Boston, MA

Winthrop Shores Dr. and Deer Island

This is the most scenic run you’ll every do around a waste treatment plant. Winthrop is a seaside community located adjacent to East Boston. We’ve put together a nice waterfront run of up to 8 miles incorporating the Winthrop waterfront and then the perimeter path around Deer Island, which features fantastic ocean views.

Start at Winthrop Shores Drive and run for 1 mile along the water toward Deer Isle. At Winthrop Head, use Beacon St. to get onto Shirley Ave., where you’ll leave the waterfront for ~2 miles. Includes a little jaunt out to Coughlin Park along Bay View Ave. and Grand View Ave. Then, enjoy the 2.5 mile loop of Deer Isle. This is a waster treatment plant which has a spectacular path around the perimeter, with 360° water views. Return to the start.

Options: You can just do laps around Deer Isle, ~2.5 miles each.

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Essentials
  • 7.8 miles for both Winthrop & Deer Isle, out and back
  • 181 feet
  • Winthrop Shores Dr. or Deer Isle
  • Good parking at Deer Isle