Ashland Vendor Season is Back

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.

Apply to vend

📅 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!

Apply to vend

📅 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.

Apply to vend

📅 November 22, 2–5 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.

Apply to vend

📅 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.

Apply to vend

📅 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

Apply to vend

💼 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.”

Sponsor Downtown Ashland Association

Ashland Museum wins 2025 "You've Been Noticed Award"

The Ashland Museum at 105 Hanover Avenue in historic downtown Ashland, Virginia

Downtown Ashland Association is proud to announce the Ashland Museum as the recipient of the 2025 You’ve Been Noticed Award, recognizing an exceptional contribution to the heart and history of downtown Ashland. This honor spotlights organizations making inspiring investments in their commercial properties and in the vitality of our beloved small town.

Ashland Museum accepts the 2025 You’ve Been Noticed Award during Downtown Ashland Association’s Toast of Downtown.

Presented to the Ashland Museum during Downtown Ashland Association’s annual Toast of Downtown celebration, the award drew cheers from neighbors, business owners, sponsors, and local press. Guests toasted the Museum's achievements with drinks from Caboose Market & Café, Center of the Universe Brewing Company, and signature Shaken Not Spurred cocktails—true to the spirited charm of Ashland.

The idea for an Ashland Museum gathered momentum during the 150th celebration of Ashland in 2008. Formally established as a nonprofit in 2010, the Ashland Museum opened its first exhibits in 2012 at 105 Hanover Ave. and has become a vibrant anchor for history, culture, and community programming. Its collaboration with Downtown Ashland Association began with the placement of the town’s first bronze historic marker at Cross Brothers Grocery in 2012. Since then, the Museum has helped install six additional markers and co-created the Art McKinney Historic Preservation and Stewardship Award to honor those who carry forward Ashland’s architectural legacy.

Untold Stories in Ashland, Virginia

The Museum’s dedication to storytelling has led to impactful partnerships, including Untold Stories, an ongoing series created with the Hanover County Black Heritage Society and Hanover Arts & Activities Center to share honest, interwoven narratives of growing up Black and white in Ashland.

Among their recent projects is the Secretariat Racing Into History monument, now installed downtown. Sculpted by Jocelyn Russell, the statue honors the legendary Triple Crown winner, who was born and raised nearby at The Meadow, the horse farm of Ashland native and Randolph-Macon College alum Christopher Chenery. The Museum was instrumental in the monument’s fundraising efforts and continues to house Secretariat artifacts at 105 Hanover Ave.

The Ashland Museum at 105 Hanover Avenue in historic downtown Ashland, Virginia

The Ashland Museum continues to lead with vision, offering walking tours, cemetery tours, history talks, trivia nights, and even a 1926 caboose for hands-on exploration. They’re also helping shape the future of the Mid-Atlantic Railroad Park, a dynamic interpretive space telling the story of Ashland’s deep railroad roots and national impact.

“We are very pleased to receive this award from the Downtown Ashland Association,” said Randy Lewis, President of the Ashland Museum Board of Directors. This recognition affirms the mission to collect, preserve, and share Ashland’s unique stories, past and present.

Located in the heart of the “Center of the Universe,” the Ashland Museum invites residents and visitors alike to step into the stories that shaped our town—and to support their mission through individual and business memberships. For more information, visit ashlandmuseum.org.

On The Fly Events Brings Big Smiles to Back-to-School Season

On The Fly Events in historic downtown Ashland.

As school doors swing open and students gather for a brand-new academic year, On The Fly Events is rolling in with a mission: to make back-to-school season more joyful than ever before. Through their state-of-the-art Game Truck parties and interactive inflatable experiences, On The Fly Events is redefining what it means to bring a school community together — one game, one smile, and one bounce at a time.

From elementary school field days to middle and high school community fun days, On The Fly Events has already made a splash across the region, working with school systems in Richmond, Hanover, Henrico, Westmoreland, King William, King and Queen, and Caroline counties to create vibrant, kid-focused entertainment experiences. Whether it's a back-to-school fundraiser, a school carnival, or a just-because celebration, their mobile entertainment options turn everyday school events into lifelong memories. One enthusiastic student summed it up best, “This is the best day ever!”

