Driving time from White Plains: 1 hour 40 minutes
Tiny Bonfiglio & Bread is the ultimate weekend-retreat bakery/café (an urban yet country vibe, wonderful homemade breads) for carb-loading before a day of exploration along the city’s mile-long downtown. Two words: cinnamon buns.
photo courtesy red chair on Hudson
Window shop and gallery hop along Warren Street. Stop at Red Chair on Warren for 17th- to 19th-century Swedish, Belgian, and French pieces for your kitchen and dining room, or George Antiques for 19th- and 20th-century furniture and decorative items.
Give your feet a rest — and admire the town’s myriad of architectural styles — at 7th Street Park, a modest green space dating back to the 1780s, crisscrossed by obsolete train tracks.
A husband-wife team with buzzy Manhattan kitchen pedigrees run Swoon Kitchenbar, a pasture-to-plate eatery with earthy pâtés, artisan cheeses, and a robust French-focused wine list (lunch weekends only).
photo courtesy swoon kitchenbar
Docked at the base of Warren Street, hop aboard a Hudson Cruises charter at Riverfront Park and come to appreciate why there’s an artists’ school named after this body of water (May through Oct only).
A 12-minute drive brings you to Olana Historic Site, where you can view the work of Frederic Edwin Church, a master of the aforementioned Hudson River School, and tour his Victorian/Middle Eastern-inspired villa set on 250 incredible acres.
End with nose-to-tail dining at Fish & Game, a 2016 James Beard Award winner for Best Chef Northeast. Or, Club Helsinki Hudson offers regional American (mainly Creole, low-country Carolina) cuisine in an 1860s bus garage.
photo courtesy of david lee
Visit on the first Saturday of December, when the Hudson Opera House’s annual Winter Walk transforms Warren Street into a holiday playground, with a musical parade, fireworks, jugglers, dancers, and horse-drawn carriages.