Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis keeps its ghosts close to the bar. This two-hour evening walk links old taverns, a former jail, a church, government grounds, and a Prohibition-era pub, giving you a lively way to meet the city after dark. I like the mix of authentic local ghost stories and real Annapolis history, and I like that the route includes several places where you can stop for a drink.

The $36 price is fair for a small-group evening tour with a guide, especially since you visit seven historic locations. I also appreciate the flexible tone: you get spooky tales, but you are not locked into a theatrical haunted house show. The main drawback is that alcohol costs extra, and some of the stops may feel too long if you want a nonstop stream of ghost stories.

Key points to know before you book

• Seven historic stops: The route includes Middleton Tavern, the Old Annapolis Jail, Reynolds Tavern, St. Anne’s Parish, Rams Head Tavern, Government House, and Galway Bay.
• Drinks are optional and extra: The $36 ticket covers the guide and tour, but not alcoholic beverages.
• Ryan has earned special praise: If Ryan leads your outing, expect a patient and pleasant guide who can make the pub stops especially enjoyable.
• A 6:00 pm start: The timing works well for an evening in Annapolis, with the tour ending back at the original meeting point.
• A maximum of 25 people: This is not a private walk, but the group cap keeps it more manageable than a large city tour.
• Plan for walking and standing: The experience is not recommended for people with mobility impairments.

Why this Annapolis ghost walk works

I like this tour because it uses real places rather than staging a spooky set. You enter old taverns, pause outside or near historic buildings, and hear stories tied to people who lived, worked, suffered, or died in Annapolis. That gives the evening a stronger sense of place than a general ghost-story performance.

The pub-crawl format also makes the experience social. You can listen to the guide, then order a drink at selected stops if you wish. The alcohol is not part of the ticket, so you remain in control of your spending and can skip drinks entirely.

The route lasts about two hours and begins at 6:00 pm at 22 Market Space. It returns to that same meeting point. At $36 per person, the value depends on what you want from the evening. If you want an entertaining introduction to Annapolis folklore, local buildings, and tavern culture, the price is reasonable. If you mainly want a long, detailed lecture on ghost lore, the time spent in bars may feel excessive.

The tour is offered in English, with mobile ticketing. It is limited to 25 people, which gives you a better chance of hearing the guide than you would on a very large group outing. You should still expect a shared experience, not an intimate private tour.

Middleton Tavern and the spirit called Roland

The first stop is Middleton Tavern, a nearly 300-year-old building with plenty of age for a ghost story. Here, the focus is on people connected to the building and the strange activity said to remain behind.

You can go inside and order a drink while keeping an eye out for Roland, the spirit named by the staff. That detail gives the stop a personal touch. Roland is not just an unnamed presence from a guide’s script. The story is connected to the place as it functions today.

You spend about 20 minutes here. That is enough time to hear the story and settle in, but it may feel brief if you want to study the building or order something slowly. Since the drink is not included, remember that this stop can add to the evening’s cost.

I like Middleton Tavern as the opening stop because it introduces the tour’s basic pattern: old building, local tale, optional drink, then another walk through Annapolis. It also gives you an early chance to decide how much of the pub side you want to enjoy.

The Old Annapolis Jail at 136 Dock Street

At 136 Dock Street, you visit the site of the Old Annapolis Jail. The subject shifts from tavern life to confinement, accusation, and the uncertainty faced by people waiting for trial.

This is one of the more serious stops. You hear what life was like for an accused criminal before a verdict, along with stories of people who met their fate there and are still said to walk the nearby streets. The setting supports the material without needing much decoration.

The stop lasts about 20 minutes. That allows the guide to explain the jail’s role and connect it with the ghost stories surrounding the area. I would pay close attention here, since this part gives the tour more historical weight than a simple list of haunted bars.

The drawback is that the tour’s information depends heavily on the guide. One past outing was criticized for weak historical facts, while other feedback praised the guide’s pleasant manner and informative approach. That unevenness suggests you should expect the quality to depend on who leads your group.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub provide another drink stop, this time connected to one of Annapolis’ best-known legends. The wording of the experience points to a resident spirit with a reputation, so the advice is simple: keep on the spirit’s good side.

You spend roughly 20 minutes here. As with Middleton Tavern, you can order a beverage, but it is not included in your ticket. This is a useful place to pace yourself. If you plan to have a drink at every pub, the extra cost can quickly exceed the admission price.

I like the way this stop ties a famous local legend to a functioning tavern. You are not only hearing about a building’s past. You are also seeing how old Annapolis sites remain part of the city’s present-day social life.

Still, this is where some people may want more ghost content. One assessment of the tour found the stories limited and felt too much time was spent in the bars. If your priority is maximum folklore, use each pause to ask the guide questions rather than treating the stop as a long drinking break.

St. Anne’s Parish and the fire of 1858

St. Anne’s Parish changes the mood again. This nearly 300-year-old church survived a major fire in 1858, and the stop focuses on the building’s survival, the man rumored to have started the hauntings, and the spirits said to remain on the grounds.

You spend about 10 minutes here, so this is a short storytelling stop rather than an extended church visit. That brevity can work well in the middle of a pub crawl. It breaks up the tavern visits and adds a religious and civic layer to the evening.

I find this kind of stop valuable because ghost stories often make more sense when you understand the building’s past. A fire, a long-used church, and stories connected to a suspected source of the hauntings give the guide several threads to work with.

Do not expect a full church tour. The supplied details promise ghost tales and historical context, not an interior visit or a lengthy architectural explanation.

