Your Complete Guide to Annual Events in the Hudson Valley

Photo by Doug Baz

Find out whether or not your favorite Hudson Valley happenings are taking place this year — plus, COVID-19 updates you need to know.

– Fall –

September through November

Hudson Valley Wine & Food Festival
Peruse the Virtual Vendors Village and catch live streams with celebrity chefs and experts.

Basilica Soundscape
Basilica Hudson, Hudson
Mid-Sept; canceled for 2020
Festival of avant-garde music, dance, and word, housed in a renovated factory by the Hudson waterfront.

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Woodstock Film Festival. Photo by Dion Ogust

Woodstock Film Festival
Drive-in theaters and online
Sept 30–Oct 4, 2020
Festival of independent film, film-makers, and celebrities.

O+ Blo+ck Party
Oct 10, 2020
Enjoy a free Blo+ck Party held in Kingston’s Uptown neighborhood. Attendees can expect to enjoy art, music, and wellness elements at the event.

Hudson Valley Plein Air Festival
Various locations
Oct 13–18, 2020
In this 5th annual event hosted by the Wallkill River School of art, artists from around the country will paint at scenic outdoor spots throughout the Hudson Valley. The week ends with two public events; a “Quick Draw” on October 18 at the Farmers’ Market in Highland Falls, in which the public is invited to participate, and the opening exhibit of the artists’ work at the Wallkill River School of Art in Montgomery.

Best of the Hudson Valley Party
Oct 15, 2020
Discover top eateries, wineries, spas, and other local services at our annual celebration. 

Sheep and Wool Festival
Oct 17–18, 2020
This convention of farmers, artisans, and wholesalers brings together the best in wool for your enjoyment. 

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Hudson Valley Garlic Festival
Cantine Field, Washington Avenue Extension, Saugerties
Oct 2–3, 2021; canceled for 2020
Garlic-infused and flavored food, plus cooking demos, crafts, and more.

Warwick Applefest
30–98 Railroad Ave, Warwick
First Sunday in Oct; canceled for 2020
Celebrate local foods, crafts, and businesses at this family-friendly festival, with plentiful treats and multiple stages of live music.

O+ Festival
Second weekend in Oct; canceled for 2020
A groundbreaking combination of music festival and wellness exhibition, with free performances, pop-up shops, and healthcare demonstrations.

Sugar Loaf Fall Festival
Sugar Loaf
Columbus Day weekend; canceled for 2020
This artisan village stocks local crafts all year round, adding music and eats for this special festival.

FilmColumbia Film Festival
Crandell Theatre, Chatham
Starts the third week in Oct; canceled for 2020
This festival of independent film, discussions, and celebrity cameos returns for its 20th year.

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Headless Horseman Hayrides & Haunted Houses
Ulster Park
Weekends Sept–Oct
New for 2020: Dare to Ride the Horseman’s Trail, a drive-thru experience.  Gift shops and food cafés, outdoor dining only. Reservations required.

Capitol Hauntings Tour
Empire State Plaza, Albany
Weekdays in Oct; undetermined for 2020
Hear legends, folklore, and ghost stories related to the Capitol building.

Haunted History Pub Crawl
Tuesdays and Thursdays in Oct; undetermined for 2020
Docents lead brave souls through a haunted mansion and to famous ghost-occupied watering holes offering drink specials.

Great Jack O’ Lantern Blaze
Van Cortlandt Manor, Croton-on-Hudson
Various dates Sept– Nov
More than 7,000 carved pumpkins create a glowing landscape of jack o’ lantern sculptures. See COVID courtesy code at:

Irving’s Legend
The Old Dutch Church, Sleepy Hollow
Various dates Sept– Nov
Dramatic renditions bring “The Legend of Sleepy Hollow” to life with spirited acting and live music. See COVID courtesy code at:

Taste of the Hudson Valley
The Grandview, Poughkeepsie
First Sunday of Nov; canceled for 2020
Sample delish dishes paired with wines from 50 area restaurants.

Wreath Fineries at the Wineries
Along the Shawangunk Wine Trail
Weekends in late Nov and Dec; undetermined for 2020
Take a self-guided tour of 13 area vintners and receive decorative holiday souvenirs at each stop.

Hudson Valley Hullabaloo. Photo by Katie Chirichillo

Hudson Valley Hullabaloo
Andy Murphy Neighborhood Center, Kingston
Weekend before Thanksgiving; canceled for 2020
A congregation of crafts, trades, and general seasonal merriment.

Rosendale International Pickle Festival
Rosendale Recreation Center
Sunday before Thanksgiving; undetermined for 2020
Nothing goes unbrined at this celebration of the salty treat, with tastings, competitions, and more.

– Winter –

Late November through February

Basilica Farm & Flea
Basilica Hudson, Hudson
Nov 27–29 (Thanksgiving Weekend); undetermined for 2020
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 28–Nov 29, 2020 (Thanksgiving Weekend); undetermined for 2020
Shop handmade, affordable crafts from local makers.

