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Beginning to Look a Lot Like Christmas



Sinterklaas in Rhinebeck and Rhinecliff

November 8-December 4
The Town of Rhinebeck celebrates its rich heritage in Old Dutch customs at Sinterklaas. The festivities begin on November 8 with the opening of the Giant Puppet Making workshop. November 27 is the Grumpus Dance followed by the arrival of Sinterklaas by boat at 4pm at the Rhinecliff dock. The procession goes to the center of Rhinecliff ending with a reception at the Rhinecliff Hotel. At the reception there will be a performance of a classic St. George and the Dragon play and music by the Rhinebeck Choral Club. But the main event is on December 4, from 10am to midnight. During the day there will be a Bear Beauty Contest, story telling, magic show, international dance performances, festival of light, and tree lighting. In the evening is the Children’s Starlight Parade and Pageant. Free.

Downtown Unwrapped in New Paltz

November 19, 5-8pm
Downtown New Paltz and Huguenot Street will be open late to start off the holiday shopping season. The evening begins with a traditional tree lighting ceremony being held on historic Huguenot Street. View fine art from local artists all weekend, as well as guided candlelight tours of the historic houses. The town will be decorated with window displays and there will be special discounts for shoppers.
(845) 255-1660;

Dutchess Community College Holiday Craft Fair
November 27-28, 10am-4pm
Get a head start on holiday shopping at the 39th annual craft fair at Dutchess Community College in Poughkeepsie. With more than 100 artists, the fair has become a highly anticipated event as it allows people to purchase unique gifts for friends and family. All items are handcrafted, including pottery, painting, quilting, woodworking, foods, floral, and jewelry. Proceeds benefits student scholarships. $6, $4 seniors, DCC faculty, staff, students, and alumni, free for children under 12.
(845) 431-8403,

A Frosty Fest in Ulster Park
November 27-December 27, weekends and select dates
Travel through Frosty’s Enchanted Forest in a hayride or your own car with friends and family to enjoy Christmas music, dazzling holiday lights, spectacular displays, and magical animation. Take a stroll through Candy Cane Lane for more holiday music, gift shops, and a variety of fun foods. Win prizes, visit Santa at his workshop in the North Pole, and more. $10, $8 children.
(845) 339-2666,

A Gilded Age Christmas at Mills Mansion
November 28-December 26
The Greek Revival structure will be decorated to reflect the holiday season in the 19th century. Tours of the elegant estate will be given every half hour. $5 adults, children under 12 free.
(845) 889-8851;

Poughkeepsie Celebration of Lights Parade and Fireworks
December 3, 6:30pm
The 17th annual City of Poughkeepsie Celebration of Lights illuminates the downtown streets at the start of the holiday season. Festivities include a parade led by Mayor John Tkazyik and members of the Common Council. Joining in the parade will be performances by Arm-of-the-Sea Theatre and IABAS Traditional Brazilian Band with 200 children from Warring, Clinton, and Circle of Courage elementary schools. Decorated trees, window displays, giant puppets, and classic cars adorn the streets on the parade route. At 7:15pm there will be a winter fireworks display on the waterfront. Santa will be arriving on a City of Poughkeepsie fire engine.
(845) 473-5288;

Holiday House Tours at Olana
December 3-January 2
Learn how Frederic Church’s family spent the holiday at home on an hour-long tour at their lavishly decorated home. Hear Frederic’s letter to Santa Claus and what other family and visitors wrote about the experience. $9, $8 students and seniors, free for children under 12 and Olana Partnership members.
(518) 828-0135;

Winter Celebration at Lindenwald
December 3, 5:30pm-8:30pm
The home of America’s eighth president, Martin Van Buren, will be specially adorned for the holiday season. Warm yourself with hot cider in the winterized tent and gather around the bonfire with friends in front of Lindenwald. Also take part in Kinderhook Village’s candlelight walk. Reservations required. Free.
(518) 758-6986;

Cold Spring by Candlelight
December 4, 12-6pm
Enjoy walking tours of historic homes and sites during the seventh annual holiday celebration in the Village of Cold Spring. There will be homes and sites featured on the National Historic Register, holiday caroling, discounts at local stores and restaurants, holiday music, visits with Old Saint Nick, and more. The event is a benefit for children and adults with developmental disabilities. $25 adults; $20 seniors; $12 children under 12.
(845) 278-PARCx287;

Catskill Mountain Winter Holiday Train
December 4-January 2, Saturdays and Sundays
Get into the holiday spirit with a decorated train ride from Phoenicia to Boiceville. Warm up next to the caboose’s wood stove, or enjoy the festive atmosphere of the open-air flatcar. Children will also have a chance to meet Santa Claus. Trains depart on the hour from 1-4pm. $6, $4 children ages 2-11, children under 2 ride free with paying adult.
(845) 688-7400;

Winter Walk in Hudson
December 4, 5-8pm
Experience an evening of winter celebrations from First to Eighth Street where shops and galleries will be offering entertainment and refreshments for visitors. Businesses exhibit their holiday window shows and invite festival-goers to start their holiday shopping. Musical performances include, carols, jazz, folk, street-corner musicians, African drumming, and more. A fireworks display will occur at 8pm.
(518) 822-1438;

Vanderbilt Mansion Holiday Open House

December 5, 11am-4:30pm
The Vanderbilt Mansion will be decorated for the holidays in honor of Frederick and Louise Vanderbilt’s generosity  in the Hyde Park community. Tours will focus on the Vanderbilt’s Christmas visits to their estate and their tradition of presenting each child in the town of Hyde Park with a gift. Music and refreshments will be provided by the Roosevelt Vanderbilt Historical Association. Free.
(845) 229-7770;

Yuletide Tea High Tea at Wilderstein in Rhinebeck

December 11, 1pm
Celebrate the holiday season in a high social afternoon affair with fine tea, finger sandwiches, homemade cakes, and cookies. (Wilderstein mansion tours are offered on select dates from November 26 through December 27 at 1-4pm). Admission $25, $10 per child. Reservations are necessary.
(845) 876-4818;

Winterfest in Historic Chatham Village

December 12, 11am-4pm
Chatham transforms into a winter wonderland for this holiday celebration. There will be window displays, carolers, horse drawn hayrides, and a visit from Santa Clause.
(518) 392-4710;

Newburgh Candlelight House Tour
December 12, 12pm-5pm
Enjoy a tour of private homes, beginning at the Captain David Crawford House, highlighting the best of Newburgh’s rich architectural history. The holiday celebration will feature 1830’s-style decorations. $20, $25 at the door.
(854) 561-2585;

The Catskill Mountain Winter Holiday Train.
  • The Catskill Mountain Winter Holiday Train.

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