What to Do in the Hudson Valley This Weekend Oct 24 – Oct 26

From haunted cabarets to harvest fests, spooky cruises to soulful concerts—Halloween weekend in the Hudson Valley is packed with magic, music + mischief!

🧛 Woodstock, Fri Oct 24th, 7pm. Vampire Cabaret Club + Sideshow at Colony Woodstock.
Step into the shadows for a night of dark enchantment and thrilling spectacle! Info HERE.

🕷️ Poughkeepsie, Fri Oct 24th, 7pm – 9pm. Halloween Party at the Dutchess Pride Center.
Adult night Haolleen costume, games, pizza + a ghoulishly good time! Info HERE.

👹 Catskill, Fri Oct 24th, 7:30pm – 9:30pm. “Devils ‘N Details” with Peter Samelson at Bridge Street Theatre.
A new magic show by acclaimed magician Peter Samelson. Info HERE.

💬 Woodstock, Fri Oct 24th – Sun Oct 26th. Woodstock Story Fest at Mountainview Studios.
Celebrate storytelling in all its forms, with a rich mix of 16 guest presenters, regional + international voices sharing powerful, up-close story experiences. Info HERE.

🎭 Newburgh, Fri, Oct 24th – Sun, Oct 26th. Newburgh Fringe Festival by Safe Harbors of the Hudson.
Whether you’re drawn to the experimental, heartfelt, or hilariously offbeat, this vibrant showcase celebrates daring ideas and unforgettable artistry—a space where creativity reigns supreme. Info HERE.

⚓️ Kingston, Fri Oct 24th – Sun Oct 26th, 5pm – 7pm. Spooky Tales Aboard Solaris at the Hudson River Maritime Museum.
Climb aboard the solar-powered boat for a family-friendly Halloween ride filled with spooky Hudson River tales, ghostly legends + cozy treats. Info HERE.

🥀 Phoenicia, Fri Oct 24th – Sun Oct 26th, 7pm + 2pm. Little Shop of Horrors at Phoenicia Playhouse.
The cast and crew are hard at work bringing this cult-classic musical of a shy shop assistant, a mysterious plant, and a wild twist of fate to life! Info HERE.

🧗‍♂️Rosendale, Fri Oct 24th – Sun Oct 26th. Rock-tober Fest at Alpine Endeavors.
Choose from clinics covering essential rock climbing skills—intro to rock, top-roping, leading, rescue, self-reliance, multi-pitch climbs, gear placement, anchoring, and belay techniques. Info HERE.

🍬 Poughquag, Sat Oct 25th + Sun Oct 26th, 10am – 6pm. Tract-or-Treat Weekend at Barton Orchards.
A spooktacular family Halloween celebration with trick-or-treating, live music, magic, hayrides, a haunted house, corn maze, petting zoo, and more! Info HERE.

🏃‍♂️ Rosendale, Sat Oct 25th, 11am – 1pm. UlsterCorps’ 15th Annual ZOMBIE ESCAPE.
A family-friendly Halloween fundraiser, featuring a 5K trail run, 2K walk + free 1K kids’ Fun Run through scenic trails with zombies, spooky surprises + more. Info HERE.

​🍂 Poughkeepsie, Sat Oct 25th, 12pm – 5pm. 3rd Annual Harvest Fest at the Poughkeepsie Farm Project.
A celebration of food, farm, and community with live music, local bites, craft drinks, and a Makers Market—enjoy the best of the season with local flavors and good company. Info HERE.

🎃 Kingston, Sat Oct 25th + Sun Oct 25th, 2pm – 7pm + 1pm – 5pm. Halloween Fest + Parade at MyKingstonKids.
Pumpkin Carving Challenge, costume contest, parade + more! Info HERE.

🗡️ Dover Plains, Sat Oct 25th, 6:30pm – 9pm. Haunted Harvest Night at Soukup Farms.
Brave a hayride through shadowy fields to the haunted corn maze for a night of spine-chilling frights and eerie farmyard thrills! Info HERE.

🎶 Kingston, Sat Oct 25th – Sun Oct 26th, 10pm – 9am (OVERNIGHT!). Drone Sleepover at Assembly.
An immersive ambient music sleep concert from dusk until dawn hosted by @_stretchmetal. Eight artists perform continuous drone sets designed for sleep with live visual projections throughout the program. The final set serves as a wake-up dance party to welcome daybreak. Info HERE.

👻 Bearsville, Sun Oct 26th, 11am. The Rock ‘n Roll Playhouse: Music of Fleetwood Mac Halloween Bash at Bearsville Theater.
A family-friendly concert where kids 10 and under can sing, dance and play to classic rock hits in a fun, safe, volume-friendly setting! Info HERE.

🎤 Saugerties, Sun Oct 26th, 5pm – 8pm. Saugerties Sessions: Winn + Pearl + Laws at The Local.
Alt-pop-R&B artist Carly Pearl, Americana songwriter Pamela Laws + Kingston-based singer-songwriter Ginger Winn—joined by Will Bryant (keys) and Jack Petruzzelli (guitar)—come together for a soulful night of live music, food + drinks, including pierogi, beer, wine, sake + more. 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.

👉 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!