There’s something truly magical about spending the holidays in a town where every storefront tells a story. In downtown Ashland, Virginia, our shops are run by dreamers, makers, neighbors, and family-owned businesses who pour their hearts into every product, cup of coffee, handcrafted gift, and warm welcome. This Small Business Saturday, that spirit shines brighter than ever—and you’re invited to be part of it.

✨ Pop-Ups, Freebies, and a $100 Gift Certificate Giveaway

Kick off your Small Business Saturday adventure with a visit to one of our downtown pop-up spots! The Downtown Ashland Association will be making surprise appearances at local favorites like Classic Coffee, Tea & Books, Take Away, and Miss Timmies throughout the morning.

📸 Here’s how to enter our $100 giveaway:
Take a photo in downtown Ashland on Saturday, November 29, follow @AshlandVirginia on Instagram, and tag us. That’s it! You’ll be automatically entered to win a $100 Town of Ashland Gift Certificate—perfect for holiday shopping at local businesses.

☕ Bonus treat: Show up in Downtown Ashland between 10 AM–12 PM and you might just run into the Downtown Ashland Association gifting free coffees, ornaments, and more to brighten your morning.

❤️ Supporting Downtown Ashland Means Supporting Small Businesses

As a nonprofit, the Downtown Ashland Association (DAA) works year-round to lift up local businesses through free community events, small-business resources, and powerful marketing initiatives. And while end-of-year donations are always appreciated, there’s a simple, free way to make a huge impact:

👉 Follow @AshlandVirginia on Instagram.
We’re just 3K followers away from 10K, a milestone that will help us reach more residents, visitors, and small businesses with vital news, events, and marketing support at no cost to our community. Every follow amplifies the voices of our entrepreneurs and helps build a thriving, connected downtown.

✨ Explore a Hallmark-Worthy Holiday Downtown

Once you’re caffeinated and cozy, take a stroll through our historic streets, glowing with over 10,000 holiday lights stretched across two miles of festive charm. Whether you walk, jog, or cycle, every visit helps illuminate more than our decorations—it lights up the lives of the small business owners who make Ashland extraordinary.

Every purchase supports a small business—and every small business shapes the heart of Ashland.

🎨 Make It a Picture-Perfect Visit

While you’re exploring, don’t miss Ashland’s iconic public art, including Secretariat: Racing Into History and America’s longest train mural—two perfect backdrops for festive holiday photos (and your giveaway entry!).

🚆 The Most Magical Way to Arrive

Skip the parking and ride in style on Amtrak Virginia. Step off the train and into a downtown that shines like a living Hallmark movie—complete with glowing lights, local shops, hot coffee, happy neighbors, and all the warmth of a small-town holiday celebration.

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