Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Hikes
United States

Massachusetts

The best walks and hikes in Massachusetts

4.6

(1744)

18,047

hikers

2,722

hikes

Hiking in Massachusetts offers diverse landscapes, from the rolling peaks of the Berkshires in the west to the sandy coastal paths of Cape Cod in the east. The state's terrain includes forested reservations with well-marked trail networks, providing accessible routes near urban areas. Elevations vary from sea-level walks to ascents of notable peaks like Mount Wachusett. The region features mountains, hills, waterfalls, gorges, and extensive woodlands.

Best hiking trails in Massachusetts

  • The most popular hiking route is The Freedom Trail

Last updated: April 26, 2026

4.7

(62)

688

hikers

#1.

Freedom Trail

15.2km

03:57

100m

90m

Embark on a moderate urban hike along the Freedom Trail, a 9.5 miles (15.2 km) route that winds through Boston's historic heart. You will gain 318 feet (97 metres) over…

Navigate with device

Send to Phone

Save

Moderate

4.7

(93)

873

hikers

9.69km

02:31

60m

60m

Embark on The Freedom Trail, a moderate urban hike spanning 6.0 miles (9.7 km) with a gentle 197 feet (60 metres) of elevation gain. This route guides you through historic…

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

4.5

(2)

152

hikers

Embark on an easy hike around Fresh Pond Reservation, a refreshing escape in Cambridge, Massachusetts. This paved loop stretches for 3.4 miles (5.4 km) with a gentle elevation gain of…

Easy

5.0

(2)

104

hikers

Embark on an easy hike along the Charles River Pathway Short Loop, a pleasant urban route spanning 3.5 miles (5.6 km). With a minimal elevation gain of just 37 feet…

Easy

4.8

(4)

90

hikers

Embark on the Hickey and Peeskawso Peak Loop, an easy hiking route that takes you through a shady forest. You'll climb steadily, gaining 557 feet (170 metres) in elevation over…

Easy

5.0

(4)

87

hikers

Embark on an easy hike around Boston Harbor and Castle Island, a flat and accessible route spanning 2.7 miles (4.3 km) with a minimal elevation gain of just 38 feet…

Easy

4.4

(5)

82

hikers

Embark on the Lake Quannapowitt Trail for a refreshing hike that circles the water, offering continuous views of the lake. This moderate route spans 5.2 miles (8.3 km) and involves…

Moderate

4.8

(6)

75

hikers

6.22km

01:39

60m

60m

Embark on the World's End Trail, an easy hike spanning 3.9 miles (6.2 km) with a gentle elevation gain of 210 feet (64 metres). You can expect to complete this…

Easy

5.0

(5)

67

hikers

The Chestnut Hill Reservoir Trail offers an easy 2.0 miles (3.3 km) hiking experience, perfect for a quick outing. You will gain a minimal 30 feet (9 metres) in elevation,…

Easy

5.0

(4)

46

hikers

Embark on an easy hike along the Ashland Reservoir Trail, a 4.0 miles (6.4 km) loop that offers continuous scenic views of the 157-acre reservoir. You will gain a gentle…

Easy
Sign up for free to see 2,713 more hikes in Massachusetts.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Massachusetts

Hiking in Suffolk County

Hiking in Middlesex County

Hiking in Worcester County

Hiking in Berkshire County

Hiking in Norfolk County

Hiking in Plymouth County

Hiking in Barnstable County

Hiking in Essex County

Hiking in Hampshire County

Hiking in Bristol County

Other adventures in Massachusetts

The Long Trail — America's oldest long-distance path

Hiking Collection by

Jamie S.

Tips from the Community

Hans
November 15, 2025, View of the Longfellow Bridge

One of the most beautiful bridges in Boston. Heavily frequented.

Translated by Google

1

0

Reading the names on the gravestones is like a journey through history books. Visit the cemetery and see for yourself. And don't be afraid to go to the trouble of Googling some of the names.

Translated by Google

1

0

This is a multifaceted highlight. Opposite the relief is the government building, and the stairs lead into Boston Commons.

