A Haunted Date Night in Annapolis: Our Experience on the Boos & Booze Ghost Tour

Living right outside of Annapolis, MD, I sometimes forget just how much incredible history and how many hidden stories are only minutes away. Downtown Annapolis is full of charm; its colonial architecture, waterfront views, and centuries-old past draw tourists and locals alike. Recently, our family has made a point to explore more of what’s right in our own backyard and really appreciate the beauty and history surrounding us.

This October, Matt and I wanted a date night that tapped into a spookier side of Annapolis. I’ve done a few ghost tours in other cities and always loved them, but Matt had never been. So naturally, I saw this as the perfect opportunity to introduce him and enjoy a fun night out together.
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We booked the Boos and Booze tour through US Ghost Tours, and I was hoping it would live up to the others I’ve experienced. The tour meets right along Main Street, so we arrived a little early to grab a snack and a drink before our spooky adventure began.

Once the group gathered and we met our guide, we were off. Over the two-hour tour, we explored several locations throughout the city and uncovered their historical and haunted significance. Our tour guide was incredibly knowledgeable and shared stories and facts that were completely new to us, even though we’ve lived here for years.

We walked from site to site, taking in Annapolis by night and soaking up the atmosphere. A few of our stops were historic pubs, where we got to embrace the “booze” in Boos and Booze. We visited three different bars, each with its own eerie backstory, and spent time swapping thoughts with the group about everything we’d just learned. The drink breaks were perfectly timed, with enough space to relax and enjoy, but not so long that we lost the spooky momentum.

One of my favorite stops came toward the end of the night. Once it was fully dark, we stopped by the town church and learned about the graves of some of Annapolis’s earliest political figures. I pass that church constantly while running around town, yet I never thought twice about who might be buried there. Hearing their stories (no spoilers!) and exploring the grounds under the moonlight definitely added to the chilling vibe.

After the tour wrapped up, we said goodbye to our fellow ghost hunters and walked back to Middleton Tavern, one of the tour stops, to grab dinner. Haunted or not, the food was amazing and the perfect end to our night.

Overall, the tour was a blast and so well done. I learned so much and walked away with an even deeper appreciation for the history around us. Our guide was fantastic, passionate, patient with questions, and clearly an expert in her craft. And since it was Matt’s first-ever ghost tour, I was curious what he’d think. His review? Just as positive, he loved the mix of history, storytelling, and seeing the city in a whole new light.

​Overall, the tour was a blast and so well done. I learned so much and walked away with an even deeper appreciation for the history around us. Our guide was fantastic, passionate, patient with questions, and clearly an expert in her craft. And since it was Matt’s first-ever ghost tour, I was curious what he’d think. His review? Just as positive, he loved the mix of history, storytelling, and seeing the city in a whole new light.

While this made for the perfect spooky season date night, the tour runs year-round, so whether you’re a tourist or a local, it’s absolutely worth adding to your Annapolis must-do list. If you’re ready to experience the haunted history of one of America’s oldest towns… this is your sign. 👻✨