Great Runs in Portland, ME


Lobsters, lighthouse, and ocean— the things that come to mind when you think about Maine’s largest city, Portland. Tourists flock to the city to visit the historic Old Port district along Portland Harbor; the Arts District that runs along Congress St in the heart of the city; and the Portland Head Light, located in nearby Cape Elizabeth, which marks the entrance to Portland Harbor. Portland’s known for its hip culture, with a mixture of arts, outdoor activities, fashion, and amazing culinary scene, all along the quintessential Maine coast. No wonder this town was named one TripAdvisor’s Top 10 Destinations!

Portland’s running highlights center on the ocean. The Eastern Promenade and Back Cove are the must-dos from downtown. The Harborwalk is a great way to explore east and south Portland, and a lighthouse, while Cape Elizabeth features Portland’s swankiest real-estate and some lovely running. Our runs in the downtown and southern Portland areas can be standalone or easily mixed and matched.

This is a fairly small city with a compact downtown. Central Portland is a peninsula inside of I-295 and has many of the city’s commercial highlights. Cross the Casco Bay Bridge to get to South Portland and Portland Head Light. Cape Elizabeth is 8 miles south of downtown.

Portland is a northern city whose climate is influenced by the ocean. Summers are mild and pleasant, with high temperatures averaging near 80F (26C). It can get humid. Winters are very cold, but somewhat moderated by the ocean, compared to interior and northern parts of Maine. Average January highs are near freezing with lows 13F. Portland receives about 60 inches of snow a year, so snow-covered and icy roads and paths are a factor in winter. Annual precipitation averages 47.2 inches, copious year round, but the summers tend to be slightly drier. Fall is gorgeous and hangs on till the end of October.

Portland has around 66,000 full-time residents, but with the addition of its seasonal visitors and part-time residents in the summertime it can grow to two million! Portland stands as one of the few working waterfronts left in the United States, acting as New England’s largest tonnage seaport and second largest fishing port. The city is located on a peninsula in Casco Bay with access to many islands. Run your way through this historic and funky seacoast town with our iconic routes and don’t forget to stop for a lobster roll when you’re done!

Iconic Routes:

  1. South Portland Greenbelt Pathway
  2. Harborwalk Trail
  3. Eastern Promenade Trail
  4. Back Cove Trail
  5. Congress Street
  6. Cape Elizabeth
  7. Peak Island
  8. Old Port
  9. Mackworth Island Trail
  10. West End

The Routes

Eastern Promenade Trail
4.15 miles Out and Back. Parking: Commercial St. [MAP]


The Eastern Promenade Trail is one of Portland’s centerpieces, running from downtown, along the water, to Back Cove. The waterfront trail is built along an old rail corridor and offers spectacular harbor and ocean views. Highlights include ocean views, Fort Allen Park, East End Beach, and the Casco Bay Community Garden. The route starts at Commercial & India St Bus Stop (easy access for commuters or travelers without cars). At the end of Eastern Promenade Trail you’ll take a right to connect onto Bayside Trail, which will loop you onto Back Cove Trail for a short stint. You’ll then connect back onto the Eastern Promenade Trail to loop back to the start. This route is mostly flat but has a small rise near the Portland Water District treatment plant, and another near Tukey’s Bridge, before it connects to the Back Cove Trail. It can be a tad confusing when merging with the Bayside Trail around the tangle of highways. This is an out and back, or can be combined with a larger loop involving sections of the Bayside and Back Cove trails.

Back Cove Trail
3.6 miles. Start: Back Cove Park. Parking: Back Cove Park/Preble Street Extension/Payson Park [MAP]


This is one of the oldest and most popular trails in Portland. Back Cove offers amazing views of the Portland skyline, with water views for the entire 3.5 mile loop around this nearly circular estuary basin on the northern side of the City of Portland. This loop is mostly flat with a slight rise along the stretch that parallels I-295. The Back Cove Trail connects to the Bayside & Eastern Promenade Trail under Tukey’s Bridge. This paved trail traverses the heart of revitalized commercial and residential neighborhoods in Bayside and East Bayside. Back Cove Park and Edward Payson Park can be very festive on a nice day. It offers convenient access to local businesses — numerous breweries, coffee shops and stores. It’s also easily accessible to folks living or staying in West Portland. For a longer run, connect to the Eastern Promenade and Bayside trails, toward downtown.

Congress St
4.7 miles one-way [MAP] Parking: Booklawn Memorial Park


Congress St. stretches nearly 5 miles from Portland’s southwestern border through a number of neighborhoods before ending overlooking the Eastern Promenade on Munjoy Hill. It’s a good way to anchor a run in Portland. Our route trail at Booklawn Memorial Park, the westernmost most part of Congress Street. Congress Street provides a glimpse of office buildings intermingled with historically preserved buildings such as the Wadsworth-Longfellow House, the 19th century childhood home of the poet. This route also passes the Stroudwater River Resevoir and Fore River, which separates Portland and South Portland. Some side jaunts off Congress St. include Deering Park and University of Southern Maine campus (3-mile mark), Western Promenade, and some of the lovely, small streets of downtown Portland.

