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

From art-filled escapes and live music to wine tastings, holiday markets + Friendsgiving fun, the Hudson Valley has something for everyone—just in time as the season to gather together arrives. Take your pick below…

🧑‍🎨 New Paltz, Fri Nov 21st – Sun Nov 23rd. Mohonk Maker’s Weekend at Mohonk Mountain House.
Experience the Mohonk Maker’s Weekend, where you’ll immerse yourself in the creativity of the Hudson Valley with activities including local art exhibitions, hands-on workshops, exclusive demonstrations, behind-the-scenes tours, and captivating performances, ensuring a weekend filled with artistic inspiration. Info HERE.

🍷 Roxbury, Fri Nov 21st, 4pm – 6pm. Thanksgiving Wine Tasting at Roxbury Bottle Shop.
Stop in to explore wines perfectly matched to turkey, trimmings and all the cozy flavors of Thanksgiving. Info HERE.

🔭 Ancram, Fri Nov 21st, 4:30pm. Mid-Hudson Astronomical Association Monthly Star Party.
Observe the beautiful night sky at their monthly stargazing party at Lake Taghkanic State Park. This month you’ll be able to see seven planets! Free advanced registration required. Info HERE.

🖼️ Woodstock, Fri Nov 21st, 6pm – 9pm. “Calicornucopia 14” at Calico Gallery.
Opening reception for the year-end group exhibition featuring eclectic and fun works from a wide range of artists working in various mediums. All works under $300. Located above Small Talk Bar. Info HERE.

🎶 Bearsville, Fri Nov 21st, 7pm. The Lemonheads: “Love Chant” Tour at Bearsville Theater.
Returning with Erin Rae—a melodically rich, emotionally raw album that blends Evan Dando’s signature songwriting with longtime collaborators + new voices with an alternative rock edge. Info HERE.

🎤 Hudson, Fri Nov 21st, 8pm – 11pm. Ginger Winn + Lost Leaders at Park Theater.
Byron Isaacs of The Lumineers + Peter Cole reunite Lost Leaders with Ginger Winn. All share a cinematic, roots-driven sound that blends poetic lyricism, atmospheric folk, and emotionally honest storytelling. Info HERE.

🦃 Germantown, Sat Nov 22nd, 10am – 2pm. Thanksgiving Market at Gulden Farm.
We have a great lineup of vendors — along with food by Misto, beer from Vosburgh Brewing Company, and live music by Will Proper. Info HERE.

🎄 Kingston, Sat Nov 22nd + Sun Nov 23rd, 10am –  4pm. Hudson Valley Hullabaloo Holiday Market.
An annual holiday-season fav bringing 75+ makers + vintage vendors, live DJ vibes, portrait stations, permanent jewelry and diverse local eats for a vibrant, family-friendly shopping experience supporting small businesses. Info HERE.

🛍️ New Paltz, Sat Nov 22nd, 11am – 5pm. Annual Holiday Market at Twin Star Orchards.
Featuring 50+ rotating local artisans—spanning food, drinks, jewelry + clothing—with 10+ new vendors each weekend. Info HERE.

🎁 Tannersville, Sat Nov 22nd, 12pm – 4pm. Deer Mountain Inn Holiday Market.
A cozy afternoon of local shopping, handmade goods, vintage finds, and festive vibes—plus lunch if you want to make a day of it. Info HERE.

🛍️ Claverack, Sat Nov 22nd, 1pm – 4pm. Mini Market at Klocke Estate.
Guests can enjoy mulled cider or vermouth spritzes while shopping with local vendors for holiday gifts and treats, browsing limited botanical wreaths, and savoring wood-fired pizza from Chef J.S. Millie. Info HERE.

🎨 New Paltz, Sat Nov 22nd, 2pm – 4pm. Opening Reception “Collaborative Figurative Drawing Exhibition at Elting Memorial Library.
Uncover the magic of collaborative art-making among multiple artists who devoted a year to a single shared drawing—and meet the Sevenfold Guild students behind the work. Glimpse into their collaborative craft + apprenticeship program. Free! Info HERE.

🖼️ Kingston, Sat Nov 22nd, 5pm – 8pm. Opening Reception “A Glimmer of Change” at 68 Prince Street Gallery.
Featuring works by three distinct artists—Julie Evans, Murray Hochman + Catherine Howe—whose bold materials, shifting colors + iridescent surfaces feel especially resonant as winter’s shorter days lead us toward the season of light. Info HERE.

🦃 Walden, Sat Nov 22nd, 5pm – 9pm. Friendsgiving at Angry Orchard.
A festive gathering filled with cider, live music, games + seasonal comfort bites, all designed to kick off the holiday spirit with your favorite people. Info HERE.

🥕Hudson, Sun Nov 23rd, 12pm – 5pm. Queer Community Harvest Feast at Golden Kin Studio.
Join Queer Outdoor Adventures and Golden Kin for a cozy, autumn potluck where we’ll share a family-style meal, play games, and connect in community. Limited seating. More info HERE.

🎸 Saugerties, Sun Nov 23rd, 7pm. New African Orleans Alune Wade at The Local.
Alune Wade and his powerhouse band trace the musical threads between West Africa and New Orleans, blending reimagined classics from Hancock, Hendrix, and Fela with originals shaped by Alune’s own NOLA-inspired perspective. Info HERE.

👩‍🌾 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.

Photo by Hudson Valley Hullabaloo Holiday Market.

👉 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!