Late November through February

Basilica Farm & Flea

Basilica Hudson, Hudson

Nov 29–Dec 1 (Thanksgiving Weekend)

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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)

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Shop handmade, affordable crafts from local makers.


Capital Holiday Lights in the Park

Washington Park, Albany

Late Nov–Early Jan

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Pilgrimage-worthy drive-through spectacular with more than 125 displays and scenes.


A Frosty Fest

Ulster Park

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

Winter Walk


Dec 7

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.


Holiday Market

Bethel Woods

Dec 7–8

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

West Point

Early December

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

Downtown Troy

Dec 8

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

Jan 18

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


Throughout February

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

Early February

World-class jazz performers collaborate in the historic Hudson Opera House.


Teatown Hudson River Eaglefest

Croton Point Park and other locations

Early February

Live eagle shows, bird talks, viewing sites, children’s activities, and food trucks make for an exciting day.

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