Your Complete Hudson Valley Calendar of Annual Events

From a rollicking romp at the Renaissance Faire to fabulous food and music festivals, the Hudson Valley’s annual events will keep you busy all year long.



March Through Mid-June

Hudson Valley Restaurant Week

Throughout the region in March and October/November

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Chefs from more than 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

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Weekends in March

Tour the facilities and taste certified organic “from bark to bottle” maple syrups, including specialty infused and smoky types. (Various farms also partake in Maple Weekends.)

TAP: Craft Beer & Fine Food Festival

Hunter Mountain

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Last full weekend of April

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


May 26–27, June 30–July 1

(also Sept–Nov, select dates)

This picker’s paradise bursts at the seams with more than 600 vendors from eight states selling furniture, apparel, jewelry, and memorabilia.

Red Hook Apple Blossom Day

Various locations in the Village of Red Hook

May 12 (traditionally the Saturday before Mother’s Day)

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.

Crafts at Lyndhurst


May 4–6 (also  Sept 14–16)

Semiannual spring/fall artists’ gathering brims with limited-edition jewelry, handbags, glass, dishware, sculpture, furniture, and fashion in an inspired setting.

Hudson Children’s Book Festival


May 5 (traditionally, first Saturday in 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.

Hudson Valley Wine & Chocolate Festival  

Patterson Recreation Center Patterson

May 5–6

Chockablock with chocolate treats and tempting tastings of wine, cider, and ale, this Kentucky Derby-themed party awards prizes for the best hats.

Mower’s Saturday/Sunday Flea Market


Weekends, May 19–Nov 25

Kitschy statues, retro fashion and luggage, records, ethnic 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, May 26–28 (also Labor Day Weekend, Sept 1–3)

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.

Country Living Fair

Dutchess County Fairgrounds, Rhinebeck

June 1–3

Shop repurposed furniture, upcycled jewelry, and vintage textiles from some 200 vendors.

Birds of Prey Day

Green Chimneys, Brewster

June 3

More than 100 raptors captivate spectators at this annual wildlife-themed gathering, well-stocked with food trucks.

Photo by Sara Strauss

Westchester Magazine’s Wine & Food Festival

Kensico Dam Plaza, Valhalla

June 5–10

Meet top chefs, sommeliers, wine and spirits makers, and specialty food purveyors and sample their appetizing wares.

Photo by Davslens Photography

Taste of Country Music Festival

Hunter Mountain

June 8–10

All-star lineups, great grub (veggie-vegan, too!), and RV and tent camping make this multiday event a hot ticket.

Kingston Kayak Festival

Kingston Point Beach

June 9–10

Beginner to advanced kayakers take lessons on the beach or tours on the water and get the lowdown on boating safety.

Mountain Jam

Hunter Mountain

June 15–17

This weekend camping blowout features more than 50 sought-after acts on three stages.

Clearwater’s Great Hudson River Revival

Croton Point Park, Croton-on-Hudson

June 16–17

This environmentally themed songfest features national headliners and local favorites, along with dance, family-friendly programs, and river sails.


Mid-June Though August

Photo by William Marsh

Hudson Valley Shakespeare Festival

Boscobel House and Gardens, Garrison

June 7–Sept 3

Experience the Bard in this open-air tented theater, this season highlighting Richard II and Taming of the Shrew.

Caramoor Summer Music Festival

49 Girdle Ridge Road, Katonah

June 16–July 29

Shifting the spotlight this year to living composers and new ensembles, this lush estate’s world-class fest focuses on diverse musical performances.

Powerhouse Theater

Vassar College, Poughkeepsie

June 22–July 29

You might just see the next Hamilton at this six-week summer program debuting Broadway-bound plays, musical workshops, and readings.

Rhinebeck Crafts Festival

Dutchess County Fairgrounds, Rhinebeck

June 23–24

Browse handmade clothing, lighting, furniture, and pottery. Plus interactive puppet theater and face-painting for kids.

Bard Summerscape

Bard College, Annandale-On-Hudson

June 28–August 19

Experience opera, theater, dance, cabaret, film, and music, including the 29th annual Bard Music Festival,  “Rimsky-Korsakov and His World.”

An Old-Fashioned Independence Day

Clermont State Historic Site, Germantown

July 4

Costumed re-enactors demonstrate 18th-century crafts during a music-filled celebration that culminates with fireworks over the river.