Capital Holiday Lights in the Park
Washington Park, Albany
Late Nov–Early Jan
A pilgrimage-worthy, drive-through spectacular with more than 125 displays and scenes.

A Frosty Fest
Ulster Park
Weekends in late Nov through Dec; undetermined for 2020
Candy Cane Lane, Frosty’s Enchanted Forest, and visits with Santa make this spot a pleasant memory for little ones.

Sinterklaas. Photo by Doug Baz

Sinterklaas Send-off Celebration & Festival
Kingston, Nov 28, 2020
Rhinebeck, Dec 5, 2020
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 Nov 27 through Dec; undetermined for 2020
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.

Twilight Tours at Boscobel. Photo by Deborah DeGraffenreid

Twilight Tours at Boscobel House and Gardens
Late Nov to mid-Dec; undetermined for 2020
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 late Nov through early Jan; undetermined for 2020
Meet Santa, ice skate, experience rides, lights, and great food and drink, and much more.

Winter Walk
Early Dec; undetermined for 2020
Vendors, musicians, and special holiday decorations line Warren Street for Hudson’s premier street fair. Hudson Hall also hosts special music and theater performances.

Holiday Market
Bethel Woods
Dec 5–6, 2020
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 Dec; undetermined for 2020
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; undetermined for 2020
Celebrate a Gilded Age Christmas with special decorations, free tours, and performances of period-appropriate classical music.

Troy Victorian Stroll. Photo by Val Lazzari

Troy Victorian Stroll
Downtown Troy
Early Dec; undetermined for 2020
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
Mid-Jan; undetermined for 2021
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 Wingfest
Mid-Hudson Civic Center Poughkeepsie
Mid-Jan; undetermined for 2021
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 Feb; undetermined for 2021
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 Feb; undetermined for 2021
World-class jazz performers collaborate in the historic Hudson Opera House.

Teatown Hudson River Eaglefest
Croton Point Park and other locations
Early Feb; undetermined for 2021
Live bird shows, viewing sites, and more, make for an exciting day.

– Spring –

March through Mid-June

Hudson Valley Restaurant Week
Throughout the region in Mar and Oct/Nov
Chefs from about 200 participating restaurants showcase signature fare with three-course, reduced-price, prix-fixe lunch and dinner menus.

Photo courtesy of Crown Maple

Maple Weekends at Crown Maple
Dover Plains
Last two weekends in Mar
Tour the facilities and taste certified-organic “bark to bottle” maple syrups, including specialty infused and aged types. (Various farms also partake in Maple Weekends.)

Farm Film Fest
Third weekend of Mar
A festival of films devoted to farming, food, and the many issues related to each.

Woodstock Bookfest. Photo by Dion Ogust

Woodstock Bookfest
Late Mar
This festival features lectures and panel discussions from authors, publishers, and editors both local and international, on topics like mystery, health, and spirituality.

Westchester Jewish Film Festival
First two weeks of Apr
Two weeks of national premieres and international hits featuring Jewish filmmakers from throughout the world, as well as select episodes of TV.

TAP: Craft Beer & Fine Food Festival
Hunter Mountain
Last full weekend of Apr
A veritable smorgasbord is included with your tasting ticket at this long-running event, drawing revelers to taste the best of brewpubs and small breweries.

Stormville Airport Antique Show & Flea Market
Late May and various weekends through early Nov
This picker’s paradise bursts at the seams with more than 600 vendors from eight states selling furniture, apparel, jewelry, and memorabilia.

Crafts at Lyndhurst. Photo courtesy of Artrider

Crafts at Lyndhurst
Early May (also mid-Sept)
Semi-annual spring/fall artists’ gathering brims with limited-edition jewelry, handbags, glassware, dishware, sculpture, furniture, and fashion in an inspired setting.

Hudson Children’s Book Festival
Early May
Free-and-easy literary extravaganza attracts big names like Newbery medalist Kwame Alexander, Disney animator Elanna Allen, and bestselling author Nick Bruel to show and tell to young’uns.

Albany Tulip Festival
Various locations in Albany
May 8–9, 2021 (Mother’s Day weekend)
See more than 100,000 tulips and attend tulip tours, a street scrubbing, and the Royal Tulip Ball. Plus, kids’ activities, music, and food.

Red Hook Apple Blossom Day
Various locations in Red Hook
Early May
Scoop up fresh flowers or a new necklace for Mom at this lively fling, featuring more than 65 craft and food vendors, plus live Irish and country music.

Mower’s Saturday/Sunday Flea Market
Weekends mid-May 16 through Nov
Kitschy statues, retro fashion, luggage, records, textiles and baskets, and collectible bottles are just the beginning at this funky flea in a field.

Woodstock-New Paltz Art & Crafts Fairs
Ulster County Fairgrounds, New Paltz
Memorial Day weekend (also Labor Day weekend)
Yes, they have gorgeous furniture and architectural crafts, but there are also specialty foods and healthcare products to try, plus a children’s art project tent.

