In the Hudson Valley, the holiday season is more than just twinkling lights and holiday shopping. As December arrives, a mix of events bring the region to life, from lively street festivals to intimate performances of classic productions. Whether you’re sipping seasonal drinks at the Arlington Holiday Festival, enjoying a cozy show like “Doctor Marigold” in Hudson, or exploring handmade gifts at the Stissing House Craft Feast, there’s no shortage of ways to embrace the season. So bundle up, gather your loved ones, and get ready to make lasting memories at these must-see events across the Valley.
Wintertide Kingston
November 30 in Kingston Historic Waterfront District
The Kingston Waterfront Business Association’s third annual Wintertide invites locals and visitors to explore the Rondout neighborhood transformed by holiday cheer. A myriad of businesses lining Broadway, Abeel Street, West Strand, and Rondout Landing will offer everything from upcycled ornament-making and festive craft sessions to live music, mulled wine, and seasonal shopping deals. Families can enjoy storytelling at the Hudson River Maritime Museum or visit Santa at Mariner’s Harbor. The day culminates with the tree lighting at T.R. Gallo Park, accompanied by performances from The Rock Academy. A neighborhood-wide celebration, Wintertide serves as a laid-back yet lively kickoff to the season.
Hung With Care: A Very Queer Holiday Burlesque Spectacular
November 30 at Rosendale Theater
Big Gay Hudson Valley’s 12th annual Hung With Care holiday burlesque spectacular tour takes over Rosendale Theater this Thanksgiving weekend, bringing a glittering celebration of cabaret, drag, circus, and burlesque to the stage. Hosted by Paige Turner, the show promises a festive blend of cheeky humor and boundary-pushing performances. With acts from Cheeky Lane, Teasy Roosevelt, Jon Joni, Jack Barrow, Go Go Gadget, Pup Dio, and Stage Hunk, the evening delivers a playful and provocative holiday spectacle, complete with sequins and tassels. For fans of audacious, queer-infused entertainment (who are 16 and up). 8pm.
Theater on the Road’s “A Christmas Carol”
December 1-22 across the Hudson Valley
Now in its 25th year, Theater on the Road’s annual family holiday show brings Charles Dickens’s “A Christmas Carol” to life. In a twist on the classic dinner-and-a-show concept, the audience is invited to feast with the Cratchit family, enjoying scenes from the classic story as they unfold around the table. Characters like Ebenezer Scrooge, his nephew Fred, and Tiny Tim make their appearances, along with the ghosts of Christmas Past, Present, and Yet to Come. Holiday carolers add a seasonal touch to the evening’s atmosphere, creating an immersive experience that celebrates the spirit of Christmas through food and story. Performances in Rhinebeck, New Windsor, Kingston, Broadalbin, Hopewell Junction, Milton, Kerhonkson, West Park, and Eldred.
Snowflake Festival
December 6 in Uptown Kingston
Uptown Kingston’s annual Snowflake Festival weaves together a series of festive events across the neighborhood. The evening kicks off with a tree lighting ceremony on North Front Street, where Santa makes a special appearance to help usher in the season. Meanwhile, on Wall Street, the YMCA Magic Circle School Singers, CCE Energy Dance Co., Uptown Low Down Swing Dancers, and Tippy Toes Mini Ballet fill with air with music and movement. As the night continued, visitors can enjoy a Snowflake Festival flash mob dance, meet fairytale princesses, and take a horse-drawn carriage ride along John Street. Aerialist performances and flame throwers add an exciting twist to the night. The festive spirit extends through every corner of Uptown Kingston, making it a celebration for all ages.
“The Wickhams: Christmas at Pemberley”
December 6-15 at Shadowland Stages in Ellenville
“The Wickhams: Christmas at Pemberley” invites audiences back to the beloved world of Jane Austen’s Pride and Prejudice, this time from the perspective of the downstairs staff at Pemberley during the holiday season. Following the success of “Miss Bennet: Christmas at Pemberley,” this charming sequel adds a festive twist as Mr. Wickham—ever the dashing troublemaker and former nemesis of Mr. Darcy—makes a special appearance, stirring up holiday chaos. With a cast of loveable characters, including Mrs. Reynolds, the loyal housekeeper, and the spirited new servant Cassie, the play weaves a heartwarming story of family, class, and forgiveness, all wrapped in holiday cheer and classic Austen wit.
Winter Walk on Warren Street
December 7 on Warren Street in Hudson
Hudson’s 28th Winter Walk, presented by The Foundry at Hudson, returns with its signature blend of holiday magic and community spirit. The free event transforms the mile-long Warren Street into a festive wonderland complete with live music, holiday performances, and plenty of opportunities for seasonal shopping. Window displays compete for attention, while delicious treats fill the air with irresistible aromas. The highlight of the evening is a stunning fireworks display, presented by Hudson Hall. 5 to 8pm.
Arlington Holiday Festival and Eggnog Crawl
December 7 at The Garden Arts Space in Arlington
The Arlington Holiday Festival offers a day of festive activities in the heart of the village. The eggnog crawl lets visitors sample seasonal drinks from local businesses, while a fire pit provides a cozy spot for roasting marshmallows. As evening arrives, the community gathers for a tree lighting ceremony and a lively holiday parade. Local vendors will line the streets, offering holiday treats and gifts, creating a vibrant atmosphere that captures the spirit of the season. $5. 12-5pm.
“The Nutcracker”
December 7 at the Culinary Institute of America
The Hudson River Performing Arts Center and Hudson River Youth Ballet present two performances of “The Nutcracker” at the Marriott Pavilion at the Culinary Institute of America. Set in the breathtaking venue, this holiday classic follows Clara and her Nutcrackers as they battle the Rat Queen and embark on a magical journey to the Land of the Sweets.
