Massachusetts, USA

Walking Tours in Massachusetts

State in United States

Explore stunning Massachusetts, home to one of America's greatest cities: Boston. Explore history and culture while walking the streets of Boston.

Guide-book quality info for over 8,000 trails

View Walking Tours in Massachusetts on Map

View Map

City walking regions in Massachusetts

Best Walking Tours in Massachusetts

Open details for Fens and Back Bay

Fens and Back Bay

Easy
6.3 km
23 m
1.5-2h

This action-packed Boston walking Tour will show you some of the best of Boston. Explore the Greenery of The Fens and the Brownstones of the Back Bay, two of Boston's best neighborhoods. The walk stops at Isabella Stewart Gardner Museum, the Museum of Fine Arts (MFA), The Fens, Fenway Park, Kenmore Square, Newbury Street, and Copley Square before finishing at the impressive Christian Science Church.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Financial District to Theatre District

Financial District to Theatre District

Very Easy
5.2 km
32 m
1.5-2h

This Boston walking tour will allow you to explore the waterfront and Boston’s Financial District. Don’t let the name confuse you though, there are many must-see historical and fun stops in the area! After time walking through the Financial District head to the more-lively Theatre District. Filled with great restaurants and bars as well as a variety of shows, and of course historically significant buildings housing them all - this makes for a great afternoon into evening walk!

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Freedom Trail

Freedom Trail

Easy
6.7 km
71 m
1.5-2h

The best walk in Boston for history lovers, The Freedom Trail is one of Boston’s most popular walks. Follow the painted red line on the ground throughout this historic Boston walking tour and see the sites that were most instrumental in the American Revolution.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for City Hall to North End

City Hall to North End

Very Easy
3.3 km
15 m
1-1.5h

This short Boston walking tour shows off a huge number of Boston’s historical attractions. The bulk of Boston’s historical sites and tourist destinations are located around Faneuil Hall Marketplace and the North End. This area is flooded with culture, great restaurants, interesting shops, and sites dating back to the beginning of America.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Harvard to MIT

Harvard to MIT

Easy
8.5 km
10 m
2-2.5h

This Boston walking tour takes you to adjacent Cambridge, famous for Harvard Business School, Harvard University and MIT. This is an interesting area to explore, and it’s best done by walking. Across the Charles River is Boston, known for its rich history and cultural attractions, but Boston’s sites should not overshadow the ones across the river. Harvard and MIT both have their own interesting landmarks and attractions that are well worth a visit.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Emerald Necklace Walk

Emerald Necklace Walk

Hard
14.6 km
62 m
3.5-4h

This wonderful Boston walk tour allows you to explore the greenery of Boston with a long walk along the Muddy River and Boston’s best gardens and parks. Known locally as ‘The Emerald Necklace’, this walk goes through a series of green spaces meandering from Dorchester to Back Bay, providing an escape into nature while remaining in the city.

User Ratings
Overall Rating
9.8
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Charles River Walk

Charles River Walk

Easy
5.7 km
13 m
1.5-2h

This Boston walking tour takes in one of the most scenic features in Boston - the Charles River. Walking alongside the Charles is the best way to see incredible views of both Cambridge and Boston depending what side you’re on. This walk will take you by some of those perfect spots, as well as highlighting key sites on the campuses that sit beside the river - Massachusetts Institute of Technology and Boston University.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for MIT to Beacon Hill

MIT to Beacon Hill

Easy
6.1 km
46 m
1.5-2h

This is another great Boston walking tour for lovers of American History. Boston is well-known for being a historic city and most associate it with the Revolutionary War and the founding of America. When you dig deeper, though, you’ll find that Boston is really a city that has mastered the fusion of new with old. Especially with MIT making its home just across the Charles River in Cambridge, Boston has been filled with modern elements that are just as exciting as those rich with history.

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Foodie Walking Tour of Boston

Foodie Walking Tour of Boston

Moderate
8.6 km
11 m
2-2.5h

The best way to explore a city is with food. This foodie walking tour of Boston will take you to a number of amazing restaurants to show you the best of Boston’s culinary scene. For this foodie walking tour in particular, you’re going to want to make sure you start with an appetite because these are some of the best the city has to offer!

