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Portland is Maine's largest city, built on a hilly peninsula that juts into Casco Bay. A working harbor since colonial times, it has burned and rebuilt more than once, most notably after the Great Fire of 1866, which left a downtown of brick Victorian blocks. Today it pairs a fishing waterfront with a food scene far larger than its population would suggest.
The cobblestone streets of the Old Port hold restaurants, bars and shops a block from working wharves. Up the hill, the Portland Museum of Art anchors the Arts District along Congress Street, and Victoria Mansion is a lavishly decorated Italianate villa from before the Civil War. Literature fans can tour the house where Longfellow grew up, and up on Munjoy Hill a nineteenth-century maritime signal tower still keeps watch over the harbor. Residents walk along the Eastern Promenade. In neighboring Cape Elizabeth, Portland Head Light stands within Fort Williams Park, while South Portland has the compact Bug Light and Spring Point Ledge Light at the end of a granite breakwater. Ferries carry passengers out to the Casco Bay islands, including Peaks Island.
Portland suits food lovers, couples and travelers who like small, walkable cities by the sea. Summer and early fall are the liveliest seasons, and winters are cold and snowy. It also works well as a base for the southern Maine coast, including Kennebunkport and Freeport.
WiserMap travel guidePortland Maine Lobster Rolls Lighthouses and Casco BayPlan a Portland, Maine trip: the Old Port, Portland Head Light, the Eastern Promenade, Casco Bay islands and historic homes, plus lobster rolls and seasons.Read the guide
Portland's historic waterfront district, rebuilt in brick after the Great Fire of 1866, with cobbled streets, working wharves, shops, bars and some of the best restaurants in New England. Lobster rolls, oysters and craft beer are easy to find. Harbor cruises and island ferries leave nearby.
Maine's largest art museum, on Congress Square, with works by Winslow Homer, Andrew Wyeth and European masters, plus Homer's studio at Prouts Neck, toured by reservation. The surrounding Arts District holds galleries and the Maine College of Art. First Friday art walks are held monthly.
An Italian villa style mansion built from 1858 to 1860, considered one of the finest surviving pre-Civil War houses in America. Its interiors keep original painted walls, stained glass and furniture. Guided tours run from spring to autumn, and it is beautifully decorated at Christmas time.
The boyhood home of poet Henry Wadsworth Longfellow on Congress Street, built in 1785 and the oldest standing structure on the peninsula. Guided tours show family furnishings, and the Maine Historical Society runs a museum next door. The quiet garden behind the house is free to enter.
A museum of the small two-foot gauge railways that once ran across rural Maine, with historic cars and engines. Seasonal train rides run along the shore of Casco Bay on the Eastern Promenade, popular with families. Check the schedule, as trains run on limited days outside summer.
A wooden maritime signal tower on Munjoy Hill, built in 1807 to spot incoming ships and alert merchants. It is the last such tower in the country. Guided tours climb to the top for views over Casco Bay and the city. It is open seasonally, and tours fill on busy summer days.
A large park on the slopes of Munjoy Hill with lawns and walking paths overlooking Casco Bay and its islands. At the bottom are East End Beach, a boat launch and the Eastern Promenade Trail along the shore. It is a favorite place for picnics, sunset views and summer concerts.
A 3.6-mile loop path around Back Cove, a tidal basin just north of the peninsula, popular with runners, walkers and cyclists. It gives fine views back to the city skyline, especially at sunset. The path is mostly flat gravel, and parking is available at several lots along Baxter Boulevard.
Maine's most photographed lighthouse, first lit in 1791 and standing on rocky cliffs in Cape Elizabeth. Fort Williams Park around it has trails, ruins of the old fort and picnic areas, and the lightkeeper's house holds a small museum. Arrive early on summer days, and bring a jacket.
Two small lighthouses in South Portland. Bug Light is a tiny lighthouse in a park on the harbor with a memorial to the area's World War II shipyards. Spring Point Ledge Light stands at the end of a granite breakwater near Fort Preble. Both give fine views back to Portland.
Casco Bay Lines ferries run from the Old Port to several islands. Peaks Island is a short ride away, with bike rentals and a small village, while longer mail boat runs visit quieter islands. A ferry trip is a cheap way to see the harbor, its lighthouses and forts from the water.
A state park in Cape Elizabeth on a rocky headland with tide pools, picnic areas and remains of a World War II coastal defense site. The two lighthouses that give the park its name stand nearby. Bring a picnic or eat at the Lobster Shack at Two Lights next door, a classic local spot.
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