Any visit to Portland should start with a stroll around the historic Old Port (pictured above). 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.
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 (pictured below) 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.
Back to Nature: A Side Trip
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.
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.