Friday
Oceanfront views and wood-fired pizza

If you’re already in southern Maine, the drive to York and Kittery will be quick and smooth, just a 45-minute jaunt south on I-95 from Portland. Try to arrive before sunset to catch the striking oceanfront views as you pull in to the York Harbor Inn, set directly across from Harbor Beach and the Hartley Mason Reserve Cliff Walk. Check in and get settled with a drink in the main building’s 300-year-old, post-and-beam Cabin Room, complete with a roaring wood-burning fireplace and turnof-the-century trolley lamps that once lit the way for New England’s Victorian-era seaside vacationers. A white banister staircase leads to skinny hallways connecting a selection of cozy and comfortable rooms featuring fairly large outdoor decks with uninhibited views of the Atlantic.

For dinner, When Pigs Fly on Route 1 in Kittery, the venture of artisan bread-making brothers Ron and Andrew Siegel, is a must visit. You may be familiar with their 25 varieties of bread—sold at Whole Foods, Hannaford, and other Maine retailers—and it feels like an unexpected treat to walk into this modern industrial space featuring fresh bread, craft beers, draft wines, and Neapolitan pizzas baked to crispy, chewy perfection in an 800-degree, wood-fired oven. Order the Italian spicy sausage: a white pie topped with mushrooms, fresh arugula, and WPF’s smoked mozzarella, which is made fresh daily.

Saturday
Beach walks, historic sites, shopping, and local food

Wake up with warm egg sandwiches and hot coffee to go, included in your stay at the inn, and head to Long Sands Beach, a wide, mile long strand perfect for an energizing morning walk. Clamshells dug out by diligent seagulls litter the sand, which is icy in places this time of year. Surfers waiting for frigid waves evoke a confusion of seasons—and an appreciation of your warm parka.

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A 5-minute drive—or a 30-minute walk, depending on your fitness goals—brings you to Cape Neddick Light, also known as Nubble Light and one of the most picturesque beacons in Maine. In operation since 1879, Nubble is situated on a rocky island—a “nub” of land—just a couple hundred yards off the mainland. (Some former lighthouse keepers rigged up a system to cable their son over the ocean in a bucket for his daily commute to school.) This also happens to be one of the most popular scuba diving training sites in Maine, thanks to the fairly calm conditions and shallow depths of 20 to 40 feet. On an average day, you’ll find visitors sitting on the rocks with dogs and coffee, watching the waves crash against the hidden reefs from which the lighthouse has protected ships for over 100 years.

On your way into neighboring Kittery, make a quick stopover at the Old York Historical Society in York Village. There’s a nice grouping of historic sites there including Jefferds Tavern (1750), which hosts educational and public programs throughout the year; Old Gaol, the oldest prison building in Maine and now a museum of colonial and Native American artifacts; and a cemetery with the remains of some of the town’s first settlers. Kitty-corner across York Street is the oldest church in Maine in continuous use, the First Parish Church, a classic New England meetinghouse erected in 1747.

You’re probably ready for lunch, so give your tourist stomach what it wants: a basket of fried clams and a lobster roll from Bob’s Clam Hut on Route 1 in Kittery. Martha Stewart happens to be a fan of this seafood mecca, and for good reason: large lumps of fresh meat are piled into a buttery New England–style hot dog bun and placed beside a handful of thick-cut, crispy french fries.

Opportunities abound for the local shopper. Kittery Trading Post is an oasis of outdoor gear, with great deals on every brand imaginable, from Smartwool to North Face to Carhartt. In downtown Kittery, a medley of locally owned shops line Wallingford Square: elegant and contemporary home goods, office supplies, jewelry, and accessories can be found at Folk and Tayla Mac Boutique, and Yarrow offers herbal tonics and tinctures, air-purifying plants, and organic teas and honey. Further afield but worth a stop is the amusingly weird vintage shop Lost Coast, located at 230 State Road. You won’t miss it—a many-colored, modern mural by Portland artists Ryan Adams and Rachel Manly covers the building. Here you’ll find everything from a 1931 Frankenstein movie poster to an original Nintendo gaming system to midcentury modern furniture, glassware, and some excellent fashion finds, like a pair of deep blue XXHI hightop Chuck Taylors.

Or is it a cut of dry-aged beef you’d like to bring home? Maine Meat (MEat) is a whole-animal butcher shop that sources its humanely raised, hormone- and antibiotic-free beef, poultry, pork, and lamb directly from local farmers. It also offers a wide selection of cured meats, deli cuts, and local cheeses. For a caffeine (and sugar) jolt, stop in next door at Lil’s Cafe for a mouthwatering selection of pastries and breads, all made on-site. The classic cruller, thick and drippy with frosting, pairs perfectly with a fresh cup of Portland-roasted Tandem coffee.

It’s time to unwind, so head down the block to The Corner Pub, a cheery, no-frills watering hole with several local beers on tap and a full bar, as well as a free-of-charge pool table. On the front patio in the winter, warming flames lap at the freezing air from several pits spread out and surrounded by comfortable Adirondack chairs. The pub serves a selection of satisfying bar food (the tater tots have a delightfully peppery crunch). If you’re planning on more elevated fare, make reservations in advance for The Black Birch. At the time of writing, this farm-to-table gastropub offers contactless takeout only; cars idle in the snowy parking lot as patrons wait to collect their meals, such as Moroccan lamb meatballs with spiced tomato, fried garbanzos, and crumbled feta, or a whole smoked trout with apple-fennel relish and whipped garlic. Besides the dinner menu, there is also an impressive cocktail list. Try the “2 Government,” an old-fashioned–esque bourbon libation with house-made grenadine.

Sunday
Clamming and candy

You’ve done the beach and the lighthouse—now it’s time to visit the picturesque York River, which was a fluid expressway for merchant ships during the 1700s. There are lots of photo ops here, so have your camera handy. The rocky mainland jutting dramatically into the water’s edge creates lovely little inlets overlooked by beautiful big homes above. Without fail, there are people digging for clams in the muddy flats. (You may get to hear a mother shout to her young son, “That’s a keepah!”)

Head down the raised walkway and toward Wiggly Bridge, which is a lot sturdier than it sounds. Said to be the smallest pedestrian suspension bridge in the world, it leads to the forest trails of Steedman Woods nature preserve, where morning walkers make their rounds and babies slide by on sleds pulled by hale and hearty parents.

Don’t leave town without stepping into one of the biggest candy stores in Maine, Yummies Candy and Nuts on Route 1. Forty thousand pounds of packaged treats line the walls, including every kind of chocolate-covered nut, numerous flavors of Jelly Bellys, fudge, specialty chocolates, and even some vintage products. (Remember Clove gum? Apparently people chewed it to mask the smell of alcohol during Prohibition.) Here you will undoubtedly find a sweet memento from your weekend in York and Kittery.