48 Hours in Kennebunk + Kennebunkport

The picturesque Kennebunks are filled with historic charm, fishing wharfs, unique boutiques, and some of the best restaurants in southern Maine, nestled together along the coastline

Historic charm and classic cocktails

We know we’re in the Kennebunks when we start seeing the colorful directional arrows that adorn almost every intersection. My boyfriend, Brandon, and I arrive in the heart of Kennebunkport and check in at the Captain Fairfield Inn, a Lark Hotels property. Each of the nine rooms offers a stylish take on the classic New England look, with historic charm intertwined with a hip, clean modern style.

For dinner, we head to Pedro’s Mexican Restaurant in Kennebunk’s Lower Village. The outdoor patio is lined with tiki torches, colorful string lights, and artificial coconut palm trees. The inside is just as colorful and playful, with sombreros hanging from the ceiling and the walls decked with crosses, skeletons, paper flowers, and bull’s horns.

We order a blood orange margarita, a mojito, queso fundido, and carne asada tacos. Afterward, we walk to Old Vines Wine Bar for dessert and nightcaps: cinnamon churros with vanilla ice cream, a Mexican mule, and an old-fashioned.

Idyllic seaside views

We wake up to the smell of freshly brewed coffee and breakfast that is being served downstairs at the inn. We both have French toast, eggs, sausage, and cups of hot coffee.

After breakfast, we drive along scenic Ocean Avenue and scope out the architecture along the route, from old captain’s homes to modern cottages, all overlooking water. There are plenty of places to stop along this road, including near Walker’s Point, where we enjoy the view of the ocean and the Bush family compound from a bench. We continue toward the cute fish houses on stilts that surround Turbats Creek.

Still on the search for photo-worthy views, we drive to the coastal village of Cape Porpoise. Our first stop is Langsford Road Lobster and Fish House, which offers fresh seafood straight from the boat. From the back deck, we enjoy views of the harbor and surrounding islands, including Goat Island and its still-active lighthouse, built in 1833. Across the harbor is the Cape Porpoise Pier, where we see local fishermen and lobstermen at work. The Ramp Bar and Grill, Pier 77 Restaurant, and Cape Pier Chowder House have yet to open for the day.

Shopping, eating, and leisurely walks

A five-minute walk from the inn is Dock Square, a perfect place for shopping. We visit Beach Grass, a home decor and gift shop; Fine Print Booksellers, an independent bookstore; The Candyman, a popular candy shop specializing in saltwater taffy and fudge; Kate Nelligan Design, a coastal design store; Abacus, a Maine art gallery and store; Daytrip Society and Daytrip Jr., unique Maine-themed boutiques; and Minka, a home decor and lifestyle shop.

We are hungry after shopping, so we walk to Alisson’s Restaurant in Dock Square. We order two Bloody Marys, New England clam chowder, lobster bisque, the Fisherman’s Platter, and a lobster roll. After, we share an ice cream from Rococo Ice Cream and mini doughnuts from Satellite Donuts.

With our bellies full, we drive to Parsons Beach. We take advantage of the low tide and explore the wide sandy terrain. Down the road is Snug Harbor Farm, one of the most magical places in Maine. It has greenhouses, gardens, gifts, resident animals, and a plethora of succulents. Our next stop is Saint Anthony’s Franciscan Monastery, where we enjoy another peaceful walk. Afterward we visit one of the newest additions to Kennebunk, Batson River Tasting Room, for a cocktail and a beer.

Cocktails in igloos and local fare

We meet friends for a cocktail and snack at The Burleigh at the Kennebunkport Inn. During the colder months the inn sets up plastic igloos on the deck, where patrons can escape the winter weather.

We have reservations at 50 Local in Kennebunk, where we are warmly greeted by owner Merrilee Paul. The cozy restaurant has a floor-to-ceiling chalkboard featuring the names of the local farms that provide ingredients. We order the Campfire cocktail, a beet salad, beef skewers, bucatini, seafood stew, hanger steak, and panna cotta. We leave amazed and wanting more.

Breakfast and a gallery tour

We order the Full Belly Breakfast from All Day Breakfast in Kennebunk, which consists of buttermilk and blueberry pancakes, two eggs, two strips of bacon, a classic eggs Benedict, and bottomless coffee. We next tour the galleries at Maine Art Hill, which has been showcasing local artists for over 20 years.

An afternoon pick-me-up

Before we head home to Portland we stop in downtown Kennebunk and grab a delicious and flaky croissant from Boulangerie, a Proper Bakery and a latte from The Blue coffee shop. The latte is the perfect pick-me-up for our drive back home.