Williamsburg VA Engagement Photos

There’s something extra special about engagement sessions that happen in the place where a couple’s story began—and this one? It’s a perfect example. Kayla & Bob’s Williamsburg VA engagement photos were full of charm, nostalgia, and a whole lot of love.

Set against the historic beauty of Colonial Williamsburg and the familiar corners of William & Mary’s campus, their session felt like stepping into a personal rom-com-meets-college-flashback (minus the awkward freshman dorms).

A Story That Starts with Music and a Little Scheming

Kayla and Bob first crossed paths through the William & Mary Choir, but it wasn’t until sophomore year—at a welcome event—that they went from familiar faces to finally talking. They had mutual friends, neighboring dorms, and an uncanny ability to “coincidentally” show up at the same places at the same time (wink). Spoiler: friends did some behind-the-scenes matchmaking magic, and it worked.

Their first date? A perfectly-planned dorm-room binge of How to Get Away with Murder, complete with a spotless room and nervous chatter from Kayla before Bob made the first move.

From Treehouses to Trailheads

Since then, these two have shared everything from anniversary getaways in a literal treehouse vineyard to an off-road proposal adventure in Lexington, Virginia. The engagement moment? A mountaintop picnic with a waterfall hike beforehand. Neither of them can quite remember what Bob said—just that it was perfect.

Returning to Where It All Began

For their engagement photos, Kayla & Bob returned to the scenes of the early chapters of their relationship—Crim Dell Bridge, the Wren Building, the sunken gardens. These Williamsburg VA engagement photos weren’t just about capturing pretty backdrops—they were layered with memories:

• The walks home from choir
• The first text with just the right emoji
• The quiet in-between moments that built their relationship

We explored both old campus and a few Colonial Williamsburg gems, and their natural chemistry (and playful side) made every shot easy and authentic. Even though they claimed they’re not naturals in front of the camera, you’d never know it.

Adventurous, Thoughtful, and All In

As a couple, Kayla & Bob are equal parts fun-loving and grounded. They love hiking, wine tasting, podcast-listening, and cozy movie nights with their extremely vocal cat. They’re planners, deep feelers, and lifelong learners. And together, they’re building a life that blends tradition, curiosity, and joy.

Their fall Williamsburg VA engagement session was everything it should be: meaningful, relaxed, and filled with the kind of laughter and connection that only comes from knowing each other deeply.

Kayla & Bob—thank you for trusting me to capture this chapter of your journey in a place that holds so many memories. I can’t wait to see you again on your wedding day!

See more from their Williamsburg VA engagement photos below!

Love stories like Kayla & Bob’s never get old. If you’re dreaming up your own engagement session full of meaning and charm, let’s make it happen. Reach out here!

Alexis El Massih is a wedding and portrait photographer serving Washington DC, Maryland, Virginia and Greece Destinations.

---

Related Posts