Portland to Rockport, Maine

Red's Eats at Wiscasset

ROUTE: Fly into Portland and explore the city's working docks and cobblestone streets before taking Route 1 up the Atlantic coast, stopping at the fishing villages along the way.

Kick things off at the city's southside favorite 158 Pickett Street Cafe with a sourdough bagel filled with prosciutto, eggs, and pesto. Alongside a quick noon pint at J's Oyster, lose yourself in a bucket of steamed mussels, then hit Pai Men Miyake for Maine-shrimp sushi rolls and The Lobster Shack at Two Lights for clamcakes. Follow up with a late, wine-soaked dinner of small bites (try the seared rockfish and curry slaw) at Bar Lola.
Crash here: Black Point Inn, located seaside on one of the most scenic spots in New England.

Begin the day at the Standard Bakery Co. with morning buns (croissant dough studded with walnuts), then stop at Rosemont Market & Bakery in Yarmouth for car-friendly provisions like house-made roast beef and a loaf of ciabatta. Follow Route 1 until you reach Wiscasset, grab a life-changing lobster roll at Red's Eats, then detour to Boothbay Harbor for a scoop of whoopee-pie ice cream at Downeast Ice Cream Factory. Return to Route 1 and wind your way to the tip of the St. George Peninsula, where you can refuel on one of many delicious lobster dishes at Cod End, a fish market and seasonal cookhouse.
Crash here: The East Wind Inn, a former town meeting hall turned bucolic hideout.

Breakfast on blueberry pancakes at Port Clyde General Store, but save room for the Seven-Napkin burger at Owls Head General Store for lunch. Jump onto Route 73, pick up roadies (like WaldoStone Farm's Bloody Mary mix made with Pemaquid oyster juice; it's delicious even without the vodka) at Sweets & Meats Market, and turn north to Belfast. Stop at rustic vegetarian café-grocery Chase's Daily for a house-made raspberry-lemon muffin, then grab a barstool at Rockland's popular yachter hangout Primo and feast on clam pizza and chicken wings from its own roost.
Crash here: Samoset Resort, a collection of quaint, wood-shingled cottages.

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