KENNEBUNK — I distinctly sensed the thump of dance music in the distance as I hoisted a forkful of baked burrata toward my mouth. These were the bass-heavy beats you would hear at a nightclub, but that seemed rather improbable in my situation. It was a very chilly April night in Kennebunk and the sidewalks were rolled up for the night. I was eating a late dinner at an Italian restaurant called Via Sophia by the Sea.
After some careful sleuthing — meaning I stood up and walked in the direction of the music — I found the source. Downstairs in the restaurant was a tiny club called the Rabbit Hole. It’s a combination speakeasy/disco rumpus room that leans heavily on the bunny decor. Think “Alice in Wonderland,” with Alice as a cigarette girl in a gin joint. I did what any respectable travel writer would do. As soon as I finished the burrata, I went down the Rabbit Hole, danced to Beyoncé, and sipped a Futterwaken (gin, elderflower, pineapple, lime, and Prosecco). All in a day’s work, my friends.
Aside from the Rabbit Hole club, I went down other rabbit holes while exploring Kennebunk. I decided to save a careful examination of the town’s beaches for the summer but readily dove into everything else the town had to offer.
For years I paid little attention to where Kennebunk ended and Kennebunkport began. I assumed they were essentially the same. Clearly, the founders of these towns never sought out classes on branding or destination marketing back in 1653. In the late 1980s, Kennebunkport got all the glory as the Bush family summered on Walker’s Point. I once spotted Barbara Bush and her pearls driving through town as I walked by T-shirts that read “Kennebushport.”
Fodor’s lumped the two towns together in a recent write-up, calling them “the Hamptons of the Pine Tree State.” Upon seeing this, I muttered, “Oh, brother,” and threw in an eye roll for good measure. I always thought Maine was the antithesis of the Hamptons, and so I set out to prove it. While the Hamptons require a full wardrobe (I believe the color of choice this season is a neutral called “sand dollar whisper”) and an even fuller wallet, Kennebunk offers a broader budgetary range of lodging and restaurant options. Fodor’s misguided description inspired me to suss them out.
Let’s break this down into three easy-to-digest categories, beginning with eye candy for you big spenders, working down the ladder to folks who keep padlocks on their coin purses. Does anyone use a coin purse anymore? Here’s the usual disclaimer: This list is purely subjective and wholly focused on Kennebunk, not Kennebunkport, and certainly not the Hamptons.
Suggestions for Kennebunk visitors with deep pockets
The White Barn Inn & Spa: If you’re coming to Kennebunk to drop some serious ducats, this is your place. Both the inn and restaurant are dripping in accolades, and rightly so. The service is impeccable, the rooms are ridiculously cozy, and the restaurant is legendary. The menu is prix fixe, so don’t even try going à la carte. You’ll pay $165 for the basic menu and add $85 for wine pairings. The lobster menu is $245. Pricey? Yes. Worth it? Definitely.
Because one of my Kennebunk trips coincided with my birthday, I splurged, stayed at the inn, and dined in the barn. I figured you only turn 39 once, or, in my case, multiple times, so I deserved it. My room had a fireplace and a bed that put my mattress and sheets back at home to shame. If you opt to stay, you’ll pay about $1,000 a night for the least expensive room in high season. Rooms drop to about $500 a night during the dead of winter.
The Clam Shack: Any dining establishment with the word “shack” in it should, by all logic, be inexpensive. But the once plentiful New England seafood supply has shrunk in quantity and ballooned in price. The Clam Shack has been around since 1968, and the folks in the kitchen know their way around a lobster roll. Their version of the classic features chilled lobster served on a toasted round bun and topped with mayo and melted butter. If you allow yourself one splurge in Kennebunk, make it the $34 lobster roll. I’m not sure why they’re charging $22 for chicken fingers with fries and coleslaw, but both the universe and the laws of supply and demand work in mysterious ways.
Maine Art Hill: Some of you might take umbrage with Maine Art Hill falling under the “deep pockets” category. I tend to think of the seven galleries on three adjacent properties as a destination for folks with second homes in the area who need tasteful, nautical-inspired art to adorn their sitting rooms and libraries. Prices here aren’t entirely unreasonable (paintings start around $1,000, give or take), but these are investment pieces for most of us rather than casual purchases or souvenirs. However, there’s no charge for window shopping. Throw on a tasteful pair of Madras slacks and have fun.
Rosella: Kennebunk has been steadily gaining new restaurant and lodging offerings over the past two years, but I didn’t see this one coming. On June 8, New York sushi restaurant Rosella opens in the Grand Hotel downtown. The New York location of the sustainable sushi restaurant was named one of Esquire’s best new restaurants in America in 2021 and was featured as one of Michelin’s new 2021 Plate restaurants. The 28-seat Kennebunk iteration will feature a $150 omakase meal, which means you hand your dining fate over to the chef and allow him to choose your courses. There’s also an emphasis on innovative cocktails. In case you were wondering, sustainable sushi means that the fish used are species that are not overfished and are caught locally rather than shipped from Japan.
Kennebunk on a midrange budget
The Wanderer Cottages: This group of 17 cottages, designed by Mark Cotto, is intended to “channel a laid-back surf lodge meets nostalgic New England aesthetic.” Think of it as California-meets-Maine by way of West Elm, and I mean that in a good way. I stayed here last summer and space in the cabin was tight for two people and our luggage, but the fun takes place outside, weather permitting. There are fire pits, bikes, a pool, a bocce court, and breakfast is delivered to your door every morning in a basket. Prices for studio cabins during the summer will run just north of $250 a night. The property is closed from October to May. Off-season rates are under $200 a night. As an added bonus, you can go across the street to Bennett’s Sandwich Shop for a steak and cheese.
