When the days get long and the hills turn green, the Hudson Valley comes alive with music, art, theater, and delightfully weird happenings. From open-air Shakespeare to world-class bluegrass, and from experimental exhibitions to accordion-fueled parody concerts, the region’s cultural calendar is as lush and varied as the landscape itself. Whether you’re a lifelong local or just passing through, these not-to-miss events are a chance to tap into the creative pulse of the region—and maybe even dance a little under the stars
Woodstock-New Paltz Art & Crafts Fair
Celebrate creativity at the 44th annual Woodstock-New Paltz Art & Crafts Fair, returning Memorial Day weekend (May 24–26, 2025) at the Ulster County Fairgrounds in New Paltz. This renowned event showcases over 200 juried artists and craftspeople from across the nation, offering unique handmade goods ranging from ceramics and jewelry to fine art and textiles. Enjoy live music, craft demonstrations, and a variety of food and beverages, including regional wines and craft beers. A dedicated children’s tent ensures fun for the whole family.
Great Barrington Public Theater
Great Barrington Public Theater returns this summer with a bold, all-female slate of world premieres staged at the Daniel Arts Center on the campus of Bard College at Simon’s Rock. Headlining the 2025 season is “The Best Medicine” by Robin Gerber (August 1-17) a heartfelt comedy about caregiving and stand-up, directed by TV and theater vet Matthew Penn. Also on deck: Maggie Kearnan’s darkly comic “How to Not Save the World with Mr. Bezos” (June 5-27) and “Madame Mozart, The Lacrimosa” by Anne Undeland (July 10-27). Championing new work, local talent, and accessible pricing, GBPT continues to carve out space for fresh voices in the Berkshires.
Hudson Valley Shakespeare
Hudson Valley Shakespeare’s 2025 season promises a rich blend of classic and contemporary theater under its iconic open-air tent in Garrison. Kicking off with Shakespeare’s “The Comedy of Errors” (June 6–August 2), directed by Ryan Quinn, audiences can expect a whirlwind of mistaken identities and comedic chaos. Thornton Wilder’s “The Matchmaker” (June 8–August 3), the inspiration for Hello, Dolly!, follows, featuring HVS veterans Nance Williamson and Kurt Rhoads under the direction of Artistic Director Davis McCallum. The season also includes Dave Malloy’s a cappella chamber musical “Octet” (August 11–September 7), exploring technology’s impact on human connection, directed by Amanda Dehnert. Additionally, the HVS Cabaret series (August 6–9) will showcase intimate musical works-in-progress at the on-site Valley Restaurant. The season concludes with an educational production of “Julius Caesar” (September 15–October 10), directed by Raz Golden, which will tour local schools and community venues. This lineup offers a diverse theatrical experience amidst the scenic Hudson Valley backdrop.
“The Arrested Image: Identity Through the Lens of Law Enforcement”
This summer, the Samuel Dorsky Museum of Art at SUNY New Paltz presents “The Arrested Image: Identity Through the Lens of Law Enforcement” (June 14-November 2), an incisive exhibition curated by Sophie Landres. Exploring the intersection of photography and policing, the show traces the evolution of identity representation from 19th-century mugshots to contemporary biometric data. Featuring works like Harun Farocki’s I Thought I was Seeing Convicts (2000), the exhibition challenges viewers to consider pressing issues of justice, privacy, and surveillance in today’s technological landscape.
Mountain Jam
After a six-year hiatus, Mountain Jam makes its much-anticipated return to the Hudson Valley from June 20–22, at its new home on Belleayre Mountain in Highmount. This iconic festival, independently produced by its original creators and Radio Woodstock, promises an intimate experience with a stellar lineup. Headliners include the genre-blending Khruangbin on Friday, indie rockers Mt. Joy on Saturday, and jam band favorites Goose closing out the festival on Sunday. Additional acts feature Joe Russo’s Almost Dead, Trampled by Turtles, and Michael Franti and Spearhead.
“All Manner of Experiments”
This summer, the CCS Hessel Museum of Art at Bard College presents “All Manner of Experiments: Legacies of the Baghdad Group for Modern Art” (June 21-October 19), the first comprehensive US exhibition of Iraq’s influential postcolonial modernist collective. Curated by renowned scholar Nada Shabout, the show traces the Group’s visionary fusion of Islamic, Mesopotamian, and Western aesthetics from the 1950s to today. Featuring rarely seen works by artists like Jewad Selim and Dia al-Azzawi alongside archival materials and newsreels, the exhibition reframes global modernism through an Iraqi lens.
Weird Al Yankovic
“Bigger & Weirder” Tour
On July 13, musical satirist Weird Al Yankovic brings his “Bigger & Weirder” tour to Bethel Woods Center for the Arts, the site of the original 1969 Woodstock festival. Backed by his long-time band, Yankovic will serve up accordion-fueled parodies, style pastiches, and absurd original songs spanning his four-decade career—from “Eat It” to “Word Crimes.” Special guest Puddles Pity Party, the melancholy clown with a golden voice, opens the show. Expect costume changes, multimedia antics, and plenty of laughs under the stars. It’s high-octane nerdy fun in a legendary venue.
Grey Fox Bluegrass Festival
The Grey Fox Bluegrass Festival returns to Walsh Farm in Oak Hill, July 16–20, 2025, with five days of top-tier picking, jamming, and foot-stomping fun in the Catskills. Now in its 44th year, Grey Fox brings a stacked lineup: Del McCoury Band, Sam Bush Band,I’m With Her, Sierra Hull, Steep Canyon Rangers, the California Honeydrops, Della Mae, and many more. With on-site camping, instrument workshops, a family-friendly kids’ academy, and late-night sets under the stars, Grey Fox is a pilgrimage for bluegrass fans of all ages. Bring your banjo—or just your ears.
Upstate Art Weekend
Now in its sixth year, Upstate Art Weekend (July 17-21) is a self-directed celebration of contemporary art across the Hudson Valley and Catskills. Over five days, more than 130 participants—including museums, galleries, pop-ups, and artists’ studios—open their doors for special exhibitions, performances, and events. Launched by curator Helen Toomer, the weekend has become a summer highlight for art lovers, drawing visitors from near and far to explore the region’s rich creative landscape. With its mix of pastoral beauty and cutting-edge work, Upstate Art Weekend offers a compelling snapshot of the region’s thriving art scene. Plan your route and wander.
Ani DiFranco
“Unprecedented Sh!t” Tour
Folk icon and feminist trailblazer Ani DiFranco heads to Arrowood Farms in Accord on August 28 as part of her “Unprecedented Sh!t” tour, joined by genre-defying troubadour Hurray for the Riff Raff. Set amid the rolling fields and mountain views of this eco-conscious brewery and venue, the show promises an evening of incisive lyrics, political fire, and sonic intimacy. DiFranco’s storied catalog spans punk-inflected folk to jazz-funk grooves, while Hurray for the Riff Raff brings their own brand of soulful resistance. Expect community vibes, cold beer, and music with a message.
This article appears in Spring/Summer 2025.
