Friday 2 p.m. Hilly, hipster Kingston has long been an epicenter for creative change. Base yourself at the Hutton Brickyards, a contemporary 2021 cabin hotel on the riverside site of a reimagined brickworks factory. The grounds are so tranquil you may be tempted to book a spa treatment or a sauna session, then dine in.

Saturday 9 a.m. After breakfast, which arrives on your doorstep at the Brickyards, get an early start for A Day Away Kayak Rentals, about a 10-minute drive inland through the waterfront district. You’ll paddle along Rondout Creek, where British soldiers once arrived in ships to burn the town.

12 p.m. Refuel on new-school sandwiches such as grilled cheese with kimchi, or egg salad with garden radish and pea shoots at farm-fresh Village Grocery & Refillery.

Then drive around the bend to the Broadway shopping strip to stroll shops that emphasize craftsmanship: Clove & Creek stocks overall-dresses, fashion work-jackets and colorful, hand-dyed Found My Animal leashes, which are made in Kingston and help raise money for rescue organizations.

2 p.m. Another project, Branchwater Farms, 18 miles east of Kingston in Milan, comes from wine-industry professionals Robin Touchet and Kevin Pike, who make spirits using their own grain. Taste their first available releases—including a dry gin and pear brandy—in a loft above the distillery.

5 p.m. Nearby, chef Clare de Boer, co-owner of King in Manhattan, has taken the helm at historic former-inn Stissing House in Pine Plains. Ms. De Boer says she makes “luxuriously simple tavern food,” citing a smoked and glazed ham made from pigs who feed on the restaurant’s compost.

Sunday 10 a.m. Discover Kingston’s rich history as the first capital of New York state—as well as the eastern lock-end of a once-powerhouse canal to Pennsylvania— via two self-guided walking tours about Kingston’s history and architecture from Friends of Historic Kingston.

1 p.m. On the way back to New York City, stop by brewer, distiller and hops farm Arrowood Farms, where you can dine in the polished taproom, or outdoors from food trucks, and try its farmhouse-style beers.

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