Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

History gets eerie after dark. This two-hour Annapolis ghost pub crawl links old taverns, a former jail, a church, and historic government sites with local legends and time for a drink at several stops. I like the mix of real Annapolis history and spooky storytelling, and I like that the route stays in the historic center rather than sending you into a bus or private vehicle.

The $36 price is fair if you want a guided evening walk with several pub visits built in, though drinks cost extra. The main thing to consider is the pace: you spend about 20 minutes at many of the bars, so you may get less ghost lore than you hoped for if your priority is stories rather than social time.

Five things to know before you book

• Seven historic stops in about two hours: The route covers pubs, the Old Annapolis Jail, St. Anne’s Parish, and Government House.
• Drinks are not included: You pay $36 for the guide and tour, then buy your own beverages at the pubs.
• Ryan has earned strong praise: One especially positive experience singled out Ryan for patience, a pleasant manner, and informative guiding.
• The group can reach 25 people: That is small enough to feel manageable, but not the same as a private walk.
• The tour starts and ends at 22 Market Space: You meet at 6:00 pm and return to the same general starting point.
• Expect walking and standing: The tour is not recommended for people with mobility impairments.

What the $36 price really gets you

At $36 per person, this is not a cheap bar-hopping night if you count the price of drinks. It is better understood as a guided history walk with pub stops. Your ticket covers the guide, the stories, and admission to each stop, while alcoholic beverages are your responsibility.

That distinction matters. If you planned to buy a drink at every pub, your final cost could rise quickly. If you prefer one or two drinks and care most about hearing local tales, the price makes more sense.

The route gives you seven different settings in one evening. You are not paying for a single haunted building or a short talk outside one landmark. You get a look at taverns nearly 300 years old, a former jail, a church site, and places tied to Annapolis government and Prohibition history.

The tour also includes researched historical material, not only spooky claims. That balance is important. A good ghost walk should tell you what happened at a place before asking you to imagine who might still be there.

Still, the value depends on your expectations. One person found the guide pleasant but felt too much time went into each bar and not enough into ghost stories. If you want a dense parade of hauntings, this may feel slow. If you like sitting down, having a drink, and letting the evening unfold, the structure will suit you better.

Middleton Tavern and the spirit named Roland

The first stop is Middleton Tavern, a building almost 300 years old. You go inside, hear stories connected to people who lived within its walls, and have the chance to buy a drink while keeping an eye out for Roland, the spirit associated with the tavern.

This is a smart opening stop because it gets you indoors quickly. You begin with a historic pub rather than standing on a sidewalk while the guide explains the evening. The tavern setting also establishes the tour’s basic rhythm: hear a story, enter a bar, and decide if you want a drink.

The free admission is part of the ticket value, but you should remember that your beverage is separate. The staff’s name for the resident spirit gives this stop a specific character. It is more engaging than a vague claim that an old building feels haunted.

You might also find this first stop sets the tone for the entire night. The experience leans toward atmosphere and local storytelling rather than theatrical scares. Expect legends connected to real places, not a haunted-house production with actors jumping from dark corners.

The Old Annapolis Jail at 136 Dock Street

At 136 Dock Street, the route takes you to the Old Annapolis Jail. Here, the focus shifts from tavern folklore to the hard life of accused criminals waiting for trial.

That change gives the crawl some needed range. The jail stop is not simply another pub with a ghost story attached. It offers a look at the justice system and the people who passed through it, then connects those stories to claims that some of them still walk Annapolis streets.

The guide is expected to explain what life was like for people held there before their cases were decided. That context gives the haunting stories more weight. You can judge the legends for yourself instead of hearing only a list of names and spooky incidents.

The stop lasts about 20 minutes. That is enough time for a focused account, but the exact amount of detail may depend on the guide and the group. One critical experience raised concerns about weak historical facts and an unprofessional presentation, so the quality of the storytelling can matter a great deal here.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub bring you back to a drinking establishment with one of Annapolis’ best-known legends. You can order a beverage and hear about the resident spirit, whose mood you are advised not to disturb.

This stop is likely to appeal to anyone who enjoys the social side of a ghost walk. You are not only listening outdoors. You get time inside a pub, with a chance to sit down and take in the setting.

The tradeoff is clear. Twenty minutes at a bar can feel pleasant, but it also reduces the number of stories the guide can tell in a two-hour tour. If you would rather cover more haunted sites, you may wish the group moved on sooner. If you want an easy evening with history, conversation, and a drink, the pause works in your favor.

The tavern’s age and legend give the stop a strong sense of place. You are hearing about a specific building with a resident ghost story, not a general collection of supernatural tales borrowed from somewhere else.

St. Anne’s Parish and the 1858 fire

St. Anne’s Parish provides a change of mood. The church is nearly 300 years old and survived a major fire in 1858. The guide explains the man rumored to have started the hauntings, along with spirits said to remain around the grounds.

This is one of the more atmospheric stops because churches and old burial grounds naturally encourage a quieter kind of storytelling. The focus on the fire also gives the history a clear turning point. You hear how the site endured a disaster, then learn how later stories connected the church to ghosts.

The visit lasts about 10 minutes, shorter than the pub stops. That makes sense for an outdoor historical stop, but it also means you should not expect a long exploration of the church grounds. The tour provides an introduction rather than a full architectural or religious history lesson.

If you are most interested in old buildings, disasters, and local legends, this may be one of the evening’s stronger moments. If your interest is mainly in drinking and conversation, it will feel like a brief pause between taverns.

