To experience the city's busy shoreline and grand views of Casco Bay, walkers, cyclists, and in-line skaters head out on the Eastern Prom Trail.
Beginning at the intersection of Commercial and India streets, this paved trail follows the old railroad tracks of the Maine Narrow Gauge Railroad Co. & Museum. There are plenty of places with benches and tables for a picnic break along the way. From the trailhead, it's about 1¼ mi to the small East End Beach.
You can continue along the trail, pass underneath busy I-295, and reemerge at Portland's Back Cove to walk along a 6-mi loop; or you can return to the Old Port by either backtracking along the trail or heading up a grassy hill to the Eastern Promenade, a popular picnic spot and playground.
Take a left back toward the Old Port. Starting down the hill, a gazebo and several old cannons to your left indicate the small and unmarked Fort Allen Park. Use one of the coin-operated viewing scopes to view Ft. Gorges, a Civil War-era military garrison that was never used.
Where the Eastern Prom becomes Fore Street, either head straight back into the Old Port or take a left on India Street, which will bring you just about back to where you started.
Plan an hour to walk to East End Beach and back; add an hour or two if you continue along the Back Cove Trail.