Christmas City Engagement Photos in Downtown, Annapolis
Annapolis, Maryland
Just days before Christmas, I had the pleasure of photographing Tara and JP’s engagement session in downtown Annapolis. It was amazing to finally meet this lovely couple in person, especially knowing that I will be capturing their wedding at Celebrations at The Bay in July 2025.
During the initial engagement session planning, Tara and JP mentioned the time they first visited downtown Annapolis; during their annual St. Patrick’s Day events. They fell in love with the area, and knew it would be their choice location for their engagement session. This detail added an extra layer of magic to the afternoon.
We spent over two hours exploring the streets of DTA, and our first stop to warm up was Old Fox Books & Coffeehouse, a local shop. The shop’s cozy library and window nook were a perfect spot for some of my favorite photos during their engagement session in Annapolis.
Searching for a less crowded bar on a Sunday in downtown Annapolis isn’t always the easiest, but luck was on our side when we stumbled upon Harry’s Bar, tucked away upstairs in the Harry Browne’s Restaurant. With only one other couple and the bartender, we secured a drink and the owners permission and snapped some photos of Tara and JP sharing a drink. With the bar’s Christmas decorations, it fit perfectly into what they had envisioned for their engagement session.
Our adventure through downtown Annapolis wasn’t complete quite yet. We headed down to Dock Street, the main and most popular section of DTA, where Tara and JP popped a bottle of champagne to celebrate!
This session was truly an unforgettable afternoon with Tara and JP, as they made the most of their engagement session by choosing a location that was both meaningful and versatile. The love and humor they share for each other is so beautiful to witness, and I can’t wait to capture their love again at their wedding day at Celebrations at The Bay come July!
Check out their engagement session below!
Photos by: Karlie Whitt Photography
We just HAD to stop by the Downtown Annapolis Wall Mural: Located on Fleet St.
Let me help you capture your love story in Annapolis and Kent Island! Reach out to me, tell me your vision, and let’s capture some memories for you that will last a LIFETIME! Don’t let another year pass without getting photos. It’s time to invest in yourself, and making sure your life story is photographed.
Hey, I’m Karlie! A Wedding and Lifestyle Photographer, based in Norfolk, Virginia, and serving all of Virginia, Maryland, and beyond. I travel all around the East Coast for weddings and sessions. Interested in securing a date on my calendar? You found the right place!
All Photos by: Karlie Whitt Photography
