Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

If you’re wandering around Annapolis and have a taste for the mysterious — and a bit of a drink — the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl offers a lively way to explore the city’s haunted corners. Priced at just $27 per person, this roughly two-hour tour takes you through some of the city’s most historic pubs and landmarks, with ghost stories sprinkled in along the way. Led by friendly and knowledgeable guides, it’s a great option if you’re after a mix of local history, spirited tales, and cozy tavern atmosphere.

Two things we especially appreciate about this tour: first, the authentic stories and local legends that bring Annapolis’ haunted past vividly to life, and second, the charming, intimate pub stops that make the experience both fun and relaxed. The tour’s focus on history combined with a lively pub crawl makes it stand out from more typical ghost tours.

However, be aware that the price does not include drinks, so if you’re hoping for free-flowing beverages, you’ll need to budget for additional drinks. Also, while the tour is suitable for many, mobility challenges could be a concern, as some stops involve walking and standing. This experience suits travelers who are curious about local legends, enjoy historic pubs, and want a social, spirited evening in Annapolis.

Key Points

• Historic Pubs & Landmarks: The tour visits some of Annapolis’ most iconic sites, blending history with ghostly tales.
• Authentic Stories: Guides share well-researched, local ghost stories that truly add to the experience.
• Relaxed Atmosphere: The pub stops foster a cozy, social vibe perfect for mingling and enjoying a drink or two.
• Cost-Effective: At $27, it offers a fun, engaging way to explore without breaking the bank.
• Duration & Convenience: About two hours long, starting at 6 pm, with a meeting point at 22 Market Space.
• Limited Drinks Included: You’ll need to purchase your own beverages, as they’re not included in the tour price.

Exploring the Itinerary in Detail

Starting at Middleton Tavern

The tour kicks off at Middleton Tavern, a building approaching 300 years old — a real piece of Annapolis history. As you step inside, you’ll hear tales of the ghost called “Roland,” an apparition believed to haunt the tavern’s walls. The staff’s nickname for this mysterious presence hints at the kind of stories you’ll hear throughout the night. It’s a fantastic way to set the tone, combining historic architecture with ghostly lore. The visit here is about 20 minutes, and while the admission is free, the atmosphere is what makes it special.

The Old Annapolis Jail at 136 Dock Street

Next, you’ll visit the Old Annapolis Jail, where stories of those accused of crimes and awaiting trial linger in the air. This stop is about 20 minutes and offers a peek into the city’s darker past. The tales of spirits still said to walk these streets are what make this stop stand out. The story of those who met their fate here is chilling but fascinating, adding a layer of historical intrigue.

Reynolds Tavern & 1747 Pub

At Reynolds Tavern, you’ll find yourself in a setting ripe with legend — it’s one of Annapolis’ most renowned sites. The 20-minute stop here includes a beverage break, where you can soak in the atmosphere and hear about the “resident spirit” that’s said to haunt the place. It’s a good example of how local legends intertwine with the city’s social hubs.

St. Anne’s Parish

A nearly 300-year-old church, St. Anne’s Parish has survived fires and wars, and its grounds are rumored to be haunted by spirits linked to its storied past. Visitors will hear about the man who may have started the hauntings and the notable spirits lurking nearby. This stop is relatively brief, about 10 minutes, but adds a spiritual dimension to the ghost story collection.

Rams Head Tavern

This pub, with origins dating back to the 18th and 19th centuries, invites you in to hear about tragic tales linked to its past tenants and workers. The building’s layers of history make it a fitting stop to encounter petty spirits said to linger within its walls. It’s about 20 minutes long and offers another cozy, atmospheric setting.

Government House of Maryland

While not the original, the current Government House still holds historical significance and is rumored to host its own ghostly residents. A brief 10-minute stop, it offers a chance to hear stories about the spirits that are said to reside here — perfect for those interested in government history with a haunted twist.

