Ashland Teen Bootcamps Support Entrepreneurs at Every Age

Divine Assist Youth Center’s Roots & Resilience Black History Celebration

The Downtown Ashland Association continues its mission of cultivating a vibrant, entrepreneurial community with the launch of the Teen Entrepreneur Bootcamp and Pitch Competition, a multi-week program designed to empower young people ages 11 to 18 with the skills, confidence, and vision to turn ideas into action.

Hosted by Divine Assist Youth Center and Sisterly Sweets LLC in partnership with the Downtown Ashland Association, the Teen Entrepreneur Bootcamp offers hands-on workshops focused on entrepreneurship, leadership development, and confidence-building. The program culminates in a Pitch Competition where participants will present their business ideas for a chance to win a share of $2,000 in cash prizes—giving teens a real-world opportunity to practice innovation, public speaking, and strategic thinking.

Taking place February 4, 12, and 26, as well as March 5 and 19 from 5:30 to 7:30 p.m. at 106 S. James Street in Ashland, the bootcamp reflects the Downtown Ashland Association’s belief that entrepreneurship is not limited by age, but fueled by opportunity, mentorship, and community support.

Divine Assist Youth Center’s Roots & Resilience Black History Celebration

“Entrepreneurship is about planting seeds early and nurturing them with the right tools and encouragement,” said Coach Antonio Miller of Divine Assist Youth Center. “When young people are given space to explore their ideas, build confidence, and be taken seriously as innovators, it changes the trajectory of their future. This bootcamp shows our teens that Downtown Ashland believes in them—and that belief is powerful.”

Divine Assist Youth Center has long been a cornerstone of youth development in the community, providing community service opportunities, mentoring, tutoring, recreational programming, and leadership-focused initiatives that help young people thrive both academically and personally. Through this partnership, participants are supported not only as aspiring entrepreneurs, but as whole individuals discovering their strengths and voices.

Sisterly Sweets LLC brings its own entrepreneurial spirit to the program. Known in Downtown Ashland for its from-scratch desserts made with fresh ingredients and thoughtfully combined flavors, the locally owned bakery embodies the creativity, dedication, and passion that define small business success. By opening its doors and sharing its experience, Sisterly Sweets offers teens a tangible example of what it looks like to turn passion into profession.

For the Downtown Ashland Association, the Teen Entrepreneur Bootcamp is a natural extension of its ongoing efforts to support entrepreneurs at every stage—from aspiring teen founders to established small business owners. By investing in youth-focused programming, the organization reinforces its commitment to economic vitality, workforce development, and inclusive opportunity in the heart of Ashland.

As the Center of the Universe continues to grow, initiatives like the Teen Entrepreneur Bootcamp ensure that the next generation of leaders, innovators, and business owners are not only welcomed—but actively championed.

For more information and to register, visit https://www.ashlandvirginia.com/teen

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.

Ashland Train Day Showcases the Power of Community 🚂✨

Ashland Train Day through the lens of Aidan Brown

Each spring, the sound of train whistles echoing through downtown Ashland signals more than passing railcars — it signals connection, celebration, and community pride. Ashland Train Day, now in its 22nd year, has become one of Virginia’s most beloved rail‑centric events, drawing rail enthusiasts, families, and visitors from around the world to the heart of the Center of the Universe.

On Saturday, April 25, from 10 AM – 4 PM, historic downtown Ashland will once again transform into a vibrant festival space where rail history, local businesses, and community spirit converge. More than 20,000 people are expected to arrive by plane, train, shuttle, bicycle, and on foot, while millions more tune in globally through livestreams, social media, print coverage, and radio storytelling.

What makes Ashland Train Day extraordinary is not just the trains — it is the remarkable collaboration behind the scenes. Sponsors, in‑kind partners, vendors, volunteers, artists, and neighbors all play a role in creating an experience that is welcoming, inclusive, and unforgettable.

A Rail Town Like No Other 🚆🌍

Raffle - 2 Amtrak Tickets

$10.00

Enter our raffle for your chance to win TWO Amtrak tickets to anywhere along the East Coast! Whether you're dreaming of a scenic getaway, a city escape, or a coastal retreat, crack open a can of Center of the Universe Brewski and climb on board! Your ticket to ride is just a lucky draw away.