Old Port Tour
2 mile loop [MAP] Parking: Casco Bay Parking Garage


This is a nice tour of Portland’s Old Port main downtown area. Old Port is one of the most successful revitalized warehouse districts in the country. Seamlessly connected to the waterfront, Old Port is both a working waterfront and a local shopping, dining, residential, and entertainment district. Taking a walk at the water’s edge along Commercial Street provides a window into the working waterfront. Just steps from the water, you can walk down the cobblestone streets and experience the charm of this district. Along the way you’ll pass multiple wharfs, where short loops will take you out to the water’s edge. After you take a right on High St, you’ll pass Portland’s Museum of Art. A right onto Congress St, will bring you past Lincoln Park. From there you’ll take a right onto Franklin St to loop back towards the ferry terminal.

West End Tour
2.2 mile loop [MAP] Parking: Western Promenade Park


The West End neighborhood is famous for its architecture and boasts some of Portland’s largest historic homes including the historic Victoria Mansion museum. This route starts at Western Promenade Park, which overlooks the Libbytown and Stroudwater neighborhoods of Portland and beyond. A highlight of the run is the steep ascent to Bramhall Hill, where you’ll find yourself in one of the best-preserved Victorian neighborhoods in the country. At the top you’ll take a right onto Congress St. To connect the loop, take a right onto State St. and a right onto Danforth St. To extend, take a right onto Vaughn Street, connecting you back onto Bramhall, where you’ll take a left to go down the hill back towards Western Promenade. If you loop all the way back to the start, it’s 3.7 miles, otherwise the loop is 2.2 miles. Each of the streets mentioned has it’s own unique historic houses and beautiful scenery, that the West End is known for. Other opportunities to extend this run are to enjoy some of the west end streets, south of State St. and west of Danforth St.

South Portland Greenbelt Pathway
5.4 miles one-way Parking: Bug Light Park [MAP]


The Eastern Trail is a scenic ~65 mile bike route (mostly not paved) that starts at the Piscataqua River in Kittery and ends in South Portland, Maine. The Portland section of this trail incorporates the South Portland Greenbelt Pathway. We’ve mapped out a 5.4 mile one-way route, starting at Bug Light Park. This nearly 9 acre park has expansive views of Portland Harbor and the city’s skyline. It is also home to the Portland Breakwater Lighthouse, built in 1875, it is one of Maine’s most elegant lighthouses. The route heads south along the South Portland Greenbelt. At just over two miles, cross both Waterman Dr. and ME 77, then continue on the path. This is where the Eastern Trail becomes part of East Coast Greenway. After about a half mile, take a left on Chestnut St, which will bring you onto a short on-road section of residential streets. A right on N. Kelsey St. and then a quick left brings you back onto the trail. Cross at Broadway & Evans St. After 1.5 miles, you’ll enter Wainwright Athletic Complex, where restrooms are available. Run through this section until Gary Maietta Way which will bring you to the 5.4 mile point.


Haborwalk Trail
6 miles, one-way. Parking: Boat Launch up the hill from East End Beach [MAP]


The Harborwalk Trail is sort of a ‘tour de Portland’, connecting Portland’s East End beach and South Portand’s Bug Light Park, and includes paved trails, sidewalks, bridges, and portions of the South Portland Greenbelt Walkway. There are water views and a dedicated path most of the way. We’ve mapped out the 6 mile one-way route — but join at any point and do as much as you can! East End Beach is Portland’s only public beach. After your run you can swim at the sand and pebble beach while watching the sailboats bobbing on their moorings in Casco Bay. From East End Beach, the trail proceeds along the Eastern Promenade Trail to Portland’s Old Port where it joins with the sidewalk at Commercial Street . It then takes you through the bustling waterfront area where it connects to Harborview Park and onto the Casco Bay Bridge, with a scenic water crossing. Across the bridge, a ramp leads to Thomas Knight Park, South Portland ‘s waterfront market area, and the South Portland Greenbelt Walkway. The paved greenbelt trail leads to Bug Light Park.

Cape Elizabeth
6.2 miles (10k) one-way Parking: Sprague Fields [Course Map]


This is the route of the 10k Beach 2 Beacon race! Cape Elizabeth is Portland’s most affluent suburb, with lovely waterfront sections and pretty residential streets. The route begins in Cape Elizabeth near Crescent Beach State Park. You’ll proceed north and then bear right onto Old Ocean House Road, a narrow road that will rejoin Route 77. The road conditions are mixed, with downhills and a climb beginning at the halfway point of the race. From there, you’ll pass the town hall and turn right onto Shore Road, proceeding down the winding road approaching Fort Williams. The road conditions are mixed, with downhills predominating through Smugglers Cove. There are three climbing hills that dominate the approach to Fort Williams.