Galway Bay Irish Restaurant and Pub

The tour’s final stop is at this historic Irish pub that played a role during Prohibition. It’s a spot where you can sit down, relax, and imagine the secretive nights of bootlegging and speakeasy activity. The 20-minute visit here combines history with a chance to enjoy a drink, rounding out the evening on a lively note.

What Makes This Tour Stand Out?

Authentic Narratives & Local Legends: The stories shared are well-researched and rooted in Annapolis’ history, not just ghostly clichés. Guides like Ryan receive praise for their knowledge and engaging storytelling, making each tale come alive. As one reviewer put it, Ryan was a “terrific guide” who made the experience informative and fun.

Atmospheric Pubs & Historic Venues: Each stop offers a cozy, authentic setting. The pubs are described as “super cozy and quaint,” creating an intimate vibe that encourages storytelling and socializing. The inclusion of a historic Irish pub during Prohibition adds a unique flavor.

Balance of History & Entertainment: The tour masterfully combines facts and legends, giving you both a sense of the city’s past and the thrill of ghost stories. This balance ensures the experience appeals to history buffs and casual ghost enthusiasts alike.

Value for the Price: With a modest fee of $27, you’re getting approximately two hours of guided storytelling, historical insights, and prime pub stops. The tour offers a good mix of entertainment and education, especially given the friendly, professional guides.

Considerations for Travelers

While the tour is largely accessible and suitable for most, it’s worth noting that mobility issues might present some challenges, as certain stops involve walking and standing. Also, since drinks are not included, you’ll want to bring some extra cash if you plan on enjoying beverages at the pubs.

If you’re looking for a more story-focused experience with less pub time, you might find the balance here slightly leaning toward social drinking rather than a purely ghostly exploration. Conversely, if you love history, ghost stories, and cozy tavern atmospheres, this tour hits all those marks.

Who Should Consider This Tour?

This experience is ideal for history lovers who enjoy a bit of spectral storytelling, pub enthusiasts eager to experience Annapolis’ historic taverns, and groups of friends or couples wanting a fun, social evening out. It’s particularly suited for those who appreciate authenticity and well-researched stories, as well as travelers looking for a relaxed yet lively way to explore the city after dark.

FAQs

Is the tour suitable for children?
It’s generally geared towards adults, especially since drinks aren’t included and some stories might be more suited to an older audience. Kids might enjoy the historic sites and stories, but it’s best to check with the operator for specific age recommendations.

Does the tour include any drinks?
No, beverages are not included in the ticket price. You can purchase drinks at the pubs along the way to enhance your experience.

What is the meeting point?
The tour starts at 22 Market Space in Annapolis, and you’ll return to this same spot at the end of the two hours.

How far in advance should I book?
On average, travelers book about 12 days in advance, so planning ahead is recommended, especially during peak tourist seasons.

Is the tour accessible for people with mobility issues?
It’s not specifically designed for those with mobility challenges, as some walking and standing are involved. It’s best to contact the provider if you need accommodations.

What time does the tour start?
The tour begins at 6:00 pm, making it perfect for a post-dinner or early-evening activity.

Are private groups available?
While this is a public tour with a maximum of 25 travelers, private bookings might be possible — check with the provider for options.

Is tipping expected?
Tips for guides are always appreciated if you enjoyed the experience, but it’s not mandatory.

Final Thoughts

For those curious about Annapolis’ haunted past, this Boo’s and Booze Haunted Pub Crawl offers a fun, authentic, and atmospheric way to experience the city’s history and legends. It’s particularly well-suited for social travelers who love stories, historic pubs, and a spirited evening out. The knowledgeable guides, cozy stops, and engaging tales make it a memorable way to see a different side of Annapolis — one filled with ghostly whispers and lively tavern chatter. 

If you’re after a blend of history, local legend, and a relaxed pub atmosphere, this tour delivers. Just remember — come with an open mind, a sense of humor, and maybe a few extra dollars for drinks. It’s a charming, spirited adventure worth considering for your Annapolis itinerary.