As the Hudson Valley transforms with crisp autumn air and frosty winter nights, a vibrant array of events beckons locals and visitors alike. From artisanal markets and haunted hayrides to flamenco rhythms and iconic rock performances, the region’s cultural calendar is packed with unforgettable experiences. Whether you’re in the mood to shop handcrafted goods at the Field + Supply MRKT, groove to the sounds of Todd Rundgren, or immerse yourself in the eerie charm of the Headless Horseman Hayrides, the Hudson Valley offers something for everyone this season. Let the season’s magic unfold with these must-attend events!
Headless Horseman Hayrides | Ulster Park
Weekends through October 27
For over 30 years, Headless Horseman has entertained and frightened over a million guests with its haunted attractions. This year’s theme, “Darkest Offering,” is set in the town of Crow Hollow, which invites you to join in their ancient rites and festivities. For centuries, the celebration has been shrouded in secrecy but now outsiders have been asked to participate for the first time in town history! Don’t refuse the invitation to be an honored guest for Crow Hollow’s most sacred celebration.
“Bat Boy: The Musical” | Center for Performing Arts in Rhinebeck
October 11-27
Bat Boy is a comedy horror about a half-bat/half-boy creature that is discovered in West Virginia. The Rhinebeck Theater Society presents this spooky show to the community in the perfect setting of an intimate barn house theater. “Bat Boy” first premiered in 1997 on Halloween night. This rendition is directed by Lisa Delia and includes musical direction by Karen Dalmer-Sheehy, and choreography by Brooke Wallace.
Field + Supply Fall MRKT | Hutton Brickyard
October 11-13
This biannual curated makers’ market is back, hosting over 200 vendors at the gorgeous riverfront Hutton Brickyards property. Smaller items for sale include dainty brass cuffs from 8.6.4. and Skippy Cotton’s ornaments made from natural linen, organic cotton stuffing, and fragrant lavender. There’s also an array of high-end products, including handcrafted, zero waste furniture from Sawkille in Kingston. Enjoy views of the Hudson River while snacking on a sweet treat from Nancy’s of Woodstock Artisanal Creamery and listening to live music from artists like the Saints of Swing, who’ll be performing the best of swing, ballroom music, Dixieland jazz, and down-home blues.
New York State Sheep and Wool Festival | Dutchess County Fairgrounds
October 19-20
This Rhinebeck event, which celebrates the Northeast’s thriving livestock and fiber industries, offers an expansive number of activities and a one-stop shopping destination for all things fiber and fiber arts. Whether you want to fawn over little lambs in the livestock shows, browse the fleece sale, stock up on yarn, take crafting workshops, visit the petting zoo, or shop finished wool garments, there’s something for everyone. There’s also a used equipment auction where you can get everything for livestock raising and fiber crafts from lambing pens to spinning wheels and shears.
Todd Rundgren | Bearsville Theater
October 22
Playing at the Bearsville Theater is a homecoming for Rundgren, who worked at Bearsville Studio as a staff engineer and producerin the early `70s—he was dubbed Bearsville’s “boy wonder”—as well as recording his first three albums there. Rundgren’s monster hits include “I Saw the Light,” “Hello It’s Me,” and “Bang the Drum All Day.” The Rock & Roll Hall of Famer brings his all-star band (including bassist Kasim Sulton) on the “Me/We” tour to Woodstock in October.
Noirvember: Film Noir from Yesterday to Today | Jacob Burns Film Center
November 2-17
With Noirvember, the Jacob Burns Film center celebrates the iconic art of film noir with classics like Gilda, Mildred Pierce, Chinatown, and Bound. Guests can enjoy pre-screening themed “unhappy hours” at Take 3 Wine and Cafe bar. The series offers film lectures from select NYU Tisch professors during the first three Sundays of November. To kick off Noirvember, the center will screen Who Framed Roger Rabbit? for a family-friendly beginning on November 2.
