Built on a promontory with water on three sides, Portland is Maine’s largest city, but it embraces visitors with a friendly, small-town atmosphere. It’s big enough to support a vibrant cultural scene, small enough to easily navigate. The city is reputed to have the greatest number of restaurants, per capita, second only to San Francisco.
The enchanting Old Port links Portland’s downtown business district with its waterfront. This part of the city pulses with activity. Old-fashioned streetlights and brick sidewalks set the mood, boutiques and restaurants line the streets, fishing and excursion boats crowd the docks.
The Portland Museum of Art anchors the uptown Arts District. The museum houses a strong collection of European and American masterpieces with a focus on Maine art, including works by Winslow Homer, who maintained a studio at Prouts Neck, in Scarborough. The Children’s Museum of Maine, next door, is a must for kids. Nearby are the Institute of Contemporary Art, Portland Stage Company, the Center for Cultural Exchange and the State Theatre. Merrill Auditorium, in Portland City Hall, is the home of the Portland Symphony Orchestra. The Portland Opera Repertory Theatre and PCA Great Performances also stage programs here.
History and architecture buffs should consider a walking tour of the city. The Victoria Mansion is considered to be among the finest examples of Victorian villa architecture in the world. The Abyssinian Meeting House, built in 1828, was an important center of the black liberation struggle. Historic houses include the boyhood home of poet Henry Wadsworth Longfellow, the Neal Dow Memorial, home of the father of prohibition, and the 1755 Tate House, a fine example of the Georgian style.
Perhaps the best place to take in the view is the Portland Observatory. Built by Lemuel Moody in 1807, it reflects his seafaring ways: 122 tons of ballast hold it in place. A small museum highlights Moody’s contributions to Portland, and the 102-step climb to the orb deck is rewarded by 360-degree views over the city, the surrounding countryside and Casco Bay.
To the east is Cape Elizabeth, where Portland Head Light has been warning of treacherous ledges since 1791. South Portland is a major retail center. In Falmouth, you can wander the 2.5 miles of easy trails through the Gilsland Farm Sanctuary and Environmental Center. For more exercise, climb 383-foot tall Bradbury Mountain, in Pownal. Freeport is home of the always-open outdoor retailer L.L. Bean and more than 170 outlets, as well as the intriguing Desert of Maine. And in Yarmouth, home of the annual clam festival, don’t miss the DeLorme Map Store’s Eartha, the world’s largest rotating and revolving globe.