Lobster Rolls, Late Nights, and Living Large in Portland, Maine

A gentleman’s guide to Portlandia East. 

Note: This story has been expanded and updated to reflect some new attractions for 2015. 

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 summer weekend getaway. Here’s your 48-hour plan.

DAY ONE:  Portland

DO: Make the Old Port district—the waterfront cluster of the city’s coolest shops and restaurants—your home base. Visit Portland Dry Goods (pictured below) and Portland Trading Co. for waxed Barbour jackets, bespoke pocket knives, Maine-made Rancourt & Co. boat shoes, and other manly New England essentials; and drop by David Wood if you need a tie, with or without little lobsters on it. Got a hankering for some whiskey aftershave? Don’t worry: It’s handmade around the corner at Portland General Store, along with a wide range of woodsy grooming goods.

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 superior lobster rolls on a rocky outcrop overlooking the ocean—and it’s BYOB. Charter one of the Portland Schooner Company’s 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 in 2013 as one of the best new restaurants in the U.S., for the freshest local oysters and an epic version of the classic New England clam bake: steamers, mussels, lobster, potatoes, salt pork and a hard-boiled egg on a bed of rock seaweed. Next door is Hugo’s, serving refined fare farmed, fished and foraged exclusively from Maine. And don’t miss Fore Street (pictured below) an old brick artillery storage depot overlooking the wharf where you can watch wood-oven-roasted mussels and whole fish cooked to perfection by Sam Hayward, a past recipient of the James Beard Foundation’s Best Chef in the Northeast award.  

DRINK: Belly up to the bar at Portland Hunt & Alpine Club, (below) where craft cocktails are expertly served in a Scandinavian ski lodge setting, with snacks to match.Central Provisions boasts an elevated drinks menu that’s updated as nearly as frequently as the locally-sourced small plates. Liquid Riot Bottling Company distills spirits and brews beer in a cozy but cavernous 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: The new Press Hotel, a newspaper-themed spot in a building that formerly housed the Portland Press Herald, is ideally situated on the cusp of the Old Port district. The hotel’s designers cleverly riffed off the old-school journalism theme, with typewriter keys popping up in the decor, vintage desks and chairs, and guest floor hallways adorned with real Press Herald headlines, including such gems as “Elderly lobster set free” and “Man yanks skunk from jar, runs.” If you want to go even more historic (and don’t mind a 20-minute drive),  check into the grand Black Point Inn in Prouts Neck. Built in 1878, it features a roaring fireplace, cliff walk,  private beach, and a massive porch with a bar overlooking the ocean. 

Party Like a Portlander: For a perfect day of decadence, Joe Riccchio, a former chef turned food editor of Maine magazine (and bartender at boutique BBQ joint Terlingua), 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 a fresh-baked ham and cheese croissant and good, strong 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 shit out of some clay pigeons.

SEE: Cruise down to Cape Porpoise, a scenic Maine lobstering village, and stop at a beloved wharf bar called The Ramp (pictured below) that is renowned for its perfectly made 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.

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. (two mouthwatering specimens are pictured at the very top of this post). Across the marina is David’s KPT at the Boathouse, which has an exemplary raw bar and an oversized deck for boat-watching. Do 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, like the lobster with green garlic butter pictured here.

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 distinctively rustic Maine style. Be sure to hit Tides Beach Club at Goose Rocks  (below) for top-shelf cocktails at the swanky marble bar, or better yet, on the oceanside front porch. It’s the perfect end to your two-day tour.

Photos by Christopher Testani