is its versatility. Whether you’re an avid hiker, a casual jogger, a passionate cyclist, or someone who enjoys a stroll, there’s a trail or path catering to every preference

Additionally, the area’s natural beauty is complemented by spots like Spot Pond, which not only provides a serene setting for picnicking and relaxation but also offers opportunities for kayaking and fishing.

Hiking Mount Wachusett via Balance Rock, Old Indian, and Semuhenna Trail

Mount Wachusett

  • Location: Mount Wachusett, Princeton, Massachusetts
  • Distance: 3.8-mile (6.1 km) Loop
  • Hiking Duration: approx. 2 hours, 15 minutes
  • Difficulty: Moderate
  • Trail Type: Loop

Hiking Mount Wachusett via Balance Rock, Old Indian, and the Semuhenna Trail presents an invigorating experience near Westminster, Massachusetts. This loop is generally considered a moderate challenge and takes around 2 hours and 15 minutes to complete.

The trail ascends Mount Wachusett, the highest point in the state east of the Connecticut River, offering spellbinding views that stretch to the Boston skyline on clear days. Experienced hikers will find the diverse terrain engaging, with the Harrington Trail providing particularly rewarding vistas of the Wachusett Reservoir and beyond.

Mount Wachusett is a beacon for those seeking an adventurous escape within an hour’s drive from Boston. Ideal for both summer hikes and winter skiing, the mountain caters to outdoor enthusiasts of all levels. While the Pine Hill Trail offers a more leisurely ascent amid lush hardwood forests, the steeper sections leading to Wachusett’s summit via the Harrington Trail are a testament to the area’s natural beauty.

Blue Hills Reservation Hiking Trails

The Blue Hills Reservation in Milton, Massachusetts

  • Location: Milton, Massachusetts
  • Size: 7,000 acres
  • Number of Hiking Trails: 22+
  • Total Length of Hiking Trails: Over 125 miles (201 km)

The Blue Hills Reservation offers more than 125 miles (201 km) of trails that cater to outdoor enthusiasts of all levels. Among its highlights is the challenging Blue Hill Skyline Loop, favored for its rocky ledges and the opportunity to climb fire towers that offer breathtaking views of Greater Boston and its surroundings. The reservation is renowned for being a serene yet adventurous escape close to the urban expanse, with Great Blue Hill standing as its most recognizable feature, providing an excellent viewpoint over the area.

In addition to its rigorous trails, the reservation holds a place for those in search of tranquility. The 75-mile (1.2 km) Houghton’s Pond Trail is particularly beloved for its easy walk around the scenic Houghton’s Pond, making it an ideal spot for families or those preferring a less strenuous experience. The Skyline Trail, perhaps the park’s most prominent path, takes hikers across a series of rocky outcrops that reveal the natural beauty of the woods and the wider region.

Blue Hill Skyline Trail

Skyline Trail Massachusetts

  • Location: Milton, MA
  • Distance: 3 miles (4.8 km)
  • Hiking Duration: 1.5–2.5 hours
  • Difficulty: Moderate
  • Trail Type: Point-to-point

The Blue Hill Skyline Trail offers a moderate challenge, attracting hikers, cyclists, and outdoor enthusiasts seeking an immersive experience in nature. The trail’s diverse terrain includes forested paths, rocky ascents, and serene meadows, providing a rich tapestry of Milton’s natural beauty.

One of the trail’s highlights is its commanding view of Boston’s skyline from the summit of the Blue Hills range, offering a unique vista that contrasts the rugged natural landscape with the distant urban silhouette. This spectacular perspective makes the strenuous hike worthwhile, presenting an unforgettable reward for those who reach the peak. Along the way, visitors can also enjoy the trail’s multi-use aspects, including bird watching, and photography.

Mount Monadnock Hike

Mount Monadnock, New Hampshire

  • Location: New Hampshire
  • Distance: approximately 4 miles (6.4 km)
  • Hiking Duration: 3 hours
  • Difficulty: Moderate to Challenging
  • Trail Type: Out-and-back

Mount Monadnock is a pinnacle that offers more than just a climb; it provides a breathtaking view of Boston’s skyline to the east and a stunning panorama that stretches for hundreds of miles. Known as one of the most popular trails in North America, Mount Monadnock attracts many hikers, especially on weekends.

To enjoy a more solitary experience, aiming for a weekday adventure is advisable. The White Arrow, White Dot, and White Cross trails are the primary routes that lead to the summit, each offering a unique blend of scenic beauty and physical challenge, with the White Cross Trail recognized for its striking vistas and rigorous ascent.

