Arts & Culture
The Hudson Valley Fall and Winter Calendar, 2026 Into 2027
Five months of Hudson Valley programming worth building a weekend around, from the October festival crush through the December village nights and into the quiet part of winter.
The Hudson Valley runs two calendars. One is the leaf-peeper calendar that every regional magazine publishes in September and everyone within two hours of the Taconic already knows. The other starts once the foliage traffic clears, when villages that spent October at capacity go back to programming for the people who live there. The second calendar is the better one.
What follows is the fall and winter run, arranged by when it happens rather than by what it is. Every date below is what the organizer published as of early fall 2026; the ones that move year to year say so.
October: the festival crush
The 27th Woodstock Film Festival runs October 14 through 18, spread across Woodstock, Saugerties, Rosendale and Kingston, with an opening-night screening at the Community Theater in Catskill the evening of the 13th. More than 90 percent of directors attend, which is the reason to go. The post-screening conversation is the festival. Pick one village per day instead of chasing the whole program across four towns.
The New York State Sheep & Wool Festival takes the Dutchess County Fairgrounds in Rhinebeck on October 17 and 18. Hundreds of fiber artisans, livestock barns and cold-weather fairground food. Rhinebeck lodging sells out months ahead for it, so day-tripping from Kingston or Poughkeepsie is the workable plan.
The Great Jack O'Lantern Blaze runs nightly through October at Van Cortlandt Manor in Croton-on-Hudson, with select November dates through the 8th. More than 7,000 jack-o'-lanterns carved on site. Advance purchase only, nothing sold at the gate, and the late-October Saturdays go first.
November: the good two weeks
Hudson Valley Restaurant Week runs November 2 through 16 across more than 100 kitchens from Westchester to Columbia County. The fall edition beats the spring one: it lands after the foliage traffic clears and before the holiday rush, so a Saturday table at the harder rooms is gettable if you book in the first week rather than the second.
The Hudson Valley Craft Beverage Festival at Twin Star Orchards in New Paltz lands on November 1, covering cider, beer, wine, mead, kombucha, coffee and spirits in one afternoon with live music. Pours are 21+ with ID at the gate.
Thanksgiving weekend brings the Annual Holiday Craft Fair at Dutchess Community College in Poughkeepsie on November 28 and 29, free admission, and the unofficial start of the region's holiday-market season.
December: the village nights
December is when the Hudson Valley is most itself. Sinterklaas Festival Day takes over Rhinebeck's village center on December 5 with puppetry, crowns, a Grumpus parade and a children's procession. The same evening, Winter Walk closes Warren Street in Hudson to cars and fills it with street performers, storefront tableaux and choirs. Both are free. Both are the first Saturday in December, which means choosing, unless you are willing to do Rhinebeck in the afternoon and be in Hudson by dark.
The Kingston Farmers Market moves indoors to Bethany Hall at the Old Dutch Church for the winter, alternating Saturdays from December through April, 10 AM to 2 PM. It skips weeks, so check the schedule before driving up. The Catskill Mountain Railroad runs its December holiday train along the Esopus out of Kingston; weekends sell out well before December, and weeknight departures are the realistic option.
Planning notes for adults 21+
Most of the above happens outdoors, in villages, on public streets. New York state law prohibits cannabis consumption on state-owned land and in public spaces, which covers the fairgrounds, the parks and the closed-off village blocks these events run on. The licensed retail footprint across the region has filled in considerably, and hours shorten around the holidays. Verify licensed status via the OCM QR code at cannabis.ny.gov before any visit.
Edibles and a multi-hour outdoor event are a poor match for anyone who has not timed them before. Start low, go slow, and treat the onset window as the thing that determines when you leave the house rather than something to manage once you are standing in a crowd in 30-degree weather.
The full regional calendar, including what is running this week, sits on the events hub.