Portland, Maine walking tour & city guide

The Old Port

The Old Port, rebuilt in brick after a great fire in 1866, is the heart of the city. Its cobblestone streets are lined with shops, galleries, bars and seafood restaurants, and the wharves are still busy with fishing and lobster boats.

From the waterfront, ferries cross to the islands of Casco Bay, such as Peaks Island, for quiet walks and cycling.

Lighthouses

Portland Head Light, in Cape Elizabeth just south of the city, was first lit in 1791 and stands on dramatic rocks above the ocean in Fort Williams Park. Bug Light in South Portland and Spring Point Ledge Light, at the end of a breakwater, are also easy to visit.

A classic walk from the Old Port to the Eastern Promenade

Start in Monument Square and walk down Exchange Street into the Old Port, wandering along Fore Street and Commercial Street by the wharves. Continue east past the ferry terminal along the waterfront trail.

The trail leads to the Eastern Promenade, a hilltop park above the bay with views of the islands and a small beach. Climb Munjoy Hill to the Portland Observatory, a wooden signal tower from 1807. The walk is about 4 kilometers.

Visiting tips

Summer and early autumn are the best seasons, with warm days and colorful leaves in October. Winters are cold and snowy. Portland is about two hours north of Boston, and the coast continues north to Acadia National Park.