Damascus has scheduled its 2026 holiday market twice. "Dashing through Damascus: A Christmas Market" opens at the Damascus Old Mill Inn, 215 W Imboden St., from noon to 6 p.m. on Saturday, November 28. A week later, on Saturday, December 5, it opens again at the same place and the same hours. The Visit Damascus listing for both dates promises the same things: handmade gifts, vintage finds, art, homemade treats, live music and a picture with Santa.
The two Saturdays differ in what surrounds the market. On the first Saturday, downtown is busy with shopping. The second Saturday follows four days in which the town judges its lights, holds its parade, and sends runners down the Virginia Creeper Trail and then into cold water. So the useful question for anyone in Washington County planning a December is which of those two weekends you want around the market.
Two Saturdays, side by side
| Saturday, November 28 | Saturday, December 5 | |
|---|---|---|
| Christmas market at Damascus Old Mill Inn | Noon to 6 p.m. | Noon to 6 p.m. |
| Also on the calendar that day | Small Business Saturday downtown | Dashing Thru Damascus half marathon, 5K and polar plunge |
| The night before | Nothing listed yet | A Trail Town Christmas Parade, 7 p.m. |
| Holiday Lights Tour | Not started yet | Running, with contest winners already announced |
The November date falls on Small Business Saturday. The town's holiday page points shoppers downtown for outdoor gear, handcrafted goods and small-batch pet treats, and it suggests gift cards or an experience for the person who already has everything. The December date opens with the Dashing Thru Damascus race, which Visit Damascus describes as the start of the holiday shopping weekend. That makes it the busier of the two.
Visit Damascus also says it will add more events, so this table reflects the calendar as of early October.
November 28 is a downtown shopping day
On the first Saturday, the market is one stop on a walk through downtown. Most of the shops the town lists for that walk are within a few blocks of each other.
- Damascus Outfitters, 128 W Laurel Ave., sells hiking, backpacking and trail-running gear, plus footwear and apparel. Its listed hours are 9 a.m. to 6 p.m. daily.
- Traildog & Co, 132 W Laurel Ave., carries locally sourced pet food, small-batch treats, toys and gear. It's open Thursday through Monday from 11 a.m. to 6 p.m., so it's open on both market Saturdays and on parade Friday.
- Sundog Outfitter, 331 Douglas Dr., handles outdoor outfitting and trail information and lists hours of 8:30 a.m. to 6 p.m. daily.
- Trailhead Designs, also at 331 Douglas Dr., does custom screen printing, vinyl signs, stickers and laser engraving. It lists weekday hours of 9 a.m. to 5 p.m. and closes Wednesdays. If you want something personalized as a gift, a weekday visit is the safer bet.
For coffee between stops, The Coffee Thief is at 124 E Laurel Ave. Its regular hours weren't posted in the sources we checked, so look them up before you go. All of the hours above are each business's regular posted schedule. None of them has announced special holiday hours yet.
December 1 through 4, the lights and the parade
The second weekend starts building on December 1, when the Holiday Lights Tour begins. It runs through December 31, and you can walk, bike or drive the route around town.
The decorating contest attached to the tour has an early deadline. Displays have to be ready by the first Wednesday of December at 7 p.m. This year that's December 2, two days after the tour opens. Anyone within town limits can win, and there's no entry form. The categories are Best in Show, Best in Show: Business, and Most Lights.
Winners are announced before A Trail Town Christmas Parade, which steps off at 7 p.m. on Friday, December 4, on Laurel Avenue downtown. According to Visit Damascus, the parade is always held on the first Friday in December. The parade includes a float contest and the Damascus Loves Dogs Holiday Costume Contest, and Santa will be at the Fire Hall afterward. The town's event calendar lists 208 West Laurel Ave. as the venue address.
With a 7 p.m. start, dinner falls on one side of the parade or the other, and the posted Friday hours decide which.
- Damascus Old Mill Inn, 215 Imboden St., lists Friday hours of 5 to 9 p.m. That leaves time for an early meal from the pub's craft beer and bourbon list before the parade.
- Wilson's Cafe & Grill, 331B Douglas Dr., is open Friday and Saturday from 11 a.m. to 9 p.m.
- The Tipsy Bear, 338 Douglas Dr., lists Friday and Saturday hours of 11 a.m. to 11 p.m. It's the one place on this list still serving well after the parade ends.
- Damascus Diner, 109 S Shady Ave., is listed as open daily.
The Dairy King at 511 E 3rd St. is off the list this season. Visit Damascus shows it closed for winter 2026–27.
December 5, the race comes before the market
On the second Saturday, Trail Town Fitness holds Dashing Thru Damascus on the Virginia Creeper Trail. The half marathon starts at 8 a.m., the 5K at 9:30 a.m., and the polar plunge and sauna follow at 11 a.m. The event listing gives Trail Town Fitness's location as 132 W Laurel Ave. Costumes aren't required, though the Visit Damascus holiday listing says holiday spirit is "always strongly encouraged."
Registering early saves money. As of October 2026, UltraSignup lists the polar plunge at $20, the 5K at $33 and the half marathon at $77, before fees. Prices go up after November 14, and registration closes at 11:59 p.m. ET on Friday, December 4, the same night as the parade.
The plunge finishes around midday, and the Christmas market opens at noon at the Old Mill Inn. On December 5 you can run in the morning, plunge before lunch and shop all afternoon without leaving town.
The tree comes from higher up the mountain
The Christmas tree sits outside the downtown calendar. Visit Damascus notes that Fraser firs grow best above 4,500 feet and are native to only a small region of Virginia, North Carolina and Tennessee. It sends tree shoppers to choose-and-cut farms around Whitetop or to pre-cut lots near town.
The Anne & Eddie Blevins Christmas Tree Farm, at 30862 Jeb Stuart Hwy between Konnarock and Whitetop, sits about 14 miles from Damascus and sells Fraser firs as choose-and-cut or ready-to-go trees, along with wreaths, apple butter and applesauce. A regional farm guide, Visit Southwest Virginia, checked in September 2026 said the farm hadn't published its 2026 season dates or prices yet, so call before you drive up.
Plan to drive. The U.S. Forest Service has scheduled the Damascus-to-Whitetop section of the Creeper Trail to reopen March 31, 2027. Rebuild crews are still at work. The project's October 5 progress update reported 18 bridges finished and 73% of culverts installed.
Before November, and after December
October still has a couple of Damascus dates on it. The Damascus Farmers Market runs Thursday evenings from 4 to 7 p.m. through October at the Speckled Trout Annex, 106 West Laurel Ave., with a market on the calendar for October 15. Downtown trick-or-treating is on October 31, and the crosswalks are monitored from 5 to 7 p.m.
On the other end of the season, the town's holiday page points to First Day Hikes on January 1 at Grayson Highlands State Park and Hungry Mother State Park. Rangers lead hikes, and parking at Virginia State Parks is free that day.
If the Holiday Lights Tour has you thinking about what your own Damascus or Washington County home would bring once the decorations come down, Denise Blevins can give you a straight answer based on what's actually selling here. Start with the Instant Home Valuation, and Denise will follow up personally.
