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The Best Events & Fests to Hit in the Hudson Valley This Fall

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The Great Jack O’ Lantern Blaze / Photo courtesy of Historic Hudson Valley

When autumn arrives, the Hudson Valley comes alive with arts and music happenings, food and drink fun, and Halloween festivities.

Compiled by Francesca Furey with Charlotte Katz, Carly Johnson, and Hallie Milstein

Food & Drink

Fall Foliage Wine Tour

Beacon
Throughout the Fall

Dive deep into wine pairings, surrounded by stunning fall scenery. Hudson Valley Bucket List escorts you on a six-hour shuttled tour of several vineyards. You’ll sip regional wines, sample artisanal cheeses, and savor a picnic lunch — plus hear fascinating facts about the history and culture of the Valley.

Alpaca Trek & Wine Tasting

Alpaca Trek & Wine Tasting / Photo courtesy of Hudson Valley Bucket List

Alpaca Trek & Wine Tasting

Dutchess County
Throughout the Fall

This five-hour shuttled tour showcases Dutchess County’s gorgeous scenery, a tasting at a craft brewery on a historic farm site, and a catered picnic lunch. To top it off, you’ll have a chance to make the acquaintance of llamas and alpacas with names like Draco, Biscotti, and Prince Persia.

Hudson Valley Wine & Food Fest

Rhinebeck
September 11–12

Head to the Dutchess County Fairgrounds for a smorgasbord of food delights presented by a wide range of gourmet vendors — and wash it all down with samples from the Valley’s top wineries and breweries. You can even attend a cooking or wine seminar taught by some of the tops in the business (past participants have included pros from culinary TV shows like Iron Chef and Hell’s Kitchen).

7th Annual Hudson River Craft Beer Festival

Riverfront Park, Beacon
September 18

More than 90 of America’s top craft breweries will be represented, featuring almost 200 craft beers. Live music, local vendors, and delicious food are part of the fun. And if you’re a true beer aficionado, consider VIP admission to enjoy a super sampling session of brews.

Flavors of Haverstraw

Photo courtesy of Haverstraw River Arts / Rockland Tourism

Flavors of Haverstraw Food Crawl and Beer Garden

Haverstraw
September 19

Enjoy the diverse cuisine of downtown Haverstraw with samples from over a dozen restaurants for only $3-$6 per plate. Visit the outdoor craft beverage garden and sample craft brews from Rockland and the lower Hudson Valley. Live music by The Eugene Tyler Band will help kick off this community-oriented party.

Annual Hudson Berkshire Wine & Food Festival

Chatham
October 2

Explore a day packed with music, craft and artisan booths, and family-friendly fun activities. Tickets are available online for this widely attended autumn festival that presents products from award-winning regional wineries, distilleries, cideries, and craft breweries.

Beer Pairing Dinner at the Dutch Ale House

Saugerties
November 4

Winner winner, beer and dinner. The Dutch Ale House is treating guests to an autumnal four-course menu paired with craft beers from the iconic West Kill Brewing. Bring friends, or mingle with other beer lovers while sipping on a delectable selection of hard drinks and eats. Tickets are $70 a head and must be purchased in advance.

THE BURGER & BEER BLAST

The Burger & Beer Blast / Photo by Katie Chirichillo

Film

Movies on the Hudson

Cornwall-on-Hudson
September 18 and October 16

Come early to savor the sunset, then settle in on a blanket or lawn chair and enjoy an outdoor movie to toast the end of the outdoor season. September’s showing is voted by residents and yet to be determined at press time; the spooky, cult classic Poltergeist is October’s pick. Check the Cornwall-on-Hudson Special Events page on Facebook for updates.

Bizarre Bazaar

Amenia
September 25

This unique event held at Four Brothers Drive-In combines everything from craftspeople to zombies. During the day, you can browse dozens of vendors’ booths. Then after dark, see the classic scare-flick Night of the Living Dead, accompanied by a live score by the band Morricone Youth, which often composes and performs original music as audiences watch films.

Woodstock Film Festival

Woodstock
September 29–October 3

The 22nd annual Woodstock Film Fest offers a fascinating variety of films submitted by both established and aspiring creators. This gathering of aficionados of cinema and members of the film business has become a highlight of the region’s autumn arts scene.

Outdoor Movie with Upstate Films

Saugerties
October 16

This fun fundraiser at the quirky outdoor sculpture park Opus 40 includes a showing of the classic cult film Hairspray. The evening also offers pre-film music, plus drink and food offerings.

JAZZFEST WHITE PLAINS

Jazzfest White Plains / Photo by Emmet Cohen

Music

JazzFest White Plains

White Plains
September 9–12

This four-day celebration features an outstanding selection of established Westchester and New York City area jazz musicians, plus rising performers. Now in its tenth year, the festival’s programs will be presented both in-person and streamed live.

Bethel Woods Concerts

Bethel Woods Center for the Arts, Bethel
September

Grab your cowboy boots and make your way to Bethel Woods to enjoy Mr. Worldwide, country rock riffs, gritty blues-rock, and Houston flair to start off the fall. You won’t want to miss this quintessential Pavilion concert series.

