Town of Kennebunkport, Maine

Welcome to Kennebunkport

Although several routes could take you into Kennebunkport, and despite the summertime bottlenecks, there really is only one way you should go: Through Dock Square. Nestled just inland from the coast along the banks of the Kennebunk River, you’ll know you’ve arrived once you cross the midpoint of the bridge on Western Avenue (Route 9) from Kennebunk’s Lower Village—not only because of the beautiful, handmade-in-copper “Welcome to Kennebunkport” sign, but because of the subtle shift in the vibe and esthetic.

Exploring Kennebunkport Maine

Once you’ve entered Dock Square, you can easily imagine you have strolled (walking is strongly suggested—there is a paid parking lot tucked in just after Alisson’s Restaurant on the left) right into a Rockwell painting. Yes, the Square is crammed with gift shops, dining options, and galleries—but each is housed in a classic-yet-unique historic building, complete with weather-worn shingles and wooden clapboards.

Once you’ve parked, you’ll already have experienced the congested (in-season) confluence of Western Avenue, Ocean Avenue, and Spring Street—this intersection is what forms the “square” (actually a triangle). The tiny, circular median is where the town erects a huge Christmas tree every year for their famous, two-week-long Prelude—a true spectacle, complete with fireworks, to add to your travel bucket list if you haven’t checked it off already. Dust off your Bean boots and reserve a room now—because they go faster than Santa can fly.

Lodging

Speaking of lodging—Kennebunkport offers a host of higher-end hotels and B&Bs, all within walking distance of the subdued hubbub of the Square. If you want to stay close to the center of town, both the modern, boutique-y Boathouse and the historic Kennebunkport Inn offer world-class accommodations as well as top-rated dining options. Waterfront dining at the Boathouse is a culinary experience in itself, no matter what the season (you can even enjoy your oysters on the deck in February with outdoor, ski-gondola-style, heated enclosures), and the Burleigh at the Kennebunkport Inn provides a cozy, gastropub experience for all.

But if you don’t mind a bit of a stroll, you have other options. Head northeast out of the Square on Ocean Avenue and you’ll come to a stretch of striking, huge homes set back off the road on the left; included in this hillside neighborhood are the four historic hotels of the Kennebunk Captains Collection, owned by Lark Hotels…which means you can’t go wrong with any of them. Further along Ocean Ave., you’ll come to the Nonantum, a riverfront hotel that has been around since July 4, 1884 and offers excellent dining options, such as 95 Ocean, Heckman’s Pub, or Latitudes. Check out their annual Fire & Ice festivities, typically held the second weekend of Prelude.

Dining Options

Less than a quarter of a mile further is the Breakwater Inn and Spa, where you can also dine in style (waterfront, of course) at Stripers, their in-house restaurant. And just around the corner is the grand dame of the coast, the seasonal Colony Hotel, with her regal red roof and weathervane-topped turret presiding over the rocky coast along Ocean Avenue like a queen surveying her coastal court. You have several dining options here, too—although it will be hard to tear yourself from the spectacular oceanfront vista you’ll be treated to from the pool deck for long (and if you prefer sand and sea, just cross the road to the diminutive Colony “beach,” a rocky stretch of shore alongside the breakwater).

There are also dozens of other restaurants, cafes, and take-out options for you to choose from in and around Kennebunkport—too many to list here. But just to whet your whistle—try the Maine Lobster Mac ‘n Cheese at Alisson’s, the Shoreman’s Pie at Arundel Wharf (on the deck, of course), the Mediterranean Seafood Stew at the Hurricane, or the Maine Whoopie Pie or Chai Cardamom homemade ice cream at Rococo’s. And while utterly removed from the Dock Square activity, Earth at Hidden Pond is less than 10 minutes inland; the ambiance, menu, and service are beyond compare. Their lodging options are breathtakingly unique, the grounds are peaceful—and they even have three treehouse-style spas (yup, you read that right).

Cultural Attractions

Far from being a hub of raucous, noisy, arcades-and-waterparks-style attractions, Kennebunkport offers the discerning tourist a host of delightful storefronts and galleries, where an entire weekend could be spent in a haze of retail bliss. For local, handmade gifts and art, some of the options in Dock Square include Abacus (be sure to check out their annual calendar, featuring art by Dana Heacock), Compliments (their artisan-crafted lighting collections are gorgeous), the iconic, bridge-side Emporium Gift Shop (perfect for that last-minute hostess gift), and Maine-ly Drizzle, a fabulous olive oil/vinegar tasting room and foodie-gift-filled nook tucked away on the second story at 2 Ocean Avenue, right in the heart of the Square.

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