If you’re into ghost stories, historic towns, and a good pint, the Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl might catch your eye. This tour offers a mix of spine-tingling tales and lively bar stops, all set against the charming backdrop of Maryland’s capital. While it’s not a full-on haunted investigation, it promises a fun, storytelling-packed evening with a bit of a spooky twist.
What caught our attention? First, the knowledgeable guides who bring the stories to life, and the unique local drinks like the Oyster Shooter that add a flavorful touch. On the flip side, some reviews mention that the storytelling can feel a bit rushed or less dramatic than expected, which is worth considering if you’re craving a super-deep dive into ghostly lore. This tour is a great fit for those who enjoy history, a lively atmosphere, and a sprinkle of the supernatural—perfect for casual ghost enthusiasts or groups looking for a fun night out.
Key Points

- Historic charm: Walk through cobblestone streets and Georgian mansions rich with stories.
- Engaging guides: Expect knowledgeable storytellers who add personality and insight.
- Bar-hopping fun: Enjoy entry into four local bars, each with its own vibe and ghostly tales.
- Unique drinks: Try special cocktails like the Oyster Shooter for an authentic experience.
- Spooky stories and spirits: From ghostly sailors to infamous spirits like Roland, the tales are varied.
- Duration and price: At 2 hours and $30 per person, it’s an accessible, quick adventure.
What Is the Annapolis Ghosts Tour All About?

This tour is designed to blend history, ghost stories, and socializing into a manageable 2-hour walk through Annapolis’ historic district. Starting outside Middleton Tavern, you’ll meet your guide—easily spotted in a black US Ghost Adventures T-shirt and carrying a lantern—ready to share stories from the 18th century and beyond. It’s a mix of walking, storytelling, and bar-hopping, making for a lively evening.
The tour hits eight historic spots, including three bars. The first stop, Middleton Tavern, is a highlight, known for its 1750 roots and haunted tales. The guide will share credible, well-researched stories like the legend of the ghost of Roland, supposedly haunting Middleton’s. From there, you’ll head to other notable spots, learning about the city’s red light district, old jail conditions, and stories of sailors, tavern owners, and prisoners. Each stop adds a different flavor—literally and figuratively—to the experience.
For evening entertainment in Annapolis, here are other options we've explored
The Itinerary in Detail

The tour begins outside Middleton Tavern at 2 Market Place, where you’ll be greeted with your first drink. This historic tavern is a natural starting point because of its long-standing reputation and the abundance of ghost stories tied to its walls. You’ll hear about ghostly figures and perhaps even spot one yourself, according to local lore.
After Middleton’s, the route winds through seven more haunted locations. The pace is relaxed enough to soak in the stories but brisk enough to keep things lively. You get to explore some of Annapolis’ most charming cobblestone streets and see the classic Georgian-style mansions, which add to the haunting ambiance.
At each bar, you’ll enjoy entry with your ticket, and the guide will regale you with authentic ghost stories that make the drinks feel even more fitting. The stories range from ghostly bootleggers and flirtatious ladies to death row prisoners, giving a broad spectrum of Annapolis’ spooky past.
Drinking and Atmosphere

Part of the charm is the combination of storytelling with social sipping. The inclusion of four local bars means you’ll experience different atmospheres—some more lively, others more intimate. You get to try some special drinks like the Oyster Shooter, which adds a local flavor to your ghostly adventure.
While drinks are not included in the ticket price, the experience offers a chance to sample some of Annapolis’ best bars and drinks, making your night more than just stories. Keep in mind, you’ll need to purchase your own drinks, and a valid ID is required for alcohol sales.
The Guide and the Stories

