From Camper to Crown: Cherry on Top’s Journey in Shenandoah County

Sparkle and Sequins: Johanna Pearson Is Dressing Shenandoah Valley One Dream at a Time

In this episode of The Valley Today's Tourism Tuesday Shenandoah County edition, host Janet Michael and co-host Kary Haun from Shenandoah County Tourism visit Ruby Mae's to talk with owner Johanna Pearson about the newest addition to her Cherry on Top empire. 

From Camper to Storefront

When Johanna Pearson was nine years old, she fell in love with a sparkly dress at her first pageant. Two decades later, she has turned that childhood dream into two thriving boutiques in the heart of Strasburg, Virginia — and she is just getting started. Johanna launched her business in 2022 with nothing more than a renovated camper and a passion for fashion. She traveled to local fairs and festivals, debuting at Vintage in the Valley before making Mayfest and the Shenandoah County Fair staples of her calendar. The camper was small, but the vision was big.

Then, in early 2023, an opportunity knocked. Johanna heard about a vacant storefront at 132 East King Street in Strasburg and didn't hesitate. "Give it to me," she said. She renovated the space herself and opened Cherry on Top just in time for Mayfest, making the festival both her origin story and her grand opening. The boutique quickly became a destination for women seeking hand-selected clothing, locally made accessories, hypoallergenic earrings, and seasonal finds — everything from casual basics to statement pieces.

Crossing the Street to Ruby May's

As Cherry on Top flourished, Johanna's ambitions grew right along with it. She soon set her sights on a second storefront directly across the road at 115 East King Street — and Ruby Mae's was born. Named after her great-aunt Ruby Mae, the woman who first took her shopping as a little girl and sparked a lifelong love of fashion, the shop is a full-service formal wear boutique offering prom dresses, pageant gowns, cocktail attire, wedding dresses, and tuxedo rentals.

"I watch Cherry on Top from Ruby Mae's front door, and I watch Ruby Mae's from Cherry on Top's front door," Johanna laughs. "I get a lot of mileage crossing the road."

The store currently holds over 200 dresses, and Johanna carefully curates each one with a specific customer in mind. To protect her shoppers, she registers every dress by school, ensuring no two students from the same event walk in wearing identical gowns.

A Bridal Experience Like No Other

Beyond prom season, Ruby Mae's is quickly making a name for itself in the bridal market — and filling a gap that has long existed in the Shenandoah Valley. For years, local brides had to drive an hour and a half in any direction just to try on wedding gowns. Now, they don't have to.

Through a partnership with Casablanca Bridal, Johanna offers fully custom wedding gowns. Brides can mix and match necklines, sleeves, and embellishments from different styles, and their dress is made to their exact measurements — heels and all. Custom veils crafted from the same lace as the gown are available too. For brides who need something sooner, quick-turnaround options arrive in as little as two weeks.

Walk-ins are welcome Wednesday through Saturday from noon to six, but Johanna also offers bookings by appointment seven days a week. Those who reserve a time slot get the full experience: a reserved dressing room, pre-selected styles, and snacks for the whole party.

The Sparkle Challenge: Empowering the Next Generation

Johanna's story is not just about dresses — it's about what dresses represent: confidence, possibility, and the courage to dream big. That belief drives her mentorship program, the Sparkle Challenge, which she developed as her pageant platform and continues to this day.

Through the program, Johanna guides young women through career readiness, resume writing, interview prep, and volunteer opportunities. In the early days, she would dress them from her own closet for pageants, job interviews, and public appearances, showing them firsthand that professionalism and self-expression go hand in hand.

"I want to be the role model I had for these younger girls," she says. "Women can be whatever they want — whether that's owning a dress store or being an astronomer."

Her own role model? Her great-aunt Ruby Mae, of course — who, at the time of this interview, could be found working at Cherry on Top most weekday afternoons, welcoming customers alongside a circle of loyal friends.

A Hat Bar, a Laser, and What's Next

If two boutiques and a mentorship program weren't enough, Johanna also runs a custom hat bar. Using wide-brim western hats, ribbons, lace, feathers, flowers, and a laser engraver, she creates one-of-a-kind wearable art — personalized with logos, initials, and custom designs. The hat bar travels to local breweries, vineyards, and events in a second renovated camper, and it pops up monthly at Box Office Brewery from April through August.

As for what comes next? A dedicated hat bar storefront may not be far off. "Whenever there's one available," Johanna admits with a grin, "I wouldn't be against it."

Shop Local, Dress for Every Moment

Cherry on Top and Ruby Mae's are open Wednesday through Saturday, noon to six, with Sunday hours and appointments also available. Both shops maintain active online stores and social media pages where customers can browse inventory before visiting in person.

In a valley where formal wear options have historically been scarce, Johanna Pearson is not just filling a niche — she is redefining what it means to dress for the moments that matter most.