Portland has Maine's rough edges and its own urban ambition.
Discerning road-trippers would do well to set course for that other Portland—you know, the one in Maine. Besides boasting America’s best lobster rolls, the Pine Tree State is the birthplace of rugged preppy chic (and the first L.L. Bean store) and has enough open roads, ocean air, and outdoorsy activities for a thoroughly enjoyable weekend getaway. Read on for your 48-hour plan.
DAY ONE: Portland
Portland Dry Goods
DO: Make the Old Port district—the waterfront cluster of the city’s buzziest shops and restaurants—your home base. Visit Portland Dry Goods and Portland Trading Co. for waxed Barbour jackets, pocket knives, hunting boots, and other New England essentials; and drop by David Wood if you need a square-end knit tie or lobster-patterned belt to wear to dinner. Got a hankering for some whiskey aftershave? Don’t worry: It’s handmade around the corner at Portland General Store.
SEE: Drive to the Portland Head Light in Cape Elizabeth, the iconic lighthouse on the edge of town that was made famous by painter Edward Hopper. Nearby, The Lobster Shack at Two Lights serves up superb lobster rolls on a rocky outcrop overlooking the ocean—and it’s BYOB. Charter one of the Portland Schooner Company’s historic sailing yachts for a two-hour cruise around the peninsula, and bring a bag of tasty provisions from Browne Trading (where superchef Daniel Boulud buys his caviar).
EAT: Head to Eventide Oyster Co., tapped by Bon Appetit last year as one of the best new restaurants in the U.S., for the freshest local bivalves and an epic clam bake: steamers, mussels, lobster, potatoes, salt pork, and a hard-boiled egg on a bed of rock seaweed, served with drawn lemon butter. And don’t miss Fore Street, housed in an old brick artillery storage building, where you can watch your wood-oven-roasted mussels and turnspit pork loin being cooked to perfection by Sam Hayward, a past recipient of the James Beard Foundation’s Best Chef in the Northeast award.
Portland Hunt & Alpine Club
DRINK: Belly up to the bar at Portland Hunt & Alpine Club, where craft cocktails are expertly served in a Scandinavian ski lodge setting, with snacks to match. In’Finiti is another fine swillery that distills its own spirits and brews its beer in a cavernous yet cozy space with a waterfront deck. And if you crave a dizzying variety of brews, there are 75 on tap at the Great Lost Bear.
STAY: In town, book a suite at the Portland Harbor Hotel or the Portland Regency Hotel, and, if you don’t mind a 20-minute drive, check into the historic Black Point Inn in Prouts Neck, which features a roaring fireplace, a cliff walk, and a private beach.
Indulge Like a Local
For a perfect day of decadence, the host of Portland Web series Off the Wagon with Joe Ricchio suggests starting with a steaming bowl of beef pho at Saigon. “Later, I would hit Miyake for the 10-piece omakase nigiri—along with a bottle of Taru sake. That evening I’d find a perch at Central Provisions for plates of foie gras and marrow bones, washed down with a sea of French rosé. Then it’s off to the Hunt & Alpine Club for a Keiller’s Fortune, a soul-soothing cocktail driven by bourbon and egg white. Get the deviled eggs with warm brown bread and salty mushroom butter. Close out the night at The Snug drinking Jameson in reckless portions.”
DAY TWO: L.L. Bean & Kennebunkport
DO: Start with freshly baked pear tarts and locally sourced coffee at Standard Baking, Co. on the waterfront, where fishermen head out to reel in the daily catch. Then take a short drive up to the Freeport HQ of Maine’s legendary outdoor outfitter, L.L. Bean. Never mind those duck boots you can order online, and instead browse their impressive collection of Beretta and Browning shotguns. In-store experts can advise how to ship one home, but first drive over to Bean’s Outdoor Discovery School at Fogg Farm, which also rents guns, and blast the hell out of some clay pigeons.
L.L. Bean's Outdoor Discovery School at Fogg Farm
SEE: Cruise down to Cape Porpoise, a scenic Maine lobstering village, and stop at a wharf bar called The Ramp that’s renowned for its addictive Dark ‘n’ Stormy. Before you get too tipsy, head out along Ocean Avenue, which hugs the coast and takes you past the Bush family’s sprawling summer compound on the way into Kennebunkport; it’s one of the best scenic drives on the Eastern seaboard.
The Clam Shack
EAT/DRINK: Don’t miss the lobster roll at The Clam Shack, a Kennebunkport landmark since 1968 that may serve Maine’s best version of fresh lobster meat, melted butter, and mayonnaise on a round white bun. Across the marina is David’s KPT at the Boathouse, which has an exemplary raw bar and a massive deck for boat-watching. Save room for dinner at Earth at Hidden Pond, located at a luxurious lodge in the nearby woods, with a poolside bar, fire pits, and wow-factor cuisine (try the suckling pig with lemon marmalade or the lobster with green garlic butter) from rising chef Justin Walker.
Earth at Hidden Pond
STAY: Hidden Pond is a rugged-yet-elegant resort on 40 acres; guests stay in cottages with names like Lazy Days and Silent Pine, each decorated in a distinctive Maine style. Be sure to hit Tides Beach Club at Goose Rocks for cocktails at the marble-topped bar, or better yet, on the oceanside front porch.
Tides Beach Club
All Photos by Christopher Testani
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