Downtown Ashland is Officially Off to the Races

Secretariat Racing Into History in historic Downtown Ashland, Virginia

On Friday, March 27, Ashland will debut its very first 2026 Ashland Fourth Fridays, and in true Center of the Universe fashion, the celebration is arriving with a legendary head start. The kickoff weekend just so happens to coincide with the birthday of Ashland’s hometown hero, Secretariat—so naturally, Big Red is setting the pace.

From March through October, on the fourth Friday of each month from 5–8 PM (with April taking a breather ahead of Ashland Train Day), downtown Ashland will transform into a lively, walkable evening affair where shopping stays open late, farm-to-fork dining goes trackside, and the Town Hall lawn and parking lot fill with art, crafts, local businesses, games, prizes, and delightful discoveries for all ages. It’s a monthly tradition built for strolling, grazing, laughing, and lingering—no reins required.

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The inaugural Fourth Fridays celebration will be a full-stride tribute to Secretariat, in partnership with Secretariat for Virginia, who will be setting up shop in the Ashland Town Hall parking lot with their brand-new 10x10 booth and exclusive 2026 Secretariat Day merchandise. They’re also sweetening the pot with a raffle that’s sure to get hearts racing: two tickets to the beloved Big Red Bash at Oakdale, the cocktail party and fundraiser that kicks off Ashland’s annual Secretariat Birthday Celebration.

The Big Red Bash gallops in the very same weekend, taking place Friday, March 27 from 6:00–9:00 PM at Oakdale in Ashland—just follow the blue and white flags. Bash guests will enjoy generous grazing tables stacked with sumptuous charcuterie and decadent desserts, a lively bar pouring champagne, mint juleps, wine, and a signature “Big Red” beer, plus live patio music, an artsy silent auction, and a high-energy Horse Race Game. Adding an extra thrill to the evening, attendees will even meet Pepe, a real racehorse and proud descendant of Secretariat himself. Tickets are $100 per person and, in the spirit of love for Big Red, go on sale Valentine’s Day, February 14. Proceeds support the maintenance of the Secretariat Monument and Reynolds Family Plaza in Ashland, along with educational efforts celebrating the region’s renowned horse history. Raffle entries can be made at ashlandvirginia.com/raffles, with the winner contacted by email on Thursday, March 26.

Back at the heart of Fourth Fridays, the Ashland Town Hall Pavilion will set the tone for the evening with movement and music. Ashland Dance Academy opens the show with original choreography spanning ballet, hip hop, tap, and musical theatre, including a special Secretariat-themed piece set to “It’s Who You Are” by AJ Michalka—an inspiring tribute to Big Red’s enduring legacy. From there, the stage opens up for a free, family-friendly concert by Alan MacEwen of Grandson’s acclaim, perfect for spreading out a picnic blanket or pulling up a lawn chair to soak in the sounds from Ashland’s picturesque town square.

Ashland Dance Academy performs at Ashland Fourth Fridays

Around the lawn, the fun keeps trotting along. ReFunkIt brings their horseshoe set for a little friendly horsing around, Sign Gypsies of Mechanicsville creates a perfectly posable photo moment, and Girl Scouts of Virginia keep things sweet with their famously irresistible cookies. Inside, Tiny Tim’s Trains and Toys invites Fourth Friday fun-finders to paint Beyer Horses for free—proof that creativity runs on all four hooves in Ashland.

Vendors interested in joining the ride can apply at AshlandFourthFridays.com or guarantee their place by becoming a Downtown Ashland Association sponsor at ashlandvirginia.com/sponsor. Through marketing initiatives, special events, business engagement, and economic development, the Downtown Ashland Association proudly advances its nonprofit mission by deploying its time, funding, and voice on behalf of the community.

Because Ashland Fourth Fridays isn’t just an event—it’s a reflection of who we are.

We are organizers, fundraisers, and small-town cheerleaders. We are artists and farmers, government leaders and business owners, parents and grandparents. And together, we harness the power of community to build a stronger future for everyone.

So mark your calendar, grab the reins, and join us as Ashland’s newest tradition breaks from the gate—full of heart, heritage, and a whole lot of hometown horsepower.

Your 2026 Ashland Vision Board

Ashland Train Day through the lens of Rick Kidd Photography

If you’ve ever wished your vision board could come to life, 2026 in Ashland is ready to deliver. This year’s calendar is filled with moments both joyful and meaningful—events that invite you to gather, reflect, celebrate, and return again and again to the heart of the Center of the Universe.

Untold Stories at Patrick Henry High School

The magic is already underway with Gonna Be Golden Milk Chocolate Bars, available now while supplies last. Only four golden tickets remain, each hidden inside a creamy milk-chocolate bar and redeemable for extraordinary downtown prizes. It’s a sweet reminder that in Ashland, even everyday treats can hold a little surprise.

On March 1 from 4–6 PM, the community comes together for Untold Stories at Patrick Henry High School. This powerful panel features local residents sharing oral histories centered on race, community, and segregation during the 1940s–1960s—an evening of listening, learning, and honoring the voices that shaped our town.

