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!