Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis gets spooky in a very practical way: its ghost stories unfold inside old taverns, beside a former jail, and around buildings that have watched the city change for centuries. This two-hour haunted pub crawl covers seven stops, with time to hear local tales and buy a drink at several historic bars.

I like the mix of authentic local legends and real Annapolis landmarks. I also like that the route includes more than pubs, especially the Old Annapolis Jail and St. Anne’s Parish. The main drawback is pace: you may spend a good part of the evening at the bars, so book this for a social history walk, not a nonstop parade of ghost stories.

Key points before you book

• Seven historic stops in two hours: You visit five drinking establishments, the Old Annapolis Jail, St. Anne’s Parish, and Government House of Maryland.
• Drinks cost extra: The $36 tour price covers the guide and storytelling, but not beer, cocktails, or other beverages.
• Ryan is a guide to look for: Ryan has been praised for a patient, pleasant approach and for making the pub stops enjoyable.
• Stories come before scares: Expect local legends and historical background rather than a theatrical haunted-house show.
• The route returns to its start: Meet at 22 Market Space at 6:00 pm, then finish back at the same point.
• Mobility matters: The tour is not recommended for people with mobility impairments.

What $36 buys you in Annapolis

At $36 per person, this is priced as a guided walking experience with several built-in stops, not as an evening of included drinks. Your fee covers the guide, the historical commentary, and access to the organized route. You pay separately for anything you order inside the pubs.

That distinction matters. If you plan to have a drink at most of the taverns, your final cost will rise. Still, the price can make sense if you want an easy introduction to Annapolis after dark, with someone organizing the route and supplying the stories.

The tour lasts about two hours, and the listed schedule divides the time among seven locations. Five stops allow you to go inside a pub or tavern, while two are more focused on outdoor or site-based storytelling. You get enough time at each place to hear the main tale, but not enough for a long meal or a relaxed bar visit.

I would treat the $36 as the cost of a guided evening walk with optional drinks, not as a pub package. That keeps your expectations in the right place.

Starting at Middleton Tavern

The evening begins at 22 Market Space and moves first to Middleton Tavern, a building nearly 300 years old. This is a strong opening because it sets the tone: you are hearing about a working Annapolis building with layers of human stories, not visiting a staged attraction built only for scares.

Inside, you hear about people connected to the tavern and keep an eye out for Roland, the spirit staff have named as a resident presence. The stop lasts about 20 minutes. Admission is included, but your drink is not.

This is one of the better places to decide how you want to approach the evening. If you enjoy a bit of theater and atmosphere, Roland gives the stop a clear focal point. If you prefer documented history, listen for the building’s age and past use, then treat the ghostly part as local tradition rather than proven fact.

The Old Annapolis Jail at 136 Dock Street

The next stop shifts away from the tavern setting. At 136 Dock Street, you visit the Old Annapolis Jail and hear what life was like for an accused criminal waiting for trial.

That detail gives the tour a darker edge. The story is not only about spirits appearing in old rooms. It is also about fear, uncertainty, and the harsh position of people who had been accused but had not yet faced judgment. The guide connects the jail to stories of people said to remain around the streets after meeting their fate there.

You spend about 20 minutes at this stop. It is a useful change of pace after Middleton Tavern, and it helps make the crawl feel like a tour of Annapolis itself rather than a string of unrelated bars.

The practical limitation is that the supplied details do not promise an interior visit beyond the stop itself or describe displays inside. You should expect guided storytelling about the jail and its past, not a long museum visit.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub bring you back to a drinking establishment with a famous local legend. You can buy a beverage here while hearing about the spirit associated with the site.

The advice to stay on the resident spirit’s good side gives the stop a playful tone. That is typical of this experience: the stories are meant to be entertaining, but the locations are real and central to Annapolis history.

You have about 20 minutes here. That is enough time for the guide to explain the legend and for you to order something if you wish. It is not enough time for a full dinner, so eat beforehand or plan a separate meal after the tour.

This stop will suit you if you like ghost stories best when they come with a drink and a little humor. It may feel slow if you are mainly interested in hearing as many legends as possible and do not intend to order anything.

St. Anne’s Parish and the 1858 fire

At St. Anne’s Parish, the focus moves from tavern spirits to a nearly 300-year-old church. The church survived a major fire in 1858, which gives the guide a firm historical event to anchor the supernatural stories.

You hear about the man rumored to have started the hauntings, along with notable spirits said to linger around the grounds. This is a short stop of about 10 minutes, so expect a compact account rather than a full tour of the church.

I like this part because it widens the range of the evening. You are not only hearing about tavern workers and patrons. You are also considering how a major public building, a destructive fire, and old local stories became linked.

The stop is outdoors or site based in the information provided, so dress for an evening walk and do not expect the same seated break you get at a pub.

Rams Head Tavern and its petty spirits

Rams Head Tavern is another 20-minute stop, with stories about people who lived and worked in the building during the early 18th and 19th centuries. The tales turn toward tragedy and the smaller, more troublesome spirits said to occupy the walls.

