Holly Berry Trail

Join the Junior League of Kingston on their annual holiday home tour of six local homes decked out in their finest holiday splendor! Raffles and prizes available! Advance ticket purchase required. Trail-goers will claim their wristbands and trail map on December 9th at Halter Associates Realty (89 N Front Street, Kingston) starting at 10am.

$40
Event Series Holiday Market Fair

Holiday Market Fair

Historical Society of Woodstock - Eames House 20 Comeau Drive, Woodstock, NY

The Historical Society of Woodstock presents an annual holiday market for your shopping pleasure with local crafts & books, holiday cards, original artwork, wreaths, treats and a whole lot more!

Event Series Barnwood 2023 Art Show

Barnwood 2023 Art Show

Camp Kingston 36 St. James Street, Kingston, NY

Pop-up queer art show + sale, opening party, and after dark reception. Browse 200+ original works from more than 30 queer domestic + international artists and creators. Find schedule on event website linked below! This show was rescheduled from October 2023.

Free – $20
Event Series Artists & Makers Holiday Market

Artists & Makers Holiday Market

ArtPort Kingston 108 East Strand Street, Kingston, NY

Two floors of handmade items for a day of holiday shopping, food, stories, craft, holiday music, hot cocoa, and more! Visit event link below for details and a list of participating artisans.

Free entry, donations greatly appreciated

Holiday Fineries at the Wineries – Shawangunk Wine Trail

Shawangunk Wine Trail NY

Bust out your fun seasonal attire or ugly sweater (not required, but encouraged) and get a jump on your holiday wine shopping. Choose your date, itinerary, and starting winery, then head out on a self-guided wine tasting tour! Ticket includes a wine tasting glass, tasting flight at four wineries, and ornaments from each winery.

$35
Event Series Winter Market

Winter Market

Twin Star Orchards 155 N Ohioville Rd, New Paltz, United States

Shop local artisanal ciders and wines every Saturday and Sunday at the Twin Star Orchard farm market.

Holiday Hoopla – Historic Huguenot Street

Historic Huguenot Street 81 Huguenot St., New Paltz

The 4th Annual Holiday Hoopla Celebration kicks off with a parade of floats, jugglers, the Candy Cane Crew, and other surprises, followed by a Winter Carnival and tree lighting all geared to spread Holiday cheer!

The Polar Express – Catskill Mountain Railroad

Catskill Mountain Railroad 55 Kingston Plaza Road, Kingston, NY

Relive the classic story aboard THE POLAR EXPRESS™ for a magical trip to the North Pole where Santa and his Elves board the train to greet guests. Hot chocolate and a delicious cookie served by dancing chefs on your trip. Caroling and on-board entertainment. Train ride lasts approximately one hour. Reserve your timeslot in advance! […]

$34 – $53
Event Series Vanaver Caravan Presents: Into The Light

Vanaver Caravan Presents: Into The Light

Rosendale Theatre 408 Main Street, Rosendale

The family friendly pageant uplifts spirits and deepens appreciation for cultural traditions. With giant puppets and holiday songs, dances, and music traditions the performance celebrates many of the world’s traditions for bringing light, joy and beauty into the darkest part of the year. Through dance and music Into the Light honors such holidays as Christmas, Chanukah, […]

$18
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