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.

Raffle - Big Red Bash Raffle - Big Red Bash
Raffle - Big Red Bash
$10.00

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.

Wish You Were Here Variety Show Returns February 28

The Wish You Were Here Variety Show returns on Friday, February 28,  bringing an evening of live music, comedy, and storytelling to the Cultural Arts Center at Glen  Allen. Created and hosted by Bryan Dupuis, the show blends professional artistry with a deep commitment to community, offering audiences a night that is both entertaining and meaningfully human. 

The February 28 performance features a dynamic lineup including Garden Variety String  Band, Drew Dunbar, Justin Paciacco, and the COTU Players, whose sketch comedy adds a playful and unpredictable element to the night. 

Wish You Were Here Variety Show

Part concert, part comedy showcase, and part storytelling experience, Wish You Were Here is intentionally designed to feel more like a shared gathering than a traditional performance— inviting audiences to laugh, reflect, and experience something together. 

“The heart of Wish You Were Here is creating space for people to feel connected—to the artists,  to each other, and to the stories that remind us there’s a better story unfolding all around us,” said  Dupuis. 

A Collaborative Creative Process 

Each show is built collaboratively with the featured artists, allowing performers to bring their authentic voice and personality to the stage rather than fitting into a rigid format. 

“I don’t think of this as booking acts as much as curating conversations,” Dupuis explained.  “When artists are given room to be fully themselves, the audience feels that honesty  immediately.” 

Highlighting Community Impact 

In addition to showcasing live performance, the February 28 show will highlight the work of  Comfort Zone Camps, a nonprofit organization dedicated to supporting children who have experienced the death of a parent, sibling, or primary caregiver. 

Comfort Zone Camp

“One of the defining values of Wish You Were Here is using creativity to shine a light on people and organizations doing meaningful work,” said Dupuis. “Comfort Zone Camps is creating space  for kids to grieve, heal, and feel understood—and that mission aligns beautifully with what this  show is about.” 

Throughout the evening, audiences will learn more about Comfort Zone Camps and the impact of their work, reinforcing the show’s commitment to storytelling that extends beyond the stage.

An Audience-Centered Experience 

Audience response has become one of the most distinctive aspects of the Wish You Were Here experience, with laughter often giving way to moments of quiet attentiveness. 

“One of my favorite moments is when the room shifts—from laughing out loud to being completely still because a song or story just landed,” Dupuis said. “You can feel everyone  leaning in together.” 

Attendees frequently describe the show as uplifting and refreshingly different. 

“People often tell us, ‘I didn’t know I needed this,’” Dupuis added. “That’s always the hope— that people leave lighter than they arrived.” 

Rooted in Community 

Beyond entertainment, Wish You Were Here exists to celebrate creativity, generosity, and hope within the local community. 

“The goal isn’t just a great night out,” said Dupuis. “It’s reminding people that beauty, humor,  and compassion are already present around us—and worth paying attention to.” 

The February 28 performance promises a fresh mix of music, comedy, and storytelling, all delivered with warmth, humor, and heart. 

Event Details:
What: Wish You Were Here Variety Show  
When: Friday, February 28, 7PM  
Where: Cultural Arts Center at Glen Allen  
Tickets: wishyouwereherelive.com 

The Hunt Continues in Downtown Ashland ✨🍫

Downtown Ashland has officially entered its main character era, where the soundtrack swells, the villains don’t dare to even lurk in the shadows, and destiny arrives wrapped in milk chocolate. The Gonna Be Golden Chocolate Bar Hunt is unfolding like a K-Pop Demon Hunter saga — dramatic, joyful, and powered entirely by community love.

The mission is simple but the thrill is real: four Golden Tickets are still hidden somewhere downtown, waiting for the next hero to discover them. Each participating business is guaranteed to hold a Golden Ticket among their Gonna Be Golden bars, which means every stop is a new chapter. If you don’t strike gold right away, consider it an invitation to linger, explore, and fall a little more in love with everything Ashland has to offer.

