13 Hidden Gem Running Routes Around Boston

Ditch the Esplanade and try these great routes.

A workout routine is a great thing to have. Falling into a rhythm keeps you consistent, and making exercise a habit ensures it actually gets done.

But when your routine starts to feel too routine, you get bored—and that’s when you fall into a workout slump.

Runners, who tend to be creatures of habit, are especially susceptible to this phenomenon. So we consulted an expert: Mark Lowenstein, a Brookline resident who has written three books about running in Boston, and who now heads up Great Runs, a website that uncovers the best places to run in more than 150 cities worldwide.

Here, Lowenstein shares some hidden gem routes that will shake up your routine—and get you miles away from the Esplanade.


  •  Lowenstein calls Fresh Pond the “best off-road option in Cambridge, outside the Charles River Paths.” It’s roughly 2.5 miles around the pond, making it easy to adjust your mileage.
North Point Park

North Point Park photo via istock.com/drnadig


  • Yes, we know we promised to get you off the Esplanade. But if you follow the path into Charlestown, you’ll leave the crowds behind. “Just across from the Museum of Science is a real gem, North Point Park, where you can then take the pedestrian bridge to Charlestown and continue for another two-plus miles along the Harborwalk, to Spaulding Rehab [Hospital],” Lowenstein says.

East Boston:

  • Start on the waterfront path that begins at the Hyatt Harborside at Logan Airport. Follow it to Piers Park, then continue on to the East Boston Greenway, which runs parallel to Bremen Street. Follow it to East Boston Memorial Park. The total distance is roughly 2.5 miles.
  • “Drive out to Deer Island, which has a 2.6-mile path around the 60-acre park, with great water and skyline views,” Lowenstein says. “It is undoubtedly the best run you’ll ever do around a wastewater treatment plant.”
Sudbury Aqueduct

Sudbury Aqueduct photo via wikimedia commons/magicpiano


  • Try the Upper Charles River Path. “Many folks doing the Charles River Path think it ‘ends’ near Watertown Square,” Lowenstein says. “But the path continues west for six more miles, through Watertown, Waltham Center, and Newton to very near the Newton Marriott, nearly all off-road and fairly well signed.”
  • “Another hidden gem is the Aqueduct Path,” Lowenstein says, adding that it’s “a little tricky to find in parts.” Pick up the path across from the Whole Foods on Walnut Street and continue three miles to Waban, near the Starbucks.

North of Boston

  • The Mystic River Paths, winding through Medford and Somerville, offer nearly three miles of pathway stretching from Somerville’s Assembly Square to the Mystic River Reservation. Another section, running parallel to the Mystic Valley Parkway, offers 2.5 miles of paths stretching from West Medford into Arlington and Winchester, all the way to the Mystic Lakes.
  • Take the T out to Revere Beach and “run the three-mile boardwalk or enjoy the hard, packed sand.”
  • The Nahant Boardwalk, stretching from Nahant to Swampscott, boasts three miles of water views at sites including Nahant Beach, Kings Beach, and Red Rock Park.

South Boston:

  • “My favorite run in Boston is the waterfront run from Castle Island to the JFK Museum, and the UMass Boston campus,” Lowenstein says. “Five-plus miles of ocean views and off-road paths.”

South of Boston

  •  Quincy Shore Drive offers two-plus miles of waterfront running on a nice, wide sidewalk.
  • The Neponset River Greenway runs along the Red Line tracks for about three miles, “so you can do it one way and hop back,” Lowenstein suggests.


  • “Wellesley, in my opinion, is the number one suburb of Boston for running, with great trails, off-road paths, and quiet residential roads,” Lowenstein says. Try the Crosstown Trail, which covers the nearly five miles from Newton Lower Falls to Wellesley College. There are wonderful trails around Wellesley College, including 2.5 miles around Lake Waban,” he adds.