Portland, a peninsula, is surrounded by Casco Bay, a charming expanse of small islands and the green-blue Atlantic Ocean. Take it all in by running the Eastern Promenade Trail, a 4.15 mile dash that follows an old rail bed along the water’s edge and around the city’s Back Cove. The trail is paved, well-marked and mostly flat. Start at the ferry terminal and head north along Commercial Street before veering right to run alongside the train tracks.
Branching off the Eastern Promenade Trail, the Back Cove pathway rounds a tidal inlet that contours much of Portland into a peninsula. This 3.6 mile trail is by far the most popular run, featuring a well-groomed, level walkway with room for cyclists. Conveniently located next to a parking lot, and with on street parking and views of Portland’s skyline, the trail is worth the excursion even if you’re not a runner. This picks up where the Eastern Prom trail let off, and circles back onto it.
Tip to tip, Congress Street stretches 4.7 miles through Portland’s diverse neighborhoods, from suburbs to office buildings, up hills, down through the Arts District before ascending—and ending—at the Eastern Prom. Along the way are the city’s best attractions: Longfellow Square, Merrill Auditorium, the Longfellow House, the Portland Observatory, and scores of trendy restaurants along the route. If you need more miles under your belt, the Back Cove and Eastern Prom trails are near the end.
Short, simple, and sights: a run around Portland’s historic shopping center hugs the shore, passing through tall, wholesome brick factories-turned-high-end shops and apartments. The water is the highlight here, with the Casco Bay practically lapping at your feet. With numerous breweries, bars, restaurants, and boutique stores within arm’s reach, it’s a good thing this loop is so short. Starting near the ferry terminal (a good point for embarking to Peakes Island) head south along Commercial Street until you hit High Street, take a right, pass Portland’s Museum of Art and take the next right onto Congress Street. Congress Street will take you to Lincoln Park and the stately courthouses, then take Franklin Street right to complete the loop.
Calm, quiet and family-orientated, the West End is an ideal place to live and an ideal urban playground for runners. This 2.2 mile loop passes some of Portland’s great landmarks: the Victoria Mansion, the brick “cottages” on Bramhall Hill and the Western Promenade. Other than the hill, the run is mostly flat and the sidewalks are usually sparser than downtown Portland or the eastern end. Start on Commercial Street, run south to Park Street, up Spring Street, and to Waynflete School.
Few people know that the 30-minute ride off Portland’s coast to Peaks Island falls within city limits. While we don’t suggest jogging in place while you embark and wait to land, there are plenty of secluded, tree-lined, ocean-viewing streets to explore if you’re interested in an off-the-beaten-path run. A road runs the perimeter of this residential, commuter island, and a loop runs about four (mostly flat) miles. Ferries run every hour or so.
Quiet, secluded, free, and technically an island (the causeway connecting it to the mainland juts from the water on stilts), Mackworth is a prime spot to run if you like clear, wooded paths along the ocean. Named after a Maine governor (his beloved dogs and horses are buried here) the island is home to the school for the deaf. Technically Falmouth but within the waters of Casco Bay, the island is a premier place to run, and a sand beach is the perfect place to cool off afterward.