There’s something downright magical about the moment downtown Ashland lights up for the holidays. The Grand Illumination marks the official beginning of Light Up the Tracks, a season-long celebration that transforms the Center of the Universe into a twinkling winter wonderland.

On Saturday, November 22, the community will gather in Historic Downtown Ashland for an afternoon of festive fun that leads up to the big tree lighting at 5:00 PM sharp. Thanks to the support of Dominion Energy and the skilled team at Wells Tree Service, more than 10,000 lights will outline our charming historic buildings, restaurants, and shops. When the switch is flipped, you’ll feel like you’ve stepped straight into a holiday movie.

For travel made easy, let Amtrak Virginia do the driving—after all, their “sleighs” stop right in the heart of downtown, just in time for the afternoon magic to begin. Start your morning local when you fuel up with brunch or lunch at one of our downtown cafés and restaurants, whether you’re craving a big Southern breakfast, a cozy coffee, or a seasonal latte that tastes like the holidays. From 9 AM to noon, the Ashland Farmers Market will feature farm-fresh produce, baked goods, and handmade treats surrounding Town Hall at 121 Thompson Street while artists showcase Autumn in Ashland at the Hanover Arts and Activities Center. Starting at 10 AM - 4 PM, guests will be able to pop inside the cozy historic halls to browse and shop for pieces from local artists over delicious beverages and desserts.

Starting at 3 PM, explore a festive outdoor market that stretches from the Dominion Energy Innovation Center to 110 Thompson Street, featuring handmade art, crafts, specialty foods, and unique gifts from local makers. Every purchase supports a small business and helps keep Ashland’s downtown thriving through the winter season.

Santa and Mrs. Claus will be waiting at the Ashland Town Hall Pavilion, ready to greet families and hear holiday wishes while Center Street Sound Co. fills the air with timeless Christmas tunes. As the afternoon continues, enjoy performances from MKH Dabke Entertainment, the Ashland Dance Academy, and the Randolph-Macon College Choir, who will lead a community sing-along to Walking in a Winter Wonderland.

Then comes the big moment—the Ashland Town Tree lighting at 5:00 PM. As thousands of lights flicker to life across the tracks, you’ll see why downtown Ashland, Virginia has been named one of America’s top Main Streets.

Ashland Dance Academy performing at The Grand Illumination

The Grand Illumination is just the beginning. The Light Up the Tracks season continues through New Year’s, filled with heartwarming community traditions and downtown collaborations. The Kiwanis Club of Ashland’s beloved Olde Time Holiday Parade will return for the 56th year on Sunday, November 23 with local musicians, dancers, car groups, and an outdoor vendor market at 110 Thompson Street, produced by the Downtown Ashland Association. Throughout December, downtown restaurants, cafés, and boutiques keep the spirit bright with special promotions and sparkling decorations.

Carolers in historic downtown Ashland, Virginia

Starting Saturday, November 29, carolers will stroll the downtown sidewalks every Saturday evening from 5 to 7 PM, filling the streets with song. The night begins at Town Hall with a 5 PM community sing-along before the music winds its way through Library Plaza, Changing Reins, and The Henry Clay Inn. Local choirs including Good Vibrations, the Henrico Pops, Shiloh Baptist Church, and City Singers Youth Choirs will lead the way, spreading cheer from stop to stop.

And just when you think the season can’t get any sweeter, New Year’s Eve brings the Ashland Chocolate Bar Giveaway. Chocolate bars will be distributed at downtown shops, with one golden ticket hidden among them—good for an exciting downtown Ashland prize. QR code purchases support the Downtown Ashland Association with labels printed locally by Minuteman Press of Ashland and sweet support from our friends at 110 Thompson Street and the Ashland Dance Academy. Buy in cash and donate directly to stores through the hard winter months.

Whether you’re a longtime resident or a first-time visitor, Ashland’s Light Up the Tracks season is an invitation to slow down, shop small, and savor the season with neighbors who make the Center of the Universe shine.

Downtown’s calendar is glowing with holiday happenings—check AshlandVirginia.com/LightUp for an updated list of events and experiences that make this season shine.