Historic Hudson Valley Holiday Events and Happenings

Historic Hudson Valley Holiday Events and Happenings

The holiday season is quickly approaching. From upcoming holiday markets to Christmas tree lights and Hanukkah events, this season is sure to be busy but also really fun! The Historic Hudson Valley, Westchester County’s largest cultural organization, recently announced a huge roster of events to celebrate the season! Read on to check out the complete guide to all of the Historic Hudson Valley holiday events in Sleepy Hollow and Tarrytown.

Psst…looking for more holiday fun? Check out our list where you and your family can see The Nutcracker In and Around Westchester.

Historic Hudson Valley holiday
Photo by Tom Nycz

December 2-3, 9-10, 16-17 at 2:30pm, 3:45pm, and 5:00pm
Dickens’s Christmas Carol

Enjoy a performance of the Christmas Carol at the Old Dutch Church in Sleepy Hollow. Performed only by Jonathan Kruk, along with musical accompaniment by Jim Keyes, families will love watching the story Ebenezer Scrooge unfold.

Additionally, Jonathan performs roles of the ghosts of Christmas Past, Present, and Future, and Tiny Tim. Ticket prices are $47 for adults and $42 for children under 18. Ages 10 and up. Philipsburg Manor, 381 N Broadway, Sleepy Hollow, NY.

December 16th
Victorian Christmas Celebration

Get transported to the past in this self-paced festive tour of the Washington Irving’s Sunnyside. Enjoy holiday decor, hot chocolate, and seasonal treats. Plus, enjoy making holiday paper crafts and other special pop-up events. This includes a Make Your Own Pomander class on December 9th, and a Holiday Tea Party on December 16th. Tickets are $35-$85 per person. 3 W Sunnyside Ln, Irvington, NY 10533

Saturdays and Sundays until December 17 from 10:00am-6:00pm
The Holiday Boutique at the Philipsburg Manor Museum Shop

Find a unique gift for your loved one at the Holiday Boutique at the Philipsburg Manor Museum Shop. Discover local foods such as Hudson Valley-inspired and holiday-themed merchandise. Additionally, this includes artisan foods, books, candles, and handcrafted jewelry. 381 N. Broadway, Sleepy Hollow, NY.

The special events schedule is as follows:

Saturday, December 2, 1-2pm: Hot Cocoa and Cider Bar: Enjoy these classic winter drinks, along with all the mix-ins! $5 per person.

Saturday, December 9, 1-3pm: Make Your Own Pomander: Families will learn how to craft this traditional holiday decoration. $10 per person.

Historic Hudson Valley holiday
Winter Tours of Philipsburg Manor

Weekends, December 2nd-December 17th
Winter Tours of Philipsburg Manor

In 1750, Philipsburg Manor was home to 23 enslaved individuals known to have lived and labored there. Interestingly, this is the country’s first living history museum focused on slavery in the North.  Tickets are $15 for adults, $12 for seniors and young adults, and $10 for children. Tours are free for Historic Hudson Valley Members. Additionally, admission is timed. Philipsburg Manor, 381 North Broadway (Route 9) in Sleepy Hollow, NY.

Weekends, December 2nd-December 17th
Winter Tours of Union Church of Pocantico Hills

View the stunning stained-glasses windows by European masters Henri Matisse and Marc Chagall. Tickets are $10 per person. Union Church of Pocantico Hills is at 555 Bedford Road, Tarrytown, NY.

Victorian Christmas Celebration
Guests enjoy candlelight tours of Washington Irving’s Sunnyside in Irvington, NY on December 3, 2022.

Weekends, December 2nd-December 17th
Winter Tours of Washington Irving’s Sunnyside

Learn more about Washington Irving in his picturesque estate. Plus, the house and the furnishings, many of which are original to Irving, have been restored to their 1850s character. Tickets are $15 for adults, $12 for seniors and young adults, and $10 for children. Admission is by timed ticket only. 3 W Sunnyside Lane, Irvington, NY

Special Holiday Events

Families can also enjoy a range of special events happening throughout the month. This includes the following:

Saturday, December 2, 1-2pm: S’mores Bar: Families will have a sweet time making their own s’mores! $5 per person.

Saturday, December 2, 5-8pm: Hot Cocoa Under the Stars: Warm up during your holiday shopping at this one-night-only extended-hours shopping event! $5 per person.

Saturday, December 9, 12-3pm: Holiday Tea Party: Get in the holiday spirit as you sip Harney & Son’s Holiday Tea. Plus, enjoy sweet treats in their greenhouse. $20 per person

Saturday, December 16, 12-3pm: Cake Pop Decorating: Families can participate in this hands-on class with local baker, Patty Pops. Plus, learn how to make three different festive designs. $35 per person.