8 Beautiful Running Routes In Boston

For a city that hosts one of the most watched marathons of the year, it is natural for there to be a strong running community in Boston. But sometimes to locals, Boston can feel cramped and crowded. Runners know all too well the struggle of running through Downtown, especially right after work. Of course, Boston crowds are nothing compared to some cities, and Bostonians have the benefit of having a number of open spaces of which to take advantage. Now that summer is ending, grab your running shoes and hit these eight beautiful outdoor trails.

Boston Esplanade

This could be one of the most popular running routes in Boston, so if you don’t like a crowd, avoid this route during peak times, like at the end of a workday or late morning on weekends. The 1.5-mile stretch of park runs along the Charles River and offers a spectacular view of the cityscape. Alternatively, cross the Mass Ave bridge and run down the Cambridge side of the river to run parallel to the Esplanade – you’ll have a view from across the river and an extended run.
Distance: 1.5 miles

Jamaica Pond

Commonwealth Avenue

Commonwealth Avenue is one of the best-known streets in Boston, and the straight road through Back Bay makes it the perfect running track. Run in the middle park area of the Comm. Ave Mall, and you’ll be surrounded by trees, picturesque Back Bay brownstones, and an eight-block stretch before you hit a turn. Since the road is broken up by perpendicular streets, you’ll often see runners use the park section for sprints, pausing at each street if cars have the right of way.
Distance: .8 miles

Fresh Pond

This reservoir and park in Cambridge feature a popular 2.25-mile path for strolling, running, and dog walking. While the pond is strictly a reservoir today for the city of Cambridge, it was once used to harvest ice in the wintertime for shipping around the nation. The pond itself is 55 acres, and the entire surrounding land spans 162 acres.
Distance: 2.25 miles

Memorial Drive

One of the best parts about Memorial Drive is the Sunday closures. Every Sunday, from late April to the beginning of November, the Department of Conservation closes the street from 11:00 a.m. to 7:00 p.m., leaving it free for pedestrians. When it’s open to motor traffic, it still makes a great running trail, following the Charles River, similar to the layout of the Esplanade.
Distance: 3.9 miles

1. Boston Common and Public Garden

Park, Memorial

While this location definitely appears on the shorter side, it can make a great makeshift track in a pinch. A circle of the Common and Garden totals 1.5 miles, complete with challenges like the menacing Beacon Hill. Come spring, you may see marathon trainers tackling this hill, and it’s an oft-used location for fitness groups like The November Project.
Distance: 1.5 miles

Day Boulevard

Unfortunately, while plenty of these trails follow the water’s edge, it can be tough to find a beach in the city fit for running. Thanks to the William J. Day Boulevard in South Boston, this problem is solved. The 2.6-mile trail passes by Moakley Park and stretches to Pleasure Bay, ending at Castle Island, which makes a great running route in itself.
Distance: 2.6 miles

Boston Harborwalk

This is another route to plan before going, as at the height of the summer tourist season, it can get crowded in spots. The advantage of the Boston Harborwalk is that you can really make it any distance you would like. Currently, 38 miles of the walk connects the North End, Downtown, South Boston, and Dorchester. When the revitalization project is completed, the walk will include 47 miles from Dorchester to East Boston. If you’re not sure where to start, try taking off from the New England Aquarium, which runs all the way to the Seaport District. If you wanted to make it a loop, you could even circle back through the Rose Kennedy Greenway.
Distance: 38 miles to choose from

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.