A Game-Changer for School and Community Events

On The Fly Events climate-controlled mobile Game Truck

At the heart of On The Fly Events is their climate-controlled mobile Game Truck, delivering video game truck rentals near you with all the bells and whistles. Featuring six HD televisions, immersive LED lighting, thumping music, and the latest gaming consoles — including PlayStation 5s, Xbox Series Xs, and Nintendo Switches — this video game theater on wheels offers unlimited play access and hours of pure fun.

And thanks to their expert Game Coaches, event organizers don’t have to lift a finger. “We manage the entire experience so hosts can actually enjoy their event,” said a team On The Fly Events. “It’s play without the stress — and fun that meets you wherever you are.”

Building Futures Through Play

Whether kids are racing through a 70-foot inflatable obstacle course or cheering on friends in a game of Mario Kart, On The Fly Events believes in the power of play to build connections and confidence. “Play is the universal language,” said the team. “And when kids are laughing, connecting, and challenging themselves, they’re learning in the most joyful way possible.”

The company’s modular obstacle course can be rented in sections or as one epic stretch of excitement — perfect for schools, festivals, or neighborhood community fun days.

On The Fly Events Joins Downtown Ashland Association as Gold Sponsor

This fall, On The Fly Events is leveling up again — this time as a Gold Sponsor of Downtown Ashland Association (DAA). Locals can catch them in action at two of the town’s biggest events:

“Downtown Ashland Association is so grateful to call On The Fly Events a gold sponsor,” said DAA Executive Director "Coach" Antonio Miller. “Now we can ensure there’s engaging, family-friendly entertainment at our cherished community events. Whether they inflate it or bring their own Game Truck, we know we’re going to have a great time with our neighbors — and with On The Fly Events.”

The Future is Bright — and On The Fly

With a growing reputation and a proven track record of making kids (and parents) say “wow,” On The Fly Events is quickly becoming a go-to partner for anyone planning back-to-school events and community fun days. Because at the end of the day, it’s more than just games. It’s about building futures through play — and growing On The Fly.

Book On The Fly Events

🍲 Submit Recipes for New Cookbook

Ashland Town Council member Pam Sopall tests pies at the Ashland Fourth of July Parade and Celebration

Dust off your grandmother’s pie recipe, document that go-to weeknight dinner, or finally share your secret sangria: the Downtown Ashland Association is calling on community members to submit recipes, desserts, and drinks for the 2025 Ashland Cookbook Collection!

Now through November 1, 2025, friends of Ashland are invited to submit their culinary creations at www.ashlandvirginia.com/cookbook. Whether it’s a cherished family favorite, a new twist on a local classic, or a dish that just tastes like “home,” your contribution will help shape a legacy book that captures the town’s unique flavor—literally.

From longtime residents to newcomers and even those simply inspired by Ashland, everyone is welcome to share their recipes. All skill levels are encouraged to participate—whether your dessert is toddler-tested or Top Chef-worthy, we want to include it.

The Iron Horse Restaurant’s hot grill

“This isn’t just a cookbook,” says Downtown Ashland Association’s Director of Operations, Louise “Lou” Keeton. “It’s a snapshot of who we are, what we grow, and how we come together around food. Even though I’m no chef, I’m thrilled to help build something that highlights the people and places behind every bite.”

The 2025 Ashland Cookbook will feature not only recipes from community members but also spotlights on the local farmers, bakers, grocers, and restaurants where ingredients and flavors can be found right here in town.

“We want everything we cook up to feed back into our community,” says Executive Director “Coach” Antonio Miller. That’s why all proceeds from the cookbook will directly support free family events and small business support led by the Downtown Ashland Association, a nationally accredited Main Street America™ nonprofit.

The finished cookbook will be printed locally by Minute Men Press of Ashland, just in time for holiday giving. Whether you're shopping for foodies, hometown lovers, or history buffs, this keepsake will be a gift from the heart of the Center of the Universe.