Rams Head Tavern and its petty spirits

At Rams Head Tavern, the tour turns to people who lived and worked in the building during the early 18th and 19th centuries. You hear tragic stories connected to the site and learn about the petty spirits believed to remain inside.

The word petty gives this stop a different flavor from the jail and church stories. Not every haunting needs to involve a grand curse or a dramatic death. Small, troublesome spirits can make a story more playful and memorable.

You get another 20-minute pub stop here. The practical question is how many drinks you want to purchase during the evening. Since beverages are not part of the tour fee, you may want to set a spending limit before you arrive.

The strongest part of this stop is the combination of working lives and ghost lore. The building is presented through the people who lived and worked there, which can make the setting feel more human. The drawback remains the same: time spent inside the pub means less time for additional locations or longer stories.

Government House and Annapolis power

The Government House of Maryland is not the original government house, but the building at the site carries its own history and ghost stories. The visit lasts about 10 minutes.

This stop broadens the tour beyond taverns and places of confinement. You get a glimpse of Annapolis as a center of government, then hear how public buildings can collect their own legends. The contrast is useful. It reminds you that the city’s ghost stories are tied not only to bars and old tragedies, but also to civic power.

Because the tour does not enter every site for a long visit, you should think of this as a guided exterior story rather than a full house tour. The value comes from the context and the guide’s explanation, not from extended time inside the building.

Galway Bay and Prohibition history

The final stop is Galway Bay Irish Restaurant and Pub. Here, the story moves to Prohibition history, and you are invited to sit down and have a drink at a site connected to that period.

This is a strong ending for a pub crawl because it returns the experience to food, drink, and social history. The stop is not only about spirits. It also points to a time when alcohol was restricted and places serving it had to operate in difficult conditions.

The phrase do what others could not gives this stop a playful edge, but the historical subject is more substantial than the joke. Prohibition stories show how ordinary people and businesses responded to changing laws. That kind of local detail can be more memorable than a generic haunted-house tale.

The 20-minute stay gives you time to settle in at the end of the route. You may want to order a drink here, especially since the tour returns to its starting point afterward. Just remember that the beverage remains your own expense.

Guide quality can shape the whole evening

A ghost tour rises or falls on its guide. The best feedback praised Ryan for being patient, pleasant, and informative. That is especially valuable on a pub crawl, where the guide has to manage a moving group, coordinate stops, and keep the stories clear over the noise of busy bars.

The experience is advertised with friendly, researched guiding and authentic local ghost stories. Those are useful promises, but the actual presentation may vary. One poor experience described a young guide who seemed unprofessionally dressed, offered weak historical facts, and did not appear expected at the establishments.

That criticism is serious because the pubs are central to the tour. If the group arrives awkwardly or the guide seems unprepared, the evening loses much of its charm. I would book this expecting a casual walking tour, not a formal lecture or polished stage show.

The group size can reach 25 people. That is not enormous, but it is large enough that you may stand behind other people or need to stay close to hear every word. A smaller group would make the old buildings and pub visits feel more personal, but the maximum size remains reasonable for a city walk.

Timing, meeting point, and practical concerns

The tour begins at 6:00 pm at 22 Market Space in Annapolis and ends back at the meeting point. The round trip makes planning easier. You do not need to arrange a ride from a distant final stop, and the route stays near public transportation.

The tour lasts about two hours. Seven stops in that window mean the walk has a steady structure, even with time inside the pubs. Some stops last 10 minutes, while the taverns generally receive 20 minutes.

You should wear shoes suitable for walking and expect periods of standing. The experience is not recommended for people with mobility impairments. Service animals are allowed, and most people can take part.

Confirmation is sent within 48 hours of booking, subject to availability. You can cancel for a full refund up to 24 hours before the start time. Cancellations or changes made inside that 24-hour window are not refunded or accepted, so keep the local start time in mind.

Who will enjoy this Annapolis ghost tour?

I would recommend it to you if you want three things in one evening:

• A guided walk through old Annapolis
• Local ghost stories tied to named buildings
• Time to buy a drink and relax inside historic pubs

It works well for couples, friends, and visitors who want an easy introduction to the city after dark. You do not need to be a serious believer in ghosts. The historical setting and pub visits provide enough reason to go.

You may want to skip it if you dislike drinking environments, need a fully accessible route, or prefer a tightly packed history tour with little downtime. The tour is also not ideal if you expect drinks to be included in the $36 price.

Should you book the Boos & Booze crawl?

Book this tour if you want a social evening built around old Annapolis buildings, local legends, and several chances to buy a drink. The strongest reasons to go are the varied route, the nearly 300-year-old sites, the Old Annapolis Jail, and the praise for Ryan’s patient, informative guiding.

Think twice if you want nonstop ghost stories or exact historical depth at every stop. The pub time is part of the appeal, but it can also feel like lost storytelling time. At $36, the experience is a fair buy when you treat it as a guided historic pub walk, with drinks added separately.

FAQ

How much does the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl cost?

The tour costs $36 per person. Alcoholic beverages are not included, so you pay separately for any drinks you order.

How long does the tour last?

The tour lasts approximately two hours.

Where does the tour start?

The tour starts at 22 Market Space, Annapolis, Maryland 21401, at 6:00 pm.

Where does the tour end?

The activity ends back at the meeting point.

Is the tour offered in English?

Yes. The tour is offered in English.

How many people can join the tour?

The tour can accommodate a maximum of 25 people.

Can I cancel for a refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations or changes made less than 24 hours before the start time are not refunded or accepted.