Kennebunkport is the perfect spot for a weekend getaway up to Vacationland, though there’s enough to do to last you an entire week (or more). Be sure to check out Federal Jack’s for a pint (or three) and charter a sunset sail on the Pineapple Ketch to discover why this town has been the longtime summer home for the Bush family. Though most popular in the summertime, it’s gorgeous to visit year-round. Roughly two hours north of Boston, and five hours north of New York City, this resort town in Southeastern Maine is worth the trip.
PUT ‘EM BACK
Federal Jack’s // 8 Western Ave, Kennebunk, Maine 04043
Federal Jack’s (also known as Fed’s) is practically a required visit when traveling to Kennebunkport. Drop in during the weekends for live music and dancing: a DJ plays every Friday and Saturday night. There is also a Tuesday Trivia contest held weekly, and, if you feel like coming back again, become a member of the Mug Club: $3 beer, a free tee-shirt, and your own numbered mug to be reserved behind the bar just for you. What more could you want?
The Pilot House // State Route 9, Kennebunk, Maine 04043
The ideal local bar in KPT. The Pilot House is perfect for those looking for 50 cent jello shots and $2 Miller Lites—and who isn’t looking for that? A big U-shaped bar takes up the majority of the space, so pull up a stool and mingle with some locals.
Old Vines Wine Bar // 173 Port Road, Lower Village, Kennebunk, Maine 04043
For a classier option, head over to the Old Vines Wine Bar for some vino. If you’re visiting in the warmer months, grab a table at one of the picnic tables outside and keep your eyes peeled—Adrian Grenier has been known to frequent the spot.
The Colony Hotel // 140 Ocean Ave, Kennebunkport, Maine 04046
If you’re looking for a bar with a view, look no further than the Colony Hotel. Go there at sunset for cocktails by the pool or in the hotel’s Marina Room. If you’re in town on Friday night, head over for the Mariner’s Buffet (also known as heaven: $40 all-you-can-eat lobster and steak).
Nunan’s Lobster Hut // 9 Mills Rd., Kennebunkport, Cape Porpoise
Nunan’s is a favorite local spot: the row-house style building has a lobster net on the ceiling. The hut has long, bench-style seating and serves lobsters any way you want: steamed, in a stew, on a roll, or in a salad. Two miles from Dock Square, the restaurant is definitely recommended for a visit. Word to the wise: the hut is cash-only and serves beer and wine.
The Landing // 157 Summer Street, Kennebunk, Maine 04043
The Landing is a locally-owned country store that has been around for over 100 years. The chowder and convenience store is a great spot for some chowdahh and a beer.
Mabel’s Lobster Claw // 124 Ocean Ave, Kennebunkport, Maine 04046
Open April through October, stop by Mabel’s for an old-fashioned feast of Maine seafood standbys. Try the traditional baked stuffed lobster (with bread filling) or the sea scallops. There’s also an ice cream spot right next door for dessert.
Old Salt’s Pantry // 5 Ocean Ave, Kennebunkport, Maine 04046
This local spot is exactly what it sounds like—located right in the heart of the port, stop by for a lobster roll or some chowder. Try to go on a sunny day, as indoor seating is limited.
The Clam Shack // 2 Western Avenue, Kennebunk, Maine 04043
The Clam Shack is a must-go tourist spot in Kennebunkport. Check out the traditional fried clams.
David’s // 21 Ocean Ave, Kennebunkport, Maine 04046
Another casual, easy spot for a great dinner in the center of town. The building was once rundown, but has since been renovated and is located in the Boathouse Oceanfront hotel, which is also a great place to stay.
White Barn Inn // 37 Beach Ave, Kennebunk, ME 04043
This is simply the fanciest place in Kennebunkport, and perfect for a date night. Open year-round, especially recommended in the fall or winter, when you can dine by the fire.
Earth at Hidden Pond // 354 Goose Rocks Road, Kennebunkport, Maine 04046
Another high-end option for dinner in KPT. Secret tip: request to have a private dinner in the Potting Shed.
