If the idea of coastal New England brings up seriously preppy thoughts—such as the Kennedys lounging inside private compounds, mint-green khakis embroidered with mini whales and an endless array of fried seafood dishes—then you’ve probably been to a number of cities in coastal New England. To escape these overly touristy stops (sorry, Cape Cod), keep heading north, all the way up the coast, to Portland, Maine. The largest city in Maine (with 62,000 people, it’s home to a quarter of the state’s population), Portland offers all the charm of an East Coast seaside city without the overabundance of all things prep.
Despite its hefty—by Maine standards—population, Portland is pretty small, so if possible, skip the rental car and take a shuttle from Portland International Jetport. Most of the city’s action centers around the Old Port neighborhood, where bed and breakfasts compete with boutiques, lobster shacks and brewpubs for the attention of visitors. Start off with a walk down to the water and stop into the Portland Lobster Company (180 Commercial St, 207-775-2112) to sample the quintessential food of coastal New England: the lobster roll. Chow down on toasted white bread topped with buttery, sweet lobster with sides of fries and coleslaw.
From there, walk southwest up to Victoria Mansion (pictured, 109 Danforth St, 207-772-4841), for an inside peek at Portland’s Victorian history. Forty-five minute guided tours are the perfect length to take in the extravagantly decorated historical mansion, which still has all of its original furnishings dating back to the 1860s.
Save a few hours to stroll through the Old Port neighborhood. With brick sidewalks and tall, stately buildings lining the streets, it has quite the European air. Start at Exchange Street and make your way over to Commercial, which runs along the Harbor. Many of the restaurants here, like The Dry Dock (84 Commercial St, 207-774-3550, $4.50/beer), offer seating on the decks in back—the perfect spot to enjoy a predinner drink (try the locally brewed Allagash White) while you watch lobstermen haul in the day’s catch.
That catch most likely will be what’s featured on the menu at Fore Street restaurant (288 Fore St, 207-775-2717, $28 average entree). People start lining up at 5pm to snag a walk-in table for what will arguably be your best meal in Portland. A better plan is to call exactly two months before you want to dine, which is the earliest they start accepting reservations. As a reward for scoring a table, you’ll be treated to fresh, local food that’s prepared simply—but brilliantly. Think briny-fresh oysters, sardines straight from a wood-burning oven and a perfectly cooked pork loin with fresh sauerkraut.
As far as lodging goes, Portland’s options run from the fancy Eastland Park Hotel (157 High St, 207-775-5411, $200 a night), to the funky Pomegranate Inn (9 Neal St, 207-772-1006, $185–$295 a night). Be warned that funky doesn’t necessarily mean inexpensive, and room rates can shoot up based on local events and seasonality.
Skip breakfast at your hotel and opt for the simple morning fare at Standard Baking Company, located beneath Fore Street (75 Commercial St, 207-773-2112). A cup of coffee served black is the perfect counter to a sugary-sweet rhubarb pastry or rugalach. Then it’s time to visit one of Maine’s most recognizable landmarks…the L.L. Bean flagship store and its accompanying outlet (95 Main St, Freeport, 207-559-0747) in Freeport, a few miles up the road. There’s no public transportation to get there, but taxis are plentiful. Don’t worry if your style is more caviar than granola. In this outlet city, you’ll also find high-end brands such as Coach (48 West St, 207-865-1772), Dooney & Bourke (56 Main St, suite 11, 207-865-1366) and Burberry (42 Main St, 207-865-4400) outlets.
The capitalism of the morning calls for something a little more refined in the afternoon. Give yourself about two hours in the three-story Portland Museum of Art (7 Congress Sq, 207-775-6148), which offers a lovely selection of art from Maine and afar. A new exhibition, “Landscapes from the Age of Impressionism,” opens September 25.
Just up the street from the museum of art is 555 (555 Congress St, 207-761-0555, $25 average entree), the home of Steve Corry, a Food & Wine best new chef from 2007. Like Fore Street, the restaurant puts emphasis on simple, local ingredients, but where Fore Street holds back on whimsy, 555 charges full-steam ahead, with dishes like pepper-encrusted diver scallops in a carrot-vanilla emulsion and “Milk and Cookies”—light-as-air pistachio meringues with milk panna cotta sandwiches inside. Just don’t eat so much that you can’t fit into your pastel colored khakis—should you decide to indulge your inner prepster, in honor of vacationing on the New England coast.