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The charms of Hidden Pond, an exclusive wooded retreat in Kennebunkport, are easy to enjoy. From the moment you turn down the drive, the forest starts to close around you. Bungalows are tucked privately in deeply forested glens. You can sit on your private screen porch and listen to birds and squirrels cheeping and rustling in the trees and perhaps glimpse a pair of deer venturing out into a clearing.

And sip on a custom cocktail while admiring your new nautical attire – if you book the property’s Sail Away with Sperry package. Now through the end of September, guests choosing this package will each get a pair of Sperry Top Siders – the classic boat shoes will help you fit right in while strolling Kennebunkport.

Photograph by Jeanne O’Brien Coffey

Crafted to help keep your footing while boating, they are de rigueur for the included sailing trip on the Schooner Eleanor. While this gaff-rigged schooner was custom built by Capt. Rich Woodman in 1999, it is in every way evocative of the yachts of the 1930s—when Sperry Top Siders debuted—from the teak cockpit to the hand-carved trail boards. The sailing trip lasts from 90 minutes to two hours, depending upon where the wind takes you, and may breeze by anything from the mansions lining the shores to schools of dolphins. Capt. Woodman grew up in these waters – his grandfather actually built schooners at the turn of the last century – and he’s happy to share stories, or just allow guests to enjoy the peaceful experience of cruising under four majestic sails.  

The Schooner Eleanor leaves from downtown Kennebunkport, where parking can be challenging – luckily Hidden Pond has that covered. Guests can enjoy a complimentary shuttle for the 15-minute ride into town. The shuttle can also drop guests at Hidden Pond’s sister property, The Tides Beach Club, right on the storied Goose Rocks Beach. There, guests can take advantage of provided lounge chairs and towels on the powdery sand.

Photograph courtesy of Hidden Pond

Of course, you’ll have to share your shoe size when booking the package, as the Top Siders, along with some other Sperry swag, will be waiting in your room, along with a custom foot scrub from Hidden Pond’s Tree Spa. And a cocktail – perhaps made with ingredients fresh from the resort’s extensive organic gardens. Guests are invited to tour the gardens and sample anything they’d like – late season tomatoes, perhaps some blackberries or basil.

The gardens also form the backbone of the menu at Earth, the resort’s farm-to-fork prix fixe restaurant. Fairy lights, lush plants, and tree branches inside evoke a rustic woodland retreat, while dishes like halibut in a rich corn sauce and barley risotto with wild mushrooms celebrate the seasons.

Like everything else at the resort, the food at Earth is ideal for easing the transition from summer to fall. The property’s two outdoor pools (one for everyone, and one for adults-only) are heated, nightly bonfires serve up s’mores while chasing away the evening’s chill, and the accommodations offer cozy fireplaces and snug blankets.

Hidden Pond’s Sail Away With Sperry package, valid through Sept. 29, 2023, is valid for bookings of three or more nights, and includes a 15 % room discount off the standard daily rate. For details or to book, visit or call 877-618-0032.