"Your favorites will be back and we'll have new activities as well!" That was Destination Downtown Waynesboro's promise for Winterfest on Saturday, November 28, 2026. On the same event page, the first favorite listed now carries two words in capital letters: SOLD OUT.
The Cookie Trail gave ticket holders a baker's dozen of decorated holiday cookies collected from 13 downtown businesses. Those tickets are gone. No other event on DDW's schedule is marked sold out, and this year's new events stretch the day at both ends. The first one starts at 10:30 a.m. on the Greenway, and the last one is a tree lighting at 5:30 p.m. For Cherry Orchard households heading downtown for Small Business Saturday, the planning now comes down to timing. A few events need a registration or a small fee, and on parade day the street closures start hours before the first float.
Thirteen Cookies, and What Stays Open Without Them
Destination Downtown Waynesboro, the nonprofit that promotes downtown businesses and events, built the Cookie Trail as a shopping route. Ticket holders pick up a bag at the DDW Info Booth at 503 W. Main Street starting at 11 a.m., then collect wrapped cookies along the way. The listed stops include Boutique in the Boro, adorn., Rusticae, the Augusta County Rail Road Museum, the Shenandoah Valley Art Center on South Wayne Avenue, The Russell Museum, The French Press, Initial Inspiration, Stone Soup Books, Shelf Indulgence, Crack O' Dawn and the Waynesboro Watershed Coalition.
The Cookie Trail runs 11 a.m. to 4 p.m., so its stops are along the same blocks shoppers will be walking anyway. A cookie bag was never required to go inside.
The rest of the day leans toward events with no ticket at all. DDW lists Meet Santa as free. Santa is at The Russell Museum from 11 a.m. to 1 p.m., and the listing invites photos with kids, pups or both. Story time with Santa follows at Stone Soup Books from 1:30 to 2:15 p.m. Waynesboro Parks and Recreation brings fire pits and supplies for free DIY s'mores from 11 a.m. to 4 p.m. in Bruce Alley, beside the P. Buckley Moss Gallery. The listing says plainly that the s'mores are not in Lumos Plaza. A DIY ornament station with the Office on Youth shares Bruce Alley during the same hours. City Hall has artificial snow and a giant snow globe bounce house all day, with a suggested $2 donation for photos.
The New Events Make a Longer Day
DDW marks three events as new this year. One adds a reason to arrive early, one adds a reason to stay until evening, and the third fills the middle of the day.
Time | Event | Where | Cost as listed |
|---|---|---|---|
10:00–11:00 a.m. | Cocoa and Cookies with the Princesses | The Russell Museum | $25 per child, one adult included |
10:30–11:00 a.m. | Trot and Toddy Fun Run or Walk (new) | Constitution Park Pavilion | Pay what you will, registration required |
11:00 a.m.–1:00 p.m. | Meet Santa | The Russell Museum | Free |
11:00 a.m.–4:00 p.m. | Farmers Holiday Market (new) | 522 W. Main Street | No ticket listed |
11:00 a.m.–4:00 p.m. | DIY s'mores | Bruce Alley | Free |
11:00 a.m.–5:00 p.m. | Wassail Trail | Passports at 503 W. Main Street | $5, 21 and older |
1:30–2:15 p.m. | Story time with Santa | Stone Soup Books | Free |
5:30 p.m. | Tree Lighting (new) | Constitution Park | No ticket listed |
The Trot and Toddy begins half an hour before the main festivities. The course goes three-quarters of a mile out along the Greenway and three-quarters of a mile back, 1.5 miles in all. DDW points out that this is roughly half a 5K, so no training is needed. Every participant gets a Santa hat. Participants 21 and older also get a Wassail Trail passport, and those under 21 get a Kids Wassail passport. Costumes are encouraged, from Santa to characters from "The Grinch."
The Waynesboro Farmers Market's Holiday Market sets up at 522 W. Main Street, right beside The Russell Museum. It mixes returning favorites with new artisan vendors and has a reindeer food activity for kids. Vendors can apply by emailing [email protected].
The day closes at Constitution Park, where Waynesboro Parks and Recreation holds an old-fashioned tree lighting at 5:30 p.m. DDW describes it as the event that wraps up Winterfest. The fun run starts at the Constitution Park Pavilion and the tree lighting ends in Constitution Park, so a family that does both begins and ends the day in the same place.