🎟 Your golden ticket includes:
🚆 Two Amtrak tickets valid for any East Coast destination
🍻 $25 Center of the Universe Brewing Company Gift Card
🧢 5 Brewski Hats
📅 Redeemable for up to one year from the issue date
⚠️ Some blackout dates apply (mostly federal holidays)

Don’t miss your chance to embark on the journey of a lifetime—grab your raffle tickets now before this opportunity leaves the station! 🚉💨

Raffle proceeds benefit Downtown Ashland Association’s non-profit mission.

The winner will receive an email from Downtown Ashland Association on Friday, April 24.

Purchase

Downtown Ashland holds a rare distinction as one of the few towns in America where an active Amtrak station, operating since the 1920s, runs directly through the center of town. Powerful Amtrak and CSX trains roll past sidewalk cafés, railside dining, and locally owned boutiques filled with toys, antiques, equestrian goods, art, and gifts. For railfans unable to attend in person, the beloved Virtual Railcam offers a front‑row seat from anywhere in the world.

Ashland Train Day elevates this everyday magic into a once‑a‑year celebration that highlights not only rail history, but also the businesses, organizations, and people who make Ashland special year‑round. Through the Downtown Ashland Association’s expansive media reach — spanning digital platforms, print features, and radio partnerships like K101.2 POP Richmond’s Happy Hour Vibes — the event shines a spotlight on the community far beyond town limits.

Amtrak Virginia Helps Set the Pace 🚉💙

As a presenting sponsor, Amtrak Virginia plays a central role in Ashland Train Day, reinforcing the importance of rail travel to the event’s identity. In celebration, Amtrak Virginia is raffling off two round‑trip tickets anywhere along the East Coast, delighting attendees and underscoring the ease of arriving by train.

For many visitors, Amtrak is the preferred way to experience Train Day. Riders enjoy parking‑free travel straight into downtown Ashland, scenic views along the route, and a warm welcome as railfans wave them into the historic station. The Ashland stop is part of Amtrak Virginia’s Northeast Regional Route, connecting the town to destinations including Hampton Roads, Williamsburg, Richmond, Washington, D.C., Baltimore, Philadelphia, New York, and Boston.

Amtrak Virginia further supports accessibility by promoting traveler‑friendly fare programs, including the Virginia Anytime Fare with 15 percent savings, a student discount offering 15 percent off with valid identification, a child discount allowing one child ages two to twelve to ride for half price with each paying adult, and Share Fares, which provide group discounts of up to 60 percent for parties of eight or more.

Community Partners Bring the Experience to Life 🤝🎉

Raffle - Wild Bill's Mugs

$5.00

🚂 All aboard the refreshment express! 🥤
Wild Bill’s Soda is rollin’ into town for Ashland Train Day on April 25 with craft sodas made for slow sippin’ and fast refillin’! 💨💛

We’re rafflin’ TWO legendary Wild Bill mugs—and the lucky winners get FREE refills all Train Day long! 🍒🍋🍉
That’s one refreshin’ ride you don’t wanna miss.

🎟️ Enter now for $5
Then giddy up to the food court and sip like a soda sheriff. 🤠🥤

Raffle proceeds benefit Downtown Ashland Association’s non-profit mission.

The winner will receive an email from Downtown Ashland Association on Friday, April 24.

Purchase

Ashland Train Day comes to life through generous in‑kind contributions that support everything from volunteer care to entertainment and accessibility. Chick‑fil‑A ensures volunteers start the day energized by providing a complimentary breakfast buffet inside the Dominion Energy Innovation Center.

Families are invited to explore the lively Kids Zone inside the Ashland Branch Library, sponsored by New Community Church. The space features a looping kiddie train and an inflatable obstacle course and bounce house made possible through the enthusiastic in‑kind support of On The Fly Events VA, known for delivering engaging, high‑quality event experiences across the region.

Music fills the air thanks to Center Street Sound Co, which donates DJ services throughout the day inside the Ashland Town Hall Pavilion. Just outside, Free Jambalaya hosts a free live sidewalk concert near its Slipped Disc studio beside the Ashland Theatre, adding rhythm and energy to the streets of downtown.

Inclusivity remains a cornerstone of the event, with the Autism Society of Central Virginia offering a sensory‑friendly, quiet space overlooking the trains for guests seeking a calmer environment. Adding a dash of fun and fundraising, Wild Bill’s Soda is raffling off two custom Ashland Train Day mugs — complete with free refills all day — with proceeds supporting the Downtown Ashland Association and helping keep Train Day free for everyone.