Don’t wait—submissions close November 1, 2025. Visit www.ashlandvirginia.com/cookbook to add your recipe and become a part of Ashland’s delicious story.

Your Whistle-Stop Guide to Ashland Fourth Fridays: July 25 Edition

Ashland Fourth Fridays in historic downtown Ashland, Virginia

All aboard for an unforgettable evening in the Center of the Universe! 🌍 From toe-tapping tunes and local eats to creative treats and mystery guest sightings, Ashland Fourth Fridays on July 25 from 5–8 PM at Ashland Town Hall Lawn is the perfect summer celebration for all ages. Here’s your guide to the night’s highlights—you’ll want to save this one for your pre-party planning! 🗓🎈

Hanover’s Got Talent winner Hannah Armpriester.

🎸 Let the Music Play
Kick things off at 5 PM sharp with a high-energy showcase from the talented students of Ashland Dance Academy. Tap, jazz, ballet—they’ll be bringing the moves and the sparkle to the Ashland Town Hall Pavilion stage. 💃
Then settle in for an instrumental jam session like no other, as The Blue Guitar performs from 5:15–8 PM with dynamic covers of your favorite pop, R&B, rock, and jazz hits. It’s the kind of summer soundtrack you’ll want to hum all the way home.
Stick around for a grand finale performance by Hanover’s Got Talent soaring singing winner Hannah Armpriester. 🎶🌅

🚚 Savor the Flavor
Ashland’s farm-to-fork restaurants stay packed on Fourth Fridays—and for good reason! If you’re looking for a delicious detour, stop by our visiting food trucks offering everything from crepes to Filipino cuisine and dreamy ice cream delights. 🍨🍴 Come hungry and leave with a happy heart (and a full belly).

And don’t forget to raise a glass to style—Shaken Not Spurred will be serving up marvelous mocktails and retro flair from their converted horse trailer beverage truck. ✨ It’s a sip-and-stroll experience like no other! 🍹🐎

🎨 Local Treasures & Artistic Pleasures
This is your moment to shop small and shine bright! ✨ Browse handcrafted jewelry, original artwork, woodwork, fresh flower bouquets 💐, and all the handmade magic Ashland has to offer. You'll find treasures you won't be able to resist—and won’t be able to find anywhere else.

While you shop, cool off with a complimentary water bottle from Cornerstone Church, who will be spreading kindness and hydration across the lawn. Stop by Downtown Ashland Association’s Cool Zone and mist off July heat.💧💛

🎭 Get a Little Spooky…
For those craving a little mystery, RED VEIN Escape is offering immersive escape room games just steps away from the main lawn. 🔍 Their haunted halls are also the jumping-off point for the Ashland Haunted History Tours, where you can take a spine-tingling stroll through the town’s past. 👻 It’s thrills, chills, and clues—if you dare.

📸 Star Sighting Alert!
Who’s that posing for selfies on Thompson Street? 👀 You’ll have to come see for yourself! Our mystery celebrity guest will be on hand at 110 Thompson Street for photo ops and fan fun. Strike a pose—it might just be your most iconic Fourth Friday moment yet! 🌟📷

Rantrak outside of Tiny Tim’s Trains & Toys at Ashland Fourth Fridays

🚂 Tiny Trains & Painted Ponies
Stop by Tiny Tim’s Trains and Toys for a double dose of delight! Outside, the incredible team from Rantrak will be running their magical model train display—a miniature world that’s sure to wow railroad lovers of all ages. Inside, young creatives can paint their own Breyer Horse model, a neigh-borhood favorite that’s sure to spark imagination. 🐴🎨

🌳 Make It a Picnic Party
Bring a blanket, round up your crew, and spend the evening surrounded by music, movement, and community. Whether you're enjoying live performances, shopping for local gems, or just lounging in the summer sun, Ashland Fourth Fridays is the place to be. 🧺🌞

See you on the lawn, July 25 from 5–8 PM!
You never know what you'll discover—but we do know it’ll be marvelous, musical, and Center of the Universe-level magical. 💫