Walking Tours in Boston, Massachusetts

This list shows the most popular Walking Tours in Boston, Massachusetts based on user reviews, votes, and mobile downloads. Plan your next trip with EveryTrail guides by downloading a guide to your mobile phone with the EveryTrail iPhone or Android app.
Sort: show community trips
Update on map move
Guides
The Freedom Trail
The Freedom Trail
Boston, Massachusetts, United States
 
Moderate: 2.5 miles, Half day
Explore the Roots of the American Revolution with this historic Boston walk

Nothing tops the Boston Freedom Trail as an introduction to the history and popular sites of Boston. This 2.5-mile walk will take you past 16 significant landmarks, each of which played major roles in the years leading to the American Revolution and the early years of the United States. You will see many churches, cemeteries and meeting halls while...
Shopping: From Faneuil Hall to Newbury Street
Shopping: From Faneuil Hall to Newbury Street
Boston, Massachusetts, United States
 
Easy: 4.3 miles, Half day
Shops, markets, public parks, history and options for a meal

This shopping trip takes you from bustling Faneuil Hall to trendy Newbury Street, with some suggested green spaces to rest in along the way as well as some tips on where to dine or quench your thirst. Shopping can be an exhausting business! This route passes many famous Boston landmarks, so you can combine your shopping trip with some sightseeing.
Boston's Freedom Trail
Boston's Freedom Trail
Boston, Massachusetts, United States
 
Easy: 3.4 miles, Half day
Discover the roots of the revolution and Boston's rich history on this popular walk.

The Freedom Trail is more than a collection of historic sites related to the American Revolution or a suggested itinerary connecting Boston’s unique neighborhoods. It’s a chance to walk in the footsteps of our forefathers—literally, by following a crimson path on public sidewalks—and pay tribute to the figures all school kids know, like Paul...
Exploring Boston's North End
Exploring Boston's North End
Boston, Massachusetts, United States
 
Easy: 0.8 miles, Full day
The “Big Dig” reconnected downtown to the isolated North End peninsula, bringing fresh energy to the neighborhood.

This Italian neighborhood is full of new must-hit spots.
Seaport District Harbor Walk
Seaport District Harbor Walk
Boston, Massachusetts, United States
 
Easy: 1.5 miles, Full day
A waterfront walkway with parks, museums, public art, cafes and views

Concerned that there are only five spots on this guide? It's a bit deceptive actually. With the museums and sightseeing opportunities along this route, you may not get to all of them. Boston's HarborWalk is a public walkway along the waterfront, with parks, public art, seating areas, cafes, exhibit areas, interpretive signage, water transportation...
Public Garden Monument Walking Tour
Public Garden Monument Walking Tour
Boston, Massachusetts, United States
 
Easy: 1.0 miles, 1-3 hours
Monuments, sculptures beckon in Boston Public Garden

Follow this guide through the Boston Public Garden to visit all the major sculptures and monuments in the area. I've provided links in order of the route; you will see them within the description section of this guide.
Boston Bikes at Night Guide
Boston Bikes at Night Guide
Boston, Massachusetts, United States
Easy: 7.6 miles, 1-3 hours
Enjoy Boston's beautiful waterfront as the sun sets.

Enjoy Boston's beautiful waterfront as the sun sets. Look out at the harbor from Black Falcon Pier, take in the modern architecture of the Institute of Contemporary Art, and return to the North End just as the night is truly beginning.
Paul Revere Ride to Freedom Bike Tour
Paul Revere Ride to Freedom Bike Tour
Boston, Massachusetts, United States
Moderate: 47 miles, Half day
This guide takes you from the Old North Church in Boston’s North End and follows Revere’s ride on April 18, 1775.

