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two goats touching noses with the "Upstate Weekend Plans" text written across the Hudson Valley, NY photo.

What to Do in the Hudson Valley This Weekend Feb 21 – Feb 23

By inside + out | February 19, 2025

Got cabin fever? Come out + play! From Art with Goats, live music, Black Artivist showcase, Winter Wassail Fest to a Spring Celebration of Light… There’s something for everyone. Take your pick below…

💘 Marlboro, Fri Feb 21st, 11am – 4pm. Annual Valentine’s Day Wine & Cheese Pairing at Benmarl Winery.
Join Benmarl Winery for their Annual Valentine’s Day Wine & Cheese pairing every weekend in February, as they celebrate their love for local delights! Info HERE.

✊🏽 Kingston, Fri Feb 21st, 3pm – 6pm. “And Still We Rise” ARt Opening at Arts Society of Kingston.
AND STILL WE RISE draws inspiration from the indomitable spirit and perseverance of the Black community throughout history and into the present. Info HERE.

🧀 Hyde Park, Fri Feb 21st, 6pm – 7:30pm. Sake + Cheese Workshop at Dassai Blue Sake Brewery.
A cheese expert from @thecornercounter and a sake expert will take you on an interactive journey of pairing sake with cheese! Info HERE.

🎶 Woodstock, Fri Feb 21st, 7pm. Hayley Jane with Ginger Winn at Colony Woodstock.
Hayley blends 60s + 70s rock, pop, folk, blues + soul with theatrical flair, captivating audiences via electrifying performances, sharp wit + Vaudevillian storytelling. Singer-songwriter Ginger Winn will join her after just finishing a tour with the Gypsy Kings. She will preview new releases. Info HERE.

💃 Stone Ridge, Fri Feb 21st, 7pm – 9pm. Medicine Disco at the Kiva.
Medicine Disco is a structured dance ritual that blends mindfulness, movement + music. It’s 15% meditation, stretching + musculoskeletal activation, 85% guided dance with a live DJ and 0% forced vibes. Think of it as the best night out dancing—but this time, you’re actually prepared for it. Info HERE.

🪡 Red Hook, Sat Feb 22nd, 11am – 2pm. Stitch It Out at Red Hook Library.
Come stitch and twitch your heart out with the LGBTQIA+ community in a safe space. Bring your own project + supplies or use the guidance, yarn and equipment available—whatever you need to get creative! Info HERE.

❄️ Roxbury, Sat Feb 22nd, 11:30am – 6pm. Annual Snow Pope Love Run at Plattekill Mountain.
Celebrate the life and legacy of Penny Henry, our Snow Pope + guardian angel with dancing, drinks specials, a special ski run + more! Info HERE.

🎨 Kingston, Sat Feb 22nd, 3pm. Annual Black Artivist Experience + Vendor Fair.
Artists who use their art to uplift, motivate and inspire personal + social change will bring to light the diverse experiences of the black community expressed through song, poetry, dance, imagery, music, arts, crafts, clothing + more! Info HERE.

🐐 Napanoch, Sat Feb 22nd + Sun Feb 23rd. 4pm + 2pm. Art with Heart: Paint with Rescue Goats at Frederick Farm Goat Sanctuary.
A non-traditional art class in a laid-back atmosphere for anyone who wants to be creative + have a fun time. Plus, everything is better with GOATS! Info HERE.

⛷️ Stamford, Sat Feb 22nd, 4pm. Nordic Nights at OSMOS Station.
Arts & Rec hosts creative community events in the Catskills. This is a wintertime cross-country outing. Info HERE.

🪼Kingston, Sat Feb 22nd, 5pm – 8pm. Great Jell-O Jamboree at The Fuller Building.
Creating a one-of-a-kind celebration in support of interns, artists + students with a Jell-O sculpture competition, music, art, belly dancing, food, cocktails + more! Info HERE.

🍎 Walden, Sat Feb 22nd, 5pm – 9pm. Wassail Winter Fest.
The festival will include live music, outdoor games + competitions, a bonfire, chanting through the orchard with lit torches, the release of our Wassail Wooden Sleeper cider, a specialty food menu + more! Info HERE.

🏮 Beacon, Sat Feb 22nd, 5:30pm. Beacon Spring Celebration of Light: Year of the Snake!
Say goodbye to the Dragon and welcome the coming spring + Year of the Snake. Enjoy lantern displays, sip tea + savor delicious bites by the fire. Dress warmly + dance as the DJ fills the night with music. Let’s celebrate light, hope, and community together! Info HERE.

🥖 Woodstock, Sun Feb 23rd. 6pm – 8:30pm. BreakBread World Potluck + Conversation.
We invite you to join your fellow Woodstock area friends, family, and neighbors in active and inspired conversation around a prompt about “home” while breaking bread together. Info HERE.

🎸 Kingston, Sat Feb 22nd, 8pm – 11pm. Laszlo Lang at Night Swim.
Having grown up surrounded by music and festivals his whole life, Laszlo has channeled the inspiration into a one-man band playing heavy blues + hard rock. Info HERE.

🎹 Woodstock, Sat Feb 22nd, 8pm, Marco Benevento at Levon Helm Studios.
When it comes to creativity and bold experimentation, few can match the imagination and the recorded legacy laid down by keyboard wizard Marco Benevento. Read more HERE and come see the magic! Info HERE.

👨‍🌾 Explore the Bounty of Winter at Hudson Valley Farmers Markets.
Support small local farms that foster a sense of community + promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

Photo by Frederick Farm Goat Sanctuary

👉 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!

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