Barry Farmer of The Barry Farmer Morning Show happened upon their Golden Ticket at Ash & Olive

Already, a few legendary moments have been written into Golden Ticket lore. Ashland Dance Academy sold out of their bars at lightning speed, where a tiny dancer with unmistakable star power uncovered the Golden Ticket and chose to exchange it for a $50 gift card to Tiny Tim’s Trains & Toys. Ash & Olive set the trend, selling out completely on their first night when a crowd of neighbors poured into the delicious restaurant. When Barry Farmer of The Barry Farmer Morning Show happened upon their Golden Ticket and claimed the Ash & Olive gift card reward like fate itself had tuned in.

When Wagner Jewelers sold out of their chocolate bars, their Golden Ticket found a thoughtful home at Chirp, where the winner stocked up on bird seed to help feathered friends flourish through the winter months. Over at Miss Timmie’s, the Golden Ticket winner leaned fully into the moment, using their prize to select beautifully curated antiques that felt as timeless as the story itself.

Now, the spotlight shifts — because the hunt is far from over.

Miss Timmie’s Golden Ticket winner

At Homemades by Suzanne, a full basket of chocolate bars remains, along with a Golden Ticket waiting patiently among fresh fare, boxed lunches, catering favorites, gift baskets, homemade breads, and bakery treats made from scratch with love. Just down the street, RefunkIt hums with creative energy, offering carefully chosen funk, handcrafted art, and gifts from Virginia and beyond, plus a still-undiscovered Golden Ticket tied to a mystery prize guaranteed to be one of a kind.

Tiny Tim’s Trains & Toys continues to feel like a wonderland straight out of a collector’s dream, filled with toys and model trains in Ashland’s historic downtown, and with a few bars still left, the next Golden Ticket reveal could happen at any moment. Chirp, beloved for its special formulas, feeders, and all things birding that support native species and backyard habitats, has already awarded its prize — yet its Golden Ticket remains hidden, quietly waiting for the right person to notice.

Adding a bold new beat to the story, Los Regios Tienda Latina has joined the hunt with their own stack of Gonna Be Golden Bars and a Golden Ticket just waiting to be found. A visit there promises far more than chocolate alone, with warm fresh tortillas, international candies, heavenly pastries, groceries, colorful piñatas, and festive party supplies filling the shelves. Their highly acclaimed food truck adds another layer of magic, serving authentic Mexican dishes that transport taste buds straight to the heart of Mexico for breakfast, lunch, and dinner.

Ashland Dance Academy golden ticket winner

Once a Golden Ticket is discovered, the ending is yours to choose. Winners can redeem their ticket for a free month of dance classes from Ashland Dance Academy, the ultimate Homemades Snack Pack from Homemades by Suzanne featuring chicken salad, rolls, and chocolate chess pie, or a $40 basket of heartfelt treasures from Take Away, Ashland’s newest card and gift shop. Those drawn to the unexpected may find their way back to RefunkIt, where a mystery prize awaits — eclectic, thoughtful, and impossible to duplicate.

Joining the adventure is easy. Simply visit participating downtown Ashland locations, pick up a Gonna Be Golden milk-chocolate bar, and scan the QR code on the back of the Minuteman Press of Ashland wrapper to pay — or hand over cash if you prefer. Every purchase doubles as a donation to Downtown Ashland Association, supporting free community events, entrepreneur resources, and powerful media that continues to uplift Ashland’s Main Street.

This golden saga is made possible thanks to the generosity and creativity of sponsors Ashland Dance Academy and Minuteman Press of Ashland, who donated their talents to bring the Gonna Be Golden Chocolate Bars to life. With every bar purchased, shoppers become part of the story — champions of small businesses, believers in community, and heroes in a downtown worth celebrating.

The bars are disappearing. The tickets are hiding. The music is building.

The only question left is whether you will be the next to go golden in Downtown Ashland.

