September through mid-November

Hudson Valley Wine & Food Fest

Dutchess County Fairgrounds Rhinebeck

Sept 7–8


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Expo of New York State wines, plus food trucks and vendor concessions.


Basilica Soundscape

Basilica Hudson

Sept 13–15


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Festival of avant-garde music, dance, and word, housed in a renovated factory by the Hudson waterfront.


Hudson River Craft Beer Festival

Beacon Riverfront Park, Beacon

Sept 14


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Nearly 100 breweries participate with games, music, and food.


Headless Horseman Hayrides & Haunted Houses

Ulster Park

Sept 20–Nov 30


Pretend to be a character in a horror movie on this 65-acre interactive haunted campus.


Hudson Valley Garlic Festival

Cantine Field, Washington Avenue Extension, Saugerties

Sept 28–29


Garlic-infused and flavored food, plus cooking demos, crafts, and more.


TerrorDome Haunted Scream Park

Fearless Farms, Newburgh

Oct 5–27, Fri–Sun


Brave the Barn of Terror, try to survive Zombie Tag, and hide in Flashlight Woods at this haunted attraction.


Capitol Hauntings Tour

Empire State Plaza, Albany

Weekdays in October


Hear legends, folklore, and ghost stories related to the Capitol building.


Haunted History Pub Crawl

Tuesdays and Thursdays in October



Docents lead brave souls through a haunted mansion and to famous ghost-occupied watering holes offering drink specials.


Woodstock Film Festival

Theaters in Woodstock and Rhinebeck

Oct 2–6


Festival of independent film, film-makers, and celebrities descends on the Valley for its 19th year.


photo by Jennifer Mitchell


Historic Hudson Valley Events



Great Jack O’ Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson

Sept 28–Nov 24 (some dates are weekends only)

Surreal, glowing landscape of jack o’lanterns.


Irving’s Legend (pictured above)

The Old Dutch Church, Sleepy Hollow

Oct 4–Nov 3

Dramatic renditions bring The Legend of Sleepy Hollow to life with spirited acting and live music.


Horseman’s Hollow

Philipsburg Manor, Sleepy Hollow

Weekends from Oct 4–Nov 3

Flee from the Headless Horseman and a variety of terrifying creatures throughout the historic manor’s grounds.


Warwick Applefest

30–98 Railroad Ave, Warwick

Oct 6


Celebrate local foods, crafts, and businesses at this family-friendly festival, with plentiful treats and multiple stages of live music.


Hudson Valley Plein Air Festival

SUNY Orange, Middletown

Oct 8–13


Inspired by the Hudson River School of landscape art, artists from the Wallkill River School of Art paint beautiful outdoor locations. Exhibit and sale at OCCC’s Orange Hall Gallery.


Best of the Hudson Valley Party

Poughkeepsie Grand Hotel Poughkeepsie

Oct 10


Discover top eateries, wineries, spas, and other local services at our annual celebration.


O+ Festival


Oct 11–13


A groundbreaking combination of music festival and wellness exhibition, with free performances, pop-up shops, and health care demonstrations.


Sugar Loaf Fall Festival

Sugar Loaf

Oct 12–14 (Columbus Day weekend)


This artisan village stocks local crafts all year round, adding music and eats for this special festival.


FilmColumbia Film Festival

Crandell Theatre, Chatham

Oct 18–27


This festival of independent film, discussions, and celebrity cameos returns for its 20th year.


Hudson Valley VegFest

BSP Backroom, Kingston

Oct 19


This Mecca for vegetarians/vegans features cooking classes, vendors, activists, dancing, theater, and art.


Sheep and Wool Festival

Dutchess County Fairgrounds Rhinebeck

Oct 19–20


This convention of farmers, artisans, and wholesalers brings together the best in wool for your enjoyment.


Taste of the Hudson Valley

The Grandview, Poughkeepsie

Nov 4


Sample delish dishes paired with wines from 50 area restaurants.


Wreath Fineries at the Wineries

Along the Shawangunk Wine Trail

Nov 23–24, Dec 7–8, Dec 14–15


Take a self-guided tour of 13 area vintners and receive decorative holiday souvenirs at each stop.


Hudson Valley Hullabaloo

Andy Murphy Neighborhood Center Kingston

Nov 23–24


A congregation of crafts, trades, and general seasonal merriment.


Rosendale International Pickle Festival

Rosendale Recreation Center

Nov 24


Nothing goes unbrined at this celebration of the salty treat, with tastings, competitions, and more.

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