4 Day Weekend Travel Guide to Kennebunkport, Maine


Kennebunkport is one of New England’s premier summer destinations. It is ideal for long weekends by the beach or for relaxing in its lush countryside. This is what makes the destination so unique and fascinating: take a lobster excursion in the morning, take a bike ride in the afternoon and watch the sunset during happy hours by the beach. Here’s how to have the perfect weekend in Kennebunkport, Maine.

How to get there

For the majority of visitors, Kennebunkport is a relatively smooth ride. Bostonians can arrive after 90 minutes on I-95; other New England cities average about three hours; even New Yorkers can do it in less than five hours (the same for foreign tourists from Montreal). But for those who come from further afield, there is also Portland International Jetport (PWM). It’s just under 30 minutes south of Kennebunk and is a convenient option for connecting the rest of the country to this coastal town.

Where to stay

Yachtman Hotel & Marina Club

Yachtman Hotel & Marina Club

As a port town, people inevitably flock to Kennebunk to experience its seaside landscape, including beaches, harbors and lighthouses, but also a charming town center aptly named Dock Square. Built around the Kennebunk River which flows into the Atlantic and some of the area’s famous beaches like Goose Rocks, it’s the perfect base for any beginner. In this case, check in the Navigator is your best bet; Slightly removed from the main square, the harbor property is an eight-minute walk from town. It’s only a three-minute bike ride to the center (which also serves as a popular pastime and mode of transportation in Kennebunk).

Nautical bungalows offer a playful splash of color against sliding glass doors that open to your private patio along the hotel’s on-site marina. For guests looking to mingle, the Yachtsman offers a private marina bar for guests only, or their floating “pool boat,” the S.S. Sundaze, which is the place to be on a summer weekend. And for any guests looking to get away from marina life, Yachtsman partners with neighboring Kennebunkport Marina, to offer rentals to explore the area’s waterways at your own pace.

hidden pond

About 15 minutes from Dock Square, it’s a stark contrast to the waterfront appeal of Kennebunkport, but it has an allure 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 daily delivery of coffee and pastries to your door) .

Each accommodation has a name rather than an impersonal number that another guest has checked in and out and is surrounded by nearly four acres of lush forest. The cabins offer outdoor showers, gas fireplaces and a veranda equipped with cozy blankets for a cozy experience. Decor wise, 20 of the bungalows have just been revamped by menswear designer Todd Snyder, depicting three of Maine’s main themes – country, mountain and seaside – once again linking the separate location from Kennebunkport. There are two pools on the property, multiple fire pits with daily s’more kits provided, and a farm-to-fork restaurant concept that serves breakfast but is renowned for its evening tasting menu.

What to do

To the beach

Whenever you visit Kennebunkport, you just have to visit the beach—Goose rocks beach, To be precise. The three-mile stretch of fine sand along a calm cove is an idyllic way to kill a few hours on a sweltering summer day, as is an off-season beach stroll. You will notice that beachfront properties are rare, as the lots are orderly, ensuring views and privacy are protected along this popular site.

Rugosa Lobster Tours
Rugosa Lobster Tours

Lobster Tour

Although 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 a lobster boat tour. They can learn about the specifics of Maine lobster and the restrictions surrounding permits, measurement requirements, and more. Captain Bob Danzilo at Rugosa Lobster Tours takes you to the Gulf of Maine, pulls a few traps, teaches you the basics of lobster fishing, and gives you a fun yet informative 90 minutes that will give you a whole new appreciation for the lobster you’re bound to eat on your Kennebunk trip.


Local boutiques and a fair share of classic souvenir shops populate Dock Square. If you are a buyer, you could make a day out of it. If you’re more of a stop-over type if it strikes me, you can easily visit all the stores in just a few hours. Either way, it’s worth walking around town to experience traditional Kennebunkport. If you catch a nasty spell of weather in New England, you might want to shop indoors; there are a number of antique shops around Kennebunkport that are worth visiting for unique finds.

Where to eat and drink

The clam shack

A symbol of Kennebunkport, The clam shack is recognizable by its quirky Coca-Cola-covered signage and the flurry of customers lined below waiting for fried clams and a lobster roll. While there’s definitely no “right” way to order a lobster roll, there is a Maine way. And it’s cold, with lobster and mayonnaise. If you’re more of a butter connoisseur (it’s the Connecticut way), The Clam Shack won’t judge. They have a “both” option, which combines a mayonnaise spread and a drizzle of hot butter to combine the best of both styles. Grab a local beer on tap and sit on a picnic bench while you wait for your order. Dip into the hot fried clams first, then tackle the roll.

Land at Hidden Pond

Whether you’re staying at Hidden Pond or just looking for a taste of the woodland property’s specialty farm-to-fork restaurant, be sure to arrive hungry. Earth uses farm-fresh ingredients, some even grown on site, to create an indulgent three- or four-course menu that rotates with the season. The decor and cuisine reflect its namesake, a bite-sized reminder of what fresh ingredients really taste like. Arrive early to enjoy an aperitif with house spirits at the Perfect Farm Bar. Or, stay later for a nightcap by one of the private fire pits overlooking one of the resort’s three ponds.

Arundel Wharf

With a large wooden terrace, Arundel Wharf is a casual restaurant on the quayside, ideal for a sunny lunch, a cheeky cocktail and snack at noon or a happy hour at sunset. There are plenty of appetizers to share for a large group, or even a smaller one looking to try the wealth of seafood available here. Think traditional New England steamers, shrimp cocktail, lobster stuffed avocado and mussels.

Restaurant dining room interior with wooden walls
Courtesy Image

White Barn Inn

Whether you’re celebrating a special occasion or just celebrating that you’ve landed a reservation at this fine dining restaurant, the restaurant at the White Barn Inn sets the tone for an elegant evening. The AAA Five Diamond, Forbes Five Star Restaurant is led by Executive Chef Mathew Woolf. It showcases the best of Maine’s farmers, fishers, and gatherers. It’s an old-fashioned place for the region, still encouraging gentlemen to wear jackets, and why not? Again, it’s an opportunity in itself to eat here.

Rococo ice cream

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

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