On The Fly Tapsters

Jennifer Cumming is the owner of On The Fly Tapsters.

Let's get to know Jennifer.

What’s your story?

My path into this business has been anything but linear. I originally planned to go to medical school—I studied chemistry and religious studies—but life had a different rhythm in store. I chose to homeschool our three children and travel alongside my husband during his military career, which opened up so many unexpected chapters.

Along the way, I’ve always stayed connected to creativity. I trained in ballet for years and still find peace in watercolor painting. Those outlets kept me grounded through the transitions of motherhood, caregiving, and constant change.

After my mother suffered a stroke, I became her full-time caregiver. In that intense season, I enrolled in bartending school—not because I needed a new career, but because I needed something of my own. Something creative. Something that reminded me of who I was outside of caregiving and service to others.

That decision sparked something. I fell in love with the craft, the connection, and the opportunity to bring people joy. What began as a mobile bartending company grew into something so much more—full-service catering, curated cocktail experiences, and a business built on heart, intention, and hospitality. Every part of my background—science, art, motherhood, movement—shows up in how we create, serve, and connect. I’m also currently pursuing my Master’s in Nutrition to better support our meal prep clients and those looking for real, sustainable guidance in feeding themselves and their families well.

What inspired you to start your business?

It wasn’t financial need that led me here—it was a desire to create something meaningful. My husband has always supported our family, but I felt a strong pull to build something of my own. As our business has grown, so have our goals. My husband will be retiring this spring after over 20 years of military service, and one of our shared dreams is for him to transition into the family business full time. That has become both a personal and financial goal we’re working toward together.

How has your unique identity contributed to your business?

Everything about who I am shapes the way we operate. My background in science brings precision to the process; my years in ballet and love for painting influence the way I approach aesthetics and detail. My experiences as a mother, a caregiver, and a military spouse taught me adaptability, patience, and empathy. We lead with those values in everything—from how we craft menus to how we treat our clients and team.

How do you ensure that your business maintains a welcoming and inclusive environment for all customers?

We start by listening. Every client has a unique story, and we believe hospitality should reflect that. Whether it’s accommodating dietary needs, respecting cultural traditions, or just making sure every guest feels at ease, we prioritize kindness, flexibility, and intention. We want everyone who works with us to feel seen, respected, and celebrated.

Why did you decide to expand your business in Fredericksburg?

Fredericksburg felt like the right fit from the beginning—rich in history, community-oriented, and full of creative energy. When the opportunity came to open a commercial kitchen here, it felt like more than just growth—it felt like coming home. This space allows us to not only serve our clients more efficiently but also support other food entrepreneurs and create something sustainable for the community.

What is your favorite part of owning a business in Fredericksburg and being a part of this community?

The people, hands down. There’s a sense of pride and genuine support that’s hard to find elsewhere. We’ve met so many wonderful neighbors, clients, and collaborators. Whether we’re catering a small backyard wedding or participating in a community event, there’s always a sense of connection and purpose. It’s a beautiful place to build something meaningful.

How do you keep going when times get tough?

I remind myself of the “why.” This business was built from a place of purpose and service, and that keeps me grounded. I lean on my faith, my family, and my incredible team. I also take time to slow down and reconnect with simple joys—watercolor painting, tending to my chickens, and finding peace in the everyday moments. That’s often where clarity and inspiration return.

If you could share one message with the community, what would it be?

Support each other. Whether you're chasing a dream, starting a business, or just trying to make it through the week—community matters. Show up, be kind, and don’t be afraid to create something a little outside the box. Some of the most beautiful things come from unexpected beginnings.

You can find Jennifer at 451 Central Rd., Unit D.

Visit their website to view their services and menus.

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