4-Day Weekend Travel Guide to Kennebunkport, Maine

Kennebunkport is one of the quintessential summer destinations in New England. It is perfect for long weekends near the beach or relaxing in its lush countryside. This is what makes the destination so unique and attractive – tour lobsters in the morning, go for a bike tour in the afternoon, and enjoy the sunset during happy hours on the beach. Here’s how to spend the perfect weekend in Kennebunkport, Maine.

How to get there

For the majority of visitors, Kennebunkport is a relatively smooth drive. Boston residents can arrive 90 minutes later on I-95; Other New England cities average about three hours; Even New Yorkers can get there in less than five hours (similarly to out-of-country tourists from Montreal). But for those coming from far away, there’s also Portland International Jet-Airport (PWM). Located less than 30 minutes south of Kennebunk, this is a convenient option for connecting the rest of the nation to this port city.

where to stay

Yachtingmen Hotel and Marina Club

Yachtingmen Hotel and Marina Club

As a port city, people inevitably flock to Kennebunk to experience its coastal scenery, including beaches, harbors, and lighthouses, but also the charming city center called Dock Square. Built around the Kennebunk River that flows into the Atlantic Ocean – and some of the area’s famous beaches like Goose Rocks – it’s the perfect place to start any first timer. In this case, checking into the yacht is your best bet; A little further from the main square, the property is by the port, an eight-minute walk from town. It’s only a three-minute bike ride to the center (doubles as a popular pastime and mode of transportation in Kennebunk).

Navy huts offer a pop of playful color against sliding glass doors that open onto your patio along the hotel’s on-site marina. For guests looking to mingle, Yachtsman offers a private guest-only marina bar, or a floating “pool boat,” SS SundazeIt’s the perfect place to spend a summer weekend. And for any guests looking to get away from marina life, Yachtsman partners with the nearby Kennebunkport Marina, providing rentals to explore the area’s waterways at your own pace.

hidden pond

About 15 minutes from Dock Square there is a stark contrast to Kennebunkport’s waterfront allure, yet it has a whole attraction of its own – you don’t want to miss it. Spread over 60 acres, Hidden Pond offers 36 private cabins shaped like treehouses, bungalows, and two-bedroom cottages for the ultimate secluded getaway, all with the amenities of a luxury resort (like a daily morning coffee and pastry delivery on the doorstep) .

Each property has a name – not an impersonal number that another guest checked in and out of – and is surrounded by up to four acres of lush forest. Cabins offer outdoor showers, gas fireplaces, and a screened balcony with cozy blankets for a cozy experience. As for the decor, the 20 bungalows were renovated by menswear designer Todd Snyder, depicting three of Maine’s iconic themes—the countryside, the mountain, and the coast—once again linking Kennebunkport’s iconic location together. There are two pools on the property, multiple outdoor fire pits with daily s’mores combinations available, and a farm-to-fork restaurant concept that serves breakfast, but is best known for its evening tasting menu.

What do I do

beach it

No matter when you visit Kennebunkport, you should simply visit the beach—Goose Rocks Beach, to be specific. The three-mile stretch of fine sand along a quiet inlet is the perfect way to waste a few hours on a sweltering summer day, just as it is for a stroll on the beach in the off-season. You’ll notice that beachfront properties are few and far between, with plenty being coordinated, ensuring views and privacy are protected along this popular site.

Rogosa Lobster Tours
Rogosa Lobster Tours

lobster tour

Although lobsters are a year-round menu item throughout Maine, June is the unofficial high season for the namesake variety of these red crustaceans. Summer visitors should take advantage of the warmer weather and book a lobster boat excursion. They can learn more about the idiosyncrasies of Maine lobsters, restrictions surrounding licensing, measurement requirements, and more. Captain Bob D’Anzillo puts you on Rugosa Lobster Tours in the Gulf of Maine, pulls some traps, leads you through lobster basics, and provides 90 fun and informative minutes that will give you a whole new appreciation for the lobsters you’re bound to eat during your Kennebunk trip.

Shop

Local boutiques and a fair share of classic souvenir shops abound in Dock Square. If you’re a shopper, you can make a day out of it. If you are a fan of stopping by if so, you can easily visit all the stores in just a couple of hours. Either way, it’s worth strolling around the city area to get a feel of traditional Kennebunkport. If you suffer from choppy New England weather, you may want to shop indoors; There are a number of antique stores surrounding Kennebunkport that are worth popping in for unique finds.

Where do you eat and drink?

the word shack

The Clam Shack is a symbol of Kennebunkport, recognizable by its original Coca-Cola-clad sign and the group of customers queuing beneath it waiting for fried oysters and lobster rolls. Although there is no “correct” way to order lobster rolls, there is a Maine way. That’s cool with lobster and mayonnaise. If you’re more of a butter connoisseur (that’s the Connecticut way), The Clam Shack won’t judge you. They have a “both” option, which combines a spread of mayonnaise and a drizzle of warm butter to combine the best of both styles. Grab a local beer on the draft and sit on a picnic bench while you wait for your order. Dip in the hot fried oysters first, then tackle the roll.

Land in Hidden Pond

Whether you’re staying on Hidden Pond or simply looking for a taste of the farm-to-fork restaurant on your wooded property, make sure you arrive hungry. Earth uses farm-fresh ingredients, some even produced on property, to create a three- or four-course menu that alternates with the season. Both the décor and the cuisine reflect the same name, with one bite reminding you of the taste of truly fresh ingredients. Arrive early to enjoy aperitifs and house spirits at the perfect farm bar. Or you can stay later for an alcoholic drink by one of the private fireplaces overlooking one of the resort’s three pools.

Arundel Wharf

With a spacious wooden deck, Arundel Wharf is a casual quayside restaurant perfect for a sunny lunch, a midday cocktail and snack, or sunset happy hour. There are plenty of appetizers to share for a large group, or even a smaller group looking to try the best seafood available here. Think traditional New England steamers, shrimp and avocado cocktails stuffed with lobster and mussels.

Restaurant dining room interior with wooden walls
photo courtesy

White Barn Inn

Whether you’re celebrating a special occasion, or just celebrating that you’ve made a reservation at this fine dining hot spot, the restaurant at the White Barn Inn sets the tone for an elegant evening. Forbes Five Star’s AAA Five Diamond restaurant is run by Executive Chef Matthew Wolfe. Presents the best farmers, hunters and foragers in Maine. It’s old school in the area, and they still encourage gentlemen to wear jackets, and why not? Again, it is an occasion in itself to eat here.

Rococo Ice Cream

Every coastal town needs a famous ice cream storefront, and in Kennebunkport, it’s Rococo. On any given day, this focus accommodates 14 different flavors. You’ll find signature flavors like goat cheese, chambard berry, and maple fig, as well as seasonal options. They also do an incredible Affogato. Serve espresso with your choice of mid-day ice cream.


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

Leave a Comment

Your email address will not be published.