Annapolis isn’t just about sailing and historic streets; it’s also a place where you can explore its lively drinking scene with a twist. Whether you’re into ghost stories, secret histories, or just looking for a fun night out with a local touch, Annapolis offers some memorable options. We’re particularly fond of the haunted pub crawls, which combine spooky stories with a lively bar scene.
For instance, the Original Haunted Pub Crawl takes you inside some of the oldest taverns, connecting ghost tales with a lively atmosphere. It’s an ideal way to learn about the city’s past while enjoying a few drinks.
The tours stand out for their storytelling quality and the chance to visit iconic spots like the oldest haunted pubs in downtown Annapolis.
If you prefer a more underground experience, the Hidden History Pub Crawl offers a peek at the city’s lesser-known tales along with visits to historic taverns.
For those interested in spirits and ghostly legends, Annapolis also has a tour dedicated to spirits—both the drink and the supernatural kind—that’s perfect for a daring night out. Overall, Annapolis’s drinking tours are a fascinating blend of history, folklore, and good old-fashioned fun.
1. The Original Haunted Pub Crawl by Annapolis Ghost Tours
At number one, we have the Original Haunted Pub Crawl by Annapolis Ghost Tours. For just $31 per person, this 2-hour adventure takes you through historic Annapolis’s most haunted pubs. The tour is unique because it’s the only one permitted inside the city’s oldest establishments, some of which have stories dating back hundreds of years.
Your guide shares tales of ghostly barmaids, spirits who won’t leave their beer, and legendary figures from the city’s past.
What makes this tour stand out is how it blends spooky stories with a lively pub scene, giving you about 30 minutes at each stop to enjoy a drink of your choice.
Guests often talk about the quality of storytelling—“Megan was an excellent guide,” one reviewer noted, emphasizing how they learned about Annapolis while enjoying the ghostly tales. The tour’s value comes from its combination of local history, ghost stories, and the chance to visit some unique watering holes.
It’s best suited for those who love a little thrill with their drink and are curious about Annapolis’s darker side. Expect a fun, slightly spooky evening that’s perfect for groups or solo travelers looking for something different.
Bottom Line: A well-rounded, spooky experience with a lively atmosphere—great for history buffs and ghost story lovers alike.
2. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
At number two, the Boos & Booze Haunted Pub Crawl offers a slightly more budget-friendly option at $27 per person. This tour also lasts about 2 hours and takes you inside some of Annapolis’s most historic spots, including Middleton Tavern and the Old Annapolis Jail.
The highlight here is the storytelling—learn about Roland, the mysterious spirit at Middleton Tavern, and the convict tales from the jail.
While drinks aren’t included, it’s a perfect chance to sample the city’s historic taverns and hear ghost stories that have been passed down for generations.
Guests mention that Ryan, the guide, is “very informative and patient,” making the experience engaging even for those new to ghost hunts. The tour’s strength is its focus on genuine stories and the authentic, cozy pubs that add character to the evening.
It’s best suited for travelers who want a spooky night without the extra cost of drinks, or those who prefer a more intimate, storytelling-focused experience.
Bottom Line: An affordable, story-rich ghost tour with a relaxed pace—ideal for those interested in the haunted side of Annapolis.
3. Hidden History Pub Crawl of Historic Annapolis
Number three on our list is the Hidden History Pub Crawl, which scores a perfect 5.0/5 based on a single review. For $30, this tour emphasizes lesser-known stories of Annapolis, like which tavern was a popular brothel or which founding father was chased out of town. It’s a more intimate tour that dives into the city’s secret histories and quirks.
The tour visits well-known taverns like Middleton Tavern, Rams Head, and Federal House, with about 30 minutes at each spot for drinks and stories. Your guide shares local tips for further exploration, making this a good choice if you want to combine a pub crawl with a deeper understanding of Annapolis’s unsung stories. It’s perfect for travelers who love uncovering secrets behind historic landmarks.
Bottom Line: A focused, off-the-beaten-path experience that reveals Annapolis’s unexpected stories, ideal for history enthusiasts.
4. Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Last but not least, the Ghosts: Spirits & Spirits Haunted Pub Crawl ranks fourth. For $30, this 2-hour tour combines tales of murder, debauchery, and ghostly sailors with a tasting experience. You’ll hear about ghostly bootleggers and the infamous ghost of Roland at Middleton’s Tavern, along with trying signature drinks like the Oyster Shooter.
This tour is suited for those who enjoy a bit of dramatization alongside their drinks and are curious about the paranormal stories of Annapolis.
While the reviews are mixed with a 4.2 rating, many appreciate the lively storytelling and the immersive feeling of being a paranormal investigator for an evening. It offers a lively, theatrical take on the haunted side of Annapolis, perfect if you want a more energetic tour with a focus on spirits—both the drink and ghostly kind.
Bottom Line: A lively, theatrical haunted pub crawl combining storytelling with drinks, great for adventurous travelers interested in ghost tales.
How to Choose the Right Drinking Tour in Annapolis
When selecting your ideal Annapolis drinking tour, consider your interests and how much spooky storytelling versus historical depth you want. For a classic ghostly experience with historic taverns, the Original Haunted Pub Crawl stands out. If you prefer a more relaxed, story-focused night with a local vibe, the Boos & Booze Tour offers great value.
Those interested in uncovering hidden city secrets should look at the Hidden History Pub Crawl, especially if you enjoy lesser-known tales.
Budget travelers or those wanting to combine ghost stories with a theatrical flair might enjoy the Ghosts: Spirits & Spirits tour, especially for its lively atmosphere and signature drinks. The key is matching your interest—mystery, history, or fun—and your pace.
Booking early is recommended, especially for popular tours, to secure your spot and ensure you get an experience that fits your schedule and style.
To sum it up, Annapolis offers a delightful mix of ghostly tales, historic secrets, and lively pub scenes. Whether you want a spooky, storytelling-focused evening or an energetic exploration of haunted taverns, these tours provide a memorable way to enjoy the city’s nightlife.
For a more laid-back or intense experience, each option has something unique—just pick what suits your curiosity and enjoy a different side of Annapolis.
Remember to book in advance, especially during peak times, and prepare for a fun night filled with stories, spirits, and maybe a ghost or two.