2026 Editor’s Picks: What to Do in the Hudson Valley on Jan 23 – 25

Music, movement, winter gatherings—and a classic Chili Cook-Off—fill the Hudson Valley this weekend. There’s truly something for everyone. Take your pick below…

🗓️ Whole Weekend

💒 Tarrytown, Sat Jan 24th + Sun Jan 25th, 10am – 5pm. Hudson Valley Wedding Market at Makers Central.
A wedding expo reimagined, this immersive market showcases a carefully curated selection of the Hudson Valley’s top makers—florists, designers, chefs, and artisans—inviting couples to sip, stroll, meet local talent and gather inspired ideas for a truly personal celebration. Info HERE.

🏳️‍🌈 Hunter, Sat Jan 24th + Sun Jan 25th. LOVE A Little More Ski Weekend at Hunter Mountain.
Welcoming the LGBTQ+ community and allies for a Pride-filled ski weekend with all-day riding, food and drinks, live music, raffles, and special gatherings. Info HERE.

👩‍🌾 Hudson Valley, Explore the Bounty of Winter at Hudson Valley Farmers Markets + CSAs
These cozy seasonal pop-ups turn cold-weather weekends into lively celebrations of local food, makers and culture! Info HERE.

🗓️ Friday, Jan 23rd

🎵Earlton, 6pm – 9pm. Skeeter Creek Acoustic Duo at Gray Willow.
Modern country band Skeeter Creek returns with award-nominated roots and acoustic country-rock from Dave and Renee for a lively, free show with food and beverage purchase. Info HERE.

🀄️ Red Hook, 6pm – 8pm. Queer + Trans Game Night at the Corner Counter.
Monthly game nights with drinks, freshly baked scones, and a lively mix of strategy, laughter, and community fun. Info HERE.

👢 Milton, 6pm – 9pm. Country Night at Locust Grove Brewing Co.
Country Night at Locust Grove Brewing Company brings boots, boogie, and high-energy line dancing, plus a chance to win a $300 Boot Barn gift card with a $5 cover at the door. Info HERE.

🍿 Hudson, 7:30 pm. Oscar contender “Marty Supreme” at Time & Space Limited.
Marty Mauser, a young man with a dream no one respects, goes to hell and back in pursuit of greatness, facing outrageous obstacles, unlikely allies, and a wild journey that tests his courage, ambition, and heart. Info HERE.

🗓️ Saturday, Jan 24th

🎣 Woodstock, 8am – 1pm. Youth Ice Fishing Derby at Wittenberg Sportsmen’s Club Fish Shanty.
This is always a fun, welcoming introduction to ice fishing—perfect even if you’ve never fished before, with equipment and bait provided on a first-come basis, plus prizes, trophies, free hot cocoa, and plenty of winter fun. Info HERE.

🍄‍🟫 Woodstock, 10am – 1pm. Woodstock Farm Festival at Woodstock Community Center.
Bring friends and family to this beloved local farmers market for fresh produce, eggs, fish, cheese, mushrooms, baked goods + more. Info HERE.

🏯 Kingston, 11am – 1pm. Kintsugi Class at the ReStore.
This workshop will teach the essence of ancient Japanese pottery repair techniques while promoting sustainability and healing. Info HERE.

⛵️ Kingston Roundout, 1pm – 4pm. Clearwater Open Boats at Hudson River Maritime Museum.
Join Hudson River Sloop Clearwater for a free January Open Boat with live music, kids’ activities, restoration tours, and a potluck lunch—$5 suggested donation to support their work. info HERE.

🫘 Copake, 5pm – 7pm. Chili Cook-off at Copake Grange.
A winter favorite, the Chili Cook-Off invites cooks and tasters alike to sample, vote, and enjoy a spicy evening of community fun. Info HERE.

🪈Hudson, 6pm. Columbia & District Pipe Band at Return Brewing.
The sound of live pipes is coming to Hudson!! All are welcome with FREE admission. Info HERE.

🎼 Annandale-on-Hudson, 7pm – 9pm. Dvořák + the Music of Ukraine at Fisher Center.
Ukrainian musicians Tatiana Kalinichenko and violinist Dmytro Tkachenko join TŌN at the Fisher Center for a one-night-only concert featuring Dvořák’s lyrical Violin Concerto alongside powerful works by Ukrainian composers, including two U.S. premieres. Info HERE.

🩰 Tivoli, 7pm. Maeve Gilchrist: 12 Dances at Kaatsbaan.
Harp innovator Maeve Gilchrist presents a new multidisciplinary performance born from a year-long Kaatsbaan residency, weaving monthly solo-harp compositions with site-specific sound, poetry, and visuals into a meditative reflection on time, stillness, and the beauty of the everyday. Info HERE.

🗓️ Sunday, Jan 25th

🕺 Kingston, 11am. Ecstatic Dance with Keena Maya at Assembly.
Hudson Valley Ecstatic Rhythms presents a substance-free, phone-free morning of free-form movement + community, featuring a warm-up, a live DJ set by @keena.maya and a closing sound meditation to gently land the experience. Info HERE.

🔥 Red Hook, 12pm – 8pm. Wassail Celebration at Rose Hill Farm.
Inviting the community to craft crowns and noisemakers, join a lively hilltop procession, take part in a joyful winter ceremony blessing the trees—complete with food, music + a post-ceremony gathering in the taproom. Info HERE.

🧝‍♀️ New Paltz, 1pm – 4pm. Sculpting the Sacred: Cycle Wisdom & Creative Ritual at Circle Creative Collective.
This collaborative workshop with Sasha Botanica and Diana Wassef blends menstrual cycle wisdom with hands-on ritual, guiding participants to create clay goddess or yoni-inspired figures as symbols of creativity, intuition, and cyclical presence, while enjoying a nurturing space with snacks and herbal tea. Info HERE.

🦋 Catskill, 2pm – 4pm. Social Salon at Thomas Cole Center.
Enjoy libations, a creative maker activity, and winter-themed tours at this cozy Social Salon gathering, featuring stamped card crafting and sips from @leftbankciders. 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!