Walking Tours in Boston

Region in Massachusetts, United States

There are few cities in the US with so much to see as Boston. It helps that Boston is a compact city, and you can easily walk from highlight to highlight, often quicker than taking transit or taxis. Explore Boston on a walking tour (or on a bike), and take in highlights such as Fenway Park, Back Bay, a walk along the Charles River to MIT or Harvard, the Freedom Trail or a great Italian meal in North End, Boston’s Little Italy.

Our list of the best walks in Boston has a bit of everything, from history and culture (past and current), to food, fun, and general site seeing. Each walk can be a short wander through a few neighborhoods or be turned into a whole day out, depending on how many stops you want to make. One of the best parts about each of these walks is that they can be done solo, as a group, as a pair, or with kids. So whatever your Boston trip looks like, we have got the perfect routes to see the city!

THE TOP 10 WALKS IN BOSTON

  1. Fens and Back Bay (6.3 km, 23 m, 1.5-2h): This action-packed Boston walk will explore 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.
  2. Financial District to Theatre District (5.2 km, 32 m, 1.5-2h): Starting at the waterfront, venture into Boston's financial district - the nerve center of the downtown. Don’t let the name confuse you though, there are many must-see historical and fun stops in the area! After walking the financial district, head to the 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!
  3. Freedom Trail (6.7 km, 71 m, 1.5-2h):The Freedom Trail is one of Boston’s most popular walks. Follow the signed route throughout this historic city to the sites that were most instrumental in the American Revolution.
  4. City Hall to North End (3.3 km, 15 m, 1.5-2h): This short but action-packed 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.
  5. Harvard to MIT (8.5 km, 10 m, 2-2.5h): Both Harvard University and Massachusetts Institute of Technology call Cambridge, home, making this an exciting walk to explore these centers of education. Harvard and MIT both have their own interesting landmarks and attractions that are well worth a visit.
  6. Emerald Necklace (14.6 km, 62 m, 3.5-4h): Explore the greenery of Boston with a long walk along the Muddy River and Boston’s best gardens and parks. The Emerald Necklace is a series of green spaces meandering from Dorchester to Back Bay, providing an escape into nature while remaining in the city.
  7. Charles River Walk (5.7 km, 13 m, 1.5-2h): One of the most scenic features of Boston is the Charles River. Walking alongside the river 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.
  8. MIT to Beacon Hill (6.1 km, 46 m, 1.5-2h): This great walk in Boston starts at MIT and then follows the Charles River to beautiful and historic Beacon Hill. This is a great walk in Boston, with great views.
  9. Foodie Walking Tour of Boston (8.6 km, 11 m, 2-2.5h): Boston has a lot of amazing restaurants to choose from, and 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!
  10. Boston Harbor Walk (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.

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Best Walking Tours in Boston

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.

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Open details for Planning a Trip To Boston

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