This out-and-back run takes you through the Old Port’s historic shopping district, along Portland’s working waterfront, and across the Casco Bay Bridge to South Portland. 

With Tommy’s Park behind you, go south on Exchange Street, which is home to stores such as trendy clothing retailer Bliss and jeweler D. Cole. Take a slight left at the end of Exchange, and continue down Moulton Street, across the cobblestones. Turn right onto busy Commercial Street, which puts you on the route of the Thanksgiving Day 4-miler. You’ll pass Portland’s “love locks,” padlocks that sweethearts attach to a chain-link fence, which are inspired by similar collections in Paris, New York, and other cities. After about three quarters of a mile, look for Harbor View Memorial Park, which will give you access to the Casco Bay Bridge. This bridge, built in 1997 to replace the Million Dollar Bridge, provides wide walkways and a bird’s eye view of the Portland waterfront. As you near the end of the bridge, take a left down the ramp to South Portland’s Thomas Knight Park, which is your halfway point. Take in the view, and then retrace your steps back to Portland. Across the bay to the west, you’ll see the Sprague Energy tank farm. Several large oil storage tanks bear painted designs, part of a public art installation commissioned by the Maine Center for Creativity. Return to Tommy’s Park the same way you came.