A Trail Town Christmas

December in Damascus

Trail Town USA is the place to be for the holidays! Find holiday events and specials all December long. Celebrate the holidays and see Santa at the Christmas parade, which is always on the first Friday in December. Stop by local businesses for handpicked holiday gifts. Tour the holiday lights around town. Go for a winter hike, and more!

November 2026

November/December – Choose-and-cut your own Christmas tree! Did you know? Fraser firs, also known as “the Cadillac of Christmas trees,” are native to only a small region of Virginia, North Carolina, and Tennessee. They grow best at elevations above 4,500 feet. Go to a local choose-and-cut farm around Whitetop or find a pre-cut tree near town, you can pick your very own Christmas tree to take home.

November 28 – Small Business Saturday. Shop small and support local this holiday season! Walk around downtown and shop for outdoor gear, handcrafted goods, small batch pet treats, and more. And remember – gift cards make great gifts, and for the one who already has it all, we highly recommend gifting an experience. Damascus has your holiday shopping covered!

November 28 – Dashing through Damascus: A Christmas Market at the Damascus Old Mill Inn from 12 to 6pm. Sip, shop, and snap a picture with Santa. Enjoy handmade gifts, vintage finds, art, homemade treats, and more along with live music. Come soak up the Christmas spirit. More info.

Stay tuned, more events coming soon! Email info@damascus.org to add an event to the calendar.

December 2026

December 1 to 31 – Holiday Lights Tour throughout Damascus. Walk, bike or drive to tour the lights!
To enter the Holiday Lights Decorating Contest, have decorations ready on the first Wednesday of December at 7pm. Winners will be announced before the Christmas Parade. Anyone within town limits is eligible to win (no entry form required). Prizes for winners of each category: Best in Show, Best in Show: Business, and Most Lights.

December 4 – A Trail Town Christmas Parade at 7pm in downtown Damascus, featuring a Parade Float Contest and the Damascus Loves Dogs Holiday Costume Contest. The parade will be led by the Clydesdales of Bart Long & Associates Realty and Auction, LLC. Santa will be at the Fire Hall after the parade.

December 5 – Trail Town Fitness is hosting a Dashing Thru Damascus Half Marathon, 5K, and Polar Plunge / Sauna on the Virginia Creeper Trail to kick off the holiday shopping weekend! Festive costumes and outfits are not required, but holiday spirit is always strongly encouraged. The half marathon starts at 8am and 5K starts at 9:30am, with polar plunge and sauna to follow at 11am. More info and register now.

December 5 – Dashing through Damascus: A Christmas Market at the Damascus Old Mill Inn from 12 to 6pm. Sip, shop, and snap a picture with Santa. Enjoy handmade gifts, vintage finds, art, homemade treats, and more along with live music. Come soak up the Christmas spirit. More info.

January 1 – First Day Hike at Virginia State Parks. Find a ranger led hike or choose your own adventure at nearby Grayson Highlands State Park or Hungry Mother State Park. Enjoy free parking at state parks on January 1st.

Stay tuned, more events coming soon! Email info@damascus.org to add an event to the calendar.