Where a Ticket or Registration Still Matters
Three events still involve a purchase or a sign-up, and each one handles it differently.
- Cocoa and Cookies with the Princesses costs $25 per child, and the ticket includes one adult. Each child gets cocoa, cookies, a winter magic crown and wand, and a sing-along before the princesses head out across downtown. Tickets are sold through the event's ticketing page. The ticket terms include a photography release allowing DDW and Character Connections to use event photos in promotional materials, and DDW states the photos will not be used for AI-generated content or AI image manipulation.
- The Trot and Toddy is pay what you will, but registration is required. DDW's listing links to the sign-up page.
- The Wassail Trail is the one paid event that can still be bought on the day. Passports cost $5 at the booth at 503 W. Main Street or online in advance. DDW's description promises holiday drink samples, alcoholic and nonalcoholic, from nine downtown restaurants and shops, and participants must be 21 or older. Winterfest is a DORA event, so drinks can be carried while walking downtown, and proceeds support Destination Downtown Waynesboro.
The Wassail Trail also has its own small competition. Passport holders vote for the best seasonal drink, and the winner takes home the Holiday Cheermeister award. The participating-locations list on the same page runs longer than that count of nine, naming Delly Up, Benny Stivale's, Royal India Palace, The French Press, The Russell Museum, Pyramid, Stone Soup Books, Initial Inspiration, Rusticae and the Farmers Market Winterfest Market, followed by "and more," so the final lineup may be confirmed at the booth. DDW lists Delly Up as the undefeated champion.
DDW is also recruiting Winterfest volunteers through a sign-up sheet linked from the Winterfest page on Visit Waynesboro.
A New Shop Opens Eight Days Earlier
Winterfest isn't the only downtown holiday shopping date this month. Trellis Art Collective plans a ribbon cutting and kickoff event to open its shop to the public on Friday, November 20, at 11 a.m. As the News Leader reported in May, the collective is in Suite 105c of the Virginia Metalcrafters Marketplace at 1010 E. Main St. It offers private studio space and a shared workshop, with a gallery and retail shop planned for later. That retail shop is what opens on November 20. Trellis isn't on the Winterfest route, but its shop opens just in time for holiday shopping. The date and time are posted on Trellis Art Collective's events page.
December 5 Runs on a 3 p.m. Clock
The Waynesboro Christmas Parade comes one week after Winterfest, on Saturday, December 5, at 6 p.m. downtown. Planning for this one mostly means knowing when the streets close. According to the City of Waynesboro's October 28 parade notice, streets on the parade route soft-close at 3 p.m., and after 3:30 p.m. no traffic can pass through any part of the route. Parking on the route is also prohibited after 3 p.m. A car parked on a route street at lunchtime has to be moved well before the parade starts.
The city's notice also lists these details:
- Weather date. If the weather is severe, the parade may move to Tuesday, December 8, at 6 p.m. Any change will be announced on the city's website and Facebook page.
- Toy Convoy. The Salvation Army will collect toys near the beginning of the parade for area children.
- Restrooms. Portable toilets will be at Main Street and Wayne Avenue, Arch Avenue and Main Street, and Market Avenue and 11th Street.
- Accessible viewing. A small area for wheelchair users will be on Main Street at the corner of Arch, in front of the Waynesboro Tourism building. The city asks everyone along the route to avoid standing in front of others.
- Participant deadline. Applications to march or ride in the parade are open at playwaynesboro.com and are due by 5 p.m. on Tuesday, November 24. Late applications won't be accepted.
The notice points readers to the city's Christmas Parade page for additional information. For either Saturday, Visit Waynesboro's general downtown parking guidance points to the free city-owned Arch Avenue public lot, between Constitution Park and downtown, and to public lots on Market Avenue and on Main Street across from the Wayne Theatre. Arch Avenue is also one of the corners named in the parade notice, so check the closure times before relying on that lot on December 5.
Knowing the dates and deadlines on the local calendar is part of how we work at Nest Realty - Shenandoah Valley, whether it's a parade road closure or a closing date. If friends or family are thinking about a Waynesboro move, we'd be glad to help them get to know downtown, from the Arch Avenue lot to the tree in Constitution Park. Find Your Shenandoah Valley Home.
