Woodstock Christmas Parties 2026

Prepare for the festive season at Binny's Algonquin's Holiday Tasting. This walk-around event invites guests to sample a global selection of wines, perfect for holiday gatherings and finding ideal gifts. Delicious charcuterie will be served to complement the tasting experience.

A Mommy and Me Hot Chocolate Party is a holiday social event. Attendees are encouraged to wear matching pajamas and will enjoy a hot cocoa bar, games, crafts, and a photo spot.

A 1920s Electro Christmas Swing Dance includes a 45-minute dance lesson, snacks, champagne, a professional photographer, and a photobooth. Flapper or gangster attire is encouraged.

Escape the cold and gather your loved ones for a unique, cozy experience in a heated igloo at Hidden Creek Estates. These festive, private igloos seat up to 8 guests and are beautifully decorated for the holidays. Enjoy dedicated service...

Join the Willows Academy community for their annual Holiday Prelude Benefit Dinner. This elegant evening features cocktails, a silent auction, a seated dinner, a paddle raise, live auction, and dancing. It's a wonderful opportunity to support the school while enjoying...

A breakfast buffet, holiday crafts, and a meeting with the Grinch are featured at 'Brunch with the Grinch.' Guests can take photos with the Grinch and receive a goody bag.

The Arcada's Speakeasy hosts a holiday celebration with dancing and a raffle. A plated lunch and entertainment by Edizon Dayao are provided. A cash bar is available.

A relaxed singles social mixer and Santa bar crawl for ages 30s-50s encourages festive Santa or Elf attire. The route includes Morgan's, O'tooles, and Mickey Finn's, with food and drinks for purchase.

Immediately following the Annual Woodstock Christmas Parade, families can head to the Historic Woodstock Square for a delightful 'Cookies and Churros with Santa' event. This festive gathering offers children a perfect opportunity to share their Christmas wishes with Santa, indulge...

Get ready for a naughty and nice holiday celebration at Backyard Bar's "Bad Santa" Party. This adult-themed event promises a unique twist on festive fun, offering a memorable night out with a playful and irreverent atmosphere. It's the perfect place...

Join the magic of the holiday season with a delightful Brunch with Santa at Grand Geneva Resort & Spa. This event is specially crafted for children, offering a memorable breakfast experience served right at your table. Guests are encouraged to...

Experience the festive spirit of Holly Days in Downtown Elgin, a month-long celebration designed to support local businesses. The event kicks off with the popular Holiday Cheers Beverage Crawl on Small Business Saturday, where you can sample over 20 unique...

All aboard for the Polar Express Pub Crawl in McHenry! Don your pajamas and join the festive fun, hopping between participating locations for special holiday drinks. A free trolley service makes navigating between stops easy, and all ticket holders are...

Join Santa Claus for a delightful breakfast or lunch event. Families can enjoy a festive meal, participate in holiday crafts, and create reindeer food. Each child will have a special one-on-one visit with Santa, offering a perfect opportunity for photos....

Celebrate Christmas Eve with exquisite dining experiences at Grand Geneva Resort & Spa. Choose between the festive Prime Rib and Seafood Buffet at Grand Café or gourmet meals at Geneva ChopHouse and Ristoranté Brissago. Enjoy a memorable holiday feast in...

Experience the magic of the holiday season with a special 'Breakfast with Santa' event at Lambs Farm. Guests can savor a delicious brunch, engage in festive crafts, and meet the jolly man himself. This cherished tradition offers a wonderful opportunity...