September 3: Pitbull

September 23: Chris Stapleton

September 25: The Black Crowes

September 26: ZZ Top

Highlands Bluegrass Festival

Harmony Hall, Jacob Sloat House; Sloatsburg
September 12

Lively performances from upbeat and nationally known bluegrass musicians abound at this music fest. A craft show accompanies the day of music; activities for kids and tours of the historic site add to the fun.

Basilica SoundScape: A Weekend of Music + Art

Chatham
September 17–18

This creative “anti-festival” heads outdoors this year, taking place at PS21, an open-air performance-art theater site on 100 acres of orchards and meadows. Regional musicians, poets, and artists will participate in a variety of creative offerings.

Jams in the Hamlet

Hillsdale
September 18 and October 9

Outdoor music is alive and well in this concert series held in Hillsdale’s Hamlet Park. In September, sit back and listen to Grammy nominee, Brady Ryder, and Claudia Mussen offer up a selection of exuberant family music. Then brush up on your go-to karaoke favorites for October’s community talent show. Find them on Facebook.

Woodsist Festival

Accord
September 25–26

This gathering at Arrowood Farms Brewery in Accord features musicians performing on two stages, plus craft brews and yummy food from local vendors. Sign up online to join the wait list; tickets are sold out.

Jonas Brothers Tour

Saratoga Springs
September 28

The band’s “Remember This” tour rolls into the Saratoga Performing Arts Center for one night; country pop singer Kelsea Ballerini is also scheduled to appear.

Flyday Music Festival

East Durham
October 1–3

Live performances by 21 different acts in an eclectic range of genres including funk, pop, rock, and experimental EDM offer plenty of entertainment for just about any music fan. You can also browse through vendors’ stands, sample microbrews, and munch on a meal — or try a tie-dye workshop or a calming session of yoga.

Fun in the Orchard with The Chain Gang

Poughquag
October 2–3

For more than two decades, local five-member band The Chain Gang has entertained Valley audiences with their vibrant covers of favorite rock and pop tunes. Catch them here at family-owned Barton Orchards, where you can also enjoy fresh apple pastries, cider, and other goodies in the great outdoors.

Lisa Loeb

The Emelin Theatre, Mamaroneck
October 14

Known for her hit “Stay (I Missed You)” from the movie Reality Bites, Loeb made history as the first pop singer to have a #1 single without a recording contract, and soon she will be trailblazing in the Hudson Valley, too.

City and Colour Live

Ulster Performing Arts Center (UPAC), Kingston
October 22

Canadian musician Dallas Green (known onstage as City and Colour) has been a regular in the international indie music scene for two decades. His first album, Sometimes, was certified platinum in 2006.

FRANKIE VALLI & THE FOUR SEASONS, fall

Frankie Valli & The Four Seasons / Photo courtesy of Bardavon Opera House

Frankie Valli & The Four Seasons

Ulster Performing Arts Center (UPAC), Kingston
October 24

The 1960s sensations (known to more recent fans as the “Jersey Boys”) perform their legendary tunes such as “Can’t Take My Eyes Off You” and “Big Girls Don’t Cry.”

Joan Jett & the Blackhearts

Palace Theatre, Albany
November 20

The band behind “Bad Reputation,” “I Hate Myself for Loving You,” and of course, “I Love Rock ‘N’ Roll,” is coming to Albany.

Art

Kingston Annual Fine Arts Exhibition

Arts Society of Kingston, Kingston
September 4–25

See an array of fine art, including sculptures, paintings, and photographs by local and regional artists in this juried fall exhibition. Opening and closing receptions are on September 4 and 25.

Life after the Revolution: Kate Millett’s Art Colony for Women

Samuel Dorsky Museum of Art, New Paltz
September 10–December 12

This instillation will feature never-before-seen art from influential feminist writer and activist Kate Millett, inspired by her life on her Poughkeepsie farm and art colony. The contemporary exhibit will carry queer and feminist themes and include contributions from photographer Del La Grace Volcano and filmmaker Barbara Hammer.

Patrick Rubinstein’s “New Works” Exhibit

Canfin Gallery, Tarrytown
September 18–October 10

Rubinstein’s latest kinetic compositions at the Canfin highlight a fusion of Optical, Pop and Street Art movements. Influenced by Warhol, Basquiat, and others, Rubinstein developed a signature technique — plotting double and triple overlays of images in an accordion-like configuration at 45-degree angles, which then yields multiple viewpoints of any given image.

Hudson River Skywalk Arts Festival

Rip Van Winkle Bridge, Catskill
September 19

Art and nature unite in this fall celebration: Take a stroll on the historic pedestrian bridge connecting the homes of legendary Hudson River School artists Thomas Cole and Frederic Church, then stop by the park at the bridge entrance for shopping, art lessons, and music. It’s all surrounded by the scenic backdrop of the Great Northern Catskills.

Modern Makers Market

St. Mary’s Church, Cold Spring
September 25

Peruse unique creations by more than 40 artisans at Hops on the Hudson’s final Modern Makers Market of the season. Participants include glassworkers, jewelers, and potters, plus you can enjoy live music and local food and beverages.