The Paul Revere Ride to Freedom takes you from the Old North Church in Boston’s North End and follows Revere’s ride on April 18, 1775 through Charlestown, Lexington and Concord. We recount the events leading up to the Revolutionary War and educate riders on the great history of Massachusetts in the War for Independence.
Boston's Emerald Necklace and Fall Foliage Guide
Boston's Emerald Necklace and Fall Foliage Guide
Boston, Massachusetts, United States
Moderate: 16.2 miles, 1-3 hours
Discover Frederick Law Olmsted's famous system of parks on this bicycle tour of the historic Emerald Necklace.

Discover Frederick Law Olmsted's famous system of parks on this bicycle tour of the historic Emerald Necklace. From the shaded boulevard on Commonwealth Avenue to the popular shores of Jamaica Pond to the winding paths of the Arnold Arboretum, this chain of gardens, reserves, and open space serves as an oasis in the middle of a bustling city. Come enjoy...
Back Bay with Kids
Back Bay with Kids
Boston, Massachusetts, United States
 
Easy: 1.7 miles, Half day
Have fun and frolic in this historic neighborhood.

Boston is a city of neighborhoods and a great way to introduce kids to the city is not by dragging them all over the place, but to tackle it one neighborhood at a time. The Back Bay is a charming place to start. It really was a bay, part of the Charles River. Actually, it was more of a swamp than a bay and was considered a health hazard. In the...
Biking Through the Emerald Necklace Parks
Biking Through the Emerald Necklace Parks
Boston, Massachusetts, United States
 
Moderate: 5.0 miles, Full day
Touring Boston via public parks designed by Frederick Law Olmsted

This series of parks and green spaces essentially serves as the urban Boston city dweller's backyard. Frederick Law Olmsted (yes, he designed Central Park, too) was a visionary landscape architect, and Boston is blessed that he set his sights here. This guide takes you through the five-mile park system. Pack a lunch and snacks; you'll see any number...
Commonwealth Ave Mall Monument Tour
Commonwealth Ave Mall Monument Tour
Boston, Massachusetts, United States
 
Easy: 1.0 miles, 1 hour or less
A beautiful walk from Hereford Street to the Public Garden

This guide will take you on a stroll through the history of the United States. You will pass nine different monuments commemorating events and people that changed the history of both the city of Boston and the nation. Take the time to click on each of the informative links attached to this guide for a thorough description of each monument. You will...
Boston City View Bike Route
Boston City View Bike Route
Beacon Hill, Massachusetts, United States
Easy: 9.6 miles, 1-3 hours
This tour allows you to pedal from the Italian North End and historic Beacon Hill, up to Fenway park, and beyond.

This tour allows you to pedal from the Italian North End and historic Beacon Hill, up to Fenway park, heart of Red Sox Nation, and through modern and dynamic Back Bay. Riders will see parts of Boston off the beaten path and experience the diversity of Boston’s contemporary and classic neighborhoods.
Community Solar System Trail - Boston Museum of Science
Community Solar System Trail - Boston Museum of Science
East Cambridge, Massachusetts, United States
Easy: 42 miles, Half day
Use this guide to find all the planets in the Community Solar System Trail, an accurate scale model of our solar system.

The museum of science has distributed scale models of our solar systems planets throughout the greater Boston area. Great care has been taken to place them at an accurate scale that is 400 million times smaller than the scale of our actual solar system.
Arnold Arboretum
Arnold Arboretum
Boston, Massachusetts, United States
 
Easy: 3.9 miles, Half day
Take a break from the urban life and escape to this arboretum for some solitude among the various tree species

This guide covers all the major areas of interest within the Arnold Arboretum located just south of Boston in the Forest HIlls area of Jamaica Plain. This is a great place to go if you want to escape into peaceful surroundings. There are a lot of interpretive signs about the many species of plants you will discover along the walk. Make sure to stop...
Marine Park and Castle Island Exploration
Marine Park and Castle Island Exploration
Fort Independence, Massachusetts, United States
Easy: 2.5 miles, 1-3 hours
This is a great walk around a causeway to a historic fort that you won't want to miss

This is a very beautiful area just south of Boston. You will walk around an enclosed bay past a beach, a WWII memorial and then to one of the countries most famous forts which was built to defend the city of Boston. The lawn around the fort is also perfect for a picnic lunch. Keep your eye out for planes overhead (close overhead) from Logan airport...
Exploring Boston Neighborhoods: Roslindale
Exploring Boston Neighborhoods: Roslindale
Roslindale, Massachusetts, United States
Easy: 1.3 miles, Full day
Small-town charm with big-city perks.