User Ratings
Overall Rating
10.0
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Open details for Boston Harborwalk

Boston Harborwalk

Easy
6.3 km
44 m
1.5-2h

Boston’s harbor walk is a great way to spend the day, mixing in the many wharves along the waterfront and the attractions that are near them. This is a great walk to explore Boston’s maritime history.

User Ratings
Overall Rating
9.9
Technical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Physical Difficulty
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.

Change happens, fees shouldn't

Suggested Tours

Open details for Summit Mount Olympus Trekking Tour

Summit Mount Olympus Trekking Tour

Greece
Trekking
Self-Guided
4 days
From $175
Months Tour Operates
J
F
M
A
M
J
J
A
S
O
N
D

This tour is your chance to trek one of the most mystical mountains on earth: Mount Olympus. This self-guided journey starts in Litochoro, an enchanting town at the foot of Greece’s highest peak. Then you’ll spend two days on the mountain, sleeping in a mountain hut on the second night. You should be comfortable hiking up some serious elevation on this tour to reach the summit, a worthy reward for your effort.

View More
Open details for Jericho to Jerusalem through Wadi Qelt Tour

Jericho to Jerusalem through Wadi Qelt Tour

Israel
Trekking
Self-Guided
2 days
From $190
Months Tour Operates
J
F
M
A
M
J
J
A
S
O
N
D

The incredible Jericho to Jerusalem through Wadi Qelt Hiking journey from Jericho to Jerusalem is the perfect introduction to the natural beauty of the West Bank region that spans Palestine and Israel. Journeying on foot, you’ll experience these iconic areas in a truly unique and spectacular way.

View More
Open details for Avalanche Skills Training 1 in the Canadian Rockies

Avalanche Skills Training 1 in the Canadian Rockies

2 days
From $225
Months Tour Operates
J
F
M
A
M
J
J
A
S
O
N
D

Avalanche safety is a must-have tenet of backcountry adventure and a critical step in keeping yourself and your adventure partners safe in the wintertime and shoulder season. The Avalanche Skills Training 1 in the Canadian Rockies tour is a practical chance to learn the basics of avalanche safety in one of the most beautiful mountain environments in the world.

View More
Open details for Walking and Dining in Athens Tour

Walking and Dining in Athens Tour

Greece
Walking
Self-Guided
3 days
From $225
Months Tour Operates
J
F
M
A
M
J
J
A
S
O
N
D

Athens is the oldest city in Europe and the city with the longest history! Strolling through Athens, you will be thrilled to discover this rich history as Ancient, Roman, Byzantine and modern monuments abound. Pedestrian walkways lead you through green parks connecting major sites like the Acropolis, the Acropolis Museum and the Pnyx Theater, which is considered the birthplace of democracy. Dine on multiple courses at fine restaurants and sample the fare at local taverns in each spot. A unique food-on-foot tour!

View More

Other Activities in Massachusetts

    Trip Planners

    Essential Tools for Any Adventure

    Find a hotel in some of the most beautiful locations on earth.

    Book your own car to have complete freedom on your next adventure.

    Gear-up for your next adventure.

    This page may include affiliate links. We may get a small commission for the purchases made through these links at no additional cost to you.
    We only recommend tools we personally think are great.

    Change happens, fees shouldn't

    Recent Stories

    Open details for Yosemite in Winter: Plan your Perfect Weekend

    Yosemite in Winter: Plan your Perfect Weekend

    By Lynn W
    November 3rd, 2019
    Open details for Planning a Trip To NYC

    Planning a Trip To NYC

    By Lynn W
    October 8th, 2019
    Open details for Planning a Trip To Boston

    Planning a Trip To Boston

    By Lukas Saville
    September 26th, 2019
    Open details for Yellowstone National Park Guide For 2021

    Yellowstone National Park Guide For 2021

    By Lukas Saville
    August 1st, 2019
    Detailed Route Guides
    Real GPS Coordinates
    Reliable Trail Reports
    Experienced-Based Travel Tips
    GPS App
    Extensive Travel Guides

    Subscribe to our newsletter

    Get a weekly dose of discounts and inspiration for adventure lovers

    Tours

    Routes

    Blogs