Boston City Walks promise adventure, fun, and, above all, variety. You will find busy downtown routes with shops, restaurants, amazing architecture, and walks that feel like the coast of Maine with its wild seascapes and remote islands.
Boston City Walks promise adventure, fun, and, above all, variety. You will find busy downtown routes with shops, restaurants, amazing architecture, and walks that feel like the coast of Maine with its wild seascapes and remote islands. Be prepared; Boston city walks are always full of surprises and mini-adventures. Take Castle Island, for example, once a fortress for defending Boston Harbour, with its mile-long causeway right across the ocean and spectacular views of the outer harbour, the islands, and all kinds of ocean craft. Explore the city on the Boston Harborwalk, a wonderful public walkway right in the heart of the Boston Waterfront. You will be walking on the boardwalk right at the edge of the water, meandering in an area between high-end condos, parks, wharves, marinas, cafes, and beautiful hotels and restaurants. So get ready, get your hat and a bottle of water, and let's go exploring!
Boston Freedom Trail![]() The FreedomTrail is a famous Boston historic walking trail that connects 16 historically important Boston sites. Among the most famous locations are the State House, Park Street Church, Old South Meeting House, Old State House, Site of the Boston Massacre, Paul Revere House, USS Constitution and the Bunker Hill Monument. Starting at the Boston Common, all 16 sites are marked by a brick line in the street. In Faneuil Hall, there is a visitor office for the Freedom Trail by the National Park Service where they offer free maps and guided tours. Distance: 2.4 miles Features: Paved, Streets, City, Historic, Bathrooms Directions: There are many access points to the Freedom Trail but if you like to start at the beginning on Boston Common, exit the MBTA at Park Street via the Red LIne and Green Line. Parking downtown can be tricky but there are many Parking Garages available in that area. There are also a number of Hop On - Hop Off buses available that stop at many of the trail locations |
Harbor Walk![]() The Boston Harborwalk is a wonderful public walkway right in the heart of the Boston Waterfront. You will be walking on the boardwalk right at the edge of the Boston Harbor and meandering in an out between high-end condos, parks, wharves, marinas, cafes and beautiful hotels and restaurants. The trail is part of the growing Harborwalk system that will connect 47 miles of waterfront from East Boston to Quincy. Start at the North End and follow the Harborwalk signs. Take a left turn at the second bridge on Congress Stret next to the Boston Teaparty and cross the bridge and then continue the harborwalk next to the Children's Museum and Fan Pier Park, which follows the waterfront with amazing views until you pass by the Institute of Contemporary Art (ICA). Distance: 5 miles Features: Paved, Boardwalks, Sidewalks, Scenic, Mostly Car Free, Some Crossings, Restaurants, Sites, Museums, Public Transportation, Bathrooms, Disability Access Directions: The closest Subway (T) station is the Blue line Aquarium stop. Other possibilities are Hay Market Station (Orange Line), North Station (Orange Line) or South Station (Red Line). The nearest Parking Garage is 75 State Street Parking. |
Charles River Esplanade![]() The Charles River Esplanade is probably the most popular walking trail in Boston and for good reasons. Just steps away from downtown, this green pearl meanders along the blue Charles River with sailboats darting across, tour boats plowing their trade and people just enjoying themselves picnicking, reading, running, biking or walking. You can opt for an easy walk up the river on the Boston side and maybe cross over to the Fenway area or you can be more ambitious and do the loop, crossing over to the Cambridge side on one of the bridges and then head east along the river to the Museum of Science and back to the Esplanade. Distance: Up to 16 miles of trail Features: Paved, Some Sidewalks, Waterfront, Scenic, MBTA, Bathrooms Directions: Take the Red Line to the Charles/MGH Station. Turn left as you exit the station onto Charles Street, then turn right toward the footbridge to the Esplanade. There’s limited street parking near the Hatch Shell, but the Charles Street Garage is close by, as are garages at Massachusetts General Hospital. |
Castle Island- South Boston![]() Castle Island is one of the most magical places in Boston. Originally built as a fortress to defend access to Boston harbor, it overlooks the city, the islands and the waterways around Boston. What was once a fortress, is now a state park and one of the most attractive places in Boston for walking. The causeway that now connects the island with South Boston takes you literally out sea. It is a great vantage point from which one can truly experience the beauty of the nearby islands and all the comings and goings on the busy harbor. Being a circular walking trail, it invites you to make more than one turn and get some great exercise and plenty of fresh air. Distance: 2 miles Features: Paved, Flat, Park, Concession stand, Ice Cream, Fishing pier, Parking, Bathrooms, Dogs on leash, Picnic areas, Playgrounds Directions: You can reach Castle Island with Bus 7 and 11 from South Station. There is ample parking if you come by car. |