Dudley Discoveries: Fall-ing Away: Upstate to Long Island

Dudley Discoveries: Fall-ing Away: Upstate to Long Island

It’s Dudley season, and that means stealing away to favorite spots in our favorite fleece. Dudley Stephens Co-Founders Lauren and Kaki share details on their recent getaways, from upstate NY to “the end” of Long Island, Montauk.

Lauren: Slow Down Upstate

Hotel:

The Inns of Aurora. This exquisite, magical property is like something out of a storybook from another era. It’s truly a retreat, away from it all—the setting just forces you to slow down to its pace. It was created by another female founder, Pleasant Rowland, creator of American Doll. I love her quote: “I broke a lot of the rules because I didn’t know the rules,” and her resort, so uniquely its own, reflects that mindset.

Dinner:

The resort’s restaurant, 1833, reflects the same timeless, authentic aesthetic as the rest of the property, and the farm-to-table menu is incredible. After dinner, we took to the Inns’ Fargo pub which, while far nicer than a dive bar, had that same approachable, cozy vibe.

Must-Dos:

The property is full of opportunities to enjoy nature’s slower pace. The spa is an absolute must with its zen, sort of European village vibe and other-worldly treatments. The hydrotherapy experience is truly unique—you start in the hot pool and then plunge into icy-cold water (definitely a bravery test!). It’s a little terrifying, but also totally exhilarating and restorative.

Kaki: Off-Season at the Shore

Hotel:

Gurney’s. We loved the beach by day in suits, then the firepit by night in fleece (and no crowds!)—the best of both worlds. Beach day bonus: the day beds, normally $1,000/day during high season, were free of charge! Another off-season perk was our upgrade to an oceanfront room, highly recommended since some oceanview rooms are across the parking lot.

Dinner:

This delicious little gem, Harvest on Fort Pond. Incredible family-style Italian and pizza—I get why this is a Montauk go-to. We watched the sunset while eating, then capped off the night by taking in the baseball game at local-favorite Shagwong Tavern.

Must-Dos:

Take a beach walk around the point, see the lighthouse and follow the trails through Camp Hero, where you’ll find the Montauk Air Force Station and its decommissioned satellite—the subject of Stranger Things conspiracy theories!