Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl—A Spooky History Tour with a Twist
If you’re curious about Maryland’s haunted past and want to combine that with a fun night out, the Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl offers a lively way to explore the city’s historic taverns and spooky legends. While it’s a short tour at just two hours, it manages to blend storytelling, local history, and a bit of paranormal investigation into a memorable experience.
What makes this tour appealing? First, you’ll get to hear tales of ghostly sailors, bootleggers, and flirtatious ladies that add a dark, entertaining flavor to Annapolis’ charming streets. Second, the chance to visit Middletons Tavern—a 1750 hotel rumored to be haunted—is a highlight, especially if you’re intrigued by ghostly encounters. Lastly, the unique cocktails and beers, including the infamous Oyster Shooter, are fun extras that make the experience more than just ghost stories.
However, one potential concern is the mixed quality of storytelling, as some reviews mention the stories felt sparse or less dramatic than expected. The tour’s success heavily depends on the guide’s ability to keep the tales lively and engaging.
This experience works best for travelers who enjoy a mix of history, laughs, and a ghostly atmosphere. If you’re after a serious haunted investigation or a lengthy tour, this might feel a bit light, but if you’re in town for a fun, spirited evening, it’s worth considering.
Good To Know

- Short and sweet: 2-hour walking tour packed with stories and bar visits.
- Historic charm: Explores Annapolis’ cobblestone streets and Georgian mansions.
- Authentic tales: Includes credible, well-researched ghost stories from local histories.
- Fun beverages: Four bars included, with options like the Oyster Shooter and themed cocktails.
- Guided experience: Led by knowledgeable hosts who share intriguing local lore.
- Potential variability: Storytelling quality may vary based on the guide; some reviews suggest it’s not the most dramatic.
What to Expect on the Haunted Pub Crawl

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Starting Point and First Impressions
You meet your guide outside The Federal House at 22 Market Space, Annapolis, about 15 minutes before the tour begins. Look for someone in a black US Ghost Adventures T-shirt, lantern in hand. The tour officially kicks off at 6 p.m., though some guests noted slight delays, with guides arriving a few minutes late—something to keep in mind if punctuality is important for your plans.
Once gathered, you’ll head to your first stop, Middletons Tavern, which dates back to 1750. This historic tavern is a cornerstone of Annapolis’ lively past, and it’s where the tales of ghostly residents start to unfold. The stories here are plentiful, and you’ll likely hear about the infamous spirit of Roland—an apparition linked to the tavern’s shadowy history.
Exploring Haunted Spots
From Middletons, the tour winds through seven other historic sites. These include not only bars but also notable spots like old jails and the city’s red-light district, each with their own dark stories and ghostly legends. The mix of locations adds variety—some with spooky tales, others with intriguing history—making for an engaging stroll through the streets of Annapolis.
Ghostly Encounters and Stories
The guide shares well-researched stories based on credible history, which adds authenticity. For example, one reviewer mentioned a personal spine-tingling tale from the guide that enhanced the experience. You might even get a chance to spot one of the resident spirits yourself—whether it’s a fleeting shadow or an inexplicable sense of presence, part of the fun is the possibility of a paranormal encounter.
More Great Thing To Do NearbyBar-Hopping and Unique Drinks
Three additional bars are included in the tour, giving you opportunities to sample local beers and cocktails. The Oyster Shooter is frequently highlighted as a signature drink, offering a taste of local flavor alongside your ghost stories. The tour balances storytelling with social drinking, making it a lively, convivial experience.
The Experience of Being a Paranormal Investigator
One of the unique aspects is the chance to experience what it’s like to be a paranormal investigator. While the tour isn’t a full-fledged investigation, it hints at some of the methods used by ghost hunters—like observing your surroundings or listening for unexplained sounds—which adds an interactive element.
The Value of the Tour

At $30 per person, the price is quite reasonable considering the amount of historic storytelling, bar visits, and the guided experience. The inclusion of four bars and credible history makes it a better value than many standalone pub crawls or ghost tours. If you’re visiting Annapolis and want to combine a fun night with some spooky storytelling, this tour offers a memorable way to do it.
What Travelers Say
The reviews are mixed but provide useful insights. A glowing review praised the guide, Ryan, calling him “an excellent tour guide” and affirming that the experience was “amazing.” Conversely, some found the ghost stories a bit lacking in “wow factor,” with one reviewer stating it was “one of the worst” ghost tours they had experienced, citing a late start and limited storytelling.
Most appreciated the knowledgeable guides and the opportunity to visit historic bars they hadn’t been to before. Several reviews pointed out the charm of exploring Annapolis’s streets and the fun of combining history with ghostly tales.
Practical Tips
- Arrive 15 minutes early to meet your guide.
- Wear comfortable shoes for walking on cobblestone streets.
- Bring ID if you plan to purchase alcohol.
- The tour runs rain or shine—dress accordingly.
- It’s not suitable for those with mobility issues or who can’t walk a mile comfortably.
The Sum Up

The Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl offers a lively, entertaining way to discover the city’s dark past while enjoying a few drinks. It’s perfect for those who love storytelling, historic bars, and a dash of the supernatural, all wrapped into a concise, two-hour package. The knowledgeable guides, especially Ryan, help bring the stories to life, making it a memorable night out in Annapolis.
While the ghost stories can vary in intensity, the blend of history, socializing, and the thrill of potentially spotting a spirit makes this tour a fun option for casual ghost enthusiasts and curious travelers alike. It provides a relaxed, approachable way to explore old Annapolis streets after dark, with a good balance of entertainment and authenticity.
For anyone seeking an affordable, engaging evening that combines local lore, historic charm, and a hint of the paranormal, this tour is definitely worth considering—especially if you’re staying in Annapolis for a few days and want a different kind of night out.
FAQ

Is this tour suitable for children?
The tour is aimed at adults, especially since alcohol is involved, and the stories are geared toward a mature audience. It’s not recommended for children or those sensitive to spooky themes.
How long does the tour last?
It’s a 2-hour walking tour, typically held in the evening, making it a convenient option for a post-dinner activity.
Are drinks included in the price?
No, drinks are not included. You’ll purchase your own beverages at the bars, but the tour includes entry into four local bars and some unique cocktails like the Oyster Shooter.
What should I wear?
Comfortable walking shoes are advised due to cobblestone streets, and weather-appropriate clothing is recommended since the tour takes place rain or shine.
Can I book last minute?
Yes, with the “Reserve & Pay Later” option, you can book your spot in advance and pay at a later date, providing flexibility.
What is the meeting point?
You meet your guide outside The Federal House at 22 Market Space. Look for someone in a black US Ghost Adventures T-shirt with a lantern.
Are there any age restrictions?
You need a valid ID to purchase alcohol, but the tour itself is generally suitable for adults. It’s not designed for very young children or people with mobility impairments.
What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund, giving peace of mind if your plans change.
In summary, the Annapolis Ghosts pub crawl makes for a memorable, atmospheric night exploring the city’s haunted corners, with a lively guide, historic venues, and a few drinks. It’s best suited for those who enjoy a mix of storytelling and socializing, and who don’t mind a bit of ghostly suspense.
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