Autumn into winter, the Hudson Valley hums with creativity. From Rhinebeck’s Sheep and Wool Festival to the cinematic buzz of the Woodstock Film Festival, the season brims with reasons to gather. Theatergoers can catch the satirical bite of “The Thanksgiving Play” in Ghent, while comedy takes center stage in Catskill and Kingston with the Catskills Comedy Festival and Ashley Gavin’s new show. Music lovers won’t want to miss the timeless elegance of “Swan Lake,” the restless indie charge of Modest Mouse, the boundary-breaking Silkroad Ensemble, or the New Orleans swing of the Preservation Hall Jazz Band. And in Beacon, the Bonfire ignites Main Street with art, performance, and that singular spark of Hudson Valley magic.
Woodstock Film Festival
October 15-19 at locations in Woodstock
Each fall, the Woodstock Film Festival transforms the Hudson Valley into a cinematic crossroads, drawing filmmakers and audiences from around the world. Celebrated for its fiercely independent spirit, the festival showcases a mix of narrative features, documentaries, and shorts alongside panel discussions, concerts, and parties that spill across Woodstock, Kingston, Saugerties, and Rosendale. More than a film series, it’s a gathering place for artists and fans, where emerging voices share space with established auteurs. With programming still under wraps for 2025, one thing is certain: The Woodstock Film Festival remains one of the region’s premier cultural events.
“The Thanksgiving Play”
October 17-26 at the Ghent Playhouse
This fall, the Ghent Playhouse stages Larissa FastHorse’s biting satire “The Thanksgiving Play.” A Broadway hit in 2023, the comedy skewers well-meaning attempts at “woke” theater as four white educators try to devise a politically correct Thanksgiving pageant. With no Indigenous collaborators in sight, their brainstorm sessions spiral into absurdity, exposing the hypocrisies and blind spots of cultural representation. FastHorse, the first Native American woman playwright produced on Broadway, balances humor with sharp critique, making “The Thanksgiving Play” both laugh-out-loud funny and deeply unsettling. Ghent’s production offers Hudson Valley audiences a chance to wrestle with this timely, provocative comedy.
Ashley Gavin: “Hype Man”
October 18 at Assembly
Comedian Ashley Gavin brings her brand-new show “Hype Man” to Assembly in Kingston. Known for her sharp wit and unfiltered takes on sex, gender, and modern life, Gavin has cultivated a devoted fanbase through her hit podcast “We’re Having Gay Sex” and sold-out stand-up tours. Her style is brash, brainy, and unapologetically queer, blending social critique with the energy of a hype session. At Assembly, she’ll workshop fresh material that pushes boundaries while keeping audiences doubled over in laughter. It’s a one-night chance to catch one of comedy’s fastest-rising voices at the height of her powers.
The Catskills Comedy Festival
October 18-20 at locations in Catskill
The Catskills Comedy Festival turns downtown Catskill into a playground for laughs. The inaugural weekend includes stand-up, alt-comedy, improv, Vaudeville, panels, and comedy shorts—plus an art exhibit and family events. Featured acts include “SNL” alum Colin Quinn as well as comedy vets Dave Hill, Erin Jackson, and Eddie Brill. Youth-focused moments include a Kids’ Comedy Open Mic (ages 7–14) and On the Fly Story Slam showcasing young storytellers. With much of the programming free or pay-what-you-can, this nonprofit festival means serious fun with a community-first spirit.
New York State Sheep and Wool Festival
October 18-19 at Dutchess County Fairgrounds
Rhinebeck’s Dutchess County Fairgrounds turn woolly for the New York State Sheep and Wool Festival, October 18–19. One of the largest fiber arts festivals in the country, it’s a sprawling showcase of heritage breeds, fleece competitions, shearing demos, weaving, and a juried craft fair that attracts makers and knitters from across the globe. Food vendors highlight lamb in every form, while workshops teach everything from natural dyeing to felting. Families can meet alpacas and angora rabbits, while serious fiber artists stock up for the year. It’s Rhinebeck at its coziest: equal parts farm show, craft bazaar, and harvest celebration.
“Swan Lake”
October 24 at Ulster Performing Arts Center
The Ulster Performing Arts Center hosts “Swan Lake,” brought to life by a constellation of international ballet stars. Tchaikovsky’s 19th-century masterpiece, with its tale of love, deception, and transformation, remains the touchstone of the classical ballet repertoire. Under glittering tutus and sweeping orchestral strains, the timeless drama of Odette and Siegfried unfolds with technical precision and emotional heft. UPAC’s stage becomes a mirror of moonlit waters as dancers channel the otherworldly grace that has captivated audiences for generations, reminding us why “Swan Lake” endures as ballet’s most iconic flight of fantasy.
Modest Mouse
October 28 at Ulster Performing Arts Center
Since breaking out with The Lonesome Crowded West in the late ’90s, Modest Mouse have carved a singular path—jangly guitars, jagged rhythms, and lyrics that toggle between existential dread and skewed whimsy. Their 2004 smash Good News for People Who Love Bad News yielded radio staples “Float On” and “Ocean Breathes Salty,” cementing their place in the indie canon. Still restless after nearly three decades, Isaac Brock and crew continue to evolve, ensuring their live shows crackle with urgency, unpredictability, and the kind of catharsis only they deliver.
Beacon Bonfire
November 5-9 at locations in Beacon
Beacon Bonfire lights up Main Street with four days of music, art, and spontaneous creativity in November. Think Edinburgh Fringe with a dash of Burning Man, scaled to Beacon’s mile-long stretch from Fishkill Landing to Matteawan. The festival kicks off with an opening ceremony, spills into screenings at Industrial Arts, and peaks with a 10K race to the Beacon Fire Tower and a full day of buskers, pop-ups, and cozy campfires. Some events are ticketed, many are free, and all spark that elusive Hudson Valley magic that’s turned Beacon into a creative beacon of its own.
Silkroad Ensemble
November 8 at the Mahaiwe Performing Arts Center
The Mahaiwe in Great Barrington hosts the Silkroad Ensemble, the boundary-smashing collective founded by Yo-Yo Ma. Now under the artistic direction of Rhiannon Giddens, the group continues its mission of cultural cross-pollination, weaving together musical traditions from across the globe into something altogether new. Expect an evening where Chinese pipa converses with banjo, Middle Eastern percussion underpins Celtic fiddle, and improvisation bridges centuries and continents. Known for performances that are as joyful as they are virtuosic, the Silkroad Ensemble creates a soundscape that defies borders—reminding audiences that music is one of humanity’s oldest, and most unifying, languages.
Preservation Hall Jazz Band
December 4 at Bethel Woods
The sounds of New Orleans roll into Bethel Woods with the Preservation Hall Jazz Band in December. Founded in the French Quarter in 1961, the ensemble has carried the city’s musical DNA across the globe, blending traditional Crescent City jazz with fresh influences that keep the spirit alive and evolving. Their concerts are joyous affairs—equal parts history lesson, second-line parade, and communal celebration. Expect blistering horns, syncopated rhythms, and soulful improvisation that transcend generations. As winter sets in, Preservation Hall’s unmistakable swing will warm the Catskills with a living tradition that still feels urgent, vibrant, and defiantly alive.
This article appears in Fall 2025/Winter 2026.