Rams Head Tavern and its petty spirits

At Rams Head Tavern, the stories turn toward people who lived and worked in the building during the early 18th and 19th centuries. You hear tragic accounts and may hear about the petty spirits said to remain inside.

The stop lasts around 20 minutes. This is another chance to buy a drink, but the ticket does not cover it. The mix of tragedy and minor mischief should keep the tone from becoming too grim.

The word petty matters here. Not every ghost story needs a dramatic death or a full-body apparition. Small disturbances and troublesome spirits can be more entertaining, especially in a tavern setting. If you prefer stories with a lighter edge, this may be one of the more enjoyable stops.

At the same time, the stop adds to the concern about pacing. Five 20-minute pub visits can leave less time for additional streetside stories. I would choose this tour for a balance of drinks and folklore, not for a tightly packed supernatural lecture.

Government House and the layers beneath it

The Government House of Maryland is not the original government house, but the current building has its own history and ghost stories. The tour spends about 10 minutes here.

This stop helps show that haunted Annapolis is not limited to bars and jails. Government buildings carry a different kind of story, tied to public life and the people who worked in important places. The short visit keeps the route moving while adding variety.

Because the stop is brief, you may get only the key stories rather than a detailed account of the building. That is fine if you want a broad overview of haunted sites around the city. If you want extensive architectural or political background, this tour may leave you wanting more.

Galway Bay and Annapolis during Prohibition

The final stop is Galway Bay Irish Restaurant and Pub. Here, you can sit down and have a drink at a site linked to Annapolis’ Prohibition history.

This is an effective ending because it brings the tour back to the social side of the city. You have heard about jails, fires, churches, government buildings, and tavern spirits. Now you finish at a place tied to one of the most important periods in American drinking culture.

The stop lasts about 20 minutes. You can order a beverage, but you pay separately. The experience frames Galway Bay as a place where you can do what others could not during Prohibition: have a drink.

I like this final stop because it connects the haunted pub crawl to a documented part of Annapolis’ past. It also gives you a comfortable place to finish the route before returning to the meeting point.

What the $36 ticket really covers

The admission price is $36 per person. Included are the guide, researched historical information, and local ghost stories. Admission to the locations on the route is listed as free, but drinks are not included.

That makes the price easier to judge. You are paying for the organized route and storytelling, not for a package of beverages. If you skip alcohol, $36 is a straightforward price for a two-hour guided walk. If you buy drinks at several stops, budget beyond the ticket.

The value is strongest for you if you want an evening activity that combines history and entertainment. It is weaker if you want a bar-hopping night with drinks included or a private guide focused only on supernatural tales.

The tour’s average booking time is about 10 days ahead, so I would not leave it until the last minute if your Annapolis dates are fixed. Confirmation arrives within 48 hours, subject to availability.

Practical details for a smoother evening

Meet at 22 Market Space in Annapolis for a 6:00 pm start. The tour ends back at the meeting point, which makes it easier to plan dinner, lodging, or another evening activity nearby.

The activity is conducted in English and uses a mobile ticket. It is near public transportation, and most people can take part. Service animals are allowed.

The main physical concern is mobility. The tour is not recommended for people with mobility impairments, so consider that before booking. The route includes several stops and likely requires moving between them, standing, and entering public establishments, although the supplied information does not give a precise distance or surface description.

The maximum group size is 25. That is large enough for a social atmosphere but small enough that the guide should be easier to hear than on a mass-market city walk.

The guide can make a major difference. Ryan has been singled out for being patient, pleasant, and informative, with a style that made the pub stops especially enjoyable. Another experience raised concerns about a young guide’s clothing, historical accuracy, and whether the establishments were expecting the group. I would treat that as a warning to keep expectations practical: this is a casual walking tour, and the standard may vary by guide and evening.

Free cancellation is available up to 24 hours before the start time for a full refund. Within 24 hours, cancellation changes are not accepted and the amount paid is not refunded.

Who should book the Boos & Booze crawl?

I would recommend this tour to you if you like old buildings, local legends, and a drink in a historic setting. It suits couples, friends, and visitors who want a relaxed evening activity after seeing Annapolis by day.

It is also a good fit if you prefer ghost stories with a clear connection to real places. Middleton Tavern, the Old Annapolis Jail, St. Anne’s Parish, and Government House give the route a sense of variety.

I would think twice if you have limited mobility, dislike standing, or want a private experience. I would also skip it if you want two solid hours of nonstop ghost stories. The pub stops are part of the point, and the drinks cost extra.

Should you book it?

Book the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl if you want a social, history-based evening with optional drinks and a steady run of local legends. At $36, it offers a reasonable introduction to the city’s haunted side, especially when the guide is strong.

Go in expecting a casual pub crawl, not a polished theatrical show. Ask questions, pace your drink purchases, and keep your expectations focused on atmosphere, stories, and old Annapolis buildings. If that sounds like your kind of night, this tour is worth considering.

FAQ

How long is the Annapolis Boos & Booze Haunted Pub Crawl?

The tour lasts approximately two hours.

What time does the tour start?

The tour starts at 6:00 pm.

Where does the tour begin?

You meet at 22 Market Space, Annapolis, Maryland 21401.

Where does the tour end?

The activity ends back at the meeting point.

Are drinks included in the ticket price?

No. Alcoholic beverages and other drinks are not included in the $36 ticket price.

How much does the tour cost?

The listed price is $36 per person.

How many people can join the tour?

The maximum group size is 25 people.

Is the tour offered in English?

Yes. The tour is offered in English.

Can I cancel for a full refund?

Yes, if you cancel at least 24 hours before the experience start time. Cancellations made within 24 hours are not refunded.