Win the Weekend: Build Your 4-Week AI Marketing Plan

Neighbors laugh under Your Path Counseling Center’s booth at Ashland Fourth Fridays

Are you tired of last-minute marketing panic before event weekends?

Executive Coach Dorian Cunion of Your Path Coaching and Consulting

Every month, the streets of Ashland come alive for our vibrant 4th Friday celebrations. Foot traffic peaks, energy is high, and the community gathers in the Center of the Universe. But as a local business owner or vendor, are you successfully turning that sidewalk crowd into actual storefront revenue, or are you just clearing off your sidewalk and hoping for the best?

To truly win the weekend, hope isn’t a strategy. You need a proactive roadmap, clear tactical hooks, and a repeatable system.

In this actionable marketing workshop, Executive Coach Dorian Cunion will teach you how to use the business model canvas and unlock the power of Artificial Intelligence (AI) to create a revenue-driving marketing plan.

What You Will Learn & Create:

• The One-Page 4th Fridays Blueprint: Strip away the complexity of traditional planning. You will map out your specific event goals, target audiences, operational infrastructure, and revenue targets onto a single-page strategy canvas.

• The AI Marketing Engine: Stop staring at a blank page. Learn the exact, copy-and-paste AI prompting frameworks to feed your business details into tools like ChatGPT or Gemini, instantly generating localized social media campaigns, hooks, and email copy.

• Physical Activations That Draw a Crowd: Discover experiential marketing strategies—such as sidewalk "teaser" displays, micro-events, and localized interactive contests—that organically pull casual pedestrians off the sidewalk and into your checkout line.

• The Digital Bridge: Learn how to use simple tech setups like curated QR codes and targeted social media structures to convert immediate event-day foot traffic into long-term online buyers.

• A 4-Week Social Media Calendar Blueprint: Leave with a concrete framework detailing exactly what, when, and how to post starting 30 days before the festival to build maximum local anticipation.

Who Is This Workshop For?

• Main Street retail storefronts and boutique owners are looking to maximize event hours.

• Artisans, makers, and pop-up vendors want to stand out in a crowded market.

• Local food, beverage, and service providers are looking to build strategic cross-promotions with neighboring businesses.
  
  

The Result:

You’ll walk out of this session not just with "ideas," but with a customized, AI-powered 4-week marketing roadmap built specifically for your brand. Turn your next Ashland 4th Friday into your most profitable weekend yet.

Ashland Fourth Fridays Goes Derby

Ashland Fourth Fridays in historic downtown Ashland, Virginia

Secretariat for Virginia modeling marvelous Kentucky Derby hats and styles

Ashland Fourth Fridays is trading in March showers for May flowers — and a whole lot of Derby flair. After a beloved Secretariat birthday celebration was rained out earlier this spring, downtown Ashland is making up for lost time in a big way. On Friday, May 22, 2026, from 5 to 8 PM, the Center of the Universe transforms into the center of Kentucky Derby excitement — right outside Ashland Town Hall at 121 Thompson Street, Ashland, VA. The event is completely free and family-friendly, making it the perfect springtime outing for neighbors, visitors, and horse racing fans alike.

Taking center stage in the celebration is Secretariat for Virginia, the official partner organization dedicated to honoring the legacy of the legendary Triple Crown champion who called Virginia home. Secretariat for Virginia will host an exclusive merchandise booth at the event — a rare opportunity for fans to take home officially licensed keepsakes celebrating the greatest racehorse of all time. The fun doesn't stop at shopping: Secretariat for Virginia will also award a curated gift basket to the winner of the event's signature Kentucky Derby Hat Contest. Guests are encouraged to arrive in their Derby best — the more fabulous the fascinator, the better the chances of winning.

Racing Parade presented by Ashland Dance Academy

The evening kicks off in high style with a Racing Parade presented by Ashland Dance Academy, setting an energetic and joyful tone before the main event gets underway. From there, acclaimed local act Blue Guitar takes the Ashland Town Hall Pavilion stage for a free outdoor concert that promises to be the soundtrack of the night. Whether guests are tapping their toes on the lawn or browsing the vendor lineup, live music fills the air from start to finish.

Art, craft, and food vendors will line the sidewalks of Ashland Town Hall, spill into the Town Hall Parking Lot, and stretch along Hanover Avenue — creating a festive open-air marketplace that showcases local artisans, makers, and culinary favorites. Beloved downtown Ashland shops and restaurants will also stay open late for the occasion, giving guests even more reason to linger, explore, and support the small businesses that make this community shine.

Ashland Fourth Fridays in historic downtown Ashland, Virginia

Ashland Fourth Fridays is a signature event series produced by the Downtown Ashland Association to celebrate community, local culture, and the irreplaceable spirit of life in Ashland, Virginia — a town that takes immense pride in its identity as the Center of the Universe. May's installment — with its Derby theme, Secretariat connection, live music, and festive vendors — is poised to be one of the most memorable yet.

Ashland Fourth Fridays on May 22nd is free, open to the public, and welcomes guests of all ages. The event takes place rain or shine at 121 Thompson Street, Ashland, VA 23005. Attendees are invited to follow the Downtown Ashland Association on social media for real-time updates, vendor announcements, and Derby-ready inspiration leading up to the big night.