Batson River Brewing & Distilling: The founders of Baston River also own the Wanderer Cottages, so the vibe at the restaurant just near Dock Square is similarly laid back, although the look is decidedly more Maine than California. The food here is a solid and sophisticated take on bar fare. I recommend coming for brunch with friends and splitting the duck fat cornbread, poutine, or the Carolina mustard barbecue-glazed wings. Although beer is the specialty, the cocktails are innovative. Order the Nordic Nightfall and thank me later. But the restaurant’s finest feature is its expansive, multi-level deck, complete with gas fire pits, space heaters, and blankets. Prices for most main dishes and shareable plates average around $18.
Garden Street Bowl: They had me at “luxury bowling.” Yes, that’s how the owners of Garden Street Bowl describe their lanes. Along with bowling, there’s also a gastropub with more than two dozen varieties craft beer, wine, cider, and kombucha on tap. Specialties from the kitchen include flatbreads, burgers, and adult milkshakes. But the most expensive item on the menu is the $30-an-hour bowling lanes (gulp). I didn’t let the price stop me from renting shoes that hundreds of people had worn before me and getting my 10-pin groove back. Sorry kids, there’s no candlepin here. As a former 10-pin league bowler, I realized that I was terrifically rusty and was more than satisfied to stop after one nostalgic $30 hour.
Old Vines Wine Bar: The concierge at the White Barn Inn told me that this wine-soaked stalwart is where the locals go, so I ventured in on a sleepy Monday night and ordered the tuna tartare, using it as a very flimsy excuse to sip an adult beverage. My server saw through me like a Frederick’s of Hollywood lace chemise, skipped the pretense, and steered me in the direction of cocktails. For a wine bar, the spirits program is wide-ranging and my server was very skilled deciding drinks for me based on my tastes. But before you mistake me for a total slubberdegullion, I continued down the menu with healthy choices such as the roasted carrot and quinoa salad and the Chioggia beet salad. I can understand why locals come here. It’s laid back and friendly. The menu occasionally veers into pricey territory (the pan-seared halibut is $29), but given the fresh ingredients and innovative menu — a fellow diner let me try her halibut — I had no problem with the bill. Next time I’ll lay off the cocktails and focus a bit more on the food.
The Brick Store Museum: Just to clarify, the Brick Store Museum is not a store and it does not sell bricks. Admission is $5, so it’s also an inexpensive way to acquaint yourself with the history of Kennebunk. Its focus is preserving artifacts that tell the story of Kennebunk and York County, which means there’s art, textiles, and photographs. This may not sound particularly interesting, but I found myself engrossed in reading 18th- and 19th-century letters from sailors to their wives. One in particular, dated November 1814 from James Garfield to his beloved wife read like a romance novel. “It is with regret that I have to tell you of our misfortune of being captured 30 hours after leaving you.” He then goes on tell her to sell her horse and pretty much everything else she owns and hopes that she’s in good health “as it leaves me.” I was ready to buy the rights to the letter and turn it into a PBS period drama.
Kennebunk on the cheap
The Franciscan Guest House: Even if you’re not looking to save money on lodging, I’d still recommend staying here for the novelty of it. Sure, the guest rooms were created for a boy’s boarding school in the 1950s and haven’t been updated since. There’s more paneling here than in your dad’s man cave, but it’s located on 60 pastoral acres adjacent to the Saint Anthony Franciscan Friary and along the Kennebunk River. It’s also all about the location. You can walk nearly everywhere from here. It’s also the biggest bargain in Kennebunk. Off-season rates are $129 to $199 a night. During the height of summer, rates range from $199 to $269 a night.
The Wedding Cake House: The 1825 Wedding Cake House, which was built for shipbuilder George Washington Bourne, was most recently used as an event space. It’s currently being restored, so it’s not open for tours. But, on the plus side, it’s part of Kennebunk’s Museum in the Streets. Penny pinchers rejoice! This museum is free. You can see 25 points of interest, including the oft-photographed Wedding Cake House, by following the tour. You can download the map and learn about the town’s history through its architecture. If you’re too miserly to pay for gas, ride your bike.
Squaretoes Restaurant: If you’re anything like my dad, who is as cheap as the day is long, you’ll look at the Squaretoes menu and start complaining that the French toast is $11 or the cheese omelette is $10. That may be true, however, this is not, as the French would gingerly say, petit déjeuner. There’s nothing petite about the portions here. Eating breakfast at Squaretoes means you won’t need lunch. More importantly, the restaurant, started by Paula Hunter in 2016, has some of the best blueberry pancakes I’ve ever tasted. For the record, I’ve tasted a lot of blueberry pancakes so I know whereof I speak. Like the Franciscan Guest House, Squaretoes is another place you should try regardless of your budget.
Gooch’s Beach, Middle Beach, and Mother’s Beach (plus a sliver of Parson’s Beach): The ultimate bargain in Kennebunk is the beaches. That comes with the warning that if you want to park at the beach, you’ll need to pay (sorry about that). A day pass is $25 for nonresidents. There are kiosks along Beach Avenue (they only accept debit or credit cards), or you can download the PassPortParking mobile app. Also, be forewarned that finding a parking space in July and August can be more difficult than training a cat to fetch your slippers. My advice? Ride your bike, and then stare at the waves. It’s the best show in town.