The Melody of Community: Wind Gap Music’s Story

November 24, 2025

In the heart of Shepherdstown, a new kind of music shop is humming to life — one built on passion, purpose, and a deep commitment to community. Wind Gap Music, founded by husband-and-wife team Sean and Holly Alessi, is bringing something truly special to the Eastern Panhandle: a warm, judgment-free place where people of all ages can learn, explore, and experience the joy of making music. 

For Holly, music has always felt like home. “I grew up surrounded by music,” she shared. “My grandmother played organ, my dad played bass and sang — it’s been part of me for as long as I can remember.” She picked up clarinet in grade school and never looked back, going on to perform in all-county and all-state ensembles and taking private lessons at Matt’s Music in North Tonawanda. 

By age sixteen, Holly was teaching lessons herself — and she quickly realized how much she loved it. “Being in a music shop, connecting with students, watching them grow — it never felt like work,” she said. After moving to the Eastern Panhandle six years ago, her time at Ellsworth Music expanded her knowledge even further, especially on the retail and repair side. 

Over time, the dream to blend all of these experiences — performance, teaching, retail, repair, and that classic “mom and pop” music shop energy — grew into what would one day become Wind Gap Music. 

Even the shop’s name has meaning. During one of her regular walks in Harpers Ferry, Holly read about the significance of Water and Wind Gaps along the Blue Ridge and throughout West Virginia. “It stuck with me,” she said. “We love this area, and we wanted the name to reflect the place we now call home.” 

Turning that dream into reality took encouragement from all corners — friends, family, mentors, former students, and community members who believed in the vision. There were moments when Holly and Sean considered hitting pause, especially when early opportunities didn’t feel quite right. But just when they least expected it, the right space in Shepherdstown appeared — and everything fell quickly into place. 

From that moment on, the journey was a whirlwind. “There’s so much behind-the-scenes work,” Holly said, “but it’s been the most fulfilling thing we’ve ever done.” What started as a phone call to painter Kevin Brackens in a mad dash to open in two weeks has blossomed into a thriving lesson studio with 12 dedicated teachers and more than 100 students in just a few short months. 

Shepherdstown, for Holly, always felt like the right home. “It was the first place I visited when we moved here,” she recalled. “I got coffee from Garth at Lost Dog and just felt it — the vibe, the community, the energy.” It also serves both Jefferson and Berkeley counties, which have long needed an accessible local music shop. 

The biggest challenge along the way? Simply not knowing whether the dream would work. “Our motto became, ‘we’re doing it live,’” Holly laughed. “We had no idea if students would come or if teachers would want to join us — and now we’re already facing the best challenge we could imagine: needing more space much earlier than planned.” 

Balancing a new business while both Holly and Sean maintain full-time corporate careers has meant humor, hustle, and plenty of not-so-graceful juggling. “It’s not pretty,” Holly joked. “If you’ve ever seen that Great British Bake Off clip where someone drops their dessert and just scoops it up with their hands — that’s us most days. Bone apple tea.” 
Still, the work is worth it. Their full-time jobs help Wind Gap thrive while they put systems in place to lighten the load and build toward making the shop their full-time focus someday. 

Inside Wind Gap Music, visitors find a space that feels both lively and comforting. Lessons fill the rooms with music, a cozy waiting area gives families a place to gather, and a long hallway features a rotating art wall designed by both Holly’s and Sean’s dads. Their inaugural artist? Mason Ellsworth — a showcase Holly says is worth stopping in to see even if you’re not taking lessons. 

Lessons at Wind Gap are intentionally personalized. “There is no one-size-fits-all approach to teaching music,” Holly explained. “Some students thrive with structure; others need flexibility. We adapt to each student — their goals, their personality, their learning style.” 

Accessibility is a deep part of their mission. Holly and her team work with students who’ve been turned away elsewhere, including those with autism or unique learning needs. “It’s about meeting people where they are and removing judgment from the equation,” she said. 

Wind Gap currently offers lessons in piano, voice, theory, guitar, ukulele, strings, brass, winds, and early childhood music — and they fully expect their offerings to continue growing. A passion for empowering young teachers is also baked into the business model. “We want Wind Gap to be a place where teachers can grow too,” Holly shared. 

Even as they expand, Holly and Sean are committed to keeping that “mom-and-pop” feel — warm, real, and deeply rooted in people. That includes modernizing certain systems, such as post-lesson billing, which avoids unnecessary stress and cost for families while giving teachers more flexibility. “We’re meeting people where they are,” Holly said. “That’s what makes it feel like a community space.” 

Community partnerships are already underway, with plans for summer programs, jam sessions, masterclasses, collaborations with local theater groups, musical theater camps, and even recitals held in local restaurants — giving young musicians the chance to experience a real “gig.” Their early-learner program, “Munchkins,” is already a weekend favorite. 

The response from the community has been overwhelming. “I get emotional way too often,” Holly said with a laugh. “The gratitude I feel for our teachers, our students, and their families is just… huge.” Hearing phrases like “you’re doing it right,” and “we love the vibe here” has meant everything. 

Two moments, in particular, stand out for Holly. The first was their inaugural recital at the Black Box — a full house, proud families, and her father sitting in the front row as she realized how far the dream had come in just three months. 
The second was a quiet evening running back into the shop. “I could hear music coming from every room,” she said softly. “It sounded like the classic mom-and-pop music shops I grew up in. I definitely teared up. Again.” 

If Holly had to describe Wind Gap Music in three words? Realness. Heart. Groovy. 

And her favorite instrument to play? Though her dream Backun A clarinet — a gift from Sean — holds a special place in her heart, nothing quite beats the bari saxophone. “I absolutely love playing low woodwinds,” she said. “Especially in jazz. There’s just nothing like it.” 

Wind Gap Music is more than a lesson studio — it’s a creative home, a community hub, and a bright new source of inspiration in Shepherdstown. Holly, Sean, and their team have built something truly meaningful — a place where musicians of all ages can grow, connect, and discover the joy of making music.