2026 Editor’s Picks: What to Do in the Hudson Valley on Feb 20 – Feb 22

February in the Hudson Valley is all about love, culture + community. Honor Black History Month at the Sojourner Truth Life Walk or African Drums + Dance, Flamenco + Winter Festivals, Lunar New Year Celebration + more! Something for everyone. Hot Picks below…

🗓️ Whole Weekend

❄️ Chatham, Fri Feb 20 – Sun Feb 22. The Dark: PS21’s Winter Festival.
Experience the fearless winter festival spreading across Columbia County! Over seven days, more than 60 international artists will perform 80+ shows—from theatre, dance, and music to installations in theatres, restaurants, libraries, saunas, and outdoor spaces. Explore winter as a time of community, solitude, fire, ice, darkness and light. Info HERE.

👩‍🌾 Hudson Valley, All weekend long! 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, Feb 20

🪐 Ancram, 4:30 – 9pm. Astronomy Star Gazing Party at Lake Taghkanic State Park.
Look up! Join a stargazing night hosted by the Mid-Hudson Astronomical Association—bring your own telescope or binoculars, or use ones provided. RSVP required. Info HERE.

🎙️ Saugerties, 8pm. Elisapie at The Local.
A Canadian Inuk singer-songwriter from Salluit, Nunavik, whose music blends modern indie-folk with Inuktitut language and Inuit cultural storytelling. Info HERE.

⛸️ Roscoe, 4pm – 8pm. Open Ice Skating + Après at Roscoe Mountain Club.
Glide under the glow of disco lights as music sets the mood—then warm up with drinks, bites, and cozy vibes at the après.⁠ Info HERE.

🗓️ Saturday, Feb 21

🥕 Newburgh, 10am – 2pm. Newburgh Farmers Market at the Ritz.
Shop fresh, seasonal goods from local produce + pantry staples to handmade goods and Hudson Valley specialties; every purchase supports small farms, family businesses, and independent artists. Buy local, give back, and meet the people growing your food while celebrating the craftsmanship that keeps our community thriving. Info HERE.

📜 Kingston, 11am – 5pm. 7th Annual Sojourner Truth Life Walk at Dietz Stadium.
My Kingston Kids presents a guided walk celebrating Sojourner Truth, bringing her legacy to life through storytelling, reflection, and shared history for all ages. Info HERE.

🌱 Rhinecliff, 3pm – 5pm. 9th Annual Seed Social at Morton Memorial Library.
A free community gathering with Dirty Gaia + the Morton Seed Library offering free seeds, winter sowing and connection with local seed-keepers. Plus, kids’ art-making in the Makerspace. Info HERE.

❄️ Prattsville, 4:30pm – 7pm. Sledding Social at Bearpen Mountain.
Hit the slopes for an adults-only sledding happy hour—race down the hill, then stick around for live music, drinks, and Winter Olympics festivities! Info HERE.

🧧 Beacon, 5:30pm – 8pm. Beacon Spring Celebration of Light at The Yard.
Parade through Beacon with your crew + homemade lanterns for a lively procession of light + music, then gather by the fire for tea, treats, dancing and a joyful sendoff to last year’s lantern as you welcome the Year of the Horse together. Info HERE.

🍷 Wallkill, 6pm – 11pm. Carnevale Night at Magnanini Winery.
Carnevale night is a full-on celebration of food, wine, music + dancing with the people you love. Expect a lively family-style feast, complimentary wine tasting, high-energy music by Carozza Entertainment, and a best costume contest that brings all the drama and flair. Come ready to indulge, dress up, and dance like nobody’s watching. Info HERE.

💃 Gardiner, 7pm. Tablao ~ A Peña Project at Full Circle.
Hudson Valley Flamenco Festival presents a dance + music festival that explores how flamenco can serve as a healing + unifying force within the community. Info HERE.

🤣 Montgomery, 7:30pm. Wisecrack Live Comedy at City Winery Hudson Valley.
Wisecrack is a one-of-a-kind live show blending comedy and true crime, as Hedges turns the scariest night of his life into a darkly funny stand-up set—joined on stage by podcast producer Jodi Tovay to unpack the chilling case that inspired their award-winning podcast. Info HERE.

🍿 Rosendale, 8pm. Queer Box Office presents “Moonlight” at Rosendale Theater.
The Academy Award–winning film is a lyrical coming-of-age drama following Chiron through three defining stages of his life as he navigates identity, masculinity, and love in Miami; experience this powerful story the way it’s meant to be seen: together, in community. Info HERE.

🗓️ Sunday, Feb 22

🌿 Catskill, 10am – 4pm. Basket Weaving Workshop at Kaaterskill Market.
Join artisan Renee Baumann for a full-day, hands-on workshop crafting a cattail and willow hen basket—perfect for beginners and experienced weavers alike. Inf HERE.

🪘 Beacon, 2pm. Sights and Sounds of Africa at Howland Cultural Center.
Sights and Sounds of Africa: A free youth workshop with international master drummer Kofi Donkor, introducing African drumming, culture, and communication through hands-on rhythm and movement. Info HERE.

🍿 Kingston, 3pm. Community Movie Night: Pixar ⓒ “SOUL” at UPAC.
On the brink of achieving his dream, a sudden accident sends a musician to a surreal realm where souls gain their personalities before life on Earth—forcing him to rethink ambition, purpose, and what truly makes life worth living. Free tickets available at the door! Info HERE.

Photo by NYS Parks & Historical Sites

👉 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!