Any visit to Portland should start with a stroll around the historic Old Port. Bounded by Commercial, Congress, Union, and Pearl streets, this area near the waterfront has the city's best commercial architecture, a mess of boutiques, fine restaurants, and one of the thickest concentrations of bars on the eastern seaboard. (The Old Port tends to transform as night lengthens, with crowds growing younger and rowdier.) The narrow streets and intricate brick facades reflect a mid-Victorian era; most of the area was rebuilt following a devastating fire in 1866. Exchange Street is the heart of the Old Port, with other attractive streets running off and around it.
Just outside the Old Port, don't miss the First Parish Church, at 425 Congress St., a beautiful granite meetinghouse with an impressively austere interior that has changed little since 1826. A few doors down the block, Portland's City Hall is at the head of Exchange Street. Modeled after New York City's, it was built from granite in 1909. In a similarly regal vein is the U.S. Custom House, at 312 Fore St. near the Old Port. The fine woodwork and marble floors here date to 1868.
The city's finest harborside stroll is along the Eastern Prom Pathway, which wraps for about a mile along the waterfront beginning at the Casco Bay Lines ferry terminal at the corner of Commercial and Franklin streets. This paved pathway is suitable for walking or biking, and offers expansive views of the islands and boat traffic on the harbor. The pathway skirts the lower edge of the Eastern Promenade, a 68-acre hillside park with broad, grassy slopes extending down to the water. The tiny East End Beach is also here, but the water is often off-limits for swimming (look for signs). The pathway continues on to Back Cove Pathway, a 3 1/2-mile loop around tidal Back Cove.
Atop Munjoy Hill, above the Eastern Promenade, is the distinctive Portland Observatory (tel. 207/774-5561). It's a quirky shingled tower, dating from 1807, used to signal the arrival of ships into port. Exhibits inside provide a quick glimpse of Portland's past, but the real draw is the expansive view from the top of the city and the harbor. It's open daily (when flags are flying from the cupola) from Memorial Day through Columbus Day, 10am until 5pm; the last tour leaves at 4:30pm. Admission is $6 for adults, $4 for children ages 6 to 16.
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