When couples ask what to expect during an engagement session, I always say: think of it as a date—with me third-wheeling and capturing the best parts. That’s exactly the vibe we created for this sweet couple’s Annapolis engagement photos. We started our walk near the Maryland State House, right along Maryland Avenue, and turned a simple one-hour session into a memorable adventure through some of the city’s most charming and unexpected spots.
With the historic brick walkways and soft tree-lined light, the State House area gave us that classic Annapolis feel. From there, we strolled past the colorful Bicycle Mural—a must-stop for a pop of personality. This spot is always a favorite, and it perfectly captured their playful side.
We made our way toward the docks at Ego Alley, where the breeze picked up just enough to give movement to her dress and a cinematic feel to their hugs and laughter. The soft light reflecting off the water as boats glided by gave their images such a romantic, timeless glow.
And how did this dream date night end? With espresso martinis, of course. Because nothing says celebration like a little caffeine and a lot of love. And while we’re at it—can someone please invent the affogato martini already? Ice cream and espresso? Yes, please. Count us in.
Where to Head After Your Annapolis Engagement Session
Looking to keep the date night going after your shoot? Here are some of my favorite fun and cozy downtown spots to grab a bite, a drink, or a good book:
Red Red Wine Bar – Cozy up with a flight of wines or share a flatbread under their glowing string lights.
Old Fox Books & Coffeehouse – Sip something warm while browsing hidden book treasures and local authors.
Aqua al 2 – Upscale Italian and dreamy candlelight—perfect for lingering.
Galway Bay – Traditional Irish fare and warm pub vibes right off Maryland Ave.
McGarvey’s Saloon & Oyster Bar – A staple on the water for oysters and cocktails.
The Choptank – Fresh seafood and rooftop views of the harbor.
This session reminded me how easy it is to turn everyday places into extraordinary memories—especially when you’re with your person.
Planning your own Annapolis engagement session?
Let’s create your own hour of laughter, charm, and espresso martini magic.
