The Best Walking Tours in Boston

Boston Common

Boston Common is a famous central park in downtown Boston. It's also the oldest city park in the country, dating back to 1634. The park spans 50 acres and has a botanical garden and a pond where you can enjoy the iconic experience of taking a Swan paddleboat. Visitors can also find a playground and other fun activities for kids. During the winter months, an ice skating rink is set up, and a huge Christmas tree and other decorations adorn the park.

Boston Public Garden

The Boston Public Garden, dating back to 1837, was the first botanical garden in the country. It is heavily influenced by the Victorian era with seasonally flowers that change regularly. The Boston Public Garden is an iconic park in the city with its famous Swan Boats that you can use to paddle around the pond. There are flower beds that line the paths and many places to enjoy a leisurely stroll. Boston Public Garden is a relaxed and romantic setting and you'll often see weddings or wedding pictures being taken in the park.

Freedom Trail

Boston's famous Freedom Trail is a three mile long route that goes by 16 of the city's most notable historic sites. The trail is marked by red bricks in the sidewalk and there are footprints through the street crossings. There are a number of brochures available in different places, including the city's visitor center (found in Boston Common), that will tell you about the history along the trail. Notable sites along the route include the Old Granary Burying Ground, King's Chapel Burying Ground, Old South Meeting House, and the Old State House. The route begins in Boston Common and ends across the bridge in Charlestown at the USS Constitution and Bunker Hill Monument.

The Esplanade

The Esplanade is a riverside park in the Back Bay neighborhood. It has a number of charming footbridges including Arthur Fiedler Footbridge. Within the park you'll also find the Hatch Shell bandstand, which is where the Boston Pops Orchestra holds its annual Fourth of July celebration. There are also a number of movies and concerts in the park during the warmer months. The park is a nice place to explore with a number of nice running trails, or you could enjoy a walk beside the river. Also here is the Esplanade Playground for kids which is quite large.

Spectacle Island

Spectacle Island is part of the Boston Harbor Islands National Recreation Area. It's just 20 minutes by ferry from downtown Boston and it offers a sandy oasis that's the perfect day trip from May through Columbus Day. There are lifeguards available during the summer months and a visitor center with a few exhibits. Many locals consider this to be one of the best beaches in the area. It also offers nice views of the city skyline when the weather is clear. For runners and walkers, there's a five mile loop that goes around the island.

Rose Kennedy Greenway

This stretch of interconnected parks running through Downtown Boston is a great spot for a walk, run, or even a bike ride - or for just exploring the city. Starting at the north in North End near the Haymarket T station, the connected parks and trails run south through the Waterfront and Downtown areas until they reach Chinatown Park. Along the way, visitors will find smaller parks, interactive fountains, a carousel, gardens, public restrooms, restaurants and cafes, and more. If you're wandering along the path, it's quite easy to make short detours to explore the various attractions and historical spots of Boston.

North Point Park

Located on the river, this park has a playground, jogging and biking trails, a dock for boats and stand-up-paddleboards, and some nice lawn space for relaxing. It also has great views of the water and the skyline.

Moakley Park and Carson Beach

Located in South Boston, this large park sits on the shore and has a beach and a kids playground, along with ball fields, too. The Dorothy Curran Playground has a terrific nautical theme that can keep your kids entertained for hours (and it also has a spray area in the summer months). Or, stroll over to either Carson Beach, L Street Beach, or M Street Beach on the other side of the field for some fun in the sand. The South Boston Bark Park at the upper end of the park will keep the dogs happy, too. Tennis courts, basketball courts, ball fields, and more can be found here, too. And finally, this is a good spot to hop on the trail that runs along the waterfront for your walk, run, or bike ride.

Harborwalk

The Boston Harborwalk is a nearly complete project designed to connect the waterfront walkways along the harbor. Currently, visitors can enjoy over 43 miles of walkways along the harbor, much of which runs along the main Waterfront and North End areas of central Boston near many of the city's top attractions. Along the trail, visitors can find public restrooms along with restaurants, cafes, shops, tourist attractions, marinas and wharfs, ferry terminals, and more. While it's quite easy to run and jog along the trails, bikes are only allowed along specific sections which have less pedestrian traffic. Bikes are allowed on the section from the Neponset River Greenway to Castle Island State Park. See the website and map for more details if you're looking to bike.

Castle Island Park & Fort Independence

Located in South Boston, this is part of the Boston Harbor Islands National Recreation Area. There's a nice white sand beach where you can relax. Fort Independence is a granite fort dating back to 1851. Within the park there are two walking and running trails. For the easiest and shortest option, try the Castle Island Loop. The longer trail is the Pleasure Bay Loop. There are also great areas where you can enjoy a picnic and a nice playground that is perfect for kids who like to climb, jump, and run.

Black Heritage Trail

The Black Heritage Trail is a 1.6 mile walking trail through Boston's Beacon Hill neighborhood that showcases a variety of historical sites focused on the lives of Black Americans from the time periods around the American Civil War. During this time in history, Black Americans in this area of Boston fought to abolish slavery and gain the same freedoms and rights as other Americans. Part of the trail centers on the Museum of African American History while other locations are historic residences, schools, and meeting houses.

Back Bay Fens

Where Back Bay merges into Fenway, this large green space has a variety of interesting things to do and see. In addition to walking and biking trails, visitors can explore the rose garden and World War II memorial. Also here is an area of community gardens, a playground for the kids, and ball fields.

Arnold Arboretum

The Arnold Arboretum spreads out over 281 acres and is a major horticultural research institution. The arboretum was designed by C.S. Sargent working with Frederick Law Olmsted. It was designed with a less formal intent than most botanical gardens and today it offers a relaxing place to explore and enjoy nature.