Retro Wedding Photos at the Double T Diner in Annapolis, Maryland

Weddings

November 5, 2025

As an Annapolis wedding and elopement photographer, I love flexing my creative muscles through styled shoots. This shoot at the Double T Diner in Annapolis was so much fun. I partnered with Gabby Bridge Photography to design something out-of-the-box. We wanted retro wedding photos with neon lights and a big bow, and we knew just the couple for it!

Sam and Mike are great friends of mine, and Sam owns Lovestruck Tattoo, a local Annapolis staple. They first met when Sam was working the front desk of a tattoo shop in Connecticut, and Mike was starting at the Naval Submarine School. Their brief romance ended when Mike got stationed in the south, but after ten years of being friends, he returned to Connecticut to win Sam over. They’ve been married for seven years, and considered this shoot at the Double T Diner their anniversary photos!

The Details of our Double T Diner Wedding Shoot

When we first started planning this shoot, we knew we wanted to stay local to Annapolis. We wanted to capture the energy of a courthouse elopement, since so many of those happen in our home city! Plus, diners are so cool. Where else can you get the classic retro vibes, neon lights, and fifteen different cake options? The Double T Diner is a quintessential Annapolis location. Sam, Mike, and I are regulars there, and when we asked if we could host a wedding shoot there, they were all over it! When we arrived, everyone congratulated Sam and Mike. A stranger even paid for the fries, the champagne, and the piece of cake they ordered!

I was giddy while taking these photos. The red seats and mirrored walls were the perfect backdrop for Sam and Mike’s ’60s-inspired outfits. Sam wore an Alfred Sung midi dress with a big bow in the back, paired with a veil from Ruffled Rose Veils. She looked absolutely stunning. Mike wore an all-black outfit from Express. Misha from Woodland Floral Design Co. designed Mike’s boutonniere and Sam’s stunning bouquet. We wanted to show that elopements can still have all the personality, character, and personalization as a big wedding.

Annapolis Wedding and Elopement Photography

My favorite thing about wedding and elopement photos is that they can be whatever the fuck you want. Retro photos at your local diner? Hell yeah. There are no rules. I love helping my couples develop an idea that they’re excited about. Some people love the idea of a traditional wedding, with portraits of all their favorite people. Some people want to do something unique, like skip the big wedding and eat fries instead. Whatever your vibe is, we can take wedding photos that capture it. From a courthouse elopement to the Double T Diner (or one like it!), your wedding photos should capture your love in its purest form. Explore my wedding photography services and contact me to secure your photographer for your wedding or elopement!