What to Do in the Hudson Valley This Weekend Nov 27 – Nov 30

Whether you’re kicking back with some turkeys eating “tofurky” or going full classic with all the fixins, we wish you a HAPPY THANKSGIVING with your friends, family and/or neighbors. From community dinners + Turkey Trots to local shopping spots, there’s always something happening across the Hudson Valley for everyone. Take your pick below…

THURS NOV 27th THANKSGIVING DAY EVENTS:

🏃‍♀️ Woodstock, 9am – 1pm. FAMILY of Woodstock Turkey Trot. Info HERE.

🏃‍♂️ New Paltz, 9am – 1pm. FAMILY of New Paltz Turkey Trot. Info HERE.

🏃 Windham, 9am – 11am. 3rd Annual Turkey Trot at Wylder Windham. Info HERE.

💜 Kingston, 10am – 1pm. 6th Annual Spread the Love Thanksgiving Event at Kingston Pop-Up Shop and Cafe. Info HERE.

🦃 Highland, 12:30pm – 3pm. Free Community Thanksgiving Luncheon at St Augustine Roman Catholic Church. Info HERE.

THE WEEKEND:

🛍️ Hudson, Fri Nov 28th – 30th. 10am – 5pm. Farm + Flea Holiday Market at Basilica Hudson.
A market with local, organic, sustainably made products from community-minded businesses as a meaningful alternative to Black Friday consumerism Info HERE.

🎁 Hudson, Fri Nov 28th – Sun Nov 30th, 11am – 5pm. Holiday Market at the Cannonball Factory.
Returning for another season, this cozy holiday pop-up offers four festive weekends with 75 new vendors and all the artisan eats, vintage finds, handcrafted goods, local sips, art, and home goods you need to spark your Hudson holiday magic. Info HERE.

🛍️ Milford (PA), Fri Nov 28th – Sun Nov 30th, 11am – 4pm/6pm. Living Upriver Holiday Market at Forest Hall.
A 3-day event bringing together local designers, makers + fine crafts from the Upper Delaware + Catskills region, transforming Milford’s historic Forest Hall into a festive showcase of handcrafted goods + community spirit. Info HERE.

💿 Tilson, Fri Nov 28th, 4pm – late. Freakout Spot Record Shop POP-UP at Daling’s Roadhouse.
For one night only—vinyl dig with DJs spinning + 10% of bar sales supporting their “paused” Accord shop—so come show some love + kick off the season right. Info HERE.

🎸 Woodstock, Fri Nov 28th, 7pm – 10pm. La Pucelle + Adventure at Colony Woodstock.
A globetrotting East Village rock quartet delivering pure Rock ’n’ Roll energy with a cinematic, unmistakably original sound. Info HERE.

🪇 Kingston, Fri Nov 28th, 7:30pm – 9:30pm. Pulso de Barro at Tilda’s Kitchen & Market.
Pulso de Barro unites community through inclusive music, dance, and traditional verse rooted in Jarocha and Latin American traditions, celebrating shared lineage and diverse identities. Info HERE.

🎤 Marlboro, Fri Nov 28th, 7:30pm. The Soul Experience with Corey Glover at The Falcon.
Best known as the electrifying frontman of the Grammy-winning Living Colour, Corey Glover returns to his roots with a sound that shaped his journey as an artist. Info HERE.

🛠️ West Park, Sat Nov 29th, 10am – 2pm. Esopus Repair Cafe.
Bring a beloved item to Ascension Church and let a volunteer repair it for free while you relax, mingle, and chat with your neighbors. Info HERE.

🎄Pine Plains, Sat Nov 29th, 10am – 4pm. 2nd Annual Christmas Market at Pine Plains Library.
A cozy community holiday market with 20+ vendors for what promises to be a fun day of shopping local and merriment. Info HERE.

🛍️ Kingston, Sat Nov 29th, 11am – 4pm. 6th Annual Artisans Handmade Holiday Market at Old Dutch Church.
Shop local handmade gifts, enjoy warm food and drinks, and soak in holiday music and spirit—the perfect way to kick off the season with creativity, community, and cheer. Info HERE.

🎁 New Paltz, Sat Nov 29th, 11am – 5pm. Annual Holiday Market at Twin Star Orchards.
Featuring 50+ rotating local artisans—spanning food, drinks, jewelry and clothing—with 10+ new vendors each weekend. Info HERE.

❄️ Kingston, Sat Nov 29th, 11am – 6pm. WINTERTIDE at Kingston Waterfront.
Featuring free nature-ornament making at Chicory and a roving performance by the Pop-Up Carolers. Full schedule + participating businesses Info HERE.

🖼️ Newburgh, Sat Nov 29th, 12pm – 5pm. Art + Music in Conversation at Bank Art Gallery.
A day of musical and sound performances features six collaborating musicians, composers, and wellness practitioners activating Elizabeth Arnold’s “Madre Selva” and the larger exhibit “The Shape of Memory” with meditative, multidimensional dialogues between art and sound, with performances flowing in continuous alternation from open to close. Info HERE.

🎶 Stone Ridge, Sat Nov 29th. 7pm – 10pm. Marc Black Band at Lydia’s Cafe.
Supper club with a delicious dinner + a live show including: Marc Black, Michael Esposito, Ralph Legnini and Eric Parker. Info HERE.

🛍️ Poughkeepsie, Sun Nov 30th, 9am – 4pm. Holiday Fair at Hudson Valley Pickleball + Golf Center.
Toys, crafts, clothing, jewelry, gifts, and more from 65+ amazing local artists and vendors—plus festive photos with Santa and caroling. Info HERE.

🥂 Chatham, Sun Nov 30th, 11am – 5pm. Holiday Social at Marton & Davis.
An all-day holiday celebration with custom calligraphy, festive greenery, alchemical goods, and a shop filled with the season’s best décor, treats, and gifts. Info HERE.

🛷 Kingston, Sun Nov 30th, 7:00pm. The Jinkx & DeLa Holiday Show at UPAC.
The internationally acclaimed “Jinkx & DeLa Holiday Show” returns with award-winning comedy icons BenDeLaCreme & Jinkx Monsoon delivering a wild, unpredictable wintertide adventure full of holiday chaos, comedy, and unexpected sleigh-ride surprises. 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.

👉 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!