Roslindale is a tiny corner of Boston that has a small-time neighborhood feel with big-city benefits – classy restaurants, boutique shops and foodie treats – and it borders the Arnold Arboretum, one of Boston’s best green spaces. This section of Boston, 6 miles from downtown, is tucked in between Jamaica Plain, West Roxbury and Hyde Park. Somewhat...
Lynn Heritage State Park to Nahant Bike Tour
Lynn Heritage State Park to Nahant Bike Tour
Avon Hill, Massachusetts, United States
Moderate: 36 miles, Full day
Use this guide to explore the smallest town in New England

This guide starts you off in at the Lynn Heritage State Park and Lynn Museum and takes you out to Nahant to explore the smallest town in New England. You will bike along a very long and narrow beach out to the main residential community where you will explore rocky beaches, search out a cave, visit an old artillery fort and explore the grounds of a...
Dolan Center Launch to Town Landing Lane
Dolan Center Launch to Town Landing Lane
Dedham, Massachusetts, United States
 
Easy: 1.8 miles, 1 hour or less
A very family friendly 1.8 mile paddle along a portion of the Dedham Loop Water Trail on the Charles River.

Dedham Water Trail: Dolan Launch to Town Landing is about 1.8 miles long and located in Dedham, Massachusetts. The trail is great for kayaking / canoeing and normally takes 1 hour or less.
Dedham Public Art Project
Dedham Public Art Project
Dedham, Massachusetts, United States
Easy: 10.0 miles, 1-3 hours
The rabbits have been removed for auction.

This guide will be updated in the future to include other public art in Dedham.
Minute Man National Historic Park
Minute Man National Historic Park
Minute Man National Historic Par, Massachusetts, United States
Easy: 8.2 miles, Full day
Take this tour along Battle Road to learn about the start of the Revolutionary War and the birth of our country.

Use this guide to follow the path the British took as they retreated from the North Bridge area of the Minute Man National Historic Park during the first hours of the Revolutionary War. Along the Battle Road you will follow you will pass by monuments such as where Paul Revere was Captured as well as numerous "Witness Houses" which were local homesteads...
Old North Bridge - Minute Man National Historic Park
Old North Bridge - Minute Man National Historic Park
Concord, Massachusetts, United States
Easy: 1.3 miles, Half day
Take a walk through history to the first shots of the Revolutionary War that gave birth to this country.

Take a walk/ride from downtown Concord to where the first shots of the Revolutionary War were fired at British Soldiers. You'll find several famous monuments, beautiful scenery and a lot of historical information on this journey. Bring a camera and the family along.
Stage Fort Park
Stage Fort Park
Freshwater Cove Village, Massachusetts, United States
Easy: 1.3 miles, 1-3 hours
Take the time to explore the rocky coast, soft beach and massive granite rock in this park.

This is the site of the first settlement in Gloucester. There is a beach, nature trails , ball park, and a massive rock with a plaque on it to check out. If you time it right you may find yourself in the middle of one of the many festivals the city has here.
Gloucester Biking Loop
Gloucester Biking Loop
Dogtown Commons, Massachusetts, United States
Moderate: 30 miles, Half day
Take a loop ride around the coast of Gloucester by car or bike to enjoy the coastal community life.

This is a 25-30 mile loop around Gloucester, Rockport and Anniquam. I've included a bunch of great spots that you should bike by and check out including a beach, several state parks, and a great shopping area at Bearskin Neck where you can get some fresh seafood! Make sure to stop at the beaches and enjoy yourself and if you time it right the sunset...