lamb on the rock with the "Upstate Weekend Plans" text written across the Hudson Valley, NY photo.

What to Do in the Hudson Valley This Weekend Oct 18 – Oct 20

By inside + out | October 16, 2024

Get ready for an epic weekend in the Hudson Valley, filled with laughter at the Catskills Comedy Festival, Woodstock Film Festival, NY State Sheep + Wool Fest, magic under the stars at the Opus 40 Gala, and more! There is something for everyone. Pick an event below…

🤡 Catskill, Fri Oct 18th – Sun Oct 20th. Catskills Comedy Festival is HERE!
Amazing stand-ups, improvisers, musicians, drag queens, and other funny folks are headed your way. And YES, they will host Open Mic events so you can get up and do your thing! Read more about the event in this article. Info HERE.

🎬 Woodstock, Fri Oct 18 – Sun Oct 20th. Woodstock 25th Annual Film Festival.
Series of films, forums, discussions + more taking place around the Hudson Valley from Oct 15th – 20th. Info HERE.

💃Tivoli, Fri Oct 18th, 5:30pm. Drag Bingo at Lasting Joy Brewery.
Check out the queen’s twirl for you in between bingo games, where you have a chance to win some truly fabulous prizes. Food + craft beer. Info HERE.

🌈 High Falls, Fri Oct 11th, 6pm – 8pm. Jay Blotcher on Rainbow Warrior, Gilbert Baker at Blue Heron Books.
Celebrate LGBTQ History Month and National Coming Out Day with a discussion on Gilbert Baker’s memoir, creator of the Rainbow Flag, featuring activist Jay Blotcher + author Nina Shengold. Info HERE.

🎃 Ulster Park, Fri Oct 18th, 7pm – 9:30pm. Headless Horseman Hayrides & Haunted Attractions.
Scary Halloween attractions and hayrides if you dare! Info HERE.

🦙 Rhinebeck, Sat Oct 19th + Sun Oct 20th. NY State Sheep + Wool Festival at Dutchess County Fairgrounds.
A vibrant celebration of fiber arts, farmers, animals, the global community of makers, knitters, weavers + fiber enthusiasts. Read about the event in this article. Info HERE.

🍂 Phoenicia, Sat Oct 19th, 12pm. Fallcina at Parish Field.
Community Fall-themed event with vendors, food, music + more! Info HERE.

📚 Beacon, Sat Oct 19th, 3pm – 4:30pm. “Witchlings” Celebration at Howland Cultural Center.
Stanza Books is hosting a book signing of “Witchlings 3” with Claribel Ortega + author Ryan La Sala. Info HERE.

🌈 Kingston, Sat Oct 19th, 4:45pm. WE’RE OUT HERE at the Hudson Valley LGBTQ+ Community Center.
Join them for “WE’RE OUT HERE,” a captivating shorts program that showcases a collection of bold and transformative narratives and documentaries from across the LGBTQIA+ community. Info HERE.

🍁 Saugerties, Sat Oct 19th, 5pm. Opus 40 Gala.
A magical night featuring a farm-to-table dinner, a stunning light show + live music under the stars. Info HERE.

🎸 Woodstock, Sat Oct 19th, 7pm. Rob Stoner at Colony.
Come experience the very talented singer and multi-instrumentalist Rob Stoner, who was Bob Dylan’s musical director for three tours! Info HERE.

🥒New Paltz, Sun Oct 20th, 10am – 5pm. 27th Annual Rosendale International Pickle Festival.
Over 100 vendors will sell all the goods, and there will be a home pickling contest and the Pickle Triathlon, which will include a pickle-eating contest, pickle juice drinking, and a pickle toss! Info is HERE.

🌽 Kinderhook, Sun Oct 20th, 11am – 4pm. Corn Maze!
Get lost in a corn maze at Samascott’s Garden Market. Info HERE.

🍂 Olivebridge, Sun Oct 20th, 12pm – 4pm. Fall Family Fun Fest at the Ashokan Center.
Fresh apple cider pressing, pumpkin painting, blacksmithing, broom-making, hayrides, music, food, guided hikes + fun for all ages. Info HERE.

🦪 Claverack, Sun Oct 20th, 12pm – 7pm. Oyster Party Pop Up at Cooper’s Daughter Spirits.
Feast on freshly shucked oysters, lobster rolls, caviar & chips, and more, paired with handmade cocktails, mocktails, local brews, and tasting flights of in-house spirits! Info HERE.

🫑 Kingston, Sun Oct 20th, 2pm – 3pm. Cookbook Signing + Conversation at Kingston Social.
Don’t miss out on our Cookbook Signing + Conversation with writer and chef, Emma Hearst! Chat about her new book, “Flavors From The Farm,” which uses farm-fresh ingredients. Enjoy local veggie tastings too! Info HERE.

👨‍🌾 Explore Hudson Valley’s vibrant Fall Farmers Markets + CSA, which 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.