Annapolis is a great destination for those who love to combine local history with a good drink. The city’s centuries-old pubs and taverns are perfect spots for a drinking tour, offering authentic atmospheres, compelling stories, and a chance to experience the city like a local. Whether you’re interested in spooky ghost stories or lesser-known tales of Annapolis’s past, these tours deliver memorable experiences with a drink in hand. We especially like the haunted pub crawls for their mix of history and thrills, and the Hidden History Pub Crawl for its off-the-beaten-path stories. If you’re a history buff or just want to explore Annapolis’s lively bar scene, these tours won’t disappoint.
For a well-rounded experience, check out the Original Haunted Pub Crawl by Annapolis Ghost Tours, which combines spooky stories with historic taverns. Or for a more casual night with local legends, the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl offers a fun, laid-back way to learn about the city’s haunted hotspots. Want to discover some hidden stories? The Hidden History Pub Crawl of Historic Annapolis dives into the city’s lesser-known past while giving you a taste of its authentic taverns. Below, we’ll explore each tour in detail to help you decide which one fits your style.
1. The Original Haunted Pub Crawl by Annapolis Ghost Tours
Put a spooky twist on your night with this haunted pub crawl in historic Annapolis. The tour visits three bars, pubs, or taverns known for their ghostly stories, all within the oldest parts of town. The guide shares tales of long-dead barmaids, ghostly sailors, and other spirits that supposedly linger in these historic spots. The tour lasts about 2 hours, with roughly 30 minutes at each stop, giving you plenty of time for drinks (which you purchase yourself).
What makes this tour stand out is its focus on authentic haunted locations inside the oldest pubs, with stories so vivid they’re said to “scare you sober.” The guide’s storytelling, combined with the atmospheric venues, creates a memorable blend of history and ghostly fun. Rating 4.5/5 from 12 reviews, guests praise the tour for its entertaining stories and local flavor. A typical comment: “It was a great experience to learn about Annapolis’s history and hear ghost stories. Megan was an excellent guide!”
Bottom Line: If you’re into ghost stories, historic pubs, and want a lively, quirky way to start your evening, this tour is a top choice. It combines lively storytelling with a chance to explore some of Annapolis’s most haunted watering holes.
2. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
For around $27, this 2-hour haunted pub crawl offers a relaxed way to enjoy Annapolis’s haunted spots while having some drinks and hearing ghostly tales. The tour begins at Middleton Tavern, a nearly 300-year-old building with stories of its past residents and a spirit known as “Roland.” You’ll also visit the Old Annapolis Jail, where the stories of those still reported to haunt the streets are told.
Highlights include Reynolds Tavern and the 1747 Pub, both steeped in legends, and St. Anne’s Parish, which survived a devastating fire and is said to be haunted by spirits. The tour emphasizes authentic ghost stories tied to specific venues, making it ideal for history lovers who also enjoy a drink. Reviews mention the fun and knowledgeable guide, Ryan, and note the cozy atmosphere of the pubs.
This tour isn’t about sampling drinks (drinks are purchased separately), but it’s perfect for those who want a lively, history-rich ghost experience without a heavy price tag.
Bottom Line: If you want a balanced mix of ghost tales, historic venues, and a relaxed pace, this tour offers great value and a genuine local experience.
3. Hidden History Pub Crawl of Historic Annapolis
Looking for something a little different? The Hidden History Pub Crawl focuses on lesser-known stories and the city’s more obscure corners. For $30 per person, you’ll spend roughly 2 hours visiting three historic taverns, where you’ll learn surprising facts like which pub was once a notorious brothel or which founding father was chased out of town.
The guide provides local tips for further exploration and highlights the bars’ drink specials, making it easier to enjoy a few beverages while soaking in the stories. The tour moves at a steady pace, with about 30 minutes at each stop, giving plenty of time to purchase drinks and chat with your guide about Annapolis’s quirky past.
The tour has a perfect 5-star review, with one guest calling it “a great way to see the city’s lesser-known stories,” making it ideal for history fans who want a deeper dive and to discover parts of Annapolis most travelers miss.
Bottom Line: If you’re interested in the city’s lesser-known secrets and enjoy a relaxed, storytelling-focused tour, this crawl offers a unique peek into Annapolis’s secret past.
$30.00 per person
4. Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
This tour mixes ghost stories with spirited cocktails on a lively 2-hour adventure through Annapolis’s haunted district. Starting at Middleton’s Tavern, you’ll hear tales of ghostly bootleggers, sailors, and flirtatious ladies, with the chance to search for the infamous ghost of Roland. The tour emphasizes storytelling, but also invites you to try unique drinks like the Oyster Shooter, adding a fun twist to the night.
The focus here is on the dramatic tales—think murder, debauchery, and tragic tragedies—paired with a spirited atmosphere. The tour is rated 4.2/5 from 6 reviews, with mention of its engaging stories and lively vibe. It’s perfect for travelers who want to combine history, ghostly legends, and a bit of paranormal investigation.
While the drinks are not included, the tour’s stories and the chance to try themed cocktails make it stand out. If you’re into ghostly legends with a spirited twist, this tour offers a memorable night out.
Bottom Line: For those who enjoy ghost stories with a dramatic flair and a few specialty cocktails, this tour delivers a fun, theatrical experience.
How to Choose Your Drinking Adventure in Annapolis
Picking the right tour depends on your interests and what kind of experience you’re after. If ghost stories inside historic pubs sound perfect, the Original Haunted Pub Crawl is a great choice, especially if you love spooky tales. For a more relaxed, ghostly night with a focus on local legends and no need to worry about drinking costs, the Boo & Booze Haunted Pub Crawl offers excellent value.
If your interest is in uncovering little-known stories and exploring Annapolis’s hidden past, the Hidden History Pub Crawl is ideal—and it’s the highest-rated at a perfect 5 out of 5. Lastly, for those who want a dramatized ghost story experience with themed cocktails, the Ghosts: Spirits & Spirits Haunted Pub Crawl combines storytelling with a spirited atmosphere.
Consider your budget, whether you want to include drinks or just listen to stories, and if you prefer spooky tales or secret histories. Book early, especially during peak tourist season, to secure your spot.
In summary, Annapolis offers a variety of drinking tours that cater to different interests—from haunted pubs and ghost stories to secret histories of the city’s taverns. The Original Haunted Pub Crawl is perfect for ghost enthusiasts, while the Hidden History Pub Crawl appeals to history explorers looking for lesser-known stories. Whichever you choose, you’ll enjoy a lively, authentic way to experience the city’s unique bar scene. Be sure to book ahead, and enjoy your spirited adventure in Annapolis.