The 3 Best Drinking Tours in Annapolis
Annapolis isn’t just about sailing and historic streets; it’s also a fantastic place for drinking tours that blend history, ghost stories, and good drinks. The city’s oldest pubs and taverns are rich with tales of spirits—both liquid and supernatural—and offer a fun way to explore with a little spooky twist. These tours stand out for their unique themes, engaging guides, and authentic historic venues, making them perfect for anyone interested in a memorable night out that’s more than just another bar crawl.
Whether you’re into ghost stories, haunted history, or just want to enjoy some local spirits in historic settings, Annapolis delivers. Each tour offers something different—some with a haunted twist, others with a focus on legendary tales and historic pubs. Let’s walk through each of the best options so you can choose the one that suits your mood and curiosity best.
1. The Original Haunted Pub Crawl by Annapolis Ghost Tours
At number one on our list is the The Original Haunted Pub Crawl by Annapolis Ghost Tours. This tour offers a 2-hour guided walk through historic Annapolis, weaving together ghost stories with visits to three of the city’s most haunted pubs and taverns. What makes this tour stand out is its focus on haunted locations, including the oldest and most haunted venues in downtown Annapolis. The guide shares chilling tales of long-dead barmaids, ghostly sailors, and mysterious spirits lurking in the alleys.
The experience is designed to be spooky but fun, perfect for those who enjoy a mix of history and supernatural lore. You can purchase drinks at each stop, which makes for a casual, social atmosphere. The tour’s reviews highlight the engaging storytelling and the local knowledge of guides like Megan and Cerise, who bring the stories to life.
Guests spend about 30 minutes at each location, giving plenty of time to soak in the stories and enjoy a drink or two. The tour is rated 4.5/5, with many reviewers praising its blend of history, ghost stories, and lively atmosphere. It’s a great way to start a quirky night out or to add some supernatural fun to your Annapolis visit.
Bottom Line: A highly-rated, spooky experience that combines history, ghost stories, and drinks in some of Annapolis’s most historic haunts.
2. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
Second on our list is the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl. Priced at just $27 per person, this tour is slightly less expensive and offers a similarly immersive experience. It also lasts about 2 hours and visits four historic locations filled with ghost stories and legends.
The stops include Middleton Tavern, where you can hear tales of the spirits said to haunt the nearly 300-year-old building, and the Old Annapolis Jail, haunted by the ghosts of past inmates. Reynolds Tavern and 1747 Pub are also featured, each with its own legend and eerie history. The tour emphasizes local ghost stories and provides a chance to enjoy drinks while listening to tales of the mysterious “Roland,” the spirit believed to haunt Middleton Tavern, and other spectral residents.
Guests have noted how informative and personable the guides are, with one reviewer praising Ryan for her engaging storytelling. The focus on historic sites and their haunted tales makes this tour ideal for history buffs who like a spooky twist, but it’s also perfect for anyone interested in learning about Annapolis’s layered past.
Bottom Line: A well-balanced mix of history, ghost stories, and local spirits, offering good value and a cozy pub atmosphere.
3. Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Ranking at the top with a perfect 5/5 rating, Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl is the most popular choice for ghost and history lovers. This 2-hour tour dives into tales of murder, debauchery, and haunted legends involving bootleggers, sailors, and flirtatious ladies. It features stories of the notorious ghost of Roland at Middleton’s Tavern, making it ideal for those intrigued by Annapolis’s darker stories.
The tour is slightly more interactive, encouraging participants to experience what it’s like to be a paranormal investigator. You can try special drinks like the Oyster Shooter, and visit some of the city’s most historic pubs. The experience is a great blend of history, ghost lore, and fun cocktails, suited for travelers who want a lively, storytelling adventure with a paranormal twist.
Since it’s the highest-rated tour, it’s clearly a favorite, especially for those fascinated by ghostly tales of murder and mayhem. The intimate nature of the tour and the storytelling style makes it a memorable night out.
Bottom Line: Perfect for those who want a more dramatic and lively ghost tour experience with a mix of drinks and legendary tales.
How to Choose Your Perfect Annapolis Drinking Tour
Choosing between these tours depends on what you’re most interested in. If ghost stories and haunted pubs are your main focus, the Original Haunted Pub Crawl or the Spirits & Spirits tour are excellent options. The former provides a spooky, historical walk with a fun atmosphere, while the latter offers a more immersive and lively storytelling experience. If you prefer a slightly more budget-friendly option that still delivers rich tales of Annapolis’s haunted spots, the Boos & Booze tour is a solid choice.
Consider your interest level in paranormal investigation, history, or just having a fun night with drinks and stories. For those who want to visit specific historic pubs with legendary tales, the Middleton Tavern and Reynolds Tavern stops are highlights worth noting. Booking early is advisable, especially for popular tours like the Spirits & Spirits haunted pub crawl, to secure your spot.
Final thoughts
Annapolis offers a variety of drinking tours that combine history, ghost stories, and local spirits. The Spirits & Spirits Haunted Pub Crawl stands out for its storytelling quality and high ratings, making it a great pick for lovers of dramatic ghost tales. For a more laid-back, spooky walk with historical insights, the Original Haunted Pub Crawl is ideal. Meanwhile, budget-conscious travelers will find the Boos & Booze tour offers excellent value with its engaging stops.
No matter which tour you choose, these experiences promise a fun, authentic way to explore Annapolis’s haunted side. Book early, prepare for some spooky stories, and enjoy a memorable night exploring Maryland’s historic ghostly taverns and pubs.
How to Choose Your Perfect Annapolis Drinking Tour
When selecting the best tour, think about your interests: Are you eager to hear detailed ghost stories and explore haunted pubs? The Original Haunted Pub Crawl offers spooky tales coupled with historic venues. If you want more interactive storytelling with a lively atmosphere, the Spirits & Spirits tour is your best bet. For those on a budget who still want a dose of ghostly lore in cozy pubs, the Boos & Booze tour provides solid value.
Check the tour schedules and availability, especially during peak seasons, and consider booking in advance to avoid missing out. Each tour has its own focus—whether it’s ghost stories, historic legends, or a mix of both—so pick one that matches your curiosity and energy level.
In summary, Annapolis’s drinking tours are a smart way to combine local history with some spirited fun. For a spooky night that blends storytelling, ghost lore, and drinks, the Spirits & Spirits Haunted Pub Crawl is hard to beat. If you prefer a more relaxed, historical approach, the Original Haunted Pub Crawl will satisfy your curiosity. Whichever you choose, these tours promise an entertaining and memorable way to experience Maryland’s capital city after dark. Be sure to book early and get ready for a night filled with stories, spirits, and maybe a ghost or two.