Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis is old enough to have plenty of ghosts, and this two-hour crawl puts them in the places where they supposedly linger: a nearly 300-year-old tavern, an old jail, a churchyard, and several historic pubs. You walk from stop to stop, hearing local tales while having time to order a drink at selected bars.

I like the mix of real Annapolis history and spooky folklore, and I like that the route uses places you might otherwise pass without knowing their darker stories. Guides such as Ryan can make the evening especially enjoyable, with a patient, friendly approach that leaves room for questions and conversation.

The main drawback is the pace at the pubs. You may spend a fair part of the two hours seated with a drink rather than hearing a constant stream of ghost stories. Alcohol costs extra, and the experience is not recommended for people with mobility impairments.

Key points at a glance

• Roland at Middleton Tavern: Look for the spirit staff have named Roland inside one of Annapolis’ oldest buildings.
• Seven stops in two hours: The route combines five pubs with the Old Annapolis Jail, St. Anne’s Parish, and Government House.
• Drinks are separate: Your $36 ticket covers the guide and storytelling, but not alcoholic beverages.
• Ryan is a guide to seek: The tour can benefit from Ryan’s patient, warm style, according to the available feedback.
• A walking history lesson: You hear about accused prisoners, an 1858 church fire, early Annapolis workers, and Prohibition.
• Small-group setting: The tour allows a maximum of 25 people and begins and ends at 22 Market Space.

Why this Annapolis ghost crawl works

The best thing about this experience is its setting. You are not simply standing on a street while someone recites a list of ghost names. You enter old taverns, pause outside historic buildings, and hear stories tied to the actual rooms and streets around you.

That gives the evening a useful sense of place. Middleton Tavern is not just a stop for a drink. It is a nearly 300-year-old building with tales of former occupants and a resident spirit called Roland. Reynolds Tavern and the 1747 Pub also bring the stories indoors, where the atmosphere comes from the building itself rather than from theatrical effects.

I would think of this as a history walk with a supernatural theme, not a haunted house. The material is described as researched local history and authentic ghost lore. If you want jump scares, costumed actors, or special effects, this is probably too restrained. If you enjoy hearing how old buildings acquired their legends, the format makes sense.

What the $36 price includes

At $36 per person, the tour sits in a reasonable range for a two-hour guided walk, especially because it includes several historic interiors and a guide throughout the route. You are paying for access to the stories, the planning, and the local context rather than for a meal or a package of drinks.

The value depends on how you use the pub stops. You need to budget separately for alcoholic beverages, and the tour does not include private transportation or a guide tip. If you order a drink at several stops, your final cost can rise well beyond the ticket price.

You can also treat the evening as a way to choose your next Annapolis bar. Middleton Tavern, Reynolds Tavern, Rams Head Tavern, and Galway Bay each contribute a different historical angle. I like that the crawl gives you several places to consider instead of locking the entire night into one venue.

Still, a person who wants nonstop storytelling may find the price less appealing. One available rating described the tour as pleasant but felt too much time was spent in bars and not enough time was devoted to additional ghost stories. That is a fair warning: the tour is built around pubs, so the pauses are part of the product.

Starting at Middleton Tavern

The crawl begins at 22 Market Space at 6:00 pm, then moves to Middleton Tavern. This first stop sets the tone well because the building is nearly 300 years old and tied to stories of the people who once lived and worked there.

You have about 20 minutes at the tavern. The central character is Roland, a mysterious spirit known by the staff. Keep your eyes open, but keep your expectations sensible. The tour presents Roland as part of the building’s ghost lore, not as a guaranteed apparition.

This is also your first chance to order a drink. Since beverages are not included, you can decide how much you want to spend instead of paying for a fixed drink package. If you are not drinking alcohol, the tour still works as a history walk, though the pub setting is clearly a major part of the evening.

The Old Annapolis Jail on Dock Street

The second stop takes you to 136 Dock Street, the site of the Old Annapolis Jail. Here, the focus shifts from tavern spirits to the grim experience of accused people waiting for trial.

The stop lasts about 20 minutes. You hear what life was like for people held there and learn about those who met their fate in the area. This adds a darker layer to the crawl, since the stories are linked to confinement, accusation, and death rather than only to an old building’s resident ghost.

I find this kind of stop useful because it gives the supernatural tales a human setting. You are not just hearing that a street is haunted. You are learning why stories might have remained attached to it. The description does not promise a full interior jail tour, so you should expect a guided history stop rather than a lengthy museum visit.

Reynolds Tavern and the 1747 Pub

Next comes Reynolds Tavern and the 1747 Pub, another 20-minute stop with a drink option. This is presented as the site of one of Annapolis’ best-known legends, with a resident spirit whose good side you will want to stay on.

The wording hints at a more playful tone than the jail stop. That balance matters. A full evening of grim tales could become heavy, while a little humor makes the walk easier to enjoy with a drink in hand.

You may also appreciate the change of scenery. The first two stops establish the age of Annapolis and its harder stories. Reynolds Tavern brings the crawl back to the social life of historic pubs, where legends are attached to places people still use.

The practical issue is time. Twenty minutes is enough for a story and perhaps a beverage, but not for a long meal or an extended visit. I would avoid arriving hungry and expecting the crawl to function as dinner.

St. Anne’s Parish and the 1858 fire

St. Anne’s Parish gets a shorter 10-minute stop, but the subject is important. You hear about the nearly 300-year-old church, its survival through a major fire in 1858, and the man rumored to have started the hauntings.

The stop also covers notable spirits said to remain around the grounds. Because the visit is brief, this part works best as a focused pause in the walking route. You get a compact story about disaster, blame, and lingering spirits before moving on.

Church grounds can also change the mood of a ghost tour. After several taverns, St. Anne’s provides a quieter and more solemn setting. You should expect an outdoor explanation rather than a full church visit, since no interior tour is specified.