Translated by Google

0

0

Lake Quannapowitt is a large, shallow lake at the north end of the town of Wakefield. It covers 254 acres and is about 3.6 miles around. This lake is emptied by the Saugus River.

0

0

Hans
May 25, 2025, Old North Church

One of the many historic buildings in Boston

Translated by Google

0

0

Alex
May 13, 2025, Fresh Pond

​Fresh Pond is a 155-acre reservoir surrounded by the 162-acre Fresh Pond Reservation. This body of water is an important part of Cambridge's drinking water supply, surrounded by lawns and shaded woodlands. The park is popular for walking, jogging, and birdwatching, with over 110 bird species recorded in the area. ​

1

0

You can still see this reservoir's masterfully crafted waterworks, which date all the way back to the 1860s, and a couple of aqueducts as you zip past on the 1.5-mile paved loop that circles the water. This is also a nice spot for birding, and for swimming in the summer or ice skating in the winter.

0

0

A hug reduced to the arms... Interesting idea.

Translated by Google

1

0

More Information

FAQs about hikes in Massachusetts

  • What are the typical difficulty levels for hikes in Massachusetts?
    Massachusetts offers a good range of hiking difficulties. You'll find many easy trails, perfect for casual strolls or families, with 1283 easy routes available. There are also 435 moderate options for those seeking a bit more challenge, and 95 difficult trails for experienced hikers.

  • What are some popular hiking areas in Massachusetts?
    Some of the most popular hiking areas include the historic paths around Boston like The Freedom Trail, scenic coastal routes such as the Great Island Trail loop in Cape Cod National Seashore, and the beautiful forested areas of Middlesex Fells and Blue Hills Reservation. Walden Pond State Reservation also offers popular routes.

  • What is the longest recommended hike in Massachusetts?
    The longest hike listed is the Skyline Outer Reservoir loop — Middlesex Fells, which covers an impressive 12.2 km and typically takes about 03:15 to complete.

  • Are there any short and easy hikes suitable for a quick outing?
    Absolutely! A great option for a shorter, easier hike is the Walden Pond Path loop — Walden Pond State Reservation. It's a pleasant 2.67 km route that can be completed in approximately 41 minutes.

  • When is the best time of year to go hiking in Massachusetts?
    The hiking season in Massachusetts generally runs from late spring through fall. Spring brings wildflowers, summer offers lush greenery, and autumn showcases spectacular fall foliage, making it a very popular time. Winter hiking is also possible, though some trails may require appropriate gear for snow and ice.

  • Can I find family-friendly hiking options in Massachusetts?
    Yes, many trails are suitable for families. Easy routes like the Skyline Trail Loop & Blue Hill Observatory — Blue Hills Reservation or the Walden Pond Path are excellent choices for all ages and fitness levels.

  • Are there hikes that feature waterfalls in Massachusetts?
    Yes, Massachusetts has beautiful waterfall hikes. You can explore a dedicated guide to Waterfall hikes in Massachusetts to find picturesque cascades and serene streams across the region.

  • Can I incorporate natural monuments into my hiking plans?
    Definitely. Massachusetts is home to stunning natural monuments. Look for guides on Natural Monuments in Massachusetts to discover unique geological features and scenic highlights that can be part of your hiking adventures.

  • Are there hiking trails near lakes in Massachusetts?
    Many beautiful lakes in Massachusetts offer serene hiking experiences. Check out guides focusing on Lakes in Massachusetts to find trails that wind along tranquil shores and offer opportunities for a refreshing break.

  • What is the overall rating for hiking experiences in Massachusetts by the Komoot community?
    The hiking experiences in Massachusetts are highly regarded by the Komoot community, with an excellent average rating of 4.7 out of 5 stars. Over 16,000 hikers have explored and shared their positive experiences in the region.

Frequently Asked Questions

Are there many mountains to hike in Massachusetts?

Yes, Massachusetts offers excellent mountain hiking, especially in the western part of the state. The Berkshires are home to the state's highest peak, Mount Greylock, and a scenic 90-mile section of the Appalachian Trail. For a challenging day hike with significant elevation, consider the Mount Wachusett loop via the Midstate and Semuhenna Trails in Central Massachusetts.