Vendors, Sponsors, and Neighbors Power the Day 🛍️🚂

Downtown Ashland’s intimate, walkable layout makes vendor participation especially impactful. Vendors enjoy meaningful visibility, curated placement throughout town, and the opportunity to connect directly with thousands of engaged attendees. Participation also opens the door to future Downtown Ashland Association events and ongoing promotional support.

Revival Spa vending at Ashland Train Day

Sponsorship opportunities further amplify community involvement. Silver Sponsors, including organizations such as Giving Hope Lawn Management and Macaroni Kid, receive enhanced visibility, including advertising on the Ashland Theatre’s iconic silver screen. Vendors interested in participating specifically in Ashland Train Day may apply through AshlandTrainDay.com, where invited vendors select preferred locations and pricing tiers ranging from $50 to $500 based on placement.

A Celebration Made Possible by Community 🚦✨

Ashland Train Day stands as a powerful example of what happens when a community comes together. From sponsors and in‑kind contributors to vendors, volunteers, musicians, nonprofits, and neighbors, each participant helps create an event that honors rail history while celebrating the present‑day spirit of Ashland.

As trains continue to roll through the Center of the Universe, Ashland Train Day remains a joyful reminder that collaboration, creativity, and community pride are what truly keep the town — and the event — moving forward.

More information about Ashland Train Day, including vendor and sponsorship opportunities, is available at AshlandTrainDay.com

Conductor Train Day Sponsor

$500.00

Become a sponsor for Downtown Ashland Association’s signature event - Ashland Train Day! Reach over a million viewers and 20K people in person when you become a donor to our railroad extravaganza!

Conductor Sponsors increase impact with a $500 donation, securing a dedicated social media post and a month of ads on the iconic Ashland Theatre big screen.

Purchase

Engineer Train Day Sponsorship

$1,000.00

Become a sponsor for Downtown Ashland Association’s signature event - Ashland Train Day! Reach over a million viewers and 20K people in person when you become a donor to our railroad extravaganza!

For our esteemed $1,000 donors, enjoy a comprehensive package including media promotion reaching 1.5M, a featured blog article on the Downtown Ashland Association website, recognition in our highly anticipated Get Centered Newsletter reaching over 4K readers, and a branded photography package capturing the essence of your support. 

Purchase

Stationmaster Train Day Sponsor

$5,000.00

Become a sponsor for Ashland’s signiture event - Ashland Train Day! Reach over a million viewers and 20K people in person when you become a donor to our railroad extravaganza!

For a $5,000 donation, Stationmaster Sponsors receive a dedicated Facebook and Instagram post highlighting your business or charity, reaching an audience of over 20K engaged viewers.

Purchase

Office Space Now Available in the Heart of Downtown Ashland

If your business is searching for a workspace with charm, connectivity, and unbeatable location, your next stop may be 100 South Railroad Avenue—right along the tracks in the heart of historic downtown Ashland. Thanks to Railroad Mall Properties, several office suites are now available in one of the most walkable, recognizable, and well-loved corridors in the Center of the Universe.

This prime location places your business steps away from the Town of Ashland Visitor Center, where you can travel with Amtrak Virginia, making regional travel a breeze for commuters and clients alike. Outside your door, you’ll find curated local shopping like Tiny Tim’s, vibrant public art like America’s longest railroad mural along The Caboose Market, and some of the region’s best farm-to-fork feasts like Ashland Meat Co.—perfect for lunch meetings, coffee breaks, or after-hours connections.

Available suites include a range of sizes to fit businesses at every stage:

• The Blackhawk Space (Suite #4)
  Approximately 1,000 sq ft, featuring three private offices and a reception area. Located on the Railroad Avenue side of the building, directly across from Edward Jones. Available January 1.

• Suite F
  Approximately 500 sq ft, offering an open workspace with an interior office, plus two hallway-facing windows. Located toward the back of the building on the right.

• Suite D2
  Approximately 225 sq ft, situated near the loading dock with two hallway-facing windows—ideal for a quiet, focused operation.

• Suite #5
  Approximately 125 sq ft, conveniently located just inside the parking lot entrance. A perfect landing spot for a solo professional or satellite office.

With historic character, modern convenience, and a front-row seat to one of Virginia’s most beloved small towns, these offices are a rare opportunity to put your business on the right track.

Now boarding: your next chapter in Downtown Ashland.

Interested in Leasing?

To learn more about availability or to schedule a tour, please contact:

Melanie Randall
Railroad Mall Properties
100 South Railroad Avenue
Ashland, VA 23005

p: (804) 798-1451
f: (804) 798-7072