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The Kennebunks: The Perfect New England Day Trip

Only about 80 miles outside of Boston, the quintessential neighboring New England towns of Kennebunk and Kennebunkport make a great day trip for city-dwellers looking for an escape. Think: honesty payment systems, miles of beaches, and maybe even a former President sighting or two. Summer’s end is a great time to explore the two towns. Here are our picks for where to go, what to eat, and where to sleep.


Stretch your legs after the drive by taking a long stroll on the Parson’s Way Shore Walk, a path that meanders along the coast, with competing views of the ocean and the mega mansions dotting the shore. The path is 4.8 miles round-trip.

Next, stop looking at the beaches and get on them. The Kennebunks are rife with beaches—try Kennebunk Beach for swimming (although be warned … Maine water is mighty cold, even in the summer), or Gooch’s Beach, which is popular with surfers.

You’ll need your car to get to the area, but once you reach town, you can retire it for the night. Kennebunk’s central town square (Dock Square) is small and best explored on foot. We loved the “honesty parking” available in town (in which customers are trusted to drop a cash payment into a box to pay for their parking.) Many of the farmers’ stands and yard sales that we passed were unmanned except for an honesty box as well, which speaks volumes about the Maine way of life.

There’s plenty of cute shops to while away a few hours of here. Browse everything from jewelry to art to political paraphernalia (Former President George H.W. Bush has a summer home in Kennebunkport, so I even if you don’t catch a sighting of him in town, you can buy plenty of souvenirs with his his image on it.)

Drink and Eat

Unwind and watch the sunset from a rocking chair on the wide front porch of Tia’s Topside, but be prepared to spend a lot for the ambiance. (On our visit, we were charged for ice in our drinks and “prep” for making a cocktail … in addition to the already pricey drinks.) Or try Federal Jack’s, a brew pub with a large open deck and more reasonable prices. Grab a beer flight to sample all the local brews.

When you’re ready to move on to dinner, One Dock Square, in the Kennebunkport Inn is a great option. The restaurant is tapas style, but with New England style cuisine. This makes it perfect for sharing, and a fun way to design a unique meal out of small plates and signature side dishes. Vegetarians and meat-eaters will both be happy here. The only problem? All the dishes sound so delicious, and are so inexpensive, that it’s easy to over-order. The baked haloumi drizzled with an ouzo sauce sweet and spicy Brussels sprouts (which get a delightful unexpected kick from Sriracha sauce), and the asparagus with cherry tomatoes and Parmesan are all standouts.


After a day in the sun, followed by a night of great food and drinking, a drive back to the city is the last thing that you want. Leave that for tomorrow, and spend the night at The Inn at English Meadows

This inn is a far cry from your mental image of B&Bs —there are no floral couches or dusty doilies here. Instead, you’ll stay in a newly renovated mid-1800s Greek revival home, decorated with modern furnishings.

The Inn at the English Meadows is full of unexpected elegance—from the Frette linens on the bed (to match the provided Frette robes and slippers) to the toiletries. Personally, I never know what to expect from hotel toiletries, which tend to be bar soap and harsh shampoos. Not here, where the bathroom is stocked with everything you need, including Malin—Goetz Grapefruit Face Cleanser, Vitamin E Face Moisturizer, Bergamot Body Cleanser, Vitamin b5 Body Moisturizer, Peppermint Shampoo and Cilantro Conditioner.

The beds are also way beyond a typical B&B’s ancient, creaky four-poster bed. Did you know that Vera Wang makes beds? Neither did we, but the Vera Wang beds at the English Meadows were some of the most comfortable we’d ever slept on. The rooms are equipped with plenty of modern amenities as well, like a Nespresso machine, gas fireplace, and iPod docking stations, and flat-screen TVs. Breakfast is included, and snacks like fresh-baked chocolate chip cookies and tea are laid out in the common room in the afternoon. Best of all, it’s all less than a ten-minute walk from Dock Square. (There’s free parking at the Inn—no honesty box required.)

(Photos: Caroline Morse)

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