March 31, 2026
Real Weddings
Williamsburg Winery Wedding | Kelly & Ryan
Kelly and Ryan’s Williamsburg Winery wedding in Williamsburg, VA was the perfect mix of coastal blue vibes, tradition, and a laid-back energy that made the whole day feel effortless. As a candid wedding photographer, I was there to capture all the real, in-between moments, and this day delivered from start to finish.
From their ongoing Clemson vs. South Carolina football rivalry to their shared love for their dog Pepper (who has very clearly chosen a favorite), their personalities were woven into every part of the celebration.
Engagement Session
Since Pepper was a bit too shy to make an appearance on the wedding day, she absolutely stole the spotlight during Kelly and Ryan’s engagement session. Kelly showed off her Gamecocks pride while Ryan repped his Clemson Tigers, and Pepper kept things neutral as the true MVP with her two-sided bandana. It was the perfect nod to their ongoing rivalry and such a fun way to include their favorite girl in this season of their story.
Getting Ready and Pre-Ceremony Moments
The day kicked off under full September sun, warming things up early and setting the tone for a classic late-summer day in Williamsburg. Kelly wore a beautifully embroidered A-line gown from Blue Sage Bridal. The soft cream tones and delicate detailing felt timeless and completely her. Her bridesmaids wore Hill House Matilda dresses in an apple green basket stripe with a soft floral print and smocked bodice, an unexpected but perfect choice that added personality and color to the day. Ryan kept things classic in a navy suit from Brooks Brothers, a clean and timeless look that fit seamlessly with the overall feel of the wedding.
Ceremony at Williamsburg Winery
Their Williamsburg Winery wedding ceremony took place surrounded by the natural beauty of the Tidewater region, a huge reason Kelly and Ryan chose this venue in the first place. Between the on-site lodging, wine tastings for guests, and the coastal-meets-Virginia charm, it created a full experience for everyone involved.
White and blue hydrangeas filled the space, tying in that “something blue” while also nodding to the coastal vibe the couple loved so much. The ceremony felt relaxed but meaningful, with guests fully present and soaking in every moment.
Portraits Around the Winery Grounds
As the storm started rolling in, we were able to sneak in just a few minutes of portraits in the vineyard before the rain hit. It was 100% worth it for those moody, last-minute shots.
One of the biggest priorities for Kelly and Ryan was not being pulled away from their guests for too long, and that’s exactly where my approach as a candid wedding photographer comes in. We kept things efficient, natural, and fun, allowing them to get right back to celebrating while still capturing images that felt like them.
Reception at Williamsburg Winery
Right as cocktail hour kicked off, the weather shifted into a classic Virginia summer-style thunderstorm, an unexpected twist that honestly just added to the story of the day. Guests leaned right into it, enjoying cocktail hour with cornhole boards set up for both Clemson and South Carolina, keeping that rivalry alive in the most fun way even though the dark clouds were looming on the horizon.
Inside, the celebration continued with incredible energy thanks to the live 7-piece band, The Adrian Duke Project. The dance floor filled quickly and stayed that way all night.
The desserts were a highlight, with a two-tier cake from Flour Child Bakery alongside a Clemson-themed groom’s cake featuring the iconic paw print, an absolute must for Ryan and a perfect nod to their football rivalry.
Personal Touches That Made the Day
From checking the SEC football schedule before even choosing a wedding date to incorporating subtle nods to their favorite team, Kelly and Ryan made sure their personalities were front and center.
And of course, Pepper deserves an honorable mention, not just as a beloved part of their story, but as the clear winner in the battle for Ryan’s attention.
A Day That Felt Like Them
At the heart of this Williamsburg Winery wedding was a couple who truly prioritized being present with each other and with their people. Nothing felt overdone or forced. It was intentional, relaxed, and full of genuine moments.
As a candid wedding photographer, these are exactly the kinds of weddings I love documenting, the real laughs, the quick hugs, the moments you don’t plan but never want to forget.
Vendor Team
Venue | Williamsburg Winery
Photography | Awesomesauce Photography
Planning | Two River Events
Florals | Flower Cupboard Williamsburg
Cake | Flour Child Bakery
Band | The Adrian Duke Project
Hair | Victoria Fitzgerald
Bridal Boutique | Blue Sage Bridal
Groom Attire | Brooks Brothers
If you are dreaming up a colorful celebration with or without a 4-pound ring bearer, I would love to help you document it in a way that feels real, candid, and ridiculously awesome.