Las Migas | Stissing Center
November 9
The Spanish quartet of Carolina La Chispa (vocals), Marta Robles (guitar), Alicia Grillo (guitar), and Laura Pacios (violin) comes from different cities that span not only the geography of Spain but also its cultural diversity. They all came to the group with one common passion: flamenco. Over the years, the group’s music has evolved: Latin rhythms add a happier, more upbeat sound; violin lines are more pensive; and the guitar arrangements have become more complex and intertwined, creating a fascinating blend of flamenco and Mediterranean music styles. Pine Plains.
“The Gospel According to Thomas Jefferson, Charles Dickens and Count Leo Tolstoy: Discord” | Bridge Street Theatre
November 14-24
These three historical icons come together for an 85-minute battle of wits. Discord is written by Scott Carter and is based on Jean-Paul Sartre’s No Exit through the filter of Steve Allen’s Meeting of the Minds. The play, written in 2015, is thought-provoking yet comical considering historical circumstances. The set, and props like the door without a handle and a table with a drawer that doesn’t open, add satirical elements to the show. Carmen Borgia designs and directs the Bridge Street production.
Mark Normand’s “Ya Don’t Say” Tour | Bardavon
November 15
Normand is a New York comic who has made appearances on the “Tonight Show with Jimmy Fallon” and the “Late Show with Stephen Colbert.” Originally from New Orleans, he moved to New York City right after college to get his start in the comedy scene. Since then, he has had stand-up specials on Comedy Central and Netflix as well as a self-released special “Out To Lunch” on his YouTube channel. His witty and relatable humor gained attention from other comics, like Jerry Seinfeld, who called him the “best young, up-and-coming comic.”
Dark Star Orchestra | MJN Convention Center
November 17
The premier Grateful Dead cover band—if you don’t count Dead & Company as a tribute act—has been celebrating the Dead concert experience for 30 years and makes a return visit to Poughkeepsie. For most performances, Dark Star Orchestra presents the complete original set list, song by song, and in order, while adapting their phrasing, voice arrangements and specific musical equipment for the various eras of the Grateful Dead shows in which they perform. The band has now performed over 2,500 concerts, surpassing the Dead’s own staggering concert tally of 2,318 between 1965 and 1995.
Gillian Welch and David Rawlings | Ulster Performing Arts Center
November 30
Gillian Welch’s rich and remarkable career spans over 25 years, and she and her musical partner David Rawlings are a pillar of the modern acoustic music world rooted in the sounds of Appalachia. They have been hailed by Pitchfork as “modern masters of American folk” and “protectors of the American folk song” by Rolling Stone. The duo makes tense and eerie acoustic music about desire and devastation, connecting modern music to the “old, weird America” that Greil Marcus coined about the tunes Bob Dylan and the Band created for the Basement Tapes.
“Sesame Street Live! Say Hello” | MJN Convention Center
December 4
This 90-minute family friendly show brings everyone’s favorite “Sesame Street” characters to life. The show travels all around the country inviting families everywhere to experience the performances. Elmo, Abby Cadabby, and Cookie Monster will sing and dance for the Poughkeepsie fans. After the show you can purchase merchandise like T-shirts and plush toys and even take pictures with the cast during the “Sesame Street Live!” photo experience.
“Teddy Sandoval and the Butch Gardens School of Art” | Williams College Museum of Art
Through December 22
This retrospective in Williamstown, Massachusetts is dedicated to the work of the inventive though long-overlooked Teddy Sandoval (1949–1995), who was central to Los Angeles’s queer and Chicano artistic circles and was active in both US and international avant-garde movements. The exhibition covers a quarter century of the artist’s work, revealing how Sandoval produced subversive yet playful works that explored the codes of gender and sexuality, often mining archetypes of masculinity through the signature icon of a faceless man sporting a mustache.
This article appears in Fall 2024/Winter 2025.
