Portland to Rockport, MaineRed'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.
DAY 1: PORTLAND TO SCARBOROUGH
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.
DAY 2: SCARBOROUGH TO TENANTS HARBOR
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.
DAY 3: TENANTS HARBOR TO ROCKPORT
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.