How to Spend an Off-Season Food-Packed Weekend in Kennebunkport, Maine

Wind chill and snow Days can keep beach visits icy for a while, but Kennebunkport, Maine — just an hour and a half drive from Boston — is well worth a visit even in the colder months. The southern Maine town, nestled by the ocean and the Kennebunk River, is its own microcosm at mealtime, with everything from plentiful seafood platters to decadent fudge to please the palate. Plus, the streets of Dock Square are quieter without the summer rush, but just as quaint and inviting – and you’re likely to find off-season robberies in the shops.

Plan to spend a cozy weekend there, staying in one of the city’s many inns or bed and breakfasts, like AWOL Kennebunkport, which offers both historic and modern aesthetics (choose from minimalist cabins adjoining a wooded enclave or a suite in the Melville Walker House, which dates back to 1860.) Wherever you choose to drop anchor, be sure to savor as much food as you can in these ports of call.

Watch out before you go: Common to beach towns, many restaurants in Kennebunkport are closed on Mondays, Tuesdays, and Wednesdays; be sure to call or check the schedule online before you go.

Here’s a recommended foodie itinerary for a day – or more – in the beautiful coastal city.

Breakfast and brunch

A must during your winter weekends: sleep. If you’ve decided to stay at AWOL, enjoy free breakfast delivery in the morning, a variety of sweets, spreads, toppings, Greek yogurt and fruit dishes. Accompanied by a cup of coffee next to the suite’s fireplace, it’s the perfect way to refuel and plan the day.

Morning delivery extended to AWOL, including salmon, yogurt and toast toppings.
Nathan Tavares / Eater Boston

A few steps from Dock Square, Fiafia invites you to enjoy a light breakfast. Savor smoothie bowls, like the acai OG (acai, banana, and coconut milk, topped with granola, fruit, cocoa nibs, and a drizzle of honey) or the vibrant charcoal smoothie bowl , which features activated charcoal among its ingredients, tempered with a sweet agave kick. To drink, a whole mocha menu awaits you, with seven different twists, including hazelnut chocolate and lavender white chocolate.

Caffeine lovers should take a quick trip from Dock Square to Coffee Roasters of the Kennebunks in the nearby Kennebunk, where you can grab freshly roasted coffee by the pound or hot, iced coffee from the self-serve bar, as well as sandwiches to go. As an added bonus, you can fill your cup with coffee ice cubes so your java won’t be watered down when the ice melts.


Alisson’s Restaurant is the kind of place you can sit in for hours, thanks to both its excellent seafood dishes and friendly atmosphere. Flat screens on the walls above the booths sport, while others showcase the richness of drinks on tap, both up close (like Austin Street Brewery’s barleywine Snow Blower in Portland, Maine) and distant (like the Rullquin blended sour stout from Gueuzerie Tilquin in Belgium).

French onion soup baked with chunks of bread and cheese – and of course the Maine lobster bisque – are among the must-haves, with the sauce of native Maine mussels singing along with that perfect white wine and the garlic butter magic. Hungry but undecided? The small trio of lobster rolls lets you try variations on the New England staple: there’s a classic version, a south-of-the-border lobster roll, and one made with lobster bisque.

If your lunch plans fall later, check out Pedro’s fast and satisfying Mexican restaurant, which opens at 3 p.m. marinated in tequila and garlic (served with black beans and tortillas). For heartier dishes, check out the braised cola and adobo barbacoa, served in a burrito, on a salad or with vegetables, beans and guac. If it’s Tuesday, enjoy $4 tacos and classic $7 margaritas in a lively atmosphere.

Having dinner

You don’t have to stay at the Boathouse Waterfront Hotel to dine at the restaurant (though lobster lovers might jump at the chance to stay in the hotel’s Maine Lobster Suite, complete with creative artwork on shellfish and surprises around the room, including lobster trap end tables). The waterfront restaurant serves New England fare with Asian influences, with dishes such as tamarind and lemongrass steamed mussels, togarashi-spiced salmon, and short rib ramen. Other plates cater to comfort food cravings, like the bacon-butternut squash macaroni and cheese, smothered in cheddar, smoked gouda and mornay sauce — which you definitely have to order topped with lobster. Dine in the dining room or in one of the charming private heated ski gondolas on the wraparound deck.

The Steak and Noodle Salad at the Boathouse Restaurant

The steak and noodle salad at the Boathouse Restaurant.
The boathouse restaurant

Meanwhile, the food at the Earth farm-to-fork restaurant at the luxury Hidden Pond resort is nothing short of heavenly. Offerings change frequently with what’s in season and harvested locally – including from the resort’s own organic gardens – but expect a juicy lobster caught that day, as well as a filet mignon worthy of a madness with truffle gnocchi and black trumpet mushrooms, plus scallops with prosciutto and caviar.

Save room for the exceptional homemade brioche donuts. Besides delighting the taste buds, Earth’s plates are a work of art and will leave you wondering when this place will ever earn a Michelin star.

Overhead view of a variety of modern and artistic food plates on a wooden table.

A spread of delights on Earth.
Heidi Kirn Photography


Savvy travelers to this seaside spot know to hit the Candy Man for its jewel-like chocolate truffles, classic fudge sold by the pound, and turtles (especially the dark chocolate variety). But the real treat is the huge selection of 79 flavors of salt water taffy, from fresh apricot and frosted cupcake to cinnamon bun and even pickle. (Really, try the pickle: you might actually enjoy the salty-sweet combo.) Stock up for the drive back to Boston, or — at $9.99 a pound — store a full barrel until your next trip summer in Maine.

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