Ali (she/her) and Kelly’s (he/they) elopement day was the perfect reflection of their relationship—laid-back, love-filled, and full of little details that made it completely theirs. From their dog Tatum in his tuxedo collar, to heartfelt letters from family and friends, to a surprise rainbow that showed up right after their ceremony, Ali and Kelly’s Highland Hideaways elopement in Grayson Highlands was nothing short of magical.
Getting Ready at Rumple’s Retreat
Most of Ali and Kelly’s day took place at Rumple’s Retreat, one of the many cozy Airbnbs that make up Highland Hideaways. The space feels like the ultimate mountain escape—warm wood interiors, a quiet and relaxing atmosphere, and even a spiral staircase (which we, of course, had to use for photos).
Ali and Kelly got ready together to kick off their elopement day. I was sure to document all of the meaningful details: Ali’s bouquet, Kelly’s boutonniere (which Ali helped pin on his lapel), Tatum’s little tuxedo bandana, their rings and ring box, and Ali putting on some last-minute makeup touches. Tatum was bouncing around the space, clearly excited for the day ahead, adding a playful, joyful energy to the room.
Portraits at Highland Hideaways
After getting ready, we started with some portraits on the Airbnb porch. As the sun started to poke through the clouds, we moved to another spot on the Highland Hideaways property for some backlit couple portraits. The soft glow of the sun made the moment feel magical, highlighting their connection beautifully.
We brought Tatum into a few shots, including a sweet moment with the three of them sitting on a bench together. These images perfectly captured the warmth, love, and playful energy of their little family.
Picnic Dinner and Reading Letters from Loved Ones
To play it safe with the unpredictable weather, Ali and Kelly’s picnic-style dinner was set up under cover on the porch. Everything—from plates and napkins to silverware and tablecloth—was rented from Blossom & Bliss, bringing a thoughtful and polished touch to the cozy outdoor setup.
For dessert, they had cookies made by Dessert Bar: some were heart-shaped with blue icing and their names written in cursive and others were white with the date (9.26.25) written in gray icing. The date cookies were dog-friendly, so Tatum could enjoy a treat too! And, of course, Dr. Pepper was included as their drink of choice—because nothing says “them” quite like it.
During the picnic, Ali and Kelly read some letters from family and friends, sharing moments of laughter and “awws” with each other. It was a warm, intimate way to connect before heading to the park for their ceremony.
Ceremony at Sugarland Overlook
As the evening light softened, we drove into Grayson Highlands State Park and headed toward Sugarland Overlook for their ceremony. The weather had been unpredictable all day—we adjusted their timeline three times due to storms—but it finally cooperated in the perfect way.
Their ceremony was beautifully simple and completely them. With the Blue Ridge Mountains as a backdrop, they read aloud more letters from loved ones. This is also when Ali got emotional, tearing up at one particularly heartfelt note—it was a beautiful moment that perfectly encapsulated the depth of love surrounding them.
Just as they exchanged rings, a light sprinkle started to fall. We had packed clear bubble umbrellas, which they used briefly during their first kiss. Instead of worrying about the rain, they embraced it, laughing together as the droplets fell.
Shortly afterward, a double rainbow appeared—perfectly framing the couple in the soft, glowing light. They left the umbrellas behind and celebrated in the rain, resulting in some of my favorite portraits of the year.
Ali and Kelly’s Love Story
Ali and Kelly are one of those couples who just radiate joy together. From the very beginning, their story has been about perseverance, patience, and finding ways to make even the most ordinary things fun. They met through a work friend during the peak of COVID. What started as a long-distance crush turned into a long-distance relationship, and once Ali graduated college and moved back to Roanoke, the rest was history.
They love spending time with friends and family, walking their dogs, cuddling with their cats, and playing tennis when they can. But what makes them truly unique is their deep love for each other and their ability to make every moment together—big or small—fun and meaningful.
Final Thoughts
From the very beginning, Ali and Kelly knew they wanted a day that reflected them—laid-back, heartfelt, and intentional. Even with the challenges of shifting weather and last-minute changes, they trusted the process and leaned into the joy of being together. From cuddles with Tatum on the porch at Highland Hideaways to heartfelt letters and a rainbow-filled ceremony at Sugarland Overlook, their day felt true to their story in every way.
Getting to document their Highland Hideaways elopement was such an honor. It wasn’t just about the details (though those were incredible)—it was about documenting a relationship built on laughter, perseverance, and the ability to make even the simplest moments fun. Ali and Kelly are the kind of couple who remind me why I do what I do.
Are you excited to start planning your Virginia elopement?
Planning your elopement should feel intentional, flexible, and completely true to you. No pressure, no stress—just a day filled with real connection and stunning memories.
I’d love to help you create a day like Ali and Kelly’s—one that’s flexible, personal, and rooted in what matters most. I’m Cameron (she/her), a Virginia elopement photographer and partial planner. My role goes beyond just taking photos—I help couples craft intentional timelines, adapt to unexpected changes, and make sure your day feels effortless.
Reach out to me today to schedule your free consultation call! Let’s turn your dream elopement into a reality. Curious about my packages and pricing options? Head over to my pricing page for more information. I can’t wait to hear from you and help you bring your vision to life!
More Resources & Inspiration for your Virginia elopement
Looking for more inspiration? Here are a few more elopements I’ve photographed that might spark some ideas:
- Nikki-Rose and Sean’s Grayson Highlands State Park Elopement
- FahTesha and Ashton’s Downtown Roanoke Wedding at Century Plaza
- Sarah and Russ’s Massie Gap Elopement in Grayson Highlands
- Kaitlin and Rob’s Martinsville, Virginia Elopement
- Melissa and Marshall’s Blue Ridge Mountain Wedding in Virginia
Are y’all in need of more planning help? I’ve got ya covered! Check out some of my free elopement planning resources below:
