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 Street, 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, 312 Fore Street near the Old Port. The fine woodwork and marble floors here date to 1868.

Back to Nature

Just a few miles north of Portland along Route 1 in Falmouth, the Maine Audubon Society’s Gilsland Farm Sanctuary is a lovely place to enjoy nature (and a perfect place for a picnic, if you’re so inclined). Gaze out on grassy fields, wildflowers, and tidewater. Afterward, explore the society’s intriguing displays, demonstration projects, and gift shops; this is clearly an organization that cares deeply about the state’s natural resources. What the heck? Become a member while you’re here.



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 Casco Bay and its myriad (more than one for each day of the year) islands.

Some have favorably compared this view with San Francisco’s; even if that’s stretching it a bit, you can’t go wrong here watching the weather and light come and go. The pathway skirts the lower edge of the Eastern Promenade, a 68-acre hillside park with broad, grassy slopes extending down to the water. Little East End Beach is also here, but the water is often off-limits for swimming (look for signs). 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, and then take your first left on the road down the hill to the water’s edge.


The pathway continues on to Back Cove Pathway, a 3 1/2-mile loop around tidal Back Cove, offering attractive views of the city skyline 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 (there’s enough water 2 1/2 hours before and after high tide).

Part of the pathway shares a noisy bridge with I-295, and it can be unpleasant at a dead low tide; when the tides and the weather cooperate, however, it’s a nice spot for a walk. The main parking lot is located across from Hannaford Plaza at the water’s edge. 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.


On the other end of the peninsula is the Western Promenade. (Follow Spring Street westward to Vaughan Street; turn right and then take your first left on Bowdoin Street to the Prom.) This narrow strip of lawn atop a forested bluff has sweeping views across the Fore River west to the White Mountains in the distance (you can just make out the massive outline of Mount Washington on a clear day).

The airport, Maine Mall, and paper mill in the foreground may be less than scenic, but still, it’s a great spot to watch the sun set. Around the Western Prom are some of the grandest and most imposing houses in the city that include a wide array of architectural styles, from Italianate to shingle to stick.


Take Me Out to the Sea Dogs

The Portland Sea Dogs are a minor league Double-A team affiliated with the Boston Red Sox (a perfect marriage in baseball-crazy northern New England). They play through summer at Hadlock Field (217 Park Ave.;; tel. 800/936-3647 or 207/879-9500), a delightful small stadium near downtown that still retains an old-time feel despite aluminum benches and other updating; it’s one of the better minor league parks at which I’ve ever attended a ballgame.

Activities are geared toward families, with lots of entertainment between innings and a selection of food that’s a couple of notches above basic hot dogs and hamburgers. (Try the tasty fries and sausages, and make sure you get a Sea Dog biscuit: local vanilla ice cream between two chocolate chip cookies.) You might even catch future pro stars. The season runs from around April until around Labor Day.


On the Water

Casco Bay Lines: Six of Casco Bay’s islands have year-round populations and are served by scheduled ferries from downtown Portland. Except for Long Island, the islands are part of the city of Portland. The ferries provide an inexpensive way to view the bustling harbor and get a taste of island life. Trips range from a 20-minute (one-way) excursion to Peaks Island (the closest thing to an island suburb, with 1,000 or so year-round residents) to the 5 1/2-hour narrated cruise (with a long lunch stopover) to Bailey Island (connected by bridge to the mainland south of Brunswick) and back.


All of the islands are well suited for walking; Peaks Island has a rocky back shore that’s easily accessible via the island’s paved perimeter road (bring a picnic lunch). There’s also a bike rental outfit a few blocks from the island’s ferry dock. Long Island has a good hidden beach. Cliff Island is the most remote of the six-pack, with a sedate turn-of-the-20th-century character.

Hitting the beaches

One of the supreme pleasures of visiting the Portland area is the opportunity to sample some of its many great beaches and lighthouse and ocean views. Even within Portland city limits, you can laze on the Eastern Promenade’s tiny East End Beach for free; the views are great, though swimming there is a judgment call—a wastewater treatment plant looms nearby, although after years of cleanup efforts, city officials claim it’s safe for swimming.


Across the bridge in South Portland, Willard Beach is a good neighborhood beach: small, with friendly locals, dogs, and tidal rocks to scramble over. There’s plenty of parking here.

For the best of the out-of-town beaches and views, though, strike out for Cape Elizabeth, a moneyed bedroom community just south of the city. (From Portland’s State Street, cross the Route 77 bridge going south, then follow signs.) You can choose from a trio of good beaches as you meander along Route 77, a lovely lane that occasionally recalls England with its sweeping views of marsh, ocean, or cultivated field.


Two Lights State Park (tel. 207/799-5871) is impressively scenic, and has the advantage of a decent lobster-and-seafood hut beside it: Two Lights Lobster Shack, open late March through October. The lobsters are smallish, lobster rolls meaty, clam chowder pretty good, and the views are sublime.

Farther south on Route 77, Crescent Beach State Park (tel. 207/799-5871) is a lovely mile-long curve of sand, reached by a walk through beach roses; it has ample parking, barbecue pits, picnic tables, and a snack bar. Both charge a fee from Memorial Day to Columbus Day.


The town-operated Fort Williams State Park, located on Shore Road in Cape Elizabeth just off Route 77, offers free access and sweeping vistas of craggy waves crashing onto dramatic rocks, as well as the much-photographed Portland Head Light. Two to 3 miles farther south, turn left onto Route 207 for two more options: Scarborough Beach Park, on the left, another long strip of clean sand and dunes with changing facilities ($8 for access in summer) or—a bit farther along, on the right at the end of Ferry Road—quieter Ferry Beach State Park (tel. 207/283-0067), which has good views south toward Old Orchard Beach.


Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.