Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl mixes old-city ghosts with stops for a drink. The route visits a nearly 300-year-old tavern, a former jail, an old church, and places tied to Annapolis’ Prohibition past. It is less a spooky thrill ride than an evening of stories, historic buildings, and pub time.

I like the range of stops, especially Middleton Tavern and the Old Annapolis Jail, because they give the evening two different moods: one warm and social, the other grim and unsettling. I also like that the stories are tied to real local places rather than delivered as a general collection of ghost tales.

The main caution is pacing. You spend about 20 minutes at several pubs, and drinks cost extra. If you want a fast-moving walk with a new haunted story every few minutes, this may feel slow. If you enjoy sitting down, listening, and having the option to order a drink, the rhythm makes more sense.

Key points to know before booking

• Seven historic stops: The route covers taverns, a jail, a church, Government House, and a former Prohibition site.
• Roland at Middleton Tavern: Keep an eye out for the spirit staff have named Roland while you enjoy a drink.
• Drinks are extra: The $36 tour price covers the guide and storytelling, not alcohol.
• Six o’clock start: The evening begins at 22 Market Space and ends back at the same meeting point.
• Small enough to follow: Groups are capped at 25 people, though that can still feel lively inside a pub.
• A walking tour with limitations: It is near public transportation, but it is not recommended for people with mobility impairments.

Why this Annapolis ghost tour works best after dark

Annapolis is a good setting for a haunted pub crawl because the route connects old buildings with stories that belong to those buildings. You are not simply hearing about ghosts in the abstract. You are sitting in taverns, pausing outside a former jail, and hearing about spirits linked to specific rooms, streets, and grounds.

The tour starts at 6 p.m. That gives you an evening setting without making the activity too late for dinner plans afterward. The whole outing takes about two hours, though the listed stop times add up to two hours exactly, so you should expect a fairly full schedule.

The guide is an important part of the experience. Ryan, who has led the crawl, is described as patient and pleasant, with a style that suits people who want both history and entertainment. The provider promises researched local history and authentic local ghost stories. That combination matters here. The best parts of this tour are likely to come when the guide connects a building’s past to the legend attached to it.

There has also been an uneven experience with guiding and historical detail. One poor account described an underprepared guide and weak facts, while another found the guide excellent and informative. I would treat that as a reason to keep your expectations sensible: the quality of the evening depends heavily on who leads your group.

Middleton Tavern and the spirit called Roland

The first stop is Middleton Tavern, a building nearly 300 years old. You go inside, hear stories about people connected with the building, and have the chance to order a drink while watching for Roland, the spirit associated with the tavern.

This is a smart opening stop because it sets the tone without rushing straight into the darkest material. A pub gives the group a place to gather, settle in, and learn how the evening will work. You can order a beverage, but it is not included in the $36 price.

I like the practical choice of beginning at a place with a named resident spirit. Roland gives the story a clear focus, and the tavern setting makes the opening feel social rather than theatrical. You are likely to get the most from it if you listen closely to how the guide separates the building’s known past from the stories attached to it.

The tradeoff is time. About 20 minutes here means the tour is not spending every minute walking between locations or piling up ghost stories. It is giving you room to sit and take in one place. That will please pub-crawl fans, but it may frustrate anyone who wants a rapid series of haunted accounts.

The Old Annapolis Jail at 136 Dock Street

The next stop moves into a more serious setting: the Old Annapolis Jail at 136 Dock Street. Here, the focus is on accused criminals waiting for trial and the conditions they faced before their cases were decided.

This stop adds useful context to the supernatural stories. A jail naturally brings questions of fear, punishment, uncertainty, and death. The guide also tells stories about people who met their fate here and are still said to walk the streets.

For me, this is one of the route’s strongest contrasts with the taverns. At Middleton Tavern, the ghost story comes with a drink and a welcoming interior. At the jail, the subject is confinement and accused people waiting to learn what would happen to them. You get a clearer sense of how the city’s old buildings held very different kinds of lives.

The listed time is about 20 minutes. That is enough for an explanation of the jail’s role and several related tales, but not enough for a long historical lecture. If the guide keeps the focus sharp, the stop should feel substantial. If you are hoping to tour every corner of the former jail, the description does not promise that.

Reynolds Tavern and the 1747 Pub legend

Reynolds Tavern and the 1747 Pub provide another sit-down stop, with a drink available for purchase and a renowned local legend at the center of the visit. The warning is simple: stay on the resident spirit’s good side.

The playful tone here helps keep the crawl from becoming too grim. A pub with a resident ghost gives the guide a chance to tell a story that is memorable without relying only on tragedy. It also gives you another chance to rest during the walk.

You should budget for more than the tour fee if you intend to drink at each pub. Three or four paid beverages can quickly cost more than the admission itself, depending on what you order. The sensible approach is to choose one or two stops for a drink and treat the others as storytelling locations.

This is also where the tour’s format becomes clear. You are not racing through a list of haunted addresses. The evening alternates between walking and time inside pubs. One account found the longer bar stops less appealing than additional ghost stories, so consider your own preference before booking.

St. Anne’s Parish and the fire of 1858

At St. Anne’s Parish, the emphasis shifts from tavern legends to a church that survived a major fire in 1858. You hear about the man rumored to have started the hauntings and the spirits said to linger on the grounds.

The stop lasts about 10 minutes, making it one of the shorter pauses. That is probably enough for a focused account of the fire, the supposed source of the hauntings, and a few notable spirits. You should not expect a full church tour or a long examination of the building’s past.

