Friday
Evening
Cliffside views and decadent dining

After following the winding Shore Road from downtown Ogunquit, we turn in to the stately entrance of Cliff House. This cliffside retreat recently underwent extensive renovations that transformed the long-established property into a luxury year-round resort. Our room’s sliding glass doors open up to a private deck that looks out at the Atlantic Ocean and the resort’s landscaped grounds and pool area. It’s April, so the pool is closed, but we see several guests enjoying drinks in the hot tub despite the strong breeze off the ocean.

My girlfriend, Caroline, and I have time before our dinner reservations, so we drive to Perkins Cove for drinks and harbor views. The Perkins Cove Drawbridge crosses over the entrance to the small cove where boats are moored. The pedestrian bridge can be operated by anyone to allow tall-masted boats to cruise into the cove. We follow the road around the small, boot-shaped peninsula, passing by shingled gift shops and restaurants before arriving at M.C. Perkins Cove, a popular waterfront restaurant run by two James Beard award–winning chefs, Mark Gaier and Clark Frasier. We order a half-dozen oysters and wash them down with glasses of chilled wine. Seated near the bar, we can look out at the ocean from the windows that wrap around the dining room. By the time we finish our wine, the overcast sky has turned blue from the just-set sun, covering the room in a cool hue.

From the moment we enter Northern Union, which is located in what was originally a home, we feel at ease. Owners Lauren and Matt Wickert greet us at the host stand and show us to our seats in a side dining room with just two other tables. We share a bottle of red wine from Montepulciano, Tuscany, and start with handful of decadent small plates, including foie gras torchon and duck confit on a sweet potato waffle with foie gras maple syrup. Chef Romann Dumorne’s deservedly lauded ramp soup is a special tonight, and we savor every last bit of the bright and luscious dish. We stick with duck for our entree, too, sharing a duck breast with seared endive, roasted rhubarb puree, and duck jus. For dessert, we try all three: ice cream from local honey with crushed honeycomb, a chocolate caramel tart with white chocolate–orange ice cream, and a creative version of a cheesecake with lemon-ricotta sponge cake, cheesecake spread, and blackberry sorbet.

Saturday
Morning
Coastal walks and shops

We don’t have to go far for breakfast, which we eat at Cliff House’s The Tiller Restaurant. We enjoy cold-pressed juices by the window—the bright red Beet Detox for Caroline and orange turmeric for me—as we watch waves crash on the rocks below. We keep it classic with the food, ordering a farmers’ omelet and eggs with hash and bacon. After finishing breakfast, we walk along the path below where we were just sitting. The resort
was built on cliffs, making for dramatic ocean views from nearly anywhere on the property.

After stopping in our room, we head toward Ogunquit. A cold ocean wind reminds us that it’s still not summer, but that doesn’t stop us from walking on the expansive Ogunquit Beach, which stretches from mouth of the Ogunquit River, where the main beach parking is located, to Wells to the north. We get in our car to reach the northern half, driving to a section called Footbridge Beach (named for a wooden footbridge the crosses over the river to the beach).

Back in downtown, we visit a few stores. Abacus, located in the center of town, has an extensive selection of jewelry and eclectic home goods, including life-sized bulldog “doggy banks” covered in colorful splattered paint. The company also has locations in Boothbay Harbor, Freeport, Kennebunkport, and Portland. Spoiled Rotten is located in a former home on Beach Street. The gift shop is packed with colorful, sometimes cheeky, home decor, stationery, and more (one kitchen towel declares, “Rock Out with Your Crock Out”). There are specialty food items, including shelves of Stonewall Kitchen products and samples of Mike’s Hot Honey—perfect to drizzle on pizza, we’re told.

Afternoon
Lobster rolls and oceanside drinks

We return to Perkins Cove for the opening day of Barnacle Billy’s. We order lobster rolls at the inside counter of the iconic restaurant before grabbings seats in the crowded dining room. A server stops by to take our most important order: rum punches. The strong drinks are heavily garnished with fruit and best enjoyed on the restaurant’s deck.

After arriving back at Cliff House, we put on our bathing suits, fill up paper cups with chilled Lambrusco, and don the resort’s navy-and-white gingham robes for our walk to the outdoor hot tub. Steam from the water mixes with the ocean mist blowing in over the cliff. We sink under the water to our chins as we look at the Atlantic Ocean—the only interruption in the horizon is the faint speck of Boon Island Light, the tallest lighthouse in New England.

Evening
Pizza and piano

Cornerstone Artisanal Pizza and Craft Beer, at the corner of Main and Beach Streets, offers a variety of creative stone oven–fired pizza and a smaller list of appetizers, sandwiches, and other entrees. We sit at the bar with views of the lengthy line of beer taps and the oven. Our smoked pepperoni pizza comes with a fire-roasted red sauce, and the crust is perfectly doughy and crisp.

As we cross the street to The Front Porch, we can already hear the crowd in the upstairs piano bar singing “God Bless America.” The restaurant has an impressive menu, but we’re here for the drinks and music. We grab seats at the bar and sip on a couple of the house cocktails: I order a drink of jalapeno-infused tequila, elderflower liqueur, and lime, and Caroline has a rum punch.

Sunday
Morning
Spa day and homemade sweets

We start the day as relaxing as possible with a visit to the Spa at Cliff House. We change into robes and wait in the Sanctuary Room for our massage therapists, sitting in elegant wood armchairs with linen cushions and drinking freshly brewed herbal tea. Our treatment, the Couples Cliff Side Escape, starts with an aromatherapy foot soak, glasses of prosecco, and a charcuterie plate, followed by an 80-minute massage. By the end we feel soothed, relaxed, but not quite ready to head home.

The sun is shining as we drive toward downtown and park in a lot off Shore Road. Marginal Way is a paved trail that follows the shoreline down to Perkins Cove. There are benches along the path and a few staircases that lead down to small, rocky beaches. The trail is a little over a mile long, and we’ve worked up a bit of an appetite by the time we return to our car.

The Village Food Market is the kind of market you hope to find in every town you visit. Along with grocery staples and fresh produce, the market has made-to-order sandwiches, baked goods, coffee, and a variety of beer and wine. We split a sweet Thai chicken panini and grab a bottle of grüner veltliner to take home.

One building over from the market is Bread and Roses Bakery and Harbor Candy Shop. In the latter, we check out the selection of old-school candy and buy a mix of house-made truffles. At the bakery, we grab cups of coffee for our ride home. A stack of chocolate-chip cookies wider than my hand tempts me, but I opt for a lemon square (at least there’s fruit in it, I tell myself ). With phones full of countless shots of ocean vistas and our bags of sweets, we start our drive back to Portland, ready to return to this oceanside resort town once summer arrives.