4-Day Weekend Travel Guide to Kennebunkport, Maine

Kennebunkport is one of New England’s quintessential summer destinations. It’s ideal for long weekends near the beach or relaxing in its lush countryside. That’s what makes the destination so unique and compelling—take a lobster tour in the morning, go for a bike ride in the afternoon, and catch the sunset during beachside happy hours. Here’s how to have a perfect weekend in Kennebunkport, Maine.

How to get there

For the majority of visitors, Kennebunkport is a relatively seamless drive. Bostonians can arrive after 90 minutes on I-95; other New England towns average about three hours; even New York City dwellers can make it in under five hours (likewise for out-of-country tourists from Montreal). But for those coming from farther afield, there’s also Portland International Jetport (PWM). It’s just under 30 minutes south of Kennebunk, and a convenient option for connecting the rest of the nation to this coastal town.

Where to stay

Yachtsman Hotel & Marina Club

As a port town, inevitably people flock to Kennebunk to experience its seaside scenery, including beaches, harbors, and lighthouses, but also a charming downtown aptly named Dock Square. Built around the Kennebunk River that flows out to the Atlantic—and some of the region’s famed beaches like Goose Rocks—it’s the ideal place to start for any first-timer. In which case, checking into the Yachtsman is your best bet; slightly removed from the main square, the harborside property is an eight-minute stroll to town. It’s only a three-minute bike ride into the center (doubling as a popular pastime and mode of transport in Kennebunk).

The nautical bungalows offer a playful pop of color against glass sliding doors that open up to your private patio along the hotel’s onsite marina. For guests looking to mingle, the Yachtsman offers a private marina bar for guest’s only, or their floating “pool boat,” the S.S. Sundazewhich is the place to be on a summer weekend. And for any guests looking to break away from marina life, Yachtsman partners with Kennebunkport Marina next door, to provide rentals for exploring the area’s waterways at your own speed.

Hidden Pond

About 15 minutes from Dock Square exists a stark contrast to Kennebunkport’s waterfront allure, yet it has a complete appeal of its own—one you won’t want to miss. Spread over 60 acres, Hidden Pond offers 36 private cabins in the form of treehouses, bungalows, and two-bedroom cottages for the ultimate secluded getaway, all with the amenities of a luxury resort (like a daily morning delivery of coffee and pastries at your doorstep).

Each accommodation has a name—rather than an impersonal number that another guest has checked in and out of—and is surrounded by up to four acres of lush woodlands. Cabins offer outdoor showers, gas fireplaces, and a screen porch equipped with snuggly blankets for a cozy experience. As for decor, 20 of the bungalows were just revamped by menswear designer Todd Snyder, depicting three of Maine’s prominent themes—countryside, mountainside, and seaside—once again tying the distinct locale of Kennebunkport together. There are two pools on property, multiple outdoor fire pits with daily s’mores kits provided, and a farm-to-fork restaurant concept that serves up breakfast, but is renowned for its evening tasting menu.

What to do

Beach it

Regardless of when you visit Kennebunkport, you simply must visit the beach—Goose Rocks Beach, to be specific. The three-mile stretch of fine sands along a calm inlet is an idyllic way to waste away a few hours on a sweltering summer day, just as it is for an off-season beach walk. You’ll notice beachfront properties are few and far between, as the lots are ordinated, which ensures views and privacy are protected along this popular site.

Lobster tour

Though lobsters are a year-round menu item throughout Maine, June is the unofficial peak season for the namesake variety of this red crustacean. Summer visitors should take advantage of the warmer weather and book an excursion on a lobster boat. They can learn more about the specificities of the Maine lobster and the restrictions surrounding the permits, measurement requirements, and more. Captain Bob Danzilo at Rugosa Lobster Tours puts you out into the Gulf of Maine, pulls up a few traps, walks you through the basics of lobstering, and provides a fun yet informative 90 minutes that’ll give you an entirely new appreciation for the lobster you’re bound to eat during your Kennebunk trip.

Shop

Local boutiques and a fair share of classic souvenir stores populate Dock Square. If you’re a shopper, you could make a day out of it. If you’re more of a stop-in-if-it-catches-my-eye type, you could easily visit all the stores in just a couple hours. Either way, it’s worth strolling around the town area for a sense of traditional Kennebunkport. If you catch a stretch of fickle New England weather, you might want to take your shopping inside; there are a number of antique stores surrounding Kennebunkport that are worth popping into for unique finds.

Where to eat and drink

The Clam Shack

A symbol of Kennebunkport, The Clam Shack is recognizable by its original Coca-Cola-clad signage and the flurry of customers lined up underneath it awaiting fried clams and a lobster roll. Though there is certainly no “right” way to order a lobster roll, there is a Maine way. And that’s cold, with lobster and mayo. If you’re more of a butter connoisseur (this is the Connecticut way), The Clam Shack won’t judge. They have a “both” option, which combines a spread of mayo and a drizzle of warm butter to combine the best of both styles. Grab a local beer on draft and settle into a picnic bench while you wait for your order. Dive into the hot fried clams first, then tackle the roll.

Earth at Hidden Pond

Whether you’re staying at Hidden Pond or simply seeking a taste of the wooded-property’s specialty farm-to-fork restaurant, be sure to arrive hungry. Earth uses farm-fresh ingredients, some produce even grown on property, to create an indulgent three- or four-course menu that rotates with the season. Both the decor and cuisine reflect its namesake, with one bite reminding you what fresh ingredients really taste like. Arrive early to enjoy an aperitif with house-infused spirits at the picture-perfect Farm Bar. Or, stay later for a nightcap by one of the private fireplaces overlooking one of the resort’s three ponds.

Arundel Wharf

With an expansive wooden deck, Arundel Wharf is a casual wharfside restaurant ideal for a sun-drenched lunch, cheeky midday cocktail and snack, or a sunset happy hour. There are plenty of shareable appetizers for a large group, or even a smaller one looking to try the bounty of seafood available here. Think traditional New England steamers, shrimp cocktail, lobster-stuffed avocado, and mussels.

White Barn Inn

Whether you’re celebrating a special occasion, or just celebrating that you snagged a reservation at this fine-dining hot spot, the restaurant at White Barn Inn sets the tone for an elegant evening. The AAA Five Diamond, Forbes Five Star eatery is helmed by executive chef Mathew Woolf. It showcases the best of Maine’s farmers, fishermen, and foragers. It’s an old-school spot for the area, still encouraging gentlemen to wear jackets, and why not? Again, it’s an occasion in itself to eat here.

Rococo Ice Cream

Every coastal town needs a celebrated ice cream storefront, and in Kennebunkport, it’s Rococo. On any given day, this outpost scoops up 14 different flavors. You’ll find signature flavors like goat cheese blackberry chambord and maple fig jalapeño, as well as seasonal options. They also do an incredible affogato; espresso served over your choice of ice cream for a midday pick-me-up.

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!