Photo of the massive crowds on Ashland Train Day taken by Rick Kidd
Downtown Ashland Association is proud to announce the return of highly anticipated vendor events, inviting locals and visitors alike to Shop Ashland First, savor regional flavors, and celebrate small businesses — all while enjoying free live entertainment in the Center of the Universe.
With vendor events that welcome more than 40,000 guests in person annually and reach millions of viewers regionally and internationally through TV, radio, print, and online platforms, this year’s lineup is bigger, brighter, and more business-friendly than ever before.
“Whether you're a shopper looking for the perfect handcrafted gift, or a vendor ready to amp up your work, Ashland is the place to be,” said “Coach” Antonio Miller, Executive Director for the Downtown Ashland Association. “Our vendor fairs are a celebration of what makes Ashland unique: small-town charm, big creative energy, and a community that loves to support local.”
From summer nights filled with live music and local eats, to festive holiday markets and Ashland’s world-famous Train Day, there’s truly something for everyone — and a space for every kind of maker, artist, and foodpreneur.
2025–2026 Downtown Ashland Vendor Events:
📅 August 22, 5–8 PM — Ashland Fourth Fridays Finale
Close out summer with live performances, local shopping, food trucks, and family fun at Ashland Town Hall. Highlights include Hanover’s Got Talent winner Layla Atanacio, the Ashland Song Contest grand prize reveal, and interactive entertainment like Tiny Tim’s Trains and Toys Breyer horse painting, and model trains or Ashland Haunted History Tours outside of RED VEIN Escape.
📅 September 27, 11–4 PM — Songs from the Center of the Universe Concert
Celebrate the music of Ashland at a free outdoor concert featuring live recordings by Free Jambalya. Vendors enjoy a one-of-a-kind crowd — and a booth fee of just one bag of Halloween candy!
📅 October 25, 3–7 PM — Off the Rails Beer Festival
Craft brews, local wines, and even better vibes await at this beloved boozy bash. Arts and crafts vendors and food trucks will set up shop to serve up the perfect pairings.
📅 November 25, 12–5 PM — Grand IlluminAshland
Kick off Light Up the Tracks with a holiday market, live performances, carolers, and a dazzling community tree lighting. Start your season with sparkle — and shop small while you’re at it.
📅 December 6, 11–4 PM — England Street “Christmas” Market
In partnership with Thrill of the Hunt, this vintage-inspired market begins in Ashland Town Center, making it the perfect starting point for your local holiday shopping crawl through the Center of the Universe.
📅 April 26, 10–4 PM — Ashland Train Day
An international draw and family favorite, Ashland Train Day boasts 20,000+ attendees and a marketing reach in the millions. Vendors get front-row exposure at one of the region’s most exciting and well-loved festivals
💼 Vendors: Secure Your Spot All Season Long
Apply to be considered for any or all upcoming vendor events — or skip the application process entirely and guarantee your space by becoming a Downtown Ashland Association Silver Sponsor.
Silver Sponsors enjoy perks like:
Reserved 10x10 space at all vendor events
Logo and sponsorship credit across Downtown Ashland Association’s website and promotions
Marketing that reaches millions
Even a static ad on the Ashland Theatre screen!
“Being a silver sponsor doesn’t just guarantee you a booth — it makes you a part of something bigger,” Miller adds. “You’re helping us make Ashland a thriving hub for creativity, commerce, and connection.”