The Best City Walks in Boston

Best City Walks in Boston

Looking for free things to do in Boston? Well, there is more to walk in Boston than just the Freedom Trail! You can learn more about your own neighborhood or discover new neighborhoods all while exploring Boston’s rich history. If you’re looking to show visiting friends and family around the city or are a visiting tourist yourself, these following walks showcase unique views of Boston and give you some light to moderate exercise. The best part? Walking is free and these are all accessible by the MBTA. 

Pictured is Boston's Women Memorial

Photo by USA Today

Commonwealth Ave Monument Tour is a 2.2 mile walk that goes down the Commonwealth Ave Mall, stretching from the Boston Public Garden to Massachusetts Ave, and past nine sculptures and memorials including Vendome Firefighters’ Memorial and the Boston’s Women Memorial. Planned in 1856 by Arthur Gilman, he was inspired by Parisian boulevards and London’s green spaces. Enjoy your stroll under rows of elm trees and admire the beautiful landscaped flowerbeds. This flat walk is great for all skill levels and has benches along the way to rest. 

Pictured is fountains in the Rose Kennedy Greenway

photo by the Rose Kennedy Greenway

Rose Fitzgerald Kennedy Greenway is a 1.9 mile walk on the ribbon-shaped Greenway that goes between the Italian North End and Chinatown and snakes through the Financial District and the Waterfront. Along the way you will come across Faneuil Marketplace where you can stop to shop and explore. You can even stop for a bite at one of the many food trucks on the Greenway. There’s great spots for kids too, like the Greenway Carosuel and water features that allow for a playful cool-down. 

pictured is the Boston Seaport segment of the Boston Harborwalk

Photo by Boston Seaport

Boston Harborwalk - Up for a challenge or a long-term goal? The Boston Harborwalk is a 40-mile public walkway that was designed to open up the city by connecting the public to the waterfront. The trail hugs Boston’s coastline from Chelsea Creek to the Neponset River and goes through neighborhoods including East Boston, Charlestown, North End, Downtown, Fort Point, South Boston and Dorchester. No need to do it in a day of course, as there is plenty of spots worth stopping along the way including nine public beaches like Castle Island and M Street Beach and museums including the ICA, the New England Aquarium, and the Boston Tea Party Ship & Museum. To get the best tour of Boston and hit all the landmarks, check out doing segments of this walk or make it a goal to complete it all over a period of time!

Photo by Boston Trolley Tours

The Black Heritage Trail is a 1.6-mile walking tour through Boston’s Beacon Hill and explores the history of the 19th century African American community who lived primarily on the north slope of the hill. The tour has 14 historic sites along the way including schools, churches, businesses, and residences that highlight the black community of the 1800s. Many of highlighted figures were abolitionists who housed freedom seekers in the several stations of the Underground Railroad that you will see on the tour. You may enter the Abiel Smith School and the African Meeting House. Book a tour led by a National Park Service Ranger to the full educational experience.


Photo by Emerald Necklace Conservancy

Jamaica Pond - Take a step outside the heart of Boston and take the 1.5 mile loop around Jamaica Pond. Tranquil and scenic, this loop is covered by trees and has resting spots along the way. The wide sidewalk around the pond is suitable for wheelchairs and strollers. The green space above and surrounding the pond allows for creating a day excursion with space for picnics and outdoor gatherings. Enjoy the views of the beautiful houses around the pond too!


Photo by Esplanade Association 

Charles River Esplanade is a walkway that stretches for 3 miles along the Charles River, hugging the edge of Boston with scenic views of Cambridge across the water. It is wheelchair and stroller-friendly walkway and includes a bike path (with the Beacon Street Blue Bike station nearby). Stop by Charles Street or the Back Bay beforehand for a bite to eat and enjoy your food on one of the many benches or docks. If you’re looking for an even closer view, or a different type of exercise, stop at The Community Boathouse to rent a kayak or sailboat!


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