Event At-a-Glance

What: Ashland Fourth Fridays — Derby Edition

When: Friday, May 22, 2026 | 5:00 PM – 8:00 PM

Where: Ashland Town Hall & Downtown Ashland | 121 Thompson Street, Ashland, VA 23005

Admission: Free & open to the public

Highlights: Secretariat for Virginia merchandise booth & gift basket giveaway | Kentucky Derby Hat Contest | Racing Parade by Ashland Dance Academy | Live music by Blue Guitar | Art, craft & food vendors | Late-night downtown shopping & dining

Girl Scout Cookies, and Live Music Kick Off Ashland Fourth Fridays

Spring arrives early on the streets of downtown Ashland this year. On Friday, March 27, from 5 to 8 PM, Ashland Fourth Fridays opens its 2025 season with a celebration that brings together Big Red’s Birthday weekend, the sweet tradition of Girl Scout cookie season, and a live sing-along performance that will lodge itself in your brain with the same stubborn persistence as a sleeve of Thin Mints.

At the center of the evening’s magic is a pop-up photo experience donated by Leigh Rooke, owner of Sign Gypsies Mechanicsville. Rooke is gifting Ashland Fourth Fridays custom yard sign displays throughout the entire season — a gesture as generous as it is colorful. For this first installment, guests will find a Secretariat-themed sign honoring the legendary thoroughbred’s birthday weekend alongside a cookie-themed display set up right beside the sales table of Ashland Girl Scout Troop 609. Grab a box of Samoas, strike a pose, and make a memory.

“Ashland is the Center of the Universe, and we feel the warmth and community bonds every time we come to help those in Ashland celebrate.”
— Leigh Rooke, Owner, Sign Gypsies Mechanicsville

Rooke’s connection to Ashland runs deep. Sign Gypsies Mechanicsville has shown up at Habitat for Humanity key ceremonies, sweet-sixteen celebrations, and the kind of milestone graduations from Patrick Henry High School and Randolph-Macon College that parents photograph obsessively and kids pretend to find embarrassing. The signs, she says, have a way of becoming heirlooms — framed on walls, tucked into scrapbooks, summoned each year with the familiar anticipation of “when is it coming, and what will it say?”

Victor Gottlieb performing Girl Scout Cookies

“When we attend the Habitat for Humanity homecomings celebrating the passing of the house keys to the family, I always beam with a big smile when the family wants to take pictures with our greetings. They become souvenirs in photo frames on the wall, or fill scrapbooks.”
— Leigh Rooke, Owner, Sign Gypsies Mechanicsville

If the photo spot plants a smile on your face, the live music will plant something even harder to shake. Ashland Song Contest winner Victor Gottlieb will take the stage and perform two original songs back to back: “Secretariat,” a tribute to the hometown hero of the horse world, and “Girl Scout Cookies,” an ode that may permanently rewrite the way you think about Tagalongs.

The chorus of “Girl Scout Cookies” is already earning its reputation as the earworm of the season:

“Girl Scout Cookies, I just can’t wait.
Girl Scout Cookies, they all taste great.
Girl Scouts are in town and cookies are around.
We’re glad to have you here in Ashland this year.”

Fair warning: you will not be able to stop singing “Girl Scout Cookies” for the same reason you cannot stop eating them.

Girl Scouts earning their Explore Ashland badges

Ashland Fourth Fridays has built a loyal following across Hanover County and beyond as one of the Richmond region’s most beloved free community events. Each fourth Friday from March through October — with a pause ahead of Ashland Train Day on Saturday, April 26 — downtown Ashland transforms into an open-air gathering place from 5 to 8 PM. Free live music fills the air, lawn games sprawl across the green, and Ashland Town Hall hums with local artisans, craft vendors, small business owners, and food purveyors who collectively make the case that downtown Ashland is not just the Center of the Universe but the center of everything worth doing in it.

On March 27, that universe expands to include youngest entrepreneurs selling cookies at their first public table, a birthday tribute to a legend born nearby, and a musician who turns community pride into something you can hum all the way home. Admission is free. Parking is easy. The cookies are limited, so arrive hungry.

WHAT: Ashland Fourth Fridays Season Opener — Secretariat & Girl Scout Cookie Celebration
WHEN: Friday, March 27, 2025, 5–8 PM
WHERE: 121 Thompson Street (Ashland Town Hall area)
ADMISSION: Free and open to the public

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.

Sold out

Raffle - Big Red Bash

$10.00

Enter for a chance to win two tickets to Secretariat for Virginia’s Big Red Bash cocktail party and fundraiser.

Enjoy “grazing tables” of sumptuous charcuterie and delectable desserts, a marvelous bar brimming with champagne, mint juleps, wine, and a “Big Red” beer! Live music on the patio, an artsy Silent Auction, and an exciting Horse Race Game. PLUS… a real racehorse, Pepe, who is a descendant of Secretariat!

When
Friday, March 27 from 6:00 - 9:00 pm

Where
Oakdale in Ashland. Look for the blue and white flags.

Cost
Tickets are $100/person, but you could win two for just a $10 raffle ticket! Raffle proceeds benefit Downtown Ashland Association’s non-profit mission.
The winner will receive an email from Downtown Ashland Association on Thursday, March 25, 2026.

Purchase

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.