With its cobblestone lanes and photogenic harbor, Portland’s Old Port district has long been a draw for travelers seeking a quick dose of urban New England charm before moving on to Maine’s more bucolic pleasures. These days visitors are dropping in for longer spells as Portland’s allure spreads to the Congress Street arts district and indie-spirited neighborhoods like East Bayside and Munjoy Hill. Much of that allure has to do with food. Portland’s reputation as a great dining town is well-deserved, but no one here rests on his or her laurels, least of all the chefs and restaurateurs behind renowned spots like Fore Street and Eventide Oyster Co.; both parties have recently opened new restaurants, adding to the quandary of travelers already stymied by an abundance of choices. Meanwhile, a new generation of Portlanders and newcomers is pushing the boundaries with a fresh take on everything from doughnuts to kombucha. Visitors are also discovering what residents have long loved most about their town: local art and music, gracious parks, a stunning array of 19th-century architecture and the city’s layered history.
1. 360-DEGREE VIEW, 1 P.M.
You can’t miss the red octagonal Portland Observatory rising above the wooden and brick houses and small businesses on Munjoy Hill. Climb the 104 creaking stairs of this former maritime signaling tower, built by the enterprising Capt. Lemuel Moody who, some 200 years ago, wasn’t above augmenting his business with a little income from view-seekers like you. Now, as then, one’s gaze turns to the east, to the silver waters and green islands of Casco Bay. The loquacious guides take their time pointing out lighthouses and landmarks, as appreciative of the view as you are ($10). Look for Capt. Moody’s burial site among the tombs and tilting gravestones in nearby Eastern Cemetery — threaded with paths and beloved by grave tourists. Then shake the ghostly mood with an overflowing plate of fried clams on the delightfully ramshackle patio of 3 Buoys Seafood Shanty & Grille.
2. A BRUSH WITH THE PAST, 5 P.M.
Below a row of rambling, mostly turn-of-the-last-century houses, the Eastern Promenade is one of two parks that curve around either side of old Portland. Above the bayside trail, Fort Allen Park, with its gazebo and sloping lawn, offers a serene glimpse of the bay. Several blocks away is the wood-and-brick Abyssinian Meeting House, once a hub on Portland’s Underground Railroad and one of more than a dozen sites on the city’s Freedom Trail. Portland had a robust antislavery movement and the downloadable map available at portlandfreedomtrail.org is indispensable for a thorough understanding of the city’s past.
3. HARBORSIDE, 7 P.M.
Commercial Street is the touristic heart of Portland, but don’t be deterred by the prospects of kitschiness. This harborside stretch is as inviting a tourist boulevard as you’ll find anywhere. Get off the main drag to explore wharves and docks where seaweed dries on racks and gulls poke around nets and lobster pots. Stop for a drink on the deck of Portland Lobster Co., where a local band might be playing blues or rock covers, or find a seat at the long bar at Liquid Riot Bottling Co., which, besides being a restaurant and bar, is also a distillery and brewing establishment, churning out an impressive list of libations, including beer, rum, whiskey, vodka and what its website touts as “Maine’s first Fernet.” For dinner, Scales, the latest venture of a partnership that includes the chef Sam Hayward (of Fore Street fame), recently opened in a big, light-filled space on Maine Wharf with a shiny open kitchen and views of the docks. The coastal New England menu recently included a creamy, briny lobster bisque and pan-roasted halibut with hazelnuts and brown butter. Order the Parker House rolls if only for the raw cream butter served alongside. Dinner, about $80, with drinks.
4. BREAKFAST AT SEA, 8 A.M.
Blueberry pie at Two Fat Cats Bakery. Belgian fries at Duckfat. Certain establishments have become synonymous with local treats. Now you can add doughnuts made with Maine mashed potatoes to the list. The extraordinarily moist doughnuts at the Holy Donut, in flavors like blueberry and maple bacon, draw morning lines at the Exchange Street location. Pick up a few and have breakfast at sea. With a busy day ahead, save the Casco Bay Lines’ multi-island mailboat route for another visit, and opt for the ferry to Peaks Island (itself worth a visit, but again, another time). The roughly 40-minute round trip ($7.70) offers a bracing view of busy Casco Bay and Portland’s harbor.