I like this part of the route because it broadens the setting. Taverns can make a ghost crawl feel predictable. A church introduces a different atmosphere and lets the guide tell a story shaped by fire, religious space, and public memory.

The church stop may also be better for listeners than for photographers. The appeal lies in the account you hear and the place where you hear it, not in a scheduled interior visit or a special visual presentation. Keep your attention on the guide rather than expecting a formal attraction stop.

Rams Head Tavern and the petty spirits

Rams Head Tavern brings the group back indoors for about 20 minutes. The stories concern people who lived and worked in the building during the early 18th and 19th centuries, along with petty spirits said to remain in its walls.

The phrase petty spirits suggests a lighter kind of haunting than the jail stories. That variety helps the evening. A steady run of tragic tales can become heavy, while smaller, more mischievous accounts give the group a chance to laugh.

This is another point where the pub-crawl format matters. The building is not just a backdrop. You can sit, listen, and order a beverage while the guide explains why the place has its reputation. The cost of food and drink remains separate, so plan this as an optional purchase rather than part of your ticket.

If you dislike long stops in bars, this may be the point where the schedule feels drawn out. If you value a relaxed pace and want time to talk with your group, the pause can be welcome. The maximum group size is 25, which keeps the gathering limited but does not guarantee a quiet corner.

Government House and a change in setting

The Government House of Maryland is not the original government house, but the building at the site has its own history and ghostly inhabitants. The stop lasts about 10 minutes.

This is a useful reminder that haunted Annapolis is not limited to taverns. Government buildings carry stories of power, public life, and people who worked in important places. Even with a short visit, the stop adds a different type of setting to the route.

The wording about the current building matters. You are hearing about the site and the building that now occupies it, not touring the original government house. Keep that distinction in mind so you know what kind of historical explanation to expect.

Because the stop is brief, I would listen for the central story rather than expect a large collection of legends. The value here comes from the route’s variety. After several pubs and a church, a government site gives the final stretch a new focus.

Galway Bay and Annapolis during Prohibition

The last stop is Galway Bay Irish Restaurant and Pub, where you hear about one of the important sites connected with Annapolis’ Prohibition history. You are invited to sit down and have a drink at a place where, in the story, others could not legally do the same.

This is a fitting end because it brings the evening back to the pub setting while adding a clear historical theme. Prohibition stories usually work well in a social setting, and this stop lets you consider how drinking, law, and local business once intersected.

Again, your beverage is your own expense. The tour fee pays for the guide and the organized walk, not the drinks at the stops. That makes the price fair if you see the tour as a guided evening walk with optional purchases. It is less of a bargain if you expect several drinks to be included.

The tour ends back at the original meeting point. That makes planning easier, especially if you have dinner, transport, or another evening plan nearby.

What $36 buys you, and what it does not

At $36 per person, the main value is the guide-led access to a sequence of historic places and local stories. You are paying for about two hours of organized content, not admission to a museum or a set number of drinks.

The stops themselves list no admission charge. That means the price is largely for the guide, planning, and storytelling. I think the value is reasonable for people who want structure and local context. You could walk around Annapolis independently, but you would not have the same organized route or the same explanations tied to each site.

The extra cost is easy to overlook. Alcoholic beverages are not included, and there is no private transportation. You also should plan to tip the guide separately. If you drink at several stops, your total evening cost will be well above $36.

The tour is offered in English and uses a mobile ticket. Confirmation arrives within 48 hours, subject to availability, so do not assume an instant confirmation if you are making tight plans. It is often booked about 10 days ahead, so reserving before your visit is sensible.

Who should book this haunted pub crawl?

I would choose this tour if you like local legends tied to real buildings, want an evening activity after sightseeing, and enjoy a pub stop as much as the walking portion. It suits couples, friends, and adults who prefer a guided story night to a formal history tour.

It is also a good fit if you want variety. The route includes a tavern, jail, church, government site, and restaurant pub. The tone shifts between grim, historical, and playful, rather than staying at one level of fright.

I would hesitate if you want a highly theatrical ghost show, a quick-moving route, or a serious scholarly lecture. The experience depends on the guide, and the pace includes several 20-minute pub stops. It is not recommended for people with mobility impairments, and service animals are allowed.

Should you book the Annapolis Boos & Booze crawl?

Book it if the idea of hearing ghost stories inside old Annapolis pubs appeals to you more than chasing scares. The best reasons to go are the varied route, the named spirits such as Roland, and the way the stories connect with the Old Annapolis Jail, St. Anne’s Parish, and Prohibition-era Galway Bay.

Skip it if you want every minute filled with new legends or if you do not want to pay extra for drinks. Ryan has earned praise for a patient, pleasant guiding style, but the mixed accounts about presentation and historical detail show that the guide can shape the evening.

You can cancel for a full refund up to 24 hours before the 6 p.m. start. Within 24 hours, the payment is not refunded. For most people, I would book several days ahead, arrive ready for a walking tour, and decide in advance how many drinks fit your budget.

FAQ

Where does the Annapolis Ghost Tours Boos & Booze tour begin?

It begins at 22 Market Space, Annapolis, Maryland 21401.

What time does the tour start?

The tour starts at 6:00 p.m.

How long does the haunted pub crawl last?

The experience lasts approximately two hours.

Where does the tour end?

It ends back at the original meeting point.

Are drinks included in the $36 price?

No. Alcoholic beverages are not included and must be purchased separately.

Is private transportation provided?

No. Private transportation is not included.

How large can the group be?

The tour has a maximum of 25 participants.

Is the tour offered in English?

Yes. The tour is offered in English.

Can I cancel for a full refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations within 24 hours are not refunded.