Basilica Farm & Flea
Basilica Hudson, Hudson
Nov 29–Dec 1 (Thanksgiving Weekend)
A recent addition, this fair stocks high-end teas, candles, and all manner of textiles in addition to local food.
48th Annual Holiday Craft Fair at Dutchess Community College
Nov 30–Dec 1 (Thanksgiving Weekend)
Shop handmade, affordable crafts from local makers.
Capital Holiday Lights in the Park
Washington Park, Albany
Late Nov–Early Jan
Pilgrimage-worthy drive-through spectacular with more than 125 displays and scenes.
A Frosty Fest
Weekends from late November through late December
Candy Cane Lane, Frosty’s Enchanted Forest, and visits with Santa make this spot a pleasant memory for little ones.
Photo by Doug Baz
Sinterklaas Send-off Celebration & Festival
Kingston, Nov 30;
Rhinebeck, Dec 7
Based on a Dutch tradition, this Hudson Valley original invites kids to take part in two separate days of puppetry, creation, and joy, and to take the lead during its parade of lights.
Holiday Lights in Bloom
Orange County Arboretum Montgomery
Weekends from late November through Dec 31
Garden-themed light displays in the forms of flowers, animals, and insects lead visitors down pathways and eventually to a gift shop filled with handmade holiday goods.
Photo by Deborah DeGraffenreid
Twilight Tours at Boscobel House and Gardens
Nov 29–Dec 1, Dec 6–8
A candle-illuminated mansion decorated for a 19th-century Christmas, live string music, and gingerbread-children hunts make the season merry.
Westchester’s Winter Wonderland
Kensico Dam Plaza, Valhalla
Select dates from Nov 29, 2019–Jan 4, 2020
Meet Santa, ice skate, experience dancing lights, great food and drink, and much more.
Photo by JD Urban
Vendors, musicians, and special holiday decorations line Warren Street for Hudson’s premier street fair. Hudson Hall also hosts special music and theater performances in its historic space.
This indoor-outdoor show features area vendors dispensing handmade crafts, specialty foods, and arts. For the kids are movies, carols, and pictures with Santa.
West Point Holiday Show
The West Point Band puts on an annual holiday show, free and open to the public. Expect carols, chorales, and quirky hijinks for the whole family.
Christmas Open House
Vanderbilt Mansion National Historic Site, Hyde Park
Select Dates Through Dec
Celebrate a Gilded Age Christmas with special decorations, free tours, and performances of period-appropriate classical music.
Photo by Val Lazzari
Troy Victorian Stroll
Live performances by holiday revelers and in-store specials inspire shopping and dining opportunities in downtown Troy.
Albany Chefs’ Food & Wine Festival
Hilton Albany and other venues
Early to mid-January
Wine and dine at this themed fundraiser for the arts, highlighting local restaurants and rising chefs, with fun culinary competitions and an auction.
Hudson Valley Rail Trail Winterfest
Hudson Valley Rail Trail Depot Highland
Warm up with chili and chestnuts, take a tractor ride on the trail, and more at this outdoor family fun get-together, now in its 21st year.
Hudson Valley Wingfest
Mid-Hudson Civic Center Poughkeepsie
Wing-meisters from around the country congregate to bring their spicy and sweet creations to a hungry public. Eating contests, vendors, and all manner of tips await connoisseurs.
Black History Month Kingston
A wide variety of lectures, performances, and fundraisers tell the story of Black history in Kingston, and in America. Organized by the A.J. Williams-Meyers African Roots Library.
Hudson Jazz Festival
Hudson Hall, Hudson
World-class jazz performers collaborate in the historic Hudson Opera House.
Teatown Hudson River Eaglefest
Croton Point Park and other locations
Live eagle shows, bird talks, viewing sites, children’s activities, and food trucks make for an exciting day.