At Fort Williams, you will enter through the Old Gate, following an uphill path around the old bunkers until they reach the top with its views of Casco Bay and the historic Portland Head Light.

Peaks Island
4 mile loop around the perimeter. [MAP]
Ferry Schedule. Parking: 56 Commercial Street


Peaks Island is a residential island off the coast of Portland,which offers spectacular views of Casco Bay, the Atlantic Ocean, coastal towns, and neighboring islands. The ferry connecting the island is scenic and only 20 minutes — plus it’s half the fun! The paved perimeter road offers a 4-mile, mostly flat tour of the island, half waterfront, half residential. To access the loop, walk up the hill from the dock to the first intersection. Turn right onto Island Avenue then take your second right onto Whitehead Street. From there it’s again your second right onto Seashore Avenue. Follow Seashore to its end. Turn left onto Trefethen Avenue where you will go down a steep hill. Turn left onto Island Avenue to return to the ferry.

Mackworth Island Trail
6.8 miles [MAP] Parking: Payson Park, Back Cove


Mackworth Island is an approximately 100-acre island in Falmouth, Maine, adjacent to its border with Portland. There is a footpath around the perimeter of the island with views of Falmouth, Portland, and other islands. Mackworth Island has a beautiful rocky shore and is heavily wooded, perfect for a tranquil run away from city life. A great loop is to start in Back Cove, cross the Presumpscot River, and do a quick tour of the island.

From the parking lot at Payson Park, follow Route 1 to Veranda Street. Cross the Martin’s Point Bridge and turn right on Andrews Avenue. Follow the dirt trail around Mackworth Island and retrace your steps to the start.

Run on the Beach

Old Orchard Beach (20 miles south) and Ogunquit Beach (35 miles south)

There are no really long beaches for running right in Portland. But our guide, Best Beaches for Running in New England, provides details on two of Maine’s fabulous running beaches: Old Orchard Beach (20 miles south) and Ogunquit Beach (35 miles south).


From hotels to B&Bs to lodges and cabins, Portland has something to accommodate everyone. To ensure the stay of your choice, it’s recommend that you make reservations in advance. Room availability can be limited, especially during the peak summer and fall seasons, and in the Old Port and downtown areas. If you want to be right near the running trails, look in the Back Cove neighborhood, which is bordered by the trails and Baxter Boulevard. Looking for quick access to downtown? Bayside is a centrally-located neighborhood with easy access to the heart of the city. If waterfront views are your thing, check out Munjoy Hill. It is on the eastern edge of the Portland peninsula overlooking Casco Bay and encompasses the Eastern Promenade, a scenic waterfront park with a small beach and bike path. For more information on where to stay, click here.

Running Stores/Group Runs/Community

Fleet Feet Maine Running: Originally the Maine Running Company, Fleet Feet Maine Running is Portland’s principal indie running store. Check out their various events throughout the year here. Group Runs Tuesdays and Thursdays at 6pm. They also have a store in Brunswick, ME.

RunWESTIN™: The Westin Portland Harborview Hotel has running concierges, who lead guided group runs every Tuesday and Thursday at 6:30 am (weather permitting) from their lobby. Runners of all levels are welcome.

Maine Track Club: Don’t be fooled by their name, they’re much more than track, in fact a lot of their runs are on roads! Founded in 1979, the nonprofit Maine Track Club is Maine’s largest and most active running club. They have several individual clubs that meet in and around Portland. They also hold races every month [Event Calendar]


Running Calendar, from the Maine Track Club.
Running Calendar from the Fleet Feet Maine Running

Maine Coast Marathon & Half-Marathon: Experience the coast and enjoy the beauty of springtime in Maine as you run along the coast in Kennebunk, Kennebunkport and Biddeford Pool. Do all that while running for a great cause: the Shipyard Maine Coast Half Marathon benefits Southern Maine Health Care’s Center for Breast Care. The half marathon is a relatively flat course that winds through coastline and coastal towns like Biddeford. The race start and finish is at University of New England. The Maine Coast Marathon is a USATF certified course which makes it an eligible Boston Qualifier course. It rolls through Kennebunk, Kennebunkport, Goose Rocks & Fortune Rocks Beach.


Maine Marathon: Held in October, the Maine Marathon features a moderately hilly out-and-back course for all three races — marathon, relay and half marathon. It starts and finishes along the beautiful inner bay, Back Cove. Proceeds from this year’s race will go to benefit the Dream Factory of Maine,which grants dreams to critically and chronically ill children from ages 3–18.