This story originally appeared as the Be Here Now feature of the 2024 Sept/Oct issue of Adventure Cyclist.

Perched on a peninsula in the south- western edge of Casco Bay, the city of Portland, Maine, is infused with all things ocean. Even the city’s most famous district is called the Old Port, evoking its maritime heritage. Foodies, hipsters, tourists, and fishermen mingle among stately brick buildings that rise from a maze of cobblestone streets. Overhead, squawking seagulls drift through the salt-tinged air.

Over the last couple of decades, Portland has rightfully cemented its reputation as a destination city with top-tier food, arts, and music scenes. Fortunately for those who prefer to travel on two wheels, it also serves up some tasty biking adventures.

Beginner / Day Ride

Route: Black Cove Eastern Prom

Distance: 18 miles
Elevation gain: 278 feet

For a great introduction to the city, head onto the Back Cove Trail and the Eastern Promenade Trail, and then up and over the Casco Bay Bridge into South Portland for a day ride with plenty of visual and gastronomic diversions.

The region’s original inhabitants, the Abenaki, called the area Machigonne, which means “Great Neck” in Algonquin, and this tour takes you along most of the “neck” that sticks out into the ocean. Warm up on the Back Cove Trail, a mostly flat 3.6-mile paved and crushed-stone loop that delivers views of Portland’s western skyline, before hopping onto the paved Eastern Promenade Trail and rolling into the heart of the city.

Dip your tires into the Atlantic at East End Beach and keep an eye out for Fort Gorges, which guards the entrance to Portland Harbor.

In short order, you’ll roll onto Commercial Street, which parallels Portland’s action-packed working waterfront. The vibrant strip is a great spot to lock up your bike and refuel.

Continue up Commercial Street and over the Casco Bay Bridge, a working drawbridge that connects Portland with South Portland. A protected pedestrian lane on the bridge’s northeast side allows bikes, and there are dedicated bike lanes along each side of the bridge as well. You can simply turn around at the top of the bridge once you’ve soaked in the views of Portland’s waterfront or continue into South Portland where you can make your way to Bug Light, a small lighthouse on the northern tip of South Portland.

Intermediate / Multiday Ride

Route: Lighthouses and Lobster Roll

Distance: 93.8 miles
Elevation Gain: 2,717 Feet
GPX File on Ride With GPS

This one winds along relatively flat, quiet roads, past several lighthouses, and through seaside villages before returning along the Eastern Trail, the region’s premier rail trail.

Start in Portland proper or at Bug Light (#1) in South Portland. Make your way to Spring Point Ledge Light (#2) before cranking to Cape Elizabeth and Portland Head Light (#3). Chalk up another lighthouse sighting (#4) with the Ram Island Ledge Light that marks the northern end of the main channel into Portland Harbor.

The next stop, down Route 77, is called Two Lights (#5 and #6). Although both are now off limits to the public, there are views of them from a parking area. From Two Lights, make your way to Old Orchard Beach, a classic pier complete with an amusement park and funky dive bars. Parallel the beach along Route 9 to Camp Ellis and the Saco River, which you’ll follow a few miles inland to the towns of Saco and Biddeford. Cross the river from Saco into Biddeford before quickly heading back to the coast and the communities of Biddeford Pool and Fortunes Rocks.

If you haven’t had your fill of coastal architecture, duck into the colony of Goose Rocks and then on to the village of Cape Porpoise. Be sure to ride all the way to the public dock so you can see Goat Island Light (#7). Your next stop is Kennebunkport. Just past town, take the gravel Bridle Path to Kennebunk, Kennebunkport’s inland sibling. Downtown Kennebunk is just a few miles from the Eastern Trail, so once you’re done exploring, simply work your way to the trail.

Enjoy the car-free rail trail for about eight miles to Biddeford. Once there, you’ll have to navigate some on-road riding until you meet back up with the off-road portion of the trail in Saco. Grind gravel for another 10 miles or so back to Scarborough where a quick zip south along Route 208/Black Point Road brings you to Highland Avenue’s bike lane, which you can ride all the way back to South Portland.

Groceries and Food

Portland has all the grocery options you would ever need. For fresh produce from May through November, the Portland Farmers Market operates in Deering Oaks Park from 7:00 am to 1:00 pm Wednesdays and Saturdays. Union Wharf Market curates a fine collection of local food and gifts, artisan coffee, spices, and more. Their café serves lunch as well. Browne Trading Company sells fresh fish, wine, lunch, and artisan delicacies from their Commercial Street storefront.

Go and Stay

Unfortunately, and somewhat bafflingly for locals, hotels in Portland can be remarkably pricey at all times of the year. Budget-conscious travelers should check out the Black Elephant Hostel, which provides bunk and private room options but fills up fast (they don’t allow bikes in the hostel but do have a fenced garden with a bike rack). Airbnb or Vrbo may have deals if you book early enough.

Amtrak and most major airlines serve Portland, so getting to the city is easy (just be sure you’re flying to Portland, Maine, not Portland, Oregon). It’s also right on Interstate 295, roughly two hours north of Boston.

Hotels, motels, B&Bs, and campgrounds abound along the route outlined above. In the peak summer season, reservations are mandatory, but you might be able to wing it in the spring and fall shoulder seasons.

Arts and Culture

Portland hosts a nice collection of museums, including traditional options like the Portland Museum of Art and eclectic options like the International Cryptozoology Museum, which features exhibits on Big Foot, Nessie, and other creatures that may or may not roam the earth. The Victoria Mansion provides tours of one of the best examples of pre–Civil War architecture found in New England, and the Maine Narrow Gauge Railroad Museum offers scenic rides on a historic narrow-gauge train. Check out the Portland House of Music, the nightclub Aura, or the State Theatre for music and entertainment acts if you’ve got energy left after your bike tour.

Want More Routes?

Adventure Cycling Association has created free Short Routes in partnership with the East Coast Greenway Alliance that begin (or end) in Portland, Maine. One goes from Portland, ME to Newburyport, MA, and the other is the Portland to Brunswick Maine Coastal Ride.