4 Best Sights in Portland, Maine

One of the city's most relaxing outdoor spaces, Back Cove Trail is a 3.6-mile paved loop with gorgeous views of the Cove, harbor, and downtown. It's a favorite route for walking, running, biking, and dog walking. Several benches and seasonal water fountains can be found along the trail.

The boyhood home of the famous American poet was the first brick house in Portland and the oldest building on the peninsula. It's particularly interesting, because most of the furnishings, including the young Longfellow's writing desk, are original. Wallpaper, window coverings, and a vibrant painted carpet are period reproductions. Built in 1785, the large dwelling (a third floor was added in 1815) sits back from the street and has a small portico over its entrance and four chimneys surmounting the roof. It's part of the Maine Historical Society, which includes an adjacent research library and a museum with exhibits about Maine life. After your guided tour, stay for a picnic in the Longfellow Garden; it's open to the public during museum hours.

Maine's largest public art institution's collection includes fine seascapes and landscapes by Winslow Homer, John Marin, Andrew Wyeth, Edward Hopper, Marsden Hartley, and other American painters. Homer's Weatherbeaten, a quintessential Maine Coast image, is here, and the museum owns and displays, on a rotating basis, 16 more of his paintings, plus more than 400 of his illustrations (and it offers tours of the Winslow Homer Studio in nearby Prouts Neck). The museum has works by Monet and Picasso, as well as Degas, Renoir, and Chagall. I.M. Pei’s colleague Henry Cobb designed the strikingly modern Charles Shipman Payson building.

Most visitors stumble on this stunning performance venue thanks to its national and international musical acts—and indeed, it's an ideal size and structure for that with a 3,000- to 8,000-person capacity; it's spacious but not too big to enjoy the show. But that's just the beginning of what the peninsular, waterfront spot offers, from ice skating in the winter to local craft fairs throughout the year. And on select Thursdays and Fridays from 4 pm till sunset in the summer, entry is free, dogs are welcome, and live music and lawn games are on offer with some of the city's best food trucks lining up to feed the happy crowd.