Mountain Jam
Bethel Woods
Late May
This folk rock blowout has relocated to Bethel Woods for a weekend of music, food, and camping.

Westchester Magazine’s Wine & Food Festival
Kensico Dam Plaza, Valhalla
Early Jun
Meet top chefs, sommeliers, wine and spirits makers, and specialty food purveyors and sample their appetizing wares during this multi-day festival

Trailblazer Festival. Photo by Patrick Tewey

TrailBlazer Festival
Hunter Mountain
Nashville’s finest musicians come to the area for a weekend of concerts, brews, brats, and cowboy hats. RV and tent camping make this multi-day event a hoot and a holler.

Hudson Valley Wine & Chocolate Festival
Ulster County Fairgrounds, New Paltz
Chockablock with chocolate treats and tempting tastings of wine, cider, and ale, this Kentucky Derby-themed party awards prizes for the best hats.

– Summer –

Late June through Early September

Caramoor Summer Music Festival
Late Jun–early Aug
This lush estate’s world-class music fest is expanding its lineup to include jazz, folk, flamenco, and modern classical, with a focus on groundbreaking composers.

Hudson Valley Shakespeare Festival
Boscobel House and Gardens, Garrison
Early Jun–early Sept
Experience the Bard in this open-air tented theater. This season features Cyrano, Cymbeline and, for the first time, a musical with Stephen Sondheim’s Into the Woods.

Powerhouse Theater
Vassar College, Poughkeepsie
Early Jun–late July
This six-week summer program showcases the best of modern theater, with debuts of Broadway-bound plays, musical workshops, readings, and training programs for aspiring actors and directors.

Rhinebeck Crafts Festival
Dutchess County Fairgrounds, Rhinebeck
Late Jun
Browse handmade textiles, sculpture, furniture, and pottery from more than 200 American vendors. Plus gourmet food, wine tastings, and an interactive puppet theater and face-painting for kids.

Bard Summerscape
Bard College, Annandale-on-Hudson
Late Jun–mid-Aug
The 30th iteration of this world-class festival includes opera, theater, dance, cabaret, film, and music, centered around “Korngold and His World.”

 An Old-Fashioned Independence Day
Clermont State Historic Site, Germantown
Jul 4
Costumed re-enactors demonstrate 18th-century crafts during a music-filled fest that includes fireworks.

West Point Fireworks and Band
United States Military Academy, West Point
Early Jul
Relax on lawn chairs and blankets for a 90-minute patriotic show capped off by fireworks over the Hudson.

Hudson Valley Hot Air Balloon Festival
Dutchess County Fairgrounds, Rhinebeck
More than 100 balloons take to the skies in breathtaking mass launches; tethered rides are among attractions for the crowds below the clouds.

Catskills Irish Arts Week
East Durham
Keep time to the bodhrán, learn how to step, and enjoy some of the finest traditional music on this side of the Atlantic, all in the “Ireland of the Catskills.”

Country Fairs

Orange County Fair
Late July (2021)

Putnam County 4-H Fair
Late July (2021)

Ulster County Fair
Early Aug (2021)

Dutchess County Fair
Late Aug (2021) 

Columbia County Fair
Early Sept (2021)

Our Lady of the Resurrection Monastery Vinegar Festival
Sample and buy artisanal vinegars (raspberry, sherry, and cider honey) and food created at the monastery.

Dutchess Dragon Boat Race and Festival
Hudson River Rowing Association Dock, Poughkeepsie
Strikingly painted wooden boats race for charity on the water, while demos of traditional Chinese dancing and crafts take place on land.

Rosendale Street Festival
Late Jul
A volunteer-run celebration of all things local, with food, vendors, and eight different stages of live music. Any profits fund scholarships for graduating high school students.

New York State Food Festival
Empire State Plaza, Albany
Early Aug
This free event showcases our brewers, growers, bakers, and makers, ending with a big-name performance.

12th Annual Sangria & Jazz Festival
Hudson-Chatham Winery, Ghent
Early Aug
Enjoy imaginative sangrias under a tent with live music, henna tattoos, tarot card readings, and finger foods.

Putnam County Wine & Food Fest
Patterson Fire Department
Early Aug
Bring a lawn chair and listen to local bands while you sip and sample top NYS craft beverages and edibles.

Burger & Beer Bash
Dutchess Stadium, Wappingers Falls
Date to be determined
Sample creations from the region’s top burgermeisters and wash it down with some suds, then vote for the year’s Best of Hudson Valley burger winner. This has been Zero Waste since 2018.

Hudson Valley Ribfest
Ulster County Fairgrounds, New Paltz
Late Aug
Pitmasters compete in a backyard barbecue setting for prize money and prestige.

New York Renaissance Faire
Tuxedo Park
Weekends mid-Aug–early Oct; canceled for 2020
Characters in period dress joust, play human chess, and tend booths with pub-style fare and fanciful crafts.

Summer Hoot
The Ashokan Center, Olivebridge
Late Aug
A celebration of music and nature, this bi-annual event combines live performances with food, games, and a sense of community.

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