updated 4/9/2007 10:05:18 AM ET 2007-04-09T14:05:18

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 contains 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, the crowds growing younger and rowdier.) Its narrow streets and intricate brick facades reflect the mid-Victorian era; most of the area was rebuilt following a devastating fire in 1866. Leafy, quaint Exchange Street is the heart of the Old Port, with other attractive streets running off of and around it. Learn more about the Old Port Mariner Fleet.

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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's 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's City Hall, Portland's seat of government was built of granite in 1909. In a similarly regal vein is the U.S. Custom House, at 312 Fore St. During business hours, wander inside to view its woodwork and marble floors dating back 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 (corner of Commercial and Franklin sts.). The 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. Tiny East End Beach is 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, 138 Congress St. (tel. 207/774-5561), a shingled tower dating from 1807 and used to signal the arrival of ships into port. Exhibits provide a quick glimpse of Portland past, but the real draw is the view of the city and harbor from the top. Open daily from Memorial Day to Columbus Day from 10am to 5pm; admission is $5 for adults ($4 for Portland residents) , $4 for children 6 to 16 ($2 for Portland residents), and free for children under 6.

On the other end of the Portland peninsula is the Western Promenade. (From the Old Port, follow Spring St. west to Vaughan; turn right and then take the 1st left on Bowdoin St.) A narrow strip of lawn atop a forested bluff is the actual promenade; it has views across the Fore River, which is lined with less-than-scenic light industry and commercial buildings, the White Mountains in the distance. The surrounding neighborhood is also called the "Western Prom." A walk through here reveals the grandest and most imposing houses in the city, in a wide array of architectural styles, from Italianate to shingle to stick.

On The Water
The 3 1/2-mile Back Cove Pathway loops around Portland's Back Cove, offering city skyline views across the water, glimpses of Casco Bay, and a bit of exercise. The pathway is the city's most popular recreational facility; after work in summer, Portlanders flock here to walk, bike, jog, and windsurf (2 1/2 hr. before and after high tide). Part of the pathway shares a noisy bridge with I-295, and it can be a bit smelly at very low tide, but when water and weather cooperate, it's a pleasant spot for a walk. The main parking lot is located across from a supermarket plaza at the water's edge, just off I-295. Take Exit 6 (Forest Ave. north) off I-295; turn right at the first light on Baxter Boulevard; at the next light, turn right again and park in the lot ahead on the left.

Another fine place to take in a water view is the Eastern Prom Pathway, which wraps for about a mile along the waterfront between the Casco Bay Lines ferry terminal and the East End Beach. The paved pathway is suitable for walking or biking and offers wonderful views of the islands and the boat traffic on the harbor. The easiest place to park is near the beach and boat ramp. From downtown, head east on Congress Street until you can't go any farther; turn right, then take your first left on the road down the hill to the water's edge.

Even More Historic Homes!
The Society for the Preservation of New England Antiquities (SPNEA) has two properties in Portsmouth, the Governor John Langdon House, built in 1784 at 143 Pleasant St. (tel. 603/436-3205), and the 1807 Rundlet-May House at 364 Middle St. (tel. 603/436-3205). John Langdon rose from modest origins to become a merchant, shipbuilder, Revolutionary leader, and three-term governor of New Hampshire. George Washington, who visited there in 1789, praised the house, which features a 19th-century addition by McKim, Mead, and White. The Langdon House is open June 1 through October 15, Friday through Sunday, with tours given hourly from 11am to 4pm. The Rundlet-May House was built by James Rundlet, who imported his wallpapers from England and purchased his furniture from local cabinetmakers, whose work was noted for its fine craftsmanship and striking use of veneer. Rundlet also saw to it that his house was equipped with the latest technologies of the day. The house is open June through October, the first Saturday of the month, with tours given hourly from 11am to 4pm. Admission to each house is $6, free for SPNEA members and Portland residents. For more information, visit www.spnea.org.

For more on what to see and do in Portland, ME, visit our complete guide online at http://www.frommers.com/destinations/portlandme/.

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