Monadnock’s allure is not only in its scenic beauty but also in its unique standing, isolated and majestic, rising abruptly from the landscape. This feature is what earns it the title of the most climbed mountain in North America.

The summit is often lively and filled with hikers gathering to soak in the mountain’s mystique and sweeping views.

Walking in Cape Cod National Seashore

Cape Cod National Seashore - Massachusetts

  • Location: Cape Cod National Seashore, Massachusetts, USA
  • Size: 43,607 acres (68 sq. mi.)
  • Number of Hiking Trails: 11
  • Total Length of Hiking Trails: not specified

Cape Cod National Seashore, covering the outer arm of Cape Cod, presents a mosaic of spectacular natural landscapes and historical sites. With 11 walking trails open throughout the year, visitors can explore everything from sandy dunes and salt marshes to dense woodlands and serene ponds. One standout trail, the Nauset Marsh Trail, offers peaceful walks on a boardwalk beside calm waters, making it a favorite among tranquil landscape seekers.

The seashore’s varied terrain also includes over 40 miles (64 km) of pristine Atlantic shoreline, providing not only breathtaking ocean views but also a peek into the area’s rich cultural history. The Province Lands Bike Trail, in particular, winds through picturesque dunes and provides educational exhibits on the natural and historical significance of Cape Cod.

Hiking in Mount Holyoke State Park

Peak color on the road to the summit, in western Massachusetts's J. A. Skinner State Park.

  • Location: Mount Holyoke Range State Park, Massachusetts, USA
  • Size: 3,000 acres (4.69 sq. mi.)
  • Number of Hiking Trails: Not specified
  • Total Length of Hiking Trails: More than 30 miles (48 km)

Mount Holyoke State Park offers a vivid display of nature’s artistry. The park is renowned for its 7-mile (11 km) mountain ridge line that provides stunning views and a remarkable hiking experience. Among the notable peaks, Mount Norwottuck stands out for its distinctive silhouette and panoramic vistas.

Hikers and nature enthusiasts can explore blazed trails that suit varying experience levels. Two must-visit trails include the Mount Norwottuck and Horse Caves Trail, a 4-mile (6.4 km) loop that begins and ends at The Notch Visitor Center in Amherst, Massachusetts. This trail offers an engaging adventure through diverse terrains, and visitors are encouraged to keep their eyes peeled for the unique geological formations and lush landscapes that characterize this beloved state park.

Hiking Trails in Mount Washington State Forest

Mount Shuksan reflected in Highwood Lake, Mount Baker-Snoqualmie National Forest, Washington State

  • Location: Mount Washington State Forest, Massachusetts
  • Size: 4,619 acres (7.2 sq. mi.)
  • Number of Hiking Trails: Not specified
  • Total Length of Hiking Trails: More than 30 miles (48 km)
  • Download the trail map.

Mount Washington State Forest in southwestern Massachusetts is a prime destination for outdoor enthusiasts seeking solitude and natural beauty. This extensive state forest is home to a network of trails, catering to both hikers and mountain bikers looking for an adventure amidst densely forested terrain. Among these, the South Taconic Trail is notable for its challenging hikes and stunning views that can be enjoyed along the Massachusetts-New York border.

The park’s high-elevation areas, including Alander Mountain, provide breathtaking vistas that span the tri-state area, making the exertion of the climb well worth it.

In addition to its scenic trails, Mount Washington State Forest offers visitors the opportunity to experience serene natural landscapes, rich biodiversity, and the peace of being away from urban centers.

Mass Audubon’s Ipswich River Wildlife Sanctuary Nature Trails

Mass Audubon's Ipswich River Wildlife Sanctuary, Topsfield, Massachusetts - stone bridge

  • Location: Topsfield, MA
  • Size: 1,955-acre (3.05 sq. mi.)
  • Number of Hiking Trails: 7
  • Total Length of Hiking Trails: 12 miles (about 19 km)
  • Trail Map: download Ipswich River Trail Map (740.7 kB)

Mass Audubon’s Ipswich River Wildlife Sanctuary, just a 40-minute drive from Boston, is a sanctuary that spans numerous habitats, offering a tranquil retreat into nature. Visitors can explore several miles of trails that meander through picturesque forests, vibrant meadows, and lush wetlands. The sanctuary’s trails, including the enchanting Rockery Trail with its Rocky Grotto and the serene South Esker Trail, provide ample opportunities to encounter wildlife, including the playful river otters near the Ipswich River.