“Spirit of the Holidays” Winter Walk in Tannersville
December 9 on Main Street in Tannersville
The holiday festivities in Tannersville begin on December 8 with the Winter Walk Kick-Off at 7pm at Mountain Top Library, where the Greene Room Players present “Songbirds.” Then, on December 9, the town’s “Celebrate the Spirit of the Holidays!” event takes over Main Street from 4 to 7pm, offering festive shopping, holiday activities, and family fun. Enjoy a performance of “The Nutcracker” at the Orpheum Theater at 2pm and again at 7:30pm. Between shows, join the crows for the tree lighting at 5pm, carolers, and a fireworks display at 6:45pm.
“Doctor Marigold” by Charles Dickens
December 13 at Park Theater in Hudson
“Doctor Marigold” brings Charles Dickens’s final Christmas number to the stage. Written in 1865, the story follows a cheap jack—a traveling vendor selling household wares from his cart—who, over time, learns that the people he meets along his journey have given him more than he could have imagined. The solo performance, starring John McManus, immerses audiences in the language and vivid characters of Dickensian England, where even the most flawed and struggling individuals reveal unexpected depths. With its themes of redemption and human connection, “Doctor Marigold” remains a poignant reflection on the value of simple acts of kindness. 7-10pm. $25.
Merry & Bright Holiday Concert
December 14 at Mount St. Mary College in Newburgh
The Greater Newburgh Symphony Orchestra’s Merry & Bright Holiday Concert offers a mix of seasonal music. Concert Master Adrienne Harmon will perform a special arrangement for violin and orchestra, while Principal Cello Naomi Lisowski will showcase her talent in a solo piece. The concert also features a variety of vocal performances, with the evening culminating in the traditional audience sing-along. From 4 to 6pm at Aquinas Hall, this concert blends beloved holiday classics with new arrangements, making it a highlight of the season. $10-80.
Stissing House Craft Feast
December 14 and 15 at Stissing House in Pine Plains
This holiday season, the Clare de Boer’s celebrated Stissing House restaurant will transform into a winter wonderland of handcrafted treasures. For two days—Saturday, December 14 from 12 to 6pm and Sunday, December 15 from 10 to 4pm—the air will hum with the sound of conversation, the clink of ceramics, and the earthy scent of leather and pine. Tables will be piled with exquisite textiles, handwoven baskets, knives, jewelry, and furniture, each piece telling a story. Vintage finds will mingle with new creations, as makers and collectors gather in this cozy, festive space.
A John Waters Christmas
December 16 at Old Dutch Church in Kingston
This holiday season, Big Gay Hudson Valley presents an evening with the one and only John Waters for a riotous, no-holds-barred Christmas celebration. Waters delivers two hours of irreverent humor, unapologetic holiday jeering, and his signature brand of subversive cheer. Forget the sugar and spice—this is a Christmas celebration for the bad little nonbinary boys and girls, with Waters at the helm as St. Nick the Dick. Expect bawdy humor, filthy gifts, and a chaotic good time with drag queens, holiday beatings, and a merry dose of subversion. 8pm. $45 to $85.
Unitard in “Holiday on Thin Ice”
December 20 at Unicorn Bar in Kingston
Get ready for a hilarious holiday romp when New York City’s outrageous comedy trio, Unitard, takes the stage for a twisted celebration that blends sharp wit with social, political, and sexual satire. Expect a night of riotous sketches, clever monologues, and irreverent humor from Unitard members Mike Albo, Nora Burns, and David Ilku. Special guest Gloria Gross-Glorius (aka Lex Powell) makes a rare comeback, promising a dazzling performance. Presented by Beth Lisick and Jodi Lennon, the duo who brought laughs to Saugerties with the More Than a Feeling Comedy Fest earlier this year. Doors at 7pm. Show at 8. $25 advance.
Operation Unite NY’s Kwanzaa Celebration
December 21 at Hudson Hall
Operation Unite New York hosts a Kwanzaa celebration centered on unity and African-American culture. Open to all and free of charge, the event offers an afternoon filled with arts and crafts for children, drumming, dancing, and a candle-lighting ceremony. The event will also share the Nguzo Saba, the seven principles of Kwanzaa, starting with Umoja (unity), which emphasizes the importance of unity in family, community, and nation. The day’s festivities include a performance at 4pm and a community dinner at 5:30pm.
“A Bearsville Christmas”
December 21 at the Bearsville Theater
The stage at Bearsville Theater will come alive with the spirit of the season on December 21, as “A Bearsville Christmas” delivers a night of laughter, music, and holiday magic. Featuring Chris Maxwell, Amb Parsley, and the Upstate Players, the show is part concert, part comedy, and part theatrical delight. A cozy winter evening filled with original holiday tunes from the album “A Catskill Christmas,” and special appearances from a mix of local talent and world-class musicians. With guests like AC Newman, Kip Malone, Marco Benevento, Mimi Goese, Cindy Cashdollar, and Jon Spencer, the evening promises surprise, heartfelt moments, and plenty of merriment. Doors at 7pm. $43.65 to $53.15.
“A Celtic Christmas”
December 21 at the Bardavon in Poughkeepsie
Direct from its off-Broadway run, Irish music and dance sensation A Taste of Ireland presents its holiday spectacular, “A Celtic Christmas.” Featuring former World Irish Dance champions and stars from “Lord of the Dance” and “Riverdance,” this high-energy performance transports audiences to a traditional Celtic Christmas. The show weaves together lively jigs, heartfelt ballads, and acapella tap battles, all while celebrating the warmth of the season. With a mix of folk music, electrifying rhythms, and beloved carols, “A Celtic Christmas” promises an evening of joy and wonder—filled with Irish wit and world-class talent. 7:30pm. $41 to $71.
