Maine’s largest city is scenically located on a Casco Bay peninsula. The cobblestone downtown—known simply as Old Port—is lined with art galleries, clothing boutiques, and seafood restaurants that serve up the day’s catch procured at the nearby wharves. It’s a year-round destination, but is especially lively during the summer.
One of Maine’s great icons, the picturesque white-stucco, black-capped Portland Headlight marks the entrance to the namesake city’s busy harbor, and lies just seven miles from downtown in Fort Williams Park. Incredibly, it was built in 1794 and was manned until 1989, at which time an automated beacon was installed. The small century-old keeper’s house now operates as a museum, but most visit for a stroll around the well-maintained grounds and for picnics with an unbeatable view. Head to the rocky ravine to the right of the lighthouse for a bit of sobering history; despite the head’s bright light, many met their fates on the sharp rocks below. The names of sailors and ships, including some from the1800s, are scrawled on the craggy boulders for all to remember.
Free entrance to park grounds. Admission: $2 adults; $1 children (6–18); free for children under 6.
Park grounds open year-round daily from sunrise to sunset (until 8:30 p.m. in summer); museum open June–October daily 10 a.m.–4 p.m., spring and late fall Saturday–Sunday 10 a.m.–4 p.m.
This tantalizingly retro white cement block of a restaurant enjoys a great waterside location off Commercial Street. Simply emblazoned on the outside with a bright blue J, this lively sports bar has been a favorite hangout since 1978, and not much has changed, including the staff. Here, it’s all about good drinks and fresh seafood, especially Blue Point oysters, which are bionicly shucked in the round behind the bar and served raw with horseradish-heavy cocktail sauce and lemon wedges. When it doubt, follow the locals’ lead: angle for an outdoor table (if weather permits), order a perfect martini or draft beer, and get your fill of sweet bivalves—preferably within earshot of a Red Sox game.
There’s comfort food, and then there’s Duckfat. When owner-chef Rob Evans opened this friendly all-day café just down the street from his more sophisticated restaurant, Hugo’s, in 2006, locals could not believe their taste buds—nor Evans’s near-obscene use of its namesake ingredient. He twice-cooks his star menu item—Belgian fries—in duck fat and serves them up, in paper cones, with dipping sauces like truffled ketchup or Thai chile mayo. One of its signature dishes, poutine, is a sinful soupy take on the traditional Quebecois dish, layering fries, duck fat gravy, and Maine cheese curds. There’s a good selection of from-scratch soups, salads, and hot pressed panini too. But not all the treats are savory; chocolate-dipped beignets, orange-scented churros, and real malted milkshakes made with local Smiling Hills Farm ice cream are all sugary, swoon-worthy punctuations to a rich and memorable meal.
Riding the Mailboat with Casco Bay Lines Terminal
Fare: $13 adults, $6.50 kids
In Maine, where many islands have year-round residents, there’s a good chance the mailman drives a boat. Some services have even made a nifty business of taking tourists along for the often scenic ride around rocky coves, and past charming island homes. The cluster of six islands off of the Portland Peninsula in Casco Bay has the longest-operating freight service of its kind in the country; Casco Bay Lines sells tickets for its three-hour roundtrip mail-run, which makes stops at Peak’s, Great Diamond, Little Diamond, Long, Chebeague, and Cliff islands. And don’t worry: Passengers will be expected to concentrate on the scenery, not help with heavy packages.
The Inn at Park Spring
Book a sunny room in this 1835 home within walking distance of the Old Port.
Portland Sea Dogs at Hadlock Field
The Double-A affiliate of the Boston Red Sox, the Sea Dogs play an average of 70 home games each season at Hadlock Field, just south of the Back Cove. The 7,368-seat stadium has a number of unique features, including a 37-foot replica of Fenway Park’s Green Monster; a centerfield lighthouse that pops up when a player hits a home run; and the team mascot, Slugger the Sea Dog, who roams the stadium during games. A picnic pavilion overlooks the right-field foul line, and concessions include local options like New England microbrews, fried haddock sandwiches, and Oakhurst Dairy milk and cookies.