WESTCHESTER CRAFT CRAWL, fall

Photo courtesy of Westchester Craft Crawl

Westchester Craft Crawl

Various towns in Westchester
October 2–3

Local artists launched this event in 2020 to sell their work and connect with other artists and art-lovers during the pandemic. It features eight studio stops along Westchester’s river towns, including Tarrytown, Ossining, and Cortlandt Manor. Creations feature clay, wood, fiber, metal, jewelry, glass, and mixed media.

Handcrafted Octoberfest at Rhinebeck

Rhinebeck
October 2–3

This lively autumn festival offers everything from fine art to homemade jewelry, specialty foods to apothecary goods. Kids will have a ball checking out the farm animals, while adults can appreciate a chance to sample the season’s best beer, wine, and spirits.

HUDSON VALLEY HOT-AIR BALLOON FESTIVAL, fall

Photo courtesy of the Dutchess County Regional Chamber of Commerce

Family Fun, Fairs, & Festivals

Hudson Valley Hot-Air Balloon Festival

Union Vale
September 3–5

Savor the spectacular sight of enormous hot-air balloons gracing the sky —and if that’s not breathtaking enough, you can soar up, up, and away yourself on a balloon or helicopter ride. Or if you prefer, stick to the ground and enjoy family-friendly games, hayrides, live music, and more.

SeptemberFest Street Fair

Village of Nyack
September 12

Stroll along closed-to-traffic village streets and browse through the wares of more than 300 vendors. There’s also live entertainment and plenty more. And take time to pop into the many cute Nyack shops and popular eateries offering SeptemberFest specials.

Equus Fest East

New Paltz
September 25

Lucky Star Horsemanship hosts this special fall event to enrich our horse-human experience and celebrate the rural lifestyle. This down-home day outdoors offers a host of equine-related events, businesses and vendors, along with an array of mobile food options.

Walktoberfest

Highland
October 2–3

Head to the Hudson Valley Rail Trail and the west entrance of the Walkway Over the Hudson to browse more than 100 vendors’ stands. Regional farms, breweries, wineries and distilleries will present their products; plus, you can take part in tastings, as well as browse for artwork, crafts and more.

Aerodrome Air Shows

Red Hook
Sat–Sun through October 17

Nifty historic planes and antique cars are featured at this family-friendly venue. The history of flight is showcased on Saturdays; visit on Sundays to watch a World War I dogfight spectacle. Tour the aviation museum — and you can even take a ride in a vintage biplane.

49th Annual Poughkeepsie Train and Hobby Show

Poughkeepsie
November 7

All aboard for fun at this gathering designed especially for railroad and train fans of all ages. Check out model exhibits, railroad clinics, and more at the Majed J. Nesheiwat Convention Center.

Performance

Joan Jonas

Dia: Beacon
October 8

This exhibition will feature not one or two, but three collections by Joan Jonas, iconic video and performance artist of the ‘60s and ‘70s. Dia has commissioned “The Shape, the Scent, the Feel of Things,” “Stage Sets,” and “After Mirage” for your viewing pleasure.

Chelsea Handler: ‘Vaccinated and Horny Tour’

Palace Theatre, Albany
October 15

Come see the comedian, TV host, and best-selling author’s set for lots of laughs and the ultimate post-covid comeback.

David Sedaris

Bardavon, Poughkeepsie
October 16

Author and master of humor David Sedaris is bringing his signature satire to the Queen City, where he will do a reading and Q&A. Twice included in “The Best American Essays,” Sedaris will also be signing books in the lobby after the event.

Al Franken: ‘The Only Former U.S. Senator Currently on Tour’ Tour

The Egg Center for the Performing Arts, Albany
November 6

Former Minnesota Senator Al Franken spills jokes and stories about his extraordinary life and career. An original writer for SNL, a New York Times best-selling author, a celebrated politician, and now a podcast host, Franken is sure to deliver top-notch entertainment for the politically inclined and those just looking to laugh.

THE GREAT JACK O’LANTERN BLAZE, fall

Photo courtesy of Historic Hudson Valley

Halloween

The Great Jack O’Lantern Blaze

Croton-on-Hudson
September 17–October 31; November 3–7, 10–14, 18–21

This unique Halloween-themed walk-through outdoor wonderland features 7,000 illuminated jack o’ lanterns sculpted into crazy, creative shapes including a carousel, a windmill, and even the Statue of Liberty.

Headless Horseman Hayrides and Haunted Houses

Ulster Park
Fri–Sun in October

Come for a night of spooky fun — you’ll find corn mazes, food vendors, and of course, hayrides and Halloween-themed haunted houses.

Rocky Horror Picture Show

Peekskill
October 31

What better way to spend Halloween night than at a screening of The Rocky Horror Picture Show? Buy your tickets now, then break out your stockings and stilettos for this horror comedy musical cult classic playing at the Paramount Hudson Valley theater.

Related: 7 Hudson Valley Getaways for a Beautiful, Local Escape