What are some good, easy hikes for beginners or families?

Massachusetts has many accessible trails perfect for a family outing. A classic choice is the Walden Pond Path, a relatively flat and short walk around the historic pond. For something with a bit more elevation but still manageable, the Skyline Trail Loop in the Blue Hills Reservation is a popular, well-regarded option that offers rewarding views.

Can I bring my dog on hikes in Massachusetts?

Many trails in Massachusetts are dog-friendly, but policies vary by park, so it's always best to check local regulations. The Middlesex Fells Reservation is a well-known spot where dogs are welcome, with trails like the Rock Circuit Trail loop offering a great option for you and your canine companion. Always keep your dog leashed unless in a designated off-leash area.

Are there any coastal hiking trails?

Absolutely. The eastern part of the state is famous for its coastal scenery. The Cape Cod National Seashore offers fantastic trails that combine sandy paths, salt marshes, and ocean views. A great example is the Nauset Marsh loop to Coast Guard Beach, which provides a beautiful tour of the area's unique coastal ecosystem.

What are some challenging hikes in the state?

For those seeking a challenge, the Berkshires offer rugged terrain and significant climbs. The 90-mile section of the Appalachian Trail is a classic long-distance challenge. For a tough day hike, the Mount Wachusett and Balance Rock loop provides over 300 meters of elevation gain, testing your endurance with rewarding views from the summit.

Where can I find hikes with waterfalls?

Western Massachusetts is your best bet for waterfall hikes. The state's highest and most famous waterfall is Bash Bish Falls, located in a state park on the New York border with accessible trails leading to the viewing area. While not a specific route in this guide, many trails in the Berkshires lead to smaller cascades and scenic ravines.

What is hiking in Massachusetts like?

Hiking here is incredibly diverse. You can experience rugged mountain trails in the Berkshires, explore vast forested reservations like the Blue Hills near Boston, or walk along sandy coastal paths on Cape Cod. The state has over 1,800 trails, with the majority being easy or moderate, making it accessible for all skill levels.

What do other hikers think of the trails in Massachusetts?

The trails are highly rated by the komoot community, with an average score of 4.6 stars. Hikers often praise the well-maintained paths in state reservations and the stunning variety of scenery, from the mountain vistas in the west to the unique coastal landscapes in the east.

Are there any circular walks available?

Yes, there are many excellent loop trails so you can end your hike where you started. The Walden Pond Path loop is a popular easy option. For a longer, more moderate loop, the Skyline Outer Reservoir loop in Middlesex Fells takes you through a beautiful forested landscape around a reservoir.

What should I wear for hiking in the fall?

Fall weather in Massachusetts can change quickly. It's best to dress in layers. Start with a moisture-wicking base layer, add a fleece or light insulated jacket for warmth, and bring a waterproof and windproof outer shell. Sturdy hiking shoes with good grip are essential, as trails can be covered in wet leaves. Don't forget a hat and gloves, especially for higher elevations.

Where are some popular places for hiking in Massachusetts?

Massachusetts has several highly-regarded hiking destinations across the state.

  • Blue Hills Reservation: A massive park just south of Boston, loved for its extensive trail network and views of the city skyline from Great Blue Hill.
  • Middlesex Fells Reservation: A natural haven north of Boston, popular for its trails around reservoirs and dog-friendly policies.
  • Wachusett Mountain State Reservation: A favorite in Central Massachusetts, offering challenging summit hikes with panoramic views, accessible by trail or road.
  • Purgatory Chasm State Reservation: A unique spot known for its dramatic quarter-mile-long granite chasm that you can hike through.

Most popular routes in Massachusetts

City hikes in Massachusetts

Most popular attractions in Massachusetts

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Didn’t find what you were looking for?

Check out more Hikes throughout Massachusetts below and find the perfect route in your destination.

Worcester CountyDukes CountyHampshire CountySuffolk CountyMiddlesex CountyNorfolk CountyPlymouth CountyFranklin CountyNantucket CountyBerkshire CountyHampden CountyBristol CountyEssex CountyBarnstable County

Other places to explore

Nearby adventure guides

Things to Do around Milford

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy