What to Do in the Hudson Valley This Weekend Oct 17 – Oct 19

Pick your perfect pumpkin, enjoy the fall foliage, and get ready for a weekend packed with indie films, fall galas, mindful movement and a Live Rocky Horror Picture Show cult-classic experience. From cozy fairs to the Sheep + Wool Festival, the Hudson Valley is brimming with Halloween spirit + autumn magic. Take your pick below…

? Woodstock, Fri Oct 17–Sun Oct 19. Woodstock Film Festival.
Kicking off TODAY (Wed Oct 15)! This 5-day indie celebration lights up the Valley with screenings, panels, concerts, and conversations that champion bold storytelling and films that spark change. This 2025 lineup is stellar! Info HERE.

?️ Woodstock, Fri Oct 17th – Sun Oct 19th, World Peace Mandala Celebration.
Beginning TOMORROW (Thur Oct 16th), is a 4-day celebration of Tibetan culture and spirituality. Highlights include a momo (dumpling) cooking workshop, teachings on Tibetan medicine + mandalas with Dr. Kungchok and scholar Robert Thurman, a “Songs of Peace” celebration with live music + poetry. Plus the creation and dissolution of a World Peace Sand Mandala—a beautiful symbol of harmony + impermanence. Info HERE.

? Catskill, Fri Oct 17th – 19th. Catskills Comedy Fest at Bridge Street Theatre, Avalon Lounge + Community Theatre.
A 3-day, 18 events, endless laughs! Stand-up, improv, vaudeville, panels, open mic—and so much more. Info HERE.

? Hudson, Fri – Oct 17th – Sun Oct 19th, 1pm – Late. 4th Annual Honky Tonk Market Weekend at Return Brewing.
Vintage Makers, Tintype portraits @beacontintype, live music + acts, food trucks + more! Info HERE.

? Poughquag, Fri Oct 17 + Sat Oct 18, 8pm – 10pm. Rocky Horror 50th Anniversary Live Experience at Barton Orchards.
Celebrate 50 years of cult-classic chaos with RuPaul’s Drag Race star Loosey LaDuca, outrageous costumes, sing-alongs + a costume contest with prizes! Info HERE.

? Rhinebeck, Sat Oct 18 + Sun Oct 19, 9am–5pm. Sheep + Wool Festival at Dutchess County Fairgrounds.
A cozy fall tradition featuring 300+ vendors, fiber-art lovers, farm animals and all-around autumn joy. Info HERE.

? Arkville, Sat Oct 18th, 10am – 12pm. Wild Mushroom Woods Walk at Catskill Forest.
Meet at Rider Hollow Trailhead for a guided foraging walk with Catskill Fungi’s John Michelotti to learn safe, smart mushroom identification and foraging practices. Info HERE.

? Fishkill, Sat Oct 18th + Sun Oct 19th, 11am – 5pm, Fall Harvest Fests at Fishkill Farms.
Pumpkin season is here! Pick your own perfect pumpkin—classic jack-o-lanterns or quirky “warty goblins”—and enjoy apple picking, cider sipping, corn maze, hay rides, live music, donuts + more! Info HERE.

? Kingston, Sat Oct 18th, 12pm – 4pm. Fall Fest + Food Forest Planting at Kingston Land Trust.
Enjoy pumpkin carving, face painting, live performances, tree planting, tacos & empanadas, caramel apple dunking & more! Info HERE.

​? Red Hook, Sat Oct 18th + Sun Oct 19th, 2pm. Pumpkin Bombing Airshow at Old Rhinebeck Aerodrome.
Last weekend of airshows to have some fun with pumpkin! Info HERE.

? Saugerties, Sat Oct 18, 4:30–9:30pm. Fall Foliage Gala at Opus 40.
Celebrate creativity and community under the stars with live music, mountain views and a night supporting the arts. Info HERE.

?‍♂️ New Paltz, Sat Oct 18th, 7:30pm. Rick Accomazzo Slide Show: Tobin, the Stonemasters and Me 1970-1980 at The Annex.
Rick Accomazzo shares the untold story of Tobin Sorenson, one of the fearless young climbers who revolutionized the sport in the 1970s. Part of a legendary crew that pushed the limits of free climbing, Sorenson’s story captures the spirit of adventure that inspired a new generation of climbers. Info HERE.

? Rosendale, Sun Oct 19th, 10am – 5pm. The 28th Annual Rosendale International Pickle Festival at Ulster County Fairgrounds.
Over 100 vendors offering pickles, gourmet foods, baked goods, crafts, a home pickling contest, pickle-eating + juice-drinking challenges, a pickle toss—all and more! Info HERE.

? Staatsburg, Sun Oct 19, 1–5pm. Greystone Programs’ 33rd Annual Wine Tasting + Auctions at Milea Estate Vineyard.
Sip, bid and support a great cause with curated tastings and live and silent auctions benefiting Greystone Programs. Info HERE.

? Saugerties, Sun Oct 19th, 7pm – 9pm. Desert Blues: Tarwa N-Tiniri at The Local.
Meaning “Sons of the Desert,” from Ouarzazate, Morocco, bring a new generation of desert blues inspired by Tinariwen, Tamikrest and Bombino. With guitars, percussion, a gourd, and bass, they channel the stories of nomadic people through hypnotic rhythms, mesmerizing vocals and psychedelic riffs. Their debut song Taryet has already racked up 8 million YouTube views. Live visuals by BA Miale! Info HERE.

? Explore Hudson Valley’s vibrant SPRING to FALL Farmers Markets, Marketplaces, and Community-Shared Agriculture (CSA).
Support small local farms, foster a sense of community and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

Photos by Fishkill Farms

? Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!