Peaks Island was once known as the Coney Island of Maine. Today, it is a small town neighborhood within the city of Portland, a place where kid-run lemonade stands are plentiful in summertime and you can still find flowers or honey for sale at the end of a driveway (on the honor system, of course). Tourists flock here in the warmer months to take in the views of Casco Bay, explore the few quirky museums and galleries, and get a taste for laid-back island living. The ferry—a 20-minute crossing from downtown Portland—runs rain or shine throughout the year, making this an accessible destination anytime you’re in the area. Bikes are available for rent on the island near the
ferry terminal.

The 4.0-mile bike loop follows a paved road that is mostly flat and waterfront, although it does dip into residential streets in places. The road is shared cars, but there is minimal traffic. From the intersection at Island Avenue, mount your bike and take a right. Continue for 0.2 mile and take your second right onto Whitehead Street. Bike 0.25 mile and take your second right onto Seashore Avenue; follow this street until it ends at the northeastern part of the island.

As you cruise along Seashore Avenue, look for the benches posted at scenic pullouts, offering great resting spots. The sea beyond is a mecca for wildlife and boaters. Keep your eyes pealed for seals, dolphins, and harbor porpoises popping up between Casco Bay’s prolific lobster buoys, sailboats, and tankers.

After traveling approximately 1.0 mile along Seashore Avenue, plan to dismount your bicycles and explore the Battery Steele, one of the largest gun batteries ever built in the United States. Though currently preserved as a historic site by the Peaks Island Land Preserve, the World War II battery was once considered critical to protecting Casco Bay. Signage on the west side of Seashore Avenue marks the trailhead. The trail itself is just a few hundred yards, primarily through wet lowlands, over a narrow boardwalk. The battery rises out of the scrubby vegetation like a giant mouth, ready to gobble up anything that dares to enter. This dark, damp place is best explored by older children, armed with flashlights. Those who embrace a little spelunking will love investigating the multiple rooms branching off the primary tunnel. What do they think is behind the heavy, locked doors? ECHO! ECHO…echo!

Back on your bikes, continue on Seashore Avenue to its end and turn left onto Trefethen Avenue. Go 0.1 mile down a steep hill and turn left onto Island Avenue, which leads you back to the ferry terminal. Be sure to check the returning ferry schedule in advance, as ferry times change seasonally.

The ferry runs rain or shine, so don’t be afraid to explore the island if the clouds open. When biking isn’t in the cards, plan to walk the perimeter loop, or you can always rent a covered golf cart (a popular mode of transportation on Peaks) from Island Tours (207-653-2549).

A few restaurants, gift shops, and galleries are clustered near the Peaks Island ferry terminal. Stroll along Island Avenue to find a gem gallery and the Umbrella Cover Museum. Yes, that’s right, this museum is all about sheaths that cover umbrellas! From floral and plaid covers to handmade and international ones, you’ll be surprised there is so much to know about umbrella covers!