Vendors at Ashland Train Day in historic downtown Ashland
Entrepreneurs have been looking for the right moment to claim space, build brand awareness, and plan smarter (while saving money). Downtown Ashland Association is making it happen.
At the Downtown Ashland Association (DAA), supporting small businesses isn’t a one‑off initiative—it’s a year‑round commitment. From education and exposure to real, revenue‑generating opportunities in the heart of historic downtown Ashland, DAA is proud to offer meaningful pathways for entrepreneurs to grow, connect, and be seen.
Education First: Free Entrepreneur Workshops
Free entrepreneur workshops at 6 PM on the first Wednesday of every month
Every great business starts with knowledge—and community. That’s why DAA hosts free entrepreneur workshops at 6 PM on the first Wednesday of every month inside the Ashland Branch Library. These sessions are designed to empower local and regional entrepreneurs with practical tools, shared expertise, and connections that matter.
We believe informed entrepreneurs build stronger businesses—and stronger downtowns.
From Learning to Earning: High‑Impact Vendor Events
Education is only the beginning. DAA then helps entrepreneurs turn ideas into action by creating opportunities to vend at some of the most beloved events in the Center of the Universe.
Where Entrepreneurs Show Up—and Stand Out
Ashland Fourth Fridays (March–October) mark the rhythm of the seasons in the Center of the Universe. Hosted at Ashland Town Hall, these free, family‑friendly destination events welcome spring, celebrate summer, and awe in autumn with live concerts, picnic‑perfect vibes, and entertainment that invites people to linger downtown. From face painting and dancing to the most delicious picnic fixings Ashland has to offer, Fourth Fridays create the kind of relaxed, joyful atmosphere where vendors thrive—meeting customers who are ready to explore, shop, and support small businesses.
Ashland Train Day by Rick Kidd Photography
Ashland Train Day, now in its 22nd year, is nothing short of legendary. Known around the world, this downtown‑wide railroad extravaganza transforms Ashland into a living celebration of rail history and community pride. Model trains, touch‑a‑truck style vehicles, live entertainment, giveaways, immersive history experiences, and an entire kids’ zone—complete with On the Fly bounce houses, obstacle courses, and games—fill the streets. All the while, real trains barrel through downtown, creating unforgettable moments and unmatched foot traffic for vendors.
The Grand Illumination officially ushers in the holiday season in the Center of the Universe. Hosted at the Ashland Town Hall Pavilion, this magical evening features live entertainment, traditional outdoor shopping, light‑up contests, prizes, and a breathtaking tree lighting. More than 10,000 twinkling lights outline downtown Ashland, made possible by Dominion Energy, turning the entire district into a festive marketplace where vendors connect with holiday shoppers in a truly memorable setting.
Amplification That Goes Beyond the Event
When you partner with DAA, your reach doesn’t stop at your 10x10 space.
Vendors and sponsors are amplified through a robust mix of media that extends far beyond event day. This includes digital storytelling shared locally and around the world, print features, and radio promotion on K101.2 POP Richmond, where brands are heard across the airwaves. Sponsors are also invited to attend Happy Hour Vibes Networking and Recording Parties, creating opportunities to connect, collaborate, and hear their brand amplified in real time.
Select sponsors even see their brand light up the big screen at the historic Ashland Theatre, reinforcing visibility in one of downtown’s most iconic spaces.
It’s not just vending—it’s visibility.
One Sponsorship. A Full Year of Opportunity.
Here’s where planning gets easier—and more affordable.
Rather than filling out nine separate vendor applications, waiting for invitations, and paying individual vendor fees throughout the year, businesses can secure guaranteed placement with a Downtown Ashland Association sponsorship.
Silver Sponsorship benefits include:
A guaranteed 10x10 vendor space at:
Every Ashland Fourth Fridays event (March–October)
Ashland Train Day
The Grand Illumination
A full year of visibility and support
Cost savings and simplified planning
Priority access to Downtown Ashland’s most high‑traffic events
That’s an entire year of vending opportunities—without the guesswork—in the Center of the Universe.
Now Is the Time to Claim Your Space
Downtown Ashland Association sponsorships are more than a marketing opportunity—they’re an investment in your business’s growth and a partnership with a community that shows up for its entrepreneurs.
Guarantee your place today and start planning smarter:
👉 https://www.ashlandvirginia.com/sponsor
Because when small businesses thrive, downtown thrives—and there’s no better place to shine than right here in the Center of the Universe.