16 Fun and Festive Events in the Hudson Valley This December

From caroling to Christmas scavenger hunts, there are so many holiday happenings in the Hudson Valley this December.

Snowflake Festival — Kingston

December 1, 6 p.m.

This annual event held by the Kingston Uptown Business Association returns to the historic Stockade District with holiday-themed entertainment. Full schedule of activities available online. kuba.network/snowflake

Photo by Doug Baz

Sinterklaas — Rhinebeck

December 2

Rhinebeck honors its Dutch roots with a celebration of customs from the Netherlands. Throughout the village, catch music, dance, and fire-juggling performances, children’s craft workshops, and a holiday parade and pageant to end the night. sinterklaashudsonvalley.com

Saint Nicholas Day — Rensselaer

December 2, 11 a.m.–3 p.m.

Head to the Crailo State Historic Site to participate in traditional Dutch holiday activities. The museum will have free live music, hearth-cellar baking, 17th- and 18th-century treats, crafts, self-guided tours, and even a visit from St. Nicholas. parks.ny.gov

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Allison Russell — Katonah

December 2, 8 p.m.

Join this Grammy-nominated Americana singer-songwriter for an intimate performance in the Rosen House’s Music Room. The concert will benefit Caramoor’s year-round programming and will feature a special dinner for an additional cost and a post-show reception for all. caramoor.org

Courtesy of Caramoor

Victorian Stroll — Troy

December 3, 11 a.m.–5 p.m.

The Gilded Age comes alive in Troy’s 41st annual Victorian Stroll. Downtown will be full of shops offering discounts, decorated windows, people in 19th-century dress, and live music. victorianstroll.com

Holiday Hunt in the Mansion — Poughkeepsie

December 3, 10, and 17, 12–4 p.m.

This family scavenger hunt inside the nearly 200-year-old Locust Grove Estate lets visitors look for toys and games that were enjoyed by one of the mansion’s past resident families. Items like ice skates, card games, and musical instruments will be hidden among 20 decorated Christmas trees in the house. lgny.org

Music Connects Us — Montgomery

December 3, 2 p.m.

Presented by Music for Humanity, City Winery Hudson Valley will host an afternoon of blues and soul music in the Falls Room. Performers include R&B musician Slam Allen and singer-songwriter Reggie Harris. citywinery.com

A Celebration of Local Poets — Sleepy Hollow

December 3, 4–5:30 p.m.

Toast the new prose from four local poets—Amy Holman, Silvina López Medin, Ruth Danon, and Tiffany Troy—with the program director at the Hudson Valley Writer Center. Ticket cost for the event is donation-based. writerscenter.org

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Holidelic — Tivoli

December 8–9 and 15–16, 8 p.m.

Grammy-nominated performer and percussionist Everett Bradley brings Holidelic, a holiday funk revue, to Kaatsbaan Cultural Park. In this program, Bradley plays “Papadelic,” a character that’s equal parts Santa Claus and icon George Clinton, and leads an ensemble of musicians playing funky Christmas tunes. kaatsbaan.org

Darlene Love: Love for the Holidays — Woodstock

December 9, 8–10 p.m.

Solo artist, former lead singer of The Blossoms, and Rock and Roll Hall of Famer Darlene Love takes the stage at the historic Bearsville Theater. Love will perform an array of holiday songs in this special concert, such as her hit “Christmas (Baby Please Come Home).” bearsvilletheater.com

Chatham WinterFest — Chatham

December 9

This free, all-day festival turns downtown Chatham into a winter wonderland. Event details and times available online. visitchathamny.com

Cirque Dreams Holidaze — West Point

December 10, 4 p.m.

Cirque Dreams features a line-up of circus artists for a show that blends talented acrobatics with whimsical storytelling. In Holidaze, singers, dancers, and artists dressed as penguins, toy soldiers, and reindeer present a thrilling program set to classic seasonal songs. ikehall.com

West Point
Photos courtesy of Eisenhower Hall Theatre at West Point

Festivus for the Rest of Us! With Chef Steve — Nyack

December 13, 6:30–9 p.m.

Head to RCC’s Hospitality and Culinary Arts Center for a holiday cooking lesson. Attendees will learn how to make classic dishes like herb-crusted lamb chops, baked camembert, and Maryland crab and shrimp cakes. Tickets are $75 per person. sunyrockland.edu

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Winter Around the World! — Hudson

December 16, 1–5 p.m.

Celebrate the winter solstice a few days early at Olana State Historic Site. Visit the site for free access to the house, an outdoor bonfire, live music from Heard World Jazz, and activities and games led by Olana’s educators. olana.org

The Many Moods of Christmas — Troy

December 17, 3 p.m.

Albany Pro Musica returns to the Troy Savings Bank Music Hall with their highly anticipated annual holiday concert. The choral group will perform traditional carols backed by an orchestra from the program “The Many Moods of Christmas” arranged by Robert Shaw and Robert Russell Bennett. troymusichall.org

New Year’s Eve Drag Brunch — Newburgh

December 31, 12 p.m.

Give 2023 a proper send off at Jet Set Tiki Bar’s New Year’s Eve drag brunch. The event will be hosted by Victoria Bohmore and feature special performances from Cookie Doe and Belle Pepper. Seating is limited; tickets can be reserved online. jetsettiki.com

Related: Here’s What to Do in the Hudson Valley This Week

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