Known as “The Prettiest Village in Maine,” Wiscasset is a choice town for a residential/commercial run with an old timey seaport feel. With a loop through the center of town, you can run past architectural landmarks including The Nickels-Sortwell House, Castle Tucker, the 1812 Jail, and the Octagon House. The foliage change over Wiscasset Harbor — accented by boats and railroad bridges — is not to be missed, so make sure to finish off your run with a trip to the famous Red’s Eats. The line is almost always curving around the corner, but with these views, you won’t mind waiting.

We’ve mapped out a gorgeous 5-mile run highlighting Wiscasset and over the bridge to Fort Edgecomb State Park. Start off on Main Street (Route 1) and follow it over the bridge to Davis Island (home to Fort Edgecomb State Park) for some great water views. Double back over the bridge and return via Water Street and Fore Street for a look at the historic Castle Tucker. From there, High Street will take you back to your starting point.

  • 4.6 miles, out and back
  • Main St. & Water St., Wiscasset