The phrase petty spirits suggests a lighter mood than the jail stop. Not every ghost story needs to be grim, and this part of the evening seems designed to keep the tone from becoming too heavy.

You can enter and order a drink, but again, the purchase is separate from the tour fee. If you are ordering at every pub, keep an eye on both your budget and the clock. The schedule gives each location a fixed block of time, and your group needs to stay with the guide.

This is also where the tour’s social side becomes most clear. You are moving through old pubs, hearing stories, and deciding how much you want to participate in the drinking portion. You can enjoy the history without ordering alcohol, but the setting naturally encourages a beverage break.

Government House of Maryland

The Government House stop lasts about 10 minutes. The building on the site is not the original government house, but the current structure has its own history and ghost stories.

That distinction is worth noting. The guide is not presenting the building as an unchanged relic from the earliest period. Instead, the point is that the site and the building have their own past, with reported spirits attached to them.

This is another brief storytelling stop rather than a long visit. It works as a bridge between the tavern portions and the final pub. If you prefer a tour filled with major landmarks, this stop adds civic history. If you want only dramatic hauntings, the short presentation may feel thin.

Galway Bay and Annapolis Prohibition

The final stop is Galway Bay Irish Restaurant and Pub, where the subject turns to Annapolis during Prohibition. You can sit down, order a drink, and hear about one of the city’s important sites from that period.

The prohibition connection adds a different kind of mystery. Instead of focusing only on apparitions, the tour touches on secret drinking and the people who used this place when alcohol was restricted. That gives the final stop a strong sense of place and a useful link between social history and ghost lore.

You have about 20 minutes here. It is a pleasant way to finish because you can sit, listen, and decide if you want to continue your evening after the tour. The experience ends back at the meeting point, so you are not left at a distant pub with no clear route back.

Ryan’s guide style and the group size

Guide quality matters a great deal on a ghost walk. The stories need clear delivery, and the guide must manage a moving group while dealing with public bars and busy historic sites.

Ryan has received especially warm praise for being patient, pleasant, and informative. That matters if you want time to settle in at each pub and ask a question. A good guide can also make the difference between a local legend that feels connected to its setting and one that sounds like a loose collection of spooky claims.

The experience allows up to 25 people. That is a medium-sized group. It is small enough for a guide to keep the route together, but large enough that you should not expect a private conversation at every stop.

The guide’s approach may vary. One past experience was criticized for weak historical facts, an unprofessional presentation, and poor coordination with the establishments. That concern is worth keeping in mind because this tour depends on both storytelling and smooth access to the pubs. The positive feedback for Ryan suggests that the experience can be much stronger with the right guide, but I would not assume every evening will feel identical.

How much ghost story do you get?

This is the key question. The tour offers seven locations, but the schedule also gives you time inside several bars. One experience felt that too much time was spent at each drinking stop and not enough time was given to additional ghost stories.

That is a fair concern. The structure is a pub crawl first and a ghost walk second, or at least an even blend of both. If you want a constant flow of legends, you may wish for more stops or longer storytelling at the jail, church, and Government House.

On the other hand, a slower pace can be part of the appeal. You have time to order a drink, sit down at Galway Bay, and enjoy the character of old taverns. The tour is not trying to cram every Annapolis ghost tale into two hours.

I would book it for atmosphere, local stories, and a sociable evening. I would choose a different format if my main goal were an intense, scare-focused presentation.

Timing, walking, and practical comfort

The tour starts at 6:00 pm and returns to the meeting point. Confirmation arrives within 48 hours of booking, subject to availability, and free cancellation is available until 24 hours before the start time. Within 24 hours, you cannot receive a refund, and changes are not accepted.

The route is near public transportation, which helps if you do not have a car. Private transportation is not included, but this is structured as a walking experience through central Annapolis sites.

The tour is not recommended for people with mobility impairments. The information does not give a precise walking distance, number of steps, or seating plan, so contact the provider before booking if walking between stops is a concern. Service animals are allowed, and most people can participate.

Since the evening includes several pubs, wear comfortable shoes and plan your food wisely. The schedule is too tight for a full meal at each stop, and drinks are optional purchases rather than part of the ticket.

Who should book the Annapolis ghost crawl?

I would recommend this experience to you if you enjoy old buildings, local legends, and a drink in a historic tavern. It works well for couples, friends, and adults looking for a relaxed evening activity after seeing Annapolis by day.

It also suits you if you want a guide to connect several sites. Middleton Tavern, the jail, St. Anne’s Parish, Government House, and the pubs would be harder to experience as one coherent evening without a planned route.

I would be cautious about booking if you want a polished theatrical production, a serious paranormal investigation, or a tour packed with nonstop stories. The experience has a social bar component, and the quality may depend on the guide and the evening’s coordination with each establishment.

FAQ

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

The tour lasts approximately two hours.

What time does the tour begin?

The tour starts at 6:00 pm.

Where does the tour meet?

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 $36 price?

No. Alcoholic beverages and other drinks are not included in the tour price.

How many people can join the tour?

The maximum group size is 25 people.

Can I cancel for a full refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations or changes made within 24 hours are not accepted, and the amount paid is not refunded.