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The Weekender: Kennebunkport, Maine

Here is your complete guide to experiencing the ideal long weekend in New England’s coziest town

There is perhaps no New England town quainter than Kennebunkport, Maine’s historic coastal crown jewel made up of mansions-turned-hotels, craft boutiques and small businesses, and, of course, lobster rolls galore. While some might shy away from visiting during the colder months in favor of more vacation-friendly weather, this is a year-round destination that has its own wintertime perks: snowglobe vibes, low-season rates and availability, and the same buzz about town with a bit less crowding. So zip up, pack up, and head out to this perfect seaside hideout on our 72-hour itinerary.

Friday Afternoon:

New England charm awaits at the Grand Hotel, a stately structure perched atop Chase Hill in Kennebunk, just before the bridge into Kennebunkport. The hotel is one of nine luxe properties that make up the Kennebunkport Resort Collection; here, you’ll find an art gallery, Kennebunk River views, warm hospitality, and most importantly, extremely comfortable beds. And for those who enjoy a good stroll, you’re in luck: the Grand Hotel is within walking distance of everything on your weekend itinerary.

Grand Hotel (@tghmaine)

Friday Evening:

After you’ve properly settled into your new digs, set out on foot for Kennebunkport Inn, located across the bridge in the heart of Downtown’s Dock Square area. If you’re lucky enough to catch this season’s Igloo Ice Lounge, a fur-clad outdoor wintry watering hole on the hotel’s patio, grab a pre-dinner drink (try the Destination KPT with Barr Hill Gin, honey, lemon, pear, and mint) inside one of the igloos or next to one of the roaring fire pits before heading inside for dinner at The Burleigh, where Chef Eric Murdough’s hearty coastal fare honors both the locale and the mansion’s original proprietor, Burleigh S. Thompson.

Igloo Ice Lounge (@kennebunkportinn)

Saturday Morning:

Take advantage of the peace and quiet Kennebunk has to offer and make it an alarm-free morning. Refuel after your full night’s rest with a cup of coffee and your choice of classic breakfast fare across the street at HB Provisions, a general store and longtime local favorite haunt. From there, continue your walk toward the downtown area, where small shops and businesses line the quaint streets, perfect for leisurely exploration.

Saturday Afternoon:

Lunchtime will inevitably roll around all too quickly, and you’ll have worked up an appetite worthy of a surf-and-turf spread at The Boathouse nearby. With its sprawling views of the river, this hotel restaurant is a must during any season––order a selection of raw bar classics and a lobster roll or two to start, followed by a burger, grilled pork chop, maple bourbon sirloin tips, or lobster ‘nduja mac and cheese with béchamel.

Saturday Evening:

After exploring Downtown, make your way back across the bridge and relax at the hotel or visit its art gallery. Once the clock strikes 5:00pm, set out on foot again in the opposite direction of the bustle of Downtown to find yourself at happy hour at Spat Oyster Cellar beneath Pearl Kennebunk Beach. Chef and Owner Rebecca Charles offers one of the best happy hours in town (specials include salt-crusted shrimp, chowder, Little Neck clams, and other Maine favorites alongside draft beers, wines by the glass, and cocktails). You’ll want to stay for dinner afterward; go for the smoked Atlantic salmon with johnnycake and crème fraîche, classic seafood bouillabaisse, lobster stew, and the pan-fried filet of the day. Note: Pearl and Spat will reopen for the season on April 18, 2019.

Sunday Morning:

Check out of your accommodations and hit the road, to-go coffee from HB Provisions in hand.

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