Starting in March and continuing through October, Ashland Fourth Fridays light up downtown on the fourth Friday of every month. These beloved street parties feature late-night shopping, farm-to-table fare, live music, dancing, photo-worthy moments, and the unmistakable buzz of Ashland after hours.

Ashland Fourth Fridays in historic downtown Ashland

History and hometown pride take center stage on March 28 during Secretariat Day, held at 1104 PM around the Secretariat Racing Into History monument in the Reynolds Family Plaza at Randolph-Macon College. Virginia’s only Secretariat monument comes alive with family-friendly fun, history talks, local vendors, food, merchandise, and horse-powered joy—made possible by @secretariatforvirginia.

Railfans and festival lovers alike will want to mark April 25 from 10 AM–4 PM for Ashland Train Day, the 22nd annual celebration of the town’s deep railroad roots. Expect a full day of festival fun, railroad flair, and community connection, with opportunities to get involved as a vendor, volunteer, or sponsor.

In May, big ideas take the spotlight at the Center Street Pitch Competition at the Ashland Theatre. Known as the friendliest Shark Tank in the Center of the Universe, this event champions local entrepreneurs as they pitch for major cash prizes and community support.

Light Up the Tracks through the lens of Robert Pfeifer

Summer sweetness arrives on June 6 from 10 AM–5 PM with the Ashland Strawberry Faire. A cherished tradition since 1982, this free, family-friendly festival overflows with strawberry treats, live entertainment, and activities—all while supporting scholarships and local nonprofits.

As the year winds down, Ashland turns up the glow with Light Up the Tracks, running November 21 through January 1, 2027. This mile-long holiday light display anchors six weeks of events, markets, music, and seasonal magic, powered by @dominionenergy and beloved by all ages.

In Ashland, planning your year isn’t just about dates—it’s about choosing moments. As you look ahead to 2026, we hope you’ll save space for the experiences that make the Center of the Universe feel like home.

Seize Your Space in the Center of the Universe

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

On the Fly Events on Happy Hour Vibes Networking and Recording Parties

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.

Silver Business Sponsor

$500.00

BECOME A SILVER SPONSOR

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.

Song Contest Winners Take the Stage for a Live Concert and Historic Recording

Songs from the Center of the Universe Concert on the front porch of historic Hanover Arts and Activities Center

Ashland has long inspired music in the hearts of those who stroll its picturesque streets—but now, the town’s unique charm will be immortalized in song. Join us for the Songs from the Center of the Universe concert on Saturday, September 27 at 11 AM on the front lawn of the Hanover Arts and Activities Center, where the Ashland Song Contest winners will perform their original, Ashland-inspired anthems—live and on the record.

Bring your blanket or pull up a folding chair provided by the Center, and become part of history as Free Jambalaya professionally records each performance for distribution across all major streaming platforms and airplay on K101.2 POP Richmond. It’s a free celebration of music, community, and the stories that make Ashland sing.

Sarah Forti recording her Ashland Song Contest entry

🎤 Live Music from Ashland’s Brightest Songwriters
This hometown concert features the winners of the Ashland Song Contest, each of whom captured the spirit of Ashland through melody and lyrics. From laugh-out-loud tracks to soulful serenades, the lineup includes:

• Sarah Forti, whose humorous “Don’t Drive on the Tracks” warns:
  Please don’t drive down the railroad tracks, my friend /
  They won’t get you where you’re going, in the end /
  If you’re not driving a train…

• Kevin Fergusson, who sings of Ashland’s wonder in A Day and Night in Ashland:
  I saw the Center of the Universe on view, /
  Out here in the small and precious town of Ashland.

• Beloved local musician Victor Gottlieb, who says, “I got never-ending support and inspiration all the way through this fun contest.” Victor’s songwriting nearly became a full album dedicated to Ashland itself.

Vendors set up at historic Hanover Arts and Activities Center during the Songs from the Center of the Universe Concert

✨ More Than a Concert—It’s a Celebration!
In true small-town style, the concert will be accompanied by:

• 🍽️ Farm-to-fork food trucks serving local eats

• 🛍️ Art, craft, and business vendors offering handmade and hometown goods

• 🎯 Lawn games and family-friendly fun
  
  

🚂 Arrive in style by taking Amtrak Virginia to the Ashland station—just steps from the concert—or crack open a cold one from Center of the Universe Brewing Company to toast to Ashland’s musical milestone.

Simultaneously, Ashland will welcome hundreds of Virginia Girl Scouts for Ashland Girl Scout Day, who will be exploring all the wonder the “Center of the Universe” has to offer—including this concert that adds melody to our history and helps share it with the next generation and beyond.

🎶 “We’re always delighted to discover how many people are inspired by Ashland,” says Louise Keeton, Director of Operations for Downtown Ashland Association. “It is our goal to provide a platform for these artists to be heard—not only in the Center of the Universe, but to pull everyone into our orbit. We’re so thankful to Free Jambalaya for bringing professional production to these original songs and sharing them with the world.”