5. EAST END EXPLORATION, 11 A.M.
Rent a bike at CycleMania in East Bayside and hit the trails. One choice for an hourlong ride is the Back Cove trail, which curves 3.6 miles around a circular cove. Then refresh yourself with kombucha at Urban Farm Fermentory. In a town where distilling and fermenting are apparently native skills, Urban Farm, in a warehouse-type space, is evidence of Portland’s entrepreneurial zeal. In addition to fermented tea — recent flavors included mint nettle and turmeric — you’ll find mead, hard ciders and gruit (beer with herbal flavoring). A flight is $5.
6. ASIAN LUNCH, MAINE STYLE, 1 P.M.
The seating is communal, the dishes are mismatched and the menu is irresistible at Honey Paw, from the team behind Eventide Oyster Co. and Hugo’s. Honey Paw’s East-meets-New England approach is evident in recent dishes, including smoked lamb khao soi, with house-made noodles, fermented mustard greens, lime and Burmese coconut curry, and lobster won tons with confit mushrooms (lunch, about $40). Or sample the eclectic small plates at Central Provisions, which opened to great acclaim a few years ago, not only for its dishes (like rich caramelized sheep cheese embedded with Bosc pear slices, $12), but also for its exquisite sleek-rustic interior.
7. SILK ROAD TO GOA, 2 P.M.
Opportunities abound for the weekend shopper: elegant home décor at Furniturea and Angela Adams, and puppets, puzzles and other low-tech toys (remember that Wooly Willy magnet game?) at Treehouse Toys. Or is it a 1970s ice bucket you’re after? Cocktail paraphernalia, new and nostalgic, can be found at Vena’s Fizz House: vintage lowball glasses, flasks, bitters, shrubs and infusion kits. Can’t decide? Mull it over in back where mixologists conjure creations like Silk Road to Goa, with Twenty 2 vodka (made in Maine), saffron syrup, curry bitters and other arcane ingredients, $13.50. Order the three-bean Chex mix and watch the server spritz the snack with a mist of pine bitters.
8. ARTFUL DOINGS, 3:30 P.M.
Winslow Homer was born in Massachusetts, but Maine, where he eventually moved, is the state the artist is often associated with. With its impressive Homer collection, and the weekly tours it offers to the artist’s home and studio, the Portland Museum of Art is the place to go for your Homer fix. But there’s much more beyond the brick facade on Congress Square: some 18,000 works by artists like N.C. and Andrew Wyeth, Alex Katz, Louise Nevelson, Monet, Matisse and Kandinsky, among others. Temporary shows include the current “O’Keeffe, Stettheimer, Torr, Zorach: Women Modernists in New York.” Entrance: $15. Afterward, stroll along Congress Street, with its many galleries, including She-Bear, with a strong focus on regional artists, and Space, a visual arts and performance artsvenue. Stop by the Wadsworth-Longfellow House, dating from the late 18th century. Even if you don’t tour the house where Henry Wadsworth Longfellow grew up, you can take a breather in its peaceful ornamental garden.
9. ON THE TOWN, 8:30 P.M.
At intimate Emilitsa, the plush seating and attentive service encourage diners to linger. Start with the potent house cocktail (Bombay Sapphire gin, Cointreau, moschofilero, ouzo and champagne vinegar). Recently, the menu featured a salad of local roasted red and golden beets in olive oil and muscatato vinegar, and a delicious, incredibly rich version of moussaka topped with Greek yogurtbéchamel. Dinner, about $60 with drinks. Then sample Portland’s music scene at places like One Longfellow Square and Blue. Both feature a variety of styles, including jazz, folk, rock and blues (often by such Maine artists as Samuel James).
10. BREAKFAST AT BECKY’S, 9 A.M.
There’s usually a breakfast crowd at Becky’s Diner, where locals and tourists sit at Formica tables beneath a press–tinned ceiling and fill up on buttermilk pancakes, eggs done any way you want, and huge sides of home fries. Expect a modest check and the satisfaction that you’ve experienced a Portland classic.
11. ANOTHER VIEW, 1:30 P.M.
You’ve been to the Eastern Promenade, now visit its western counterpart, by way of Danforth Street, for a glimpse of Victoria Mansion, an Italianate mansion with a grand flying staircase and lavish interiors by Gustave Herter (check victoriamansion.org for tour schedules). Continue past shady Western Cemetery to the Western Promenade. Invariably, there are artists on the grassy slopes, fixated on the distant White Mountains — yet another view, and another side of Portland.