In addition to walking the interconnecting paths and boardwalks that offer a panoramic view of the sanctuary’s diverse ecosystems, guests are invited to engage with nature through birdwatching, photography, and simply absorbing the peaceful ambiance. The Ipswich River offers a tranquil backdrop for exploration and observing local wildlife in their natural habitat.

Hiking in Noanet Woodlands

Hike in Hale Reservation, Westwood

  • Location: Dover, MA
  • Size: 600 acres (0.9 sq. mi.)
  • Number of Hiking Trails: Not specified
  • Total Length of Hiking Trails: 17 miles (27 km)

Noanet Woodlands features several miles of intricate hiking trails designed for nature lovers of all proficiencies. This wooded preserve is renowned for its stunning bird-watching opportunities and breathtaking views from Noanet Peak, a rocky ledge offering picturesque sights of the surrounding area. To fully capture the experience, visitors are advised to arrive early, especially to catch a glimpse of the Boston skyline to the north on clear days.

The property is well-appointed with bridle paths and jumps, accommodating equestrian enthusiasts alongside hikers and bird watchers. The trails lead adventurers through diverse landscapes, from dense forests to open meadows, culminating in the iconic Noanet Peak.

Martha’s Vineyard, Sandy Shores

Martha's Vineyard

  • Location: Martha’s Vineyard, MA
  • Size: 61,440 acres (96 sq. mi.)
  • Number of Hiking Trails: Not specified
  • Total Length of Hiking Trails: Miles of trails with varying lengths

Martha’s Vineyard, a picturesque island in the Atlantic just south of Cape Cod, is a cherished New England summer colony known for its quintessential charm. The island is accessible only by boat or air, making it the 58th-largest island in the United States and the third-largest on the East Coast. Its landscape is adorned with traditional New England cottages, historic lighthouses, and serene beaches, making it an idyllic retreat for travelers seeking relaxation and adventure.

Among its many attractions, Vineyard Haven serves as the island’s bustling ferry port and commercial center, offering visitors a gateway to explore the diverse experiences Martha’s Vineyard offers.

The island boasts miles of hiking trails that cater to hikers of all skill levels, weaving through wooded areas, open fields, and breathtaking seaside cliffs. These trails provide a unique opportunity to experience the island’s natural beauty, from its well-preserved farmlands to the sandy shores that line its perimeter.

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Boston Harbor Islands National Recreation Area

Georges Island, Boston Harbor Islands National Recreation Area

  • Location: Boston, MA
  • Size: 1,482 acres (2.3 sq. mi.)
  • Number of Hiking Trails: Various
  • Total Length of Hiking Trails: Not specified

The Boston Harbor Islands National Recreation Area encompasses a unique cluster of 34 islands and peninsulas off the coast of Boston, Massachusetts. This sizable park provides an exceptional escape from city life, offering a rich mix of historical sites, outdoor activities, and natural beauty. Among the most compelling attractions is Fort Warren on Georges Island, a well-preserved Civil War-era fort that invites exploration and learning about America’s past.

Visitors to the area can enjoy a diverse array of recreational activities. Hiking enthusiasts will find numerous trails traversing through lush forests and scenic coastlines, while families can relish picnicking spots with expansive views of the Boston skyline. For those interested in fishing, the clean and accessible shores offer ample opportunities.


Massachusetts is a treasure trove of natural beauty, offering an extensive network of hiking paths that stretch across state forests and stunning landscapes.

From the serene banks of the Ipswich River to the historic trails on the Boston Harbor Islands, and the picturesque peaks of Noanet Woodlands, the state is a hiker’s paradise. With hundreds of miles of trails to explore, each hike presents an opportunity to immerse oneself in the rich tapestry of nature and history that defines Massachusetts.

Whether it’s a leisurely walk through vibrant meadows, an adventurous trek up rocky ledges, or a peaceful stroll along sandy shores, the diverse hiking experiences ensure that there’s always something new to discover. Embarking on these trails connects one with the natural world and rekindles the spirit of exploration, unveiling the hidden gems of Massachusetts’ great outdoors.

Visit our guide to city hiking guides to see other destinations worth visiting.


Ralph S. is the founder of Silverlight, an avid hiker and trail runner he enjoys spending time outdoors, riding his motorcycle and swimming at the beach when he's not busy replying to customers or developing new Silverlight gear.

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