Meet Jessica Heddings

Alright – so today we’ve got the honor of introducing you to Jessica Heddings. We think you’ll enjoy our conversation, we’ve shared it below.

Jessica, so many exciting things to discuss, we can’t wait. Thanks for joining us and we appreciate you sharing your wisdom with our readers. So, maybe we can start by discussing optimism and where your optimism comes from?

My optimism really comes from a mix of legacy, determination, and survival. I’m the third generation running Island View, so I’ve seen firsthand the ups and downs that come with keeping a family business alive. That history gives me perspective — if my family could build and preserve this place through challenges, I know I can keep moving it forward.

Running a family business — especially one that’s been around for generations — means there are plenty of moments where it would be easier to walk away. But for me, optimism isn’t about ignoring challenges; it’s about believing there’s always a way forward if you’re willing to adapt and problem-solve. Every challenge we face at the venue is also an opportunity to refine how we serve people, and I think holding onto that perspective keeps me steady and motivated.

At the same time, I know there’s a fine line between survival and not knowing when to quit. That’s something I stay really aware of. I try to check in with myself constantly — is this a situation where I need to push through, or is it a moment to pivot? I don’t see quitting as failure; I see it as part of being strategic. So my optimism isn’t blind faith. It’s grounded in resilience, in being willing to fight for what matters, but also in being honest enough with myself to know when something needs to shift.

Thanks, so before we move on maybe you can share a bit more about yourself?

Island View Waterfront has been in my family for three generations, but it’s never been about the business — it’s always been about the moments we get to help create. My grandparents started it decades ago, and now I’m the third generation to take care of it. When I was growing up, this place wasn’t just a business — it was where we celebrated birthdays, crab feasts, weddings… all of it. So when I stepped into the role of running it, I knew I wasn’t just keeping the lights on, I was carrying forward a space that already holds so many stories.

What I love most about what I do is making the process easy for everyone. I try to solve problems before anyone even knows there’s one — that’s what I mean by high-touch, sometimes even unreasonable hospitality. Our couples and clients are usually the type who want their day to feel like them — relaxed, fun, memorable — and Island View makes that possible. You can have a wedding weekend with lawn games and late-night fires by the water, or a simple, cozy party where it feels like all your favorite people just came together at the best spot in town.

Right now, I’m focused on expanding that feeling of ease and connection. We’ve been growing what Island View offers — from vendor partnerships that make planning simpler, to our private café for events, and even Island View Kayaks for guests who want a little adventure on the water. My vision is to create more than a venue; it’s really about building a full Chesapeake Bay experience where people feel cared for, relaxed, and free to enjoy the moment.

At the end of the day, what I hope people know about us is that you don’t have to choose between something beautiful and something that feels real. Island View is for the kind of moments where you look around and think, ‘This is it.’ That’s what keeps me showing up every day.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

If I had to pinpoint the three qualities that shaped my journey, I’d say resilience, attention to detail, and empathy — but honestly, they all come back to one thing: faith in the process.

Resilience is about leaning into the hard. Running a family business, especially one that’s been around for generations, isn’t easy. There have been moments where it would have been way simpler to walk away, moments where everything feels stuck and heavy. But I learned early on that you can’t let yourself get stuck in the suck. You have to have faith that pushing through, even when it’s messy, will lead to a way forward. My advice for people starting out: embrace the hard parts. Sit with them. Learn from them. They’re what shape you and your work in ways that smooth sailing never will.

Attention to detail comes from wanting to make the process effortless for others. I try to solve problems before anyone even knows they exist — that’s high-touch hospitality at its core. Every small thing matters, and if you can get the details right, you create experiences that feel seamless and personal. Early on, start noticing the little things and take pride in making them perfect; it compounds in ways you can’t imagine.

Empathy is what makes all the hard work matter. Understanding the people you’re serving — their excitement, their nerves, their vision — lets you turn a day into a memory. My advice: really listen, watch, and ask questions. See the world through their eyes. That’s what turns effort into connection, and connection into trust.

All of these together — resilience, detail, empathy — are grounded in faith: faith in yourself, in your work, and in the process. If you can hold onto that while leaning into the hard, the tough moments stop being obstacles and start being opportunities.

How can folks who want to work with you connect?

Yes — I’m always looking to connect with folks who share a love for creating memorable experiences. That could be wedding and event vendors who value quality and reliability, creatives like photographers or florists who are looking for a space to bring their vision to life, or even small local businesses and entrepreneurs who want to collaborate on unique events or experiences.

I’m also really interested in corporate partnerships — especially with companies that want to celebrate their teams, host retreats, or give back in a way that supports our local community and the Chesapeake Bay. Entrepreneurship can be lonely, so I’m especially drawn to folks who want to support and grow each other, not just themselves. I want partnerships where everyone brings their skills and energy, and we help each other shine — whether that’s through events, retreats, corporate collaborations, or creative projects.

It’s important to me that our collaborations not only create meaningful experiences but also strengthen the place we call home. I’m drawn to people who are solution-oriented, passionate about what they do, and excited to bring a little creativity and fun to the table. If anyone reading this feels like we’d be a good fit to collaborate, the easiest way to connect is to reach out via email or through our website. I love hearing ideas, brainstorming ways to make things happen, and seeing how we can build experiences together that people will actually remember.

Contact Info:

• Website: https://www.islandviewwaterfrontevents.net
• Instagram: https://www.instagram.com/islandviewwaterfrontvenue/
• Linkedin: https://www.linkedin.com/in/jessica-heddings-848597123/
• Other: TikTok: https://www.tiktok.com/@islandviewwaterfront

Image Credits

https://www.laurenslinephoto.com
https://georgiaalexzandriaphoto.mypixieset.com
https://www.instagram.com/pocketwatchphoto/