10 Best Walking Trails In Boston

If you like to walk, Boston is a dream come true.  Amazing architecture, abundant green spaces and spectacular places like the waterfront make it one of the  “most walkable” cities in the world.   Even better, the availability of public transportation gives you added options to explore.
There are so many great walks in the city and the following list is just a small selection. However,  it contains a number of my personal favorites such as the Harborwalk, the Charles River Esplanade and the Emerald Necklace. All the walks listed here are wonderful and were chosen because they are fun for the whole family and because they are beautiful and guaranteed to leave you with a lasting impression.    
One final word on safety.  Boston streets can be very busy and drivers are not always courteous. So please watch out for cars, even on crosswalks. Don’t forget to be alert for bikes because there are more and more bike lanes in the city and it is easy to overlook this silent danger.   
But please, get a bottle of water and a hat and start exploring and above all, have fun!



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.
Arnold Arboretum
The Arnold Arboretum located in Jamaica Plain and Roslindale has been managing a collection of trees, shrubs, and vines since 1872. Meandering through the park are some wonderful walking trails. You will be passing through beautiful woods with flowers, exotic shrubs and ponds. What looks flat on the map is in fact somewhat hilly with Peter's hill in the south being the highest. At the beginning of the trail there is visitors center with all kinds of good information and paper maps.
Distance: 3.5 miles
Features: Park, Paved, Public Batrooms, Information Booth, Little to No Traffic, MBTA Access
Directions: Orange Line Forrest Hill Station is next to the park
East Boston Greenway
The East Boston Greenway is a fun walking trail that follows the path of the former Conrail train line and connects to a number of parks and open spaces in East Boston such as Piers Park, Bremen Street Park, Wood Island Bay Marsh and Belle Isle Marsh. At its eastern end, it joins Constitution Beach and Orient Heights Beach, great spots for swimming and plane spotting. The trail is easily reached by MBTA at both ends.
Distance: 2 miles
Features: Paved, Flat, No Cars, Parks, Beach
Directions: The trail can be accessed on both ends via MBTA. The Blue Line T station Maverick is near its Western end and the Blue Line station Orient Height is near its Eastern end. Parking may be found in the general area or alternatively at Economy Parking Garage.
Emerald Necklace Greenway
The Emerald Necklace is a walkers dream with beautiful trails across many parks starting from the center of the city. This chain of parks was designed by Frederick Law Olmsted in 1888 with the intention to create an interconnected green space that reaches from the Boston Common to Franklin park.
You will be passing through the most enchanting and varied of areas; from busy cityscapes with museums, shops and restaurants to wild nature preserves; from bucolic trails with arched bridges and flower gardens to ponds and lakes where waterfowl gathers. Most of the trails are protected from cars but there are a few street crossings and connections that need to be accomplished. A few times it can be a little tricky to make the connection from one park to another, especially near Fenway. Simply follow the map on the right and mind the signs on the road.
Distance: 6 miles
Features: Paved, Flat ,Mostly no Cars, Some Street Crossings, Parks, Ponds, Boating, Picnics, Waterfowl, Bathrooms
Directions: It is very easy to connect to the MBTA via the Park Street station on the Red Line and the Forest Hill Station of the Orange Line. The Route will take you from the Boston Common to the Back Bay Fens via Commonwealth Avenue, to the Riverway and the Olmstead Park and Jamaica Pond. From there you need to follow the Arborway road to connect the the Arboretum and if you like you can join the Arboretum trail or continue on to Franklin Park
Fresh Pond Trail, Cambridge
Fresh Pond is a small kettle-hole lake left behind from glacial times and it has been used as an ice-making operation in the 19th century. Today it is a wonderful park and a water reservoir for the city of Cambridge. Circling around the pond is a pretty walking trail that is mostly protected from the street and very kid-suitable and dog-friendly.
Distance: 2.2 miles
Features: Paved, Flat, Scenic, Bathrooms, Dogs on Leash, Dogs off Leash area
Directions: The nearest MBTA T station is about a mile away at the Porter Square Red Line station. Its about a 10 minute walk to the pond. There is some parking on the Waterworks parking lot and it may be possible to find parking nearby on the streets.
Jamaica Pond Trail
Jamaica Pond is a glacial kettle lake with great natural beauty and there is a popular walking/running trail that takes you around the lake. The trail is surrounded by a natural landscape of mature trees and shrubs. Sailboats criss-cross the lake and you can rent one at the boathouse. The fields above the Sugar Bowl are the perfect place for a picnic. The lake is stocked with fish and permits are available at the boathouse.
Distance: 1.5 miles
Features: Paved, Flat, Scenic, Waterfront, Fishing, Boating, Picnics, Bathrooms, Dogs on Leash
Directions: A 10 minute walk takes you to the Orange Line Green Station and Stony Brook Station. MBTA buses 35, 38, 39, 41, 192 stop nearby. Street parking is available and more parking is available at its Northern Side near Ward’s pond. Public bathrooms are available at the boathouse
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.