Pier 77 // 77 Pier Road, Kennebunkport, ME, 04046
For a more casual experience—and if you don’t mind waiting a bit—the Ramp is the perfect spot. The Pier 77 complex includes The Ramp Up, The Ramp Down, and Pier 77. Located in the Cape Porpoise area of KPT, all three of these places have the same menu. Though we personally recommend the Ramp Down, the space is tiny and does not take reservations. But if you end up upstairs at Pier 77, you still can’t go wrong.
GET YOUR FIX
H.B. Provisions // 15 Western Ave, Kennebunk, Maine 04043
Located right in the center of town (and walking distance from the Grand Hotel), H.B. Provisions is the quintessential country store. Perfect for coffee in the morning, and their breakfast sandwiches are a must.
Mornings in Paris // 21 Western Ave, Kennebunk, ME 04043
The Parisian answer to a Maine weekend, go there for the chocolate croissants.
Goose Rocks Beach // Kings Highway, Kennebunkport, Maine, 04046
The beach is a must-visit (during any season), and we recommend the Goose Rocks Beach for its three miles of wide sandy shoreline. Park along Kings Highway and follow one of the many paths through the dunes down to the shore. Head over to the Tides Beach Club for a cocktail once you get there.
The Tides Beach Club // 254 Kings Highway, Kennebunkport, Maine 04046
Go there for lunch or a cocktail and hang on the beach, or make a night of it and stay for dinner. It’s about fifteen minutes outside the town of KPT, and also features a hotel—a great option for a place to stay.
The Pineapple Ketch // 95 Ocean Ave, Kennebunkport, Maine
Head over to the Nonantum Resort to set out on the water aboard The Pineapple Ketch. Book in advance for a two-hour sail (we personally recommend the sunset cruise). You can park in the resort lot. If you book enough guests, you can also make it a private charter. Another option? Check out the Schooner Eleanor for a chance to get out on the water.
OFF THE GRID
Kennebunk Land Trust // 6 Brown St #2, Kennebunk, Maine 04043
The Kennebunk Land Trust is a five-mile preserve that crosses Route 9. You can run along the old railroad track, or go hiking or biking down any of the trails.
Spiller Farm // 85 Spiller Farm Ln, Wells, Maine 04090
Head out to Spiller Farm to pick strawberries, raspberries, or blueberries (depending on the season). It’s a little out of the way, so check out their website, which is updated daily to show what is in-season.
Picnic Rock // 8 Western Ave, Kennebunk, Maine 04043
This twenty-foot rock is located just off old Port Road in Kennebunkport. Picnic Rock is perfect for jumping into the ocean (though we recommend going at high tide). Bring beer, speakers, and a football (or Frisbee) to make a day out of it.
FILL YOUR BAG
Kittery Outlets // 306 US-1, Kittery, Maine 03904
Home to Barbour, Orvis, Adidas and Lululemon, this outlet just twenty minutes south of town is referred to as “America’s Maine Street for Outlet Shopping.” Head there for discontinued Barbour styles (we spotted a burnt orange jacket this June) on your way out of town.
HANG YOUR HAT
Beach House Inn // 211 Beach Ave, Kennebunk, ME 04043
The Beach House Inn is a great spot right on middle beach. Relax in a rocking chair next to the fire pit on the big wraparound porch and enjoy a cocktail at the end of your day.
Breakwater Inn & Spa // 127 Ocean Avenue, Kennebunkport, Maine 04046
If you’re looking for a luxurious experience, the Breakwater Inn & Spa is perfect—definitely book a massage and make the most of your stay.
The Cottages at Cabot Cove // 7 S Main St, Kennebunkport, Maine 04046
Want some privacy away from the bustling tourist scene? Book your own cottage at Cabot Cove and pretend that you have your own second home for the weekend.
The Grand Hotel // 1 Chase Hill Rd, Kennebunk, Maine 04043
If you’re looking for comfort and convenience, the Grand Hotel is your spot. Located right in town next to H.B. Provisions (and down the street from Federal Jack’s), the colonial décor is cozy and the location can’t be beat.
Special thanks to Will Beckham, and Morgan and John Shaddock for the insider tips!
did we miss anything? Hit us up in the comments....