Rams Head Tavern and its petty spirits

The route then reaches Rams Head Tavern for another 20-minute stop. The stories here concern people who lived and worked in the building during the early 18th and 19th centuries.

The phrase petty spirits gives this stop a lighter edge. Not every ghost story needs to involve a famous tragedy. Tales about workers and ordinary residents can make an old building feel more personal, even when the supernatural details are modest.

This is another place where you can order a beverage, though you pay separately. With five pub stops in total, you should pace yourself carefully. You do not need to buy a drink at every location, and doing so could make the evening expensive or uncomfortable.

Government House and the layers beneath it

The Government House of Maryland is a 10-minute stop. The building on the site is not the original government house, but it still carries its own history and ghost stories.

That distinction is worth noting. The tour does not rely only on the claim that an old building remains unchanged. It uses the site itself, along with the history connected to it, to explain why ghostly inhabitants are said to linger there.

This is a short stop, so you will not receive a long architectural lecture. Instead, it adds a civic and political setting to a route that has already covered taverns, a jail, and a church. The variety helps keep the crawl from feeling like seven versions of the same pub story.

Galway Bay and Annapolis Prohibition history

The final listed stop is Galway Bay Irish Restaurant and Pub, where you have about 20 minutes. The focus here is Prohibition history and the importance of the site during that period.

The hook is simple: have a drink at a place connected to a time when doing so was not legal. That gives the final pub stop a strong historical theme, even for people who are less interested in ghosts.

I like this ending because it brings the tour back to social history. Ghost stories may draw you in, but stories about how people lived, worked, drank, and broke rules can be just as memorable. Galway Bay also gives you one more chance to continue your evening after the crawl, though the activity itself returns to the original meeting point.

Walking, group size, and timing

The experience lasts about two hours and ends back at the starting point. That makes it easy to fit into an evening in Annapolis, especially if you want dinner or more drinks afterward.

The group can include up to 25 people. That is small enough for a guide to address the group, but it is not a private tour. Your experience will depend partly on how well the group keeps pace and how much conversation takes place at the pubs.

The route is near public transportation, but no private transportation is provided. You should plan on walking between stops. The tour is not recommended for people with mobility impairments, so consider the route and your comfort with walking before booking.

Service animals are allowed, and the tour is offered in English. Most people can participate, but the pub-based format and walking route are worth keeping in mind if you need frequent seating, quiet, or step-free access.

The guide can shape the whole evening

A ghost crawl depends heavily on the person telling the stories. The strongest available feedback singled out Ryan as patient, friendly, and pleasant company, with enough local information to make the pubs and stops enjoyable.

That is useful advice when you set your expectations. A guide with a warm delivery can turn a modest ghost story into a good evening. You may also find that a guide encourages questions and gives the group time to enjoy the setting rather than rushing from one tale to the next.

The quality may not be perfectly consistent. One dissatisfied account described a young guide who was dressed unprofessionally, gave weak historical information, and seemed unprepared at the establishments. Another rating found the guide pleasant but wanted more stories and less time in bars.

Those comments point to two things you can control. First, arrive ready for a social pub walk rather than a formal historical lecture. Second, if accurate historical context is your main reason for booking, ask questions during the tour and judge the experience by the guide’s answers and storytelling.

Who should book this experience

I would recommend the crawl to you if you enjoy old buildings, local legends, and a relaxed evening that mixes walking with drinks. It suits couples, small groups of friends, and visitors who want an introduction to Annapolis history without committing to a long daytime tour.

It is also a good choice if you like seeing several pubs in one evening. The route includes Middleton Tavern, Reynolds Tavern and the 1747 Pub, Rams Head Tavern, and Galway Bay, with historical sites between them.

You may want a different activity if you prefer a serious history tour with long explanations at every stop. The limited review feedback makes clear that story length can feel uneven, and the 20-minute pub pauses may seem too long if you are mainly there for ghost lore.

I would also skip it if you have mobility concerns, do not enjoy walking between locations, or want alcohol included in the ticket. The $36 price is only the entry cost, and drinks are extra.

Booking and cancellation details

You receive a mobile ticket, and confirmation arrives within 48 hours of booking, subject to availability. The tour is commonly booked around 10 days ahead, so I would not leave it until the last night of a short Annapolis visit.

You can cancel for a full refund if you do so at least 24 hours before the 6:00 pm start time. Cancellations or changes made within 24 hours are not refunded or accepted, and cut-off times follow local Annapolis time.

The meeting point is 22 Market Space, Annapolis, Maryland 21401. The activity returns there at the end, which keeps the evening simple from a transportation point of view.

Should you book the Annapolis Boos & Booze crawl?

Book it if you want local ghost stories anchored in real Annapolis places, with time to enjoy several historic pubs along the way. The Old Annapolis Jail, St. Anne’s Parish, Government House, and the old taverns give the route more substance than a basic bar crawl.

Skip it if you want a nonstop parade of hauntings or a drink package included in the $36 price. The strongest fit is someone who enjoys a friendly guide, a little folklore, and a social evening where history and pub time share the stage.

FAQ

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

The tour costs $36 per person. Alcoholic beverages, private transportation, and the guide tip are not included.

How long does the haunted pub crawl last?

The experience lasts approximately two hours.

What time and where does the tour begin?

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

Does the tour return to the starting point?

Yes. The activity ends back at the meeting point.

How many people can join the tour?

The maximum group size is 25 travelers.

Is the tour offered in English?

Yes. The experience is offered in English and includes a mobile ticket.

Can I cancel for a refund?

You can receive a full refund if you cancel at least 24 hours before the experience start time. Cancellations and changes made within 24 hours are not accepted, and no refund is provided.