Reviews highlight the guides as a standout feature. “Ryan was an excellent tour guide! We had an amazing experience,” one traveler shared. Guides are knowledgeable, engaging, and bring the stories to life, making the history feel real and immediate. They also introduce a bit of fun, allowing you to experience what it’s like to be a paranormal investigator, which adds a playful element to the night.
That said, some reviews point out that the stories can sometimes feel a bit brief or lacking the spooky ‘wow’ factor if expectations are high. One reviewer mentioned, “The stories were few and the wow factor wasn’t there,” but others found the stories interesting and the guide’s narration compelling.
More Great Tours NearbyWho Will Love This Tour

This experience is perfect if you’re looking for a casual, social night of ghost stories and drinks. It’s suited for travelers who enjoy history, a bit of the supernatural, and lively bar scenes. If you’re after a deep-dive into paranormal investigations, this might not satisfy your curiosity fully, but if you like a friendly, storytelling approach, you’ll likely find it worthwhile.
It’s not recommended for those with mobility issues since it involves walking and standing, and you’ll want to be comfortable in your shoes. Also, keep in mind that the tour takes place rain or shine, so come prepared for the weather.
- Self-Guided Scavenger Hunt: Annapolis Red Bricks & Blue Views
- The Original Walking Ghost Tour by Annapolis Ghost Tours
- Outdoor Painting Activity with a Local Artist in Annapolis
- Amazing Annapolis Scavenger Hunt
- Annapolis Historic Walking Tour at Harbor and Naval Academy
- Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Final Thoughts

The Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl offers a fun and atmospheric way to explore the city’s historic district. It balances lively storytelling, scenic streets, and a social drinking experience. The guides are a highlight, making every stop engaging and informative, while the historic sites add a tangible sense of place.
For around $30, it’s an affordable way to spend a couple of hours, especially if you enjoy local lore and a good drink. It’s best suited for those who like their ghost stories light-hearted but credible, and who appreciate a good bar crawl with a spooky twist.
While it might not satisfy hardcore ghost hunters or those expecting a highly dramatic presentation, it’s a charming, well-paced experience that reveals a different side of Annapolis—one filled with stories of sailors, jailbirds, and a few spirits lurking in the night.
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
FAQ

Is this tour suitable for families or children?
This tour is not specifically designed for children, and because it involves alcohol and walking, it’s better suited for adults.
How long does the tour last?
It lasts approximately 2 hours, making it a quick but engaging evening activity.
Do I need to pay for drinks separately?
Yes, drinks are not included in the ticket price. You’ll purchase your own at each bar.
Is there a minimum or maximum group size?
The provided information doesn’t specify group size limits, but it’s a typical small group walking tour.
Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.
Where do I meet the guide?
Outside The Federal House at 22 Market Space, Annapolis. Look for someone in a black US Ghost Adventures T-shirt with a lantern.
What should I wear?
Comfortable shoes are recommended since you’ll be walking for about two hours, and dress weather-appropriate.
Is the tour offered in languages other than English?
The tour is conducted in English.
Can I bring my ID?
Yes, you’ll need a valid ID to buy alcohol at the bars.
What if it rains?
The tour runs rain or shine, so come prepared for the weather.
All in all, if a fun, slightly spooky night exploring Annapolis’ haunted past sounds appealing, this pub crawl is worth considering. Just go in with the right expectations—entertaining stories, a lively atmosphere, and a chance to see some historic sights—and you might just have a memorable evening.
You can check availability for your dates here:More Drinking Tours in Annapolis
More Nightlife Experiences in Annapolis
More Tour Reviews in Annapolis
More Annapolis experiences we've covered
- Baltimore & Annapolis Private Day Tour
- Annapolis: Maryland State House Tour
- Annapolis: Round Trip Cruise to St. Michaels
- Annapolis Scavenger Hunt Interactive Walking Tour
- Hidden History Pub Crawl of Historic Annapolis
- Annapolis: Electric Boat Rental – Duffy Sun Cruiser – 10ppl
- Colonial Annapolis, State House & U.S. Naval Academy Tour
- Annapolis: Historic Ghost Tour
- Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
- Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
- Historic Annapolis Food Tour
- The Original Haunted Pub Crawl by Annapolis Ghost Tours