Photo by Mike Polito

Hudson Valley Hot-Air Balloon Festival

Dutchess County Fairgrounds, Rhinebeck

July 6–8

More than 100 balloons take to the skies in breathtaking mass launches;  tethered balloon rides are among the ground-based attractions for the crowds below the clouds.

West Point Fireworks and Band

United States Military Academy, West Point

July 7 (raindate July 8)

Concertgoers settle in on lawn chairs and blankets to hear a 90-minute patriotic program capped off by a fireworks salute over the Hudson.

Our Lady of the Resurrection Monastery Vinegar Festival


July 14–15

Sample and buy artisanal vinegars (including raspberry, sherry, and cider honey) and other foods created at the monastery, located on a shady country road.

Hudson Valley Chalk Festival

Water Street Market, New Paltz

July 20–22

Street artists from all over the country create colorful and colossal sidewalk art and mentor other artists — all for free!

Dutchess Dragon Boat Race and Festival

Hudson River Rowing Association Dock, Poughkeepsie

July 21

Strikingly painted wooden boats race for charity on the water, while demos of traditional Chinese dancing and crafts take place on land.

New York Renaissance Faire

Tuxedo Park

Saturdays and Sundays

August 4–September 30

Characters in period costume joust, dance around the Maypole, play human chess, and tend booths stocked with pub-style fare and fanciful crafts.

Burger & Beer Bash

Dutchess Stadium, Wappingers Falls

August 9

Sample juicy creations from the region’s top burgermeisters and wash it down with some suds, then vote for the best! More food and drink, plus music, rounds out the night.

11th Annual Sangria & Jazz Festival

Hudson-Chatham Winery, Ghent

August 11

Enjoy imaginative sangrias under a tent with live music, henna tattoos, tarot card readings, and finger foods.

Hudson Valley Ribfest

Ulster County Fairgrounds, New Paltz

August 17–19

Pitmasters compete in a backyard barbecue setting for prize money and prestige while lovers of chicken wings, beef brisket, and pork ribs have a field day.

Hudson Valley Hoot

The Ashokan Center, Olivebridge

August 24–26

Folk music fandango with square dancing, fiddlers, storytelling, and late-night jam sessions.

Putnam County Wine & Food Fest

Patterson Fire Department

Aug 25–26, 2018

Bring a lawn chair and listen to local bands while you sip and sample top New York State craft beverages and delectable edibles.

County Fairs

Orange County Fair

July 12-21

Putnam County 4-H Fair

July 27–29

Ulster County Fair

July 31–August 5

Dutchess County Fair

August 21–26

Columbia County Fair

August 29–September 3


September Through Mid-November

Hudson Valley Wine & Food Fest

Dutchess County Fairgrounds Rhinebeck

Sept 8–9

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

Hudson River Craft Beer Festival

Beacon Riverfront Park, Beacon

Sept 15

Nearly 100 craft breweries participate in a party atmosphere  with games, music, and food.

Hudson Valley Garlic Festival

Cantine Field, Washington Avenue Extension, Saugerties

Sept 29–30

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

Beacon Independent Film Festival

University Settlement Camp, Beacon

September (check website for date)

Films, food trucks, and a

filmmaker panel.

Headless Horseman Hayrides & Haunted Houses

Ulster Park

Mid-September through early November

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

TerrorDome Haunted Scream Park

Fearless Farms, Newburgh

Throughout October, Fri–Sun

Stumble through the Barn of Terror, brave Clown Alley, and mingle with mutilated patients in an on-site hospital.

Capitol Hauntings Tour

Tours begin in the North Concourse of the Empire State Plaza, Albany

Throughout October (except Sundays)

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

Haunted History Pub Crawl

Throughout October

Tours begin at Ten Broeck Mansion, Albany

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

O+ Festival


Oct 5–7

Part street fair, part wellness/healthcare services, featuring bands, artists, yoga, health exams, and more. (Also in Poughkeepsie, Aug 3–4)

Sugar Loaf Fall Festival

Oct 6–8 (Columbus Day weekend)

Shop at the artisan village and the vendor booths. Plus, great food and performing artists.