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Songs from the Center of the Universe Concert
📍 Hanover Arts and Activities Center Lawn – 500 S Center St, Ashland
🗓️ Saturday, September 27, 2025
⏰ 11 AM – Free and open to all!

Ashland Fourth Fridays Grand Finale Promises a Picture-Perfect End to Summer

Crowds shop, picnic, and gather at Ashland Fourth Fridays

Three fabulous Fourth Fridays have brought music, movement, and magic to downtown Ashland—and now it’s time for the fourth and final celebration. On Friday, August 22 from 5 to 8 PM, the community is invited to gather on the lawn of Ashland Town Hall for the Ashland Fourth Fridays Grand Finale. It’s the perfect summer send-off, brimming with neighborly fun, local flavor, and the unmistakable charm of the Center of the Universe.

Ashland Dance Academy performs at Ashland Fourth Fridays

The evening begins with a show of hometown talent on the Ashland Town Hall Pavilion stage, where Ashland Dance Academy will perform a series of original dance routines. One highlight? A special interpretation of “You Already Know,” the winning anthem from the 2024 Ashland Song Contest, written and performed by the brilliant Ginny Ray. As the dancers step off the stage, the Downtown Ashland Association will take a moment to reveal the grand prize winner of the 2025 Ashland Song Contest. The newest anthem of Ashland might even be performed live for the very first time.

2024 Ashland Song Contest winner Ginny Ray

Music continues to take center stage as Kayla Atanacio, winner of Hanover’s Got Talent, shares her award-winning song with the crowd. Then, beloved local favorites The Generations Trio will return to the stage, filling the summer air with the smooth sounds of classic jazz standards and reimagined pop hits until the sun sets on this final Fourth Friday.

While the stage entertains, more than 30 local artists, food makers, and small businesses will set up around the Town Hall lawn and parking lot. Shoppers will find everything from handcrafted housewares by C.G. Elliot Woodworking to fragrant blooms from Breemar Flower Farm, original canvas art by Richard Harding, and handcrafted soaps from Tierrapy Soaps. These are the kinds of goods that feel good to buy—not just because they’re beautiful, but because every purchase supports a real person in our community.

Local partners are going above and beyond to add comfort and care to the festivities. Cornerstone Church will be handing out cold bottles of water to help everyone beat the heat, and ARC of Hanover will welcome guests into their sensory-friendly tent, filled with calming tools and textures. They’ll also be offering a free thrift table, where families can browse and take home donated treasures at no cost. "The Arc of Hanover and Thrift Store are so pleased to be able to join in the festivities of this last of the 'Fourth Fridays,” says Diane Gallegos, Co-Executive Director/Mission, The Arc of Hanover. “We'll have our Mobile Sensory Tent for guests who may need a break from what can be an overwhelming environment, and we'll also have several rummage bins with items like what you would find at the quarterly Free Community Yard Sale events at our Thrift Store.”

Shaken Not Spurred’s Gourmet Grilled Cheese

As always, Ashland’s food scene is ready to impress. While local farm-to-fork favorites like The Caboose Market & Café, The Iron Horse, Ash & Olive, and The Henry Clay Inn offer unbeatable dinner views of trains rolling through the heart of town, the Downtown Ashland Association is also bringing in crowd-pleasing food trucks to keep everyone fueled right on site. Shaken Not Spurred will serve up gourmet grilled cheese sandwiches, Farmview Creamery will offer their signature cool treats, and Mama Vicky’s Lumpia and Filipino Cuisine will delight with savory BBQ skewers and sweet or savory lumpia made with care and tradition.

Families will want to pop into downtown shops like Take Away, which is staying open late for after-dinner browsing. Over at Tiny Tim’s Trains and Toys, little ones can paint Breyer Horses for free and marvel at the detailed model train displays. For those in the mood for a little fright with their fun, RED VEIN Escape is open for immersive games, plus they’re offering their Spirits of Railroad Avenue Haunted History Tour, a guided ghost walk through one of the oldest—and spookiest—corners of Ashland.

Celebrity guest photos at 110 Thompson

And don’t miss the festivities at 110 Thompson Street, home of the now-iconic “Welcome to the Center of the Universe” mural. Just after the Ashland Dance Academy performance, families could find free snacks, face painting, and photos with a special celebrity guest. Past stars have included Glenda the Good Witch, Lelio, and Stitch—so you never know who might make a surprise appearance to help say goodbye to summer.

Although this will be the final Fourth Friday of the year, it’s only the beginning of a bustling calendar of community events. Things kick off again on September 27 with the Songs from the Center of the Universe Concert at the Hanover Arts and Activities Center, and continue all the way through Ashland Train Day on April 25, 2026. Vendors who want to be part of the magic all year long are encouraged to become Downtown Ashland Association Silver Sponsors—and reserve their spot at events throughout the seasons. Learn more at ashlandvirginia.com/sponsor.

As summer winds down, the community is coming together one last time to celebrate all that makes Ashland shine. Whether you’re coming for the music, the food, the shopping, or simply to soak up the small-town joy—there’s a place for you at the Ashland Fourth Fridays finale. Find maps, parking, and more at AshlandFourthFridays.com