For this installment of our weekend travel guides, we’re headed to one of the most picturesque towns in all of New England: Kennebunkport, Maine. This seaside town is an appealing destination year-round, and — thanks to the quaint, walkable downtown — no car is necessary. Find out why Kennebunkport exemplifies the state nickname of Vacationland, and its motto “The Way Life Should Be”.

Though we’ve already covered the classic charms of summertime in New England, the fall is the most Instagrammable time of year to capture the spectacular changing colors of the leaves. Plus it’s more cost-efficient (but more on that later). It’s also a great place to visit over Valentine’s Day too: In February, they have an event called Paint the Town Red! Read on for more things to see and do in this gorgeous coastal town.

Where to Stay

Captain Jefferds Inn, Kennebunkport, Maine

swimming pools, then The Colony Hotel on Ocean Avenue can’t be beat. But even if you don’t book a room there, check out the surf and turf at the Mariners Buffet on Friday night to enjoy $40 all-you-can-eat lobster and steak.

The Beach House Inn boasts a gorgeous wraparound porch on middle beach in Kennebunk, and The Jeffereds Inn Bed & Breakfast offers historic accommodations such as the Captain’s House (pictured above). The Breakwater Inn & Spa is ideal for the luxury and wellness lover, while The Cottages at Cabot Cove offers privacy for the solitude-seeking traveler. Tip: Book your own cottage and pretend that it’s your second home for the weekend.

The Grand Hotel is located right downtown next to H.B. Provisions (the go-to place for breakfast sandwiches) and down the street from Federal Jack’s (where you’ll be spending your night right up until those morning hours).

Finally, as if you need another reason to visit in the fall, the Kennebunkport Resort Collection’s “Color Therapy” package is just about as enticing as the Maine foliage. The KRC offers leaf-peeping guests 25 percent off the standard mid-week rate and a $25 dining credit for any KRC restaurant. Plus, it’s totally customized: Travelers choose their favorite design palette for their stay, from the vivid hues of the Yachtsman Hotel & Marina (which was redesigned this past May) to the bright and neutral palette of The Tides Beach Club.

What to Do

Kennebunkport, Maine


Goose Rocks Beach on Kings Highway. (Go swimming, if you dare: Maine water is always cold, but refreshing!) If you do take the plunge, you can always warm up with a cocktail at the nearby Tides Beach Club and maybe stay for lunch and dinner (or even the night). It’s alarmingly easy to while away an afternoon at this restaurant and hotel.

Take it a step further and explore that Atlantic Ocean with a sail on The Pineapple Ketch or the Schooner Eleanor. After all, you are in Maine (a famously popular spot for sailors, many of whom head down to the Virgin Islands in the winter — tough life).

If you’d rather be earthbound for your activities, hike or bike along the trails of the Kennebunk Land Trust, a five-mile preserve with an old railroad track that doubles as a popular running path for Kennebunkport regulars.

Pick blueberries at Spiller Farm (or strawberries, or raspberries) — be sure to check out the daily updates on their website to see what’s in season. Then head to Picnic Rock: The 20-foot rock off old Port Road formally known as the Butler Preserve is a popular spot for cliff jumping (though, please, try to make sure it’s high tide).

If all that sounds a little too outdoorsy for you, then be thankful for the existence of US-1’s Kittery Outlets. Those seeking retail therapy can spend all day at stores such as Lululemon, Barbour, and Orvis (when in Maine, shop as the Mainiacs do).

Where to Eat and Drink

Mornings in Paris is known for their chocolate croissants, while The Clam Shack is renowned for its traditional fried clams (and known as a tourist magnet that’s still a must-visit anyway). We’re partial to Alisson’s Restaurant as a good local spot for clam chowder.

And now for the famous food you came to the state for. Visit Nunan’s Lobster Hut in Cape Porpoise to experience local-favorite lobster in any way you desire: in a stew, on a roll, in a salad, or steamed. There’s even a lobster net on the ceiling (the ultimate Maine ambiance). But note: The restaurant serves beer and wine and is cash-only. If you’re visiting between April and October, order the traditional baked stuffed lobster (with bread filling) at Mabel’s Lobster Claw.

The Old Salt’s Pantry is another favorite amongst locals, right in the heart of the port. Since there’s limited indoor seating, you’re better off heading there on a sunny day to enjoy a lobster roll and chowder outside. Or grab some chowder and beer at The Landing Store, a locally owned country store that’s over a century old.

For fancier date night options, make a reservation at either the White Barn Inn (where the fire is especially romantic in the fall and winter) or Earth at Hidden Pond (where you can request a private dinner in the Potting Shed).

The Pier 77 dining complex is a more casual option for dinner, with three restaurants of slightly different ambiance. Between The Ramp Up, The Ramp Down, and Pier 77, we prefer the Ramp Down, but since the tiny space doesn’t take reservations, it’s no big deal if you end up upstairs at Pier 77. The three restaurants are all fun and share the same menu.

Federal Jack’s (Fed’s to locals) is the spot to visit to go out at night in Kennebunkport. There’s music and dancing on weekends (a DJ every Friday and Saturday night) and a weekly Tuesday trivia contest. If you plan on spending a lot of time there, sign up for membership in the Mug Club for $50 to have a numbered mug reserved for you behind the bar at $3/beer, plus you’ll get a free T-shirt to boot.

If you’re interested in 50¢ jello shots and $2 Miller Lites, then the big U-shaped bar at The Pilot House is designed for you. For a more sophisticated night out, visit Old Vines Wine Bar in Kennebunk’s Lower Village. If it’s nice out, post up at one of the picnic tables and keep an eye out for celebs (Adrian Grenier has been spotted there).

What are your favorite places in Maine? Tag us in your go-to spots on Instagram @BritandCo.

(Photos via Getty)



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