Cape Cod, MA

Wellfleet Tour

Wellfleet is one of the prettiest towns on the lower Cape. There’s a lovely, classic main streets, and then a road along the water with shops & restaurants heading down to beautiful Wellfleet Harbor. There are a few options here:

  • Quickie 2.4 loop. Start on Main St., down Commercial/Kendrick to the harbor, and then back up Chequessett Neck Rd., back up to Main St.
  • Longer loop: 3.0 miles. At intersection with Chequessett Neck Rd., take a left on Hamblen Farm Rd., and then a right on Old Chequessett Neck Rd., back to the center of Wellfleet.

For a wonderful longer run, from Wellfleet Harbor, take a LEFT on Chequessett Neck Rd., staying along the water, and over the bridge, to the Great Island parking lot. It’s 3 miles one-way.


  • Short loop: 2.4 miles. Medium Loop: 3.0 miles; Out to Great Island: 3.0 miles one-way
  • A bit hilly
  • Main St. Wellfleet
  • Park in Wellfleet Center