Middleburg Is Hosting Its First Holiday Cookie Crawl

Less than 200 tickets are available for the inaugural event.

By Michele Kettner • Posted October 7, 2026 at 11:16 a.m.

Brent Hofacker/stock.adobe.com

If you’ve got a sweet tooth, then make plans to visit Middleburg this holiday season. The town that’s known for its holiday spirit is hosting a Middleburg Cookie Crawl on Friday, November 20, from noon to 7 p.m.

There are only 165 tickets available for purchase for the inaugural event. Tickets go on sale on Thursday, October 8, at 10 a.m.

Participants will start the day at the Castle Gallery to pick up a cookie tin, punch card, and map. Then cookie lovers can stop by all 18 participating shops to pick up a holiday treat.

Guests that visit all 18 shops can turn in their punch cards for a chance to win a $20 gift card from each of the participating shops — a total of $360. The winner also receives a parking pass for the Christmas in Middleburg parade on Saturday, December 5.

Tickets for the Middleburg Cookie Crawl are $50 per person. They include the keepsake tin designed by local artist Lydia Marie Elizabeth.

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Michele Kettner

Audience Engagement Editor

Michele Kettner joined Northern Virginia Magazine in 2020 after spending two semesters as an editorial intern at the magazine. The University of Maryland graduate is currently the audience engagement editor and covers everything from can’t-miss things to do and holiday events to new restaurant and store openings throughout Northern Virginia.