Hudson Valley Plein Air Festival

Exhibit and sale at Orange Hall Gallery, Orange County Community College, Middletown

Oct 10–14

Artists paint at inspiring Hudson Valley locations and their work is exhibited and sold to the public throughout October.

Best of the Hudson Valley Party

Poughkeepsie Grand Hotel, Poughkeepsie

Oct 11

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

Warwick Applefest

Various locations in Warwick

Oct 14

Shop for crafts, nosh, and play all day at a children’s carnival while enjoying multi-stage entertainment.

Sheep and Wool Festival

Dutchess County Fairgrounds, Rhinebeck

Oct 20–21

A convention of knitters, spinners, crocheters, and fiber junkies known for its fashion-forward vibe and llama parade.

FilmColumbia Film Festival

Chatham Village locations

Oct 20–27

See new films before they are released to the general public, and attend glam filmmaker events.

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

13 wineries along the Shawangunk Wine Trail

Nov 17–18, Dec 1–2, Dec 8–9

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

Hudson Valley Hullabaloo

Andy Murphy Neighborhood Center, Kingston

Nov 17–18 (weekend before Thanksgiving)

Makers, artists, designers, and distillers converge at this family-friendly craft gathering.

Rosendale International Pickle Festival

Rosendale Recreation Center

Nov 18 (Sunday before Thanksgiving)

Pickle-tasting and juice-drinking competitions.

Historic Hudson Valley Events


Great Jack O’Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson

September 28–November 24 (some dates are weekends only)

Surreal, glowing landscape of jack o’lanterns.

Irving’s Legend

The Old Dutch Church, Sleepy Hollow

Various dates throughout October

A dramatic performance of Washington Irving’s The Legend of Sleepy Hollow.

Photo by Tom Nycz

Horseman’s Hollow

Philipsburg Manor, Sleepy Hollow

Various dates throughout October

See the Horseman and other ghouly creatures in this maze of horrors.


Late-November Through February

Basilica Farm & Flea

Basilica Hudson, Hudson

November 23–25 (Thanksgiving weekend)

This quirky pop-up market brings together farmers, artisans, vintage collectors, chefs, and makers of handmade items in a Victorian factory.

47th Annual Holiday Craft Fair at Dutchess Community College


Nov 24–25 (Thanksgiving weekend)

Handmade crafts displayed appealingly under fairy lights.

Capital Holiday Lights in the Park

Washington Park, Albany

Nov 24–Jan 2

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 Maggie Simone

Sinterklaas Send-off Celebration & Festival


Nov 24; Rhinebeck Festival Day, Dec 1

Dazzling community event ushers in the holidays with puppetry, dance, music, and a parade.

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.

Holiday Greens Show

Hart-Cluett House, Troy

Late November through early December

Twelve rooms of a Federal-style mansion are transformed with fresh trees, greens, and flowers for the 62nd annual show by the Van Rensselaer Garden Club.

Photo by Deborah DeGraffenfied

Twilight Tours at Boscobel House and Gardens


Nov 23–25, Dec 1–2, Dec 8–9

A candle-illuminated mansion decorated for a 19th-century Christmas, live string music, and gingerbread-children hunts make the season merry.

Artisan Faire at Muscoot Farm


Early December

Browse handmade items for gift-giving like baskets, textiles, luxury soaps, pottery, and cutting boards in an early-1800s farm setting.

Troy Victorian Stroll

Downtown Troy

Dec 2

Live performances by holiday revelers and in-store specials inspire shopping and dining opportunities in downtown Troy.

Westchester’s Winter Wonderland

Kensico Dam Plaza, Valhalla

Late November through December 31

Meet Santa, ice skate, experience dancing lights, great food and drink, and much more.

Albany Chefs’ Food & Wine Fest

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.

Grafton Lakes State Park Winter Fest


Late January

Free event offers kids’ games indoors and outdoors, crafts, live animal presenters, the Polar Plunge, snowshoeing, and fun in the snow.

Photo by Tanya Metz

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.

Photo by Bridget Herlihy

Hudson Valley Wingfest

Mid-Hudson Civic Center, Poughkeepsie


More than 80 flavors of wings from Sriracha to pineapple-teriyaki are yours for the tasting.

ArtsRock Puppet Festival

BOCES Adult Ed, Nyack


Colorful sea creatures and mythical beings act out adventures on stage.

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.

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