What to Do in the Hudson Valley This Weekend Dec 5 – Dec 7

The HOLLIES are here! It’s happening, folks. Not to despair, the Hudson Valley is full of art, music, theater and hands-on experiences to take a break from the (shop….🤫shhh!). From festive markets + concerts to gallery openings + creative workshops, there’s something for everyone. Take a peek below…

🖼️ Wappingers Falls, Fri Dec 5th, 12pm – 6pm. First Fridays at CoSM.
Enjoy FREE ENTRY to CoSM + Entheon. Check out Alex Grey & Allyson Grey’s incredible artwork, and more. Info HERE.

🎄 Woodstock, Fri Dec 5th, 4pm – 8pm. 43rd Annual Holiday Open House at Village Green.
A festive evening of holiday shopping featuring local makers and artists, plus a performance by the @rockacademyofficial show band. Info HERE.

🤡 Phoenicia, Fri Dec 5th – Sun Dec 7th, 7pm + 2pm. “Fully Committed” at Phoenicia Playhouse.
A hilarious one-actor play with sharp wit and impeccable timing. Info HERE.

🎅 Woodstock, Fri Dec 5th + Sat Dec 6th, 7pm. “A Christmas Carol” at Queen of Rogues.
A special holiday treat: A Christmas Carol performed by Scott H. Severance, a master storyteller with 50 years of award-winning theater experience. After nine years touring as Scrooge in his own adaptation, he created this acclaimed one-man version that continues to captivate audiences. Info HERE.

🕯️Poughkeepsie, Fri Dec 5th, 8:30pm. Candlelight Concerts: Tribute to The Beatles at Living Water Church.
An intimate, multi-sensory concert in a warm candlelit glow, offering an immersive, atmospheric tribute to The Beatles. Info HERE.

🛍️ Tannersville, Sat Dec 6th, 9am – 3pm. Holiday Market at Fromer Market Gardens.
Enjoy local vendors, handmade gifts, hot cocoa, cookies, walking tacos, live music, and more as you shop + support your local community this holiday season. Info HERE.

🎄Arkville, Sat Dec 6th, 10am – 12pm. Wreath-Making Workshop at Catskill Forest Association.
Welcome winter with a hands-on wreath-making workshop. Create your own with fresh Catskill pine + fir, ribbons, and decorations provided. Dress warmly and bring gloves for handling needles and sap. Info HERE.

🎁 Amenia, Sat Dec 6th + Sun Dec 7th, 11am + 10am. Holiday Bazaar at Troutbeck.
Browse a mix of local shops, artisans, jewelry makers, boutiques and toys. Plus, kids’ activities + more! Info HERE.

🛍️ Beacon, Sat Dec 6th, 2pm – 6pm. Holiday Makers Market at Beacon Music Factory.
Live music, a holiday market with 11 local makers, a musical instrument petting zoo for kids, and fun craft activities throughout the afternoon. Info HERE.

🖼️ Kingston, Sat Dec 6th, 2:30pm – 4:30pm. Gallery Opening Reception Featuring Hudson Valley landscape artist Andrea M. Park, “Cloudy With a Chance of Memory” at ReStore.
Andrea’s oil and gouache paintings capture beloved Hudson Valley places—Olana, the Ashokan Rail Trail, Esopus Meadows + New Paltz. A portion of sales supports Ulster County Habitat for Humanity. Join us for an afternoon of art, refreshments and community. Info HERE.

🧑‍🎨 Woodstock, Sat Dec 6th, 3pm – 6pm. Opening Reception “Karen Whitman / Cityscape Linocuts” at Woodstock Artists Association and Museum.
Come enjoy a visit to a solo exhibition of Karen’s highly detailed and imaginative linocut cityscapes, which she prints from hand-carved blocks. Info HERE.

🎤 Chatham, Sat Dec 6th + Sun Dec 7th, 3pm. Bard Vocal Arts Program: “The Heart of A Woman” + “American Tapestry” at PS21.
Emerging singers push the boundaries of classical voice. One show explores womanhood + American experiences; the other celebrates the evolution of American vocal music. Info HERE.

❄️ Hudson, Sat Dec 6th, 5pm – 8pm. The 29th Annual Winter Walk Street Festival.
Kick off the holiday season at Hudson’s Winter Walk! Enjoy bands, dancers, choruses, circus performers, street food, horse-drawn carriage rides, holiday lights, fireworks, and festive shopping along Warren Street. Info HERE.

🎶 Kingston, Sat Dec 6th, 7pm. Holiday Sampler Performance at Holy Cross/Santa Cruz Episcopal Church.
A festive concert celebrating the 250th anniversary of the Declaration of Independence, blending colonial holiday music with sacred European Christmas traditions. Info HERE.

🎩 Washingtonville, Sat Dec 6th, 7pm – 11pm. A Dickens Mystery Dinner at Brotherhood Winery.
Experience a “whodunit… and why?” evening with a full buffet dinner + open wine tasting bar. Info HERE.

🪩 Newburgh, Sat Dec 6th, 8pm – late. HOLY HOUSE at The Ellis.
Get ready to dance the night away to a duo of high-energy DJs in a one-of-a-kind venue—a repurposed church with epic lighting, booming bass, and an unbeatable vibe! Info HERE.

🛍️ New Paltz, Sun Dec 7th, 12pm – 4pm. Winter Market at New Life Markets.
Shop vintage and Y2K clothing, browse jewelry, meet a real Santa, enjoy live music and free drinks, fill a bag with deals, explore budget-friendly piles, and snag fun giveaways. Info HERE.

🎄Hudson, Sun Dec 7th, 2pm – 4pm. Winter Social at Thomas Cole Museum.
Holiday shopping, tree + building lighting, winter tours, art making, @returnbrewing brews, @liquidfables cocktails and hot chocolate. Info HERE.

🌟 Big Indian, Sun Dec 7th, 5pm. “Festivus” at Peekamoose Restaurant + Tavern.
Three-course, Seinfeld-inspired family-style supper. Raffles, prizes, Seinfeld trivia + Elaine Dance Contest! Feats of strength and airing of grievances, of course. 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 Candlelight Concerts

👉 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!