Funding Meets Fashion at Style Cents: Women’s Career Brunch in Ashland

Dr. Karen Totten White speaking at Women Building Bridges to Business

Funding meets fashion at Style Cents: Women’s Career Brunch, an empowering, thoughtfully curated experience designed to support women entrepreneurs in building confident, sustainable businesses—inside and out. Hosted in partnership with the Downtown Ashland Association, the brunch brings together financial strategy, personal branding, and community connection during Black History Month.

Buffet by Around the Table inside the Gathering Place

Taking place Saturday, February 28 from 9:30 a.m. to 1:00 p.m. at The Gathering Place (155 Junction Drive, Ashland), Style Cents will feature holistic presentations from Dr. Karen Totten White of Emerge New Unlimited and award-winning wardrobe stylist and image consultant Anetra Byrd. Guests will enjoy a buffet brunch by Ashland’s soul food favorites, Around the Table, while engaging in meaningful dialogue, learning, and relationship-building.

“At every stage of entrepreneurship, women are balancing visibility, credibility, and financial responsibility,” said Dr. Karen Totten White, Financial Strategist and Business Growth Consultant. “Downtown Ashland Association understands how important it is to create spaces where women can grow confidently and strategically. This collaboration was inspired by a shared commitment to equipping women with real-world tools, financial clarity, and a professional presence that directly impacts business growth, leadership, and long-term success.”

Dr. Karen Totten White speaking at Women Building Bridges to Business

Dr. White’s session will focus on aligning financial decisions with business goals while strengthening confidence and leadership presence. “I want our guests to leave feeling confident, commanding, and committed,” she shared. “They’ll gain practical financial insights, mindset shifts, and style awareness that support stronger decision-making, increased income potential, and a more intentional personal brand.”

Central to the brunch is the powerful connection between money and image. “For entrepreneurs, our brand is our first impression,” Dr. White explained. “Financial literacy gives us the power to invest wisely in ourselves and our business, while fashion supports confidence, authority, and credibility. When we understand how to manage our money and present ourselves intentionally, we position ourselves for greater opportunities and sustained career growth.”

Anetra Byrd, Wardrobe Stylist, Image Consultant, and Lifestyle Architect

Joining Dr. White is Anetra Byrd, Wardrobe Stylist, Image Consultant, and Lifestyle Architect, whose work centers on authenticity, alignment, and intentional presence. “This partnership is a natural alignment of values,” Byrd said. “Ashland is a town built on authenticity, community, and intentional presence—the very principles at the core of my work.”

Byrd emphasized the importance of image in a close-knit community. “In a town like Ashland, your image is an extension of your credibility,” she said. “Whether you’re a shop owner, a professional, or a community leader, how you present yourself impacts how you’re perceived—and ultimately, how effectively you can serve and grow.”

Her presentation will guide attendees through a personalized framework for building a wardrobe that supports both professional goals and personal identity. “This isn’t just about what to wear,” Byrd explained. “It’s about creating harmony between your inner identity and your outer expression. My goal is to replace wardrobe stress with lasting clarity, so women can move through their day with confidence—whether they’re meeting clients, collaborating locally, or stepping into leadership roles.”

Both speakers highlighted the significance of hosting Style Cents during Black History Month. “Black History Month is a reminder that progress is built through knowledge, resilience, and strategic action,” said Dr. White. “The skills shared in this session—financial literacy, intentional planning, and self-presentation—help women define their futures on their own terms and build legacies for tomorrow.”

Byrd echoed that sentiment, noting the role of style in self-definition and legacy. “Style has long been a medium for claiming identity and space,” she said. “The skills we’ll cover are about curating a personal narrative with intention. In Ashland, where visibility and connection matter, how you present yourself shapes how you’re remembered and the opportunities you attract.”

Style Cents: Women’s Career Brunch invites women entrepreneurs, professionals, and leaders to invest in themselves, connect with like-minded peers, and leave with actionable tools to support long-term success.

Event Details
Saturday, February 28
9:30 a.m.–1:00 p.m.
The Gathering Place, 155 Junction Drive, Ashland, VA
  Free registration: https://www.ashlandvirginia.com/stylecents

Ashland Teen Bootcamps Support Entrepreneurs at Every Age

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.

“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