Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis mixes old taverns, a former jail and ghost stories into one evening walk. This crawl takes you to seven sites, including a pub where staff say a spirit named Roland has made himself at home. The history is part of the fun, even if you come more for a spooky tale than a serious lecture.

I like the mix of places: you get stories at pubs and historic landmarks, rather than spending the whole evening in one bar. I also like the short stops, which give you a taste of several local spots without asking you to commit to a full evening at each one.

The trade-off is that drinks are not included, and the tour spends time inside pubs. If you want a steady stream of ghost stories and historical detail, rather than breaks for a drink, this format may feel slow. The guide’s delivery also matters: Ryan has been praised for a patient, engaging approach, but feedback on the tour’s historical depth and professionalism is not uniformly positive.

Seven stops, seven stories

• Middleton Tavern: A nearly 300-year-old tavern, with a story about a spirit staff call Roland.
• The Old Annapolis Jail: Hear what it was like to wait there as an accused person awaiting trial.
• Reynolds Tavern and 1747 Pub: Drink at a site linked to one of Annapolis’ best-known legends.
• St. Anne’s Parish: Learn about the church, its survival of an 1858 fire, and its reported hauntings.
• Rams Head Tavern: Hear tales tied to people who lived and worked in the building in the 18th and 19th centuries.
• Government House: Visit the site of Maryland’s Government House, where the present building is not the original.
• Galway Bay: End with a pub stop at a site associated with Annapolis’ Prohibition history.

A ghost walk through taverns and old Annapolis

The Boos & Booze Haunted Pub Crawl is a two-hour evening tour by Annapolis Ghost Tours and Haunted Pub Crawls. It begins at 6 pm at 22 Market Space and ends back at the same meeting point. The route takes in seven historic sites, with guides telling local ghost stories alongside the history.

The format is part walking tour, part pub crawl. Several stops include time inside a tavern or restaurant, while others are brief visits to historic sites. If you like learning a little about a place before settling in for a drink, this balance can work well. If you would rather hear stories without pauses for pub visits, you may prefer a dedicated history walk.

The maximum group size is 25. That is small enough to feel more personal than a large coach tour, though a full group can still make it harder to hear in a busy pub. The tour is offered in English, and your ticket is mobile, so you can keep it on your phone.

Middleton Tavern and the spirit called Roland

The crawl starts at Middleton Tavern, a building that is nearly 300 years old. You’ll spend about 20 minutes here hearing stories tied to people who lived within its walls. The tour also introduces Roland, a spirit that staff have named and that you’re invited to keep an eye out for.

This is a strong opening stop because it sets the tone: history, a working pub and a ghost story in the same place. You can go inside and have a drink, but beverages are not included in the $36 ticket. The listed stop has no admission charge, so the ticket price pays for the guided tour rather than entry to the tavern.

Treat the spirit story as folklore, not proof of the supernatural. The appeal is in hearing how a local tale attaches itself to a real old building, then looking around with that story in mind.

At 136 Dock Street, meet the old jail

The second stop is the Old Annapolis Jail at 136 Dock St. The guide explains what life was like for an accused criminal waiting for trial, then connects the site to stories about people said to still walk the surrounding streets after meeting their fate there.

You’ll spend about 20 minutes here. This stop offers a change of pace from the taverns, and the jail’s subject matter gives the ghost stories a darker edge. It is also a reminder that an old town’s past is not only about historic buildings and notable names. Some of its stories concern people who faced uncertainty, confinement and punishment.

The information provided does not specify whether you enter the jail itself. Plan on hearing about the site, rather than assuming the tour includes a jail interior visit.

Reynolds Tavern and its 1747 Pub legend

At Reynolds Tavern and 1747 Pub, the group has another 20-minute stop and time to enjoy a beverage. The site is linked to one of Annapolis’ best-known legends, and the guide warns that you should stay on the resident spirit’s good side.

This is a useful stop for anyone who enjoys the social side of a pub crawl as much as the spooky material. You can take in the setting, hear the story and decide whether you want to order something. Again, drinks are extra, and there is no stated minimum purchase.

The amount of time spent inside a pub is worth bearing in mind. One of the main criticisms of this kind of tour is that the bar stops can take time away from additional stories. If you value atmosphere and a chance to sit down, that pause is a plus. If you want as much storytelling as possible, it may feel like a detour.

St. Anne’s Parish and the fire of 1858

The stop at St. Anne’s Parish is shorter, at about 10 minutes. Here, the guide talks about a nearly 300-year-old church that survived a major fire in 1858, as well as the man rumored to have started the hauntings and the notable spirits said to linger on the grounds.

This is one of the tour’s landmark stops rather than a pub visit. It adds a different kind of setting to the evening and gives the route a religious and civic dimension. The brief time here means the story will be concise, so it is best approached as one chapter in a larger route, not a detailed church visit.

Rams Head Tavern and old working lives

Next comes Rams Head Tavern, with about 20 minutes set aside for stories about people who lived and worked in the building during the early 18th and 19th centuries. The guide also shares tales about petty spirits said to reside there.

This stop keeps the focus on the people behind the old buildings. You are not just hearing that a place is haunted; you’re hearing stories connected to its former occupants and workers. That human element is what can make a ghost tale more than a quick scare.

As at the other taverns, this is a chance to go inside and have a drink, with the cost on you. If you are keeping a close eye on your budget, you can still join the tour without treating every stop as a round. No drinks are included in the ticket price.

Government House and Galway Bay

The tour makes a short, 10-minute stop at Government House of Maryland. The current building is not the original Government House, but it has its own history and ghostly inhabitants. This detail gives the guide a chance to distinguish between the site and the structure standing there now.

The final listed stop is Galway Bay Irish Restaurant and Pub, where the group spends about 20 minutes. The story here is tied to Annapolis’ Prohibition history, and the pub visit offers a fitting end to a tour built around buildings with old lives and lingering tales. The crawl then returns to its starting point.

The seven stops add up to about two hours. Since several visits include a pub, the evening is not simply a brisk walk from landmark to landmark. That makes it a comfortable choice if you want time to settle in, but less ideal if your main goal is maximum story content in minimum time.

What $36 gets you, and what it does not

At $36 per person, the ticket covers a guide, researched historical material and local ghost stories. It does not cover alcoholic or other beverages, private transportation or a tip for the guide. The stop descriptions list no admission charge, so you are not paying separate entry fees for the sites on this route.

The value depends on what you want from the evening. For seven stops, a two-hour guided outing and a mix of pub atmosphere and local lore, the price is reasonable if you enjoy both parts of the format. If you plan to buy drinks at several stops, budget for that separately; the total cost can rise beyond the ticket price.

The tour’s quality also rests heavily on the guide. Ryan has been described as patient and engaging, and a warm, clear guide can make a big difference when stories are the main attraction. At the same time, concerns have been raised about uneven historical detail, professionalism and whether venues were expecting the group. Keep your expectations measured: this is a themed pub crawl, not a specialist archival tour.

Timing, comfort and booking details

The tour starts at 6 pm and lasts about two hours. It begins and ends at 22 Market Space in Annapolis, near public transportation. Private transportation is not included, so make your own arrangements for getting to and from the meeting point.

The route involves several historic sites and pub stops. The tour is not recommended for people with mobility impairments, so consider that before booking. Service animals are allowed, and most people can participate.

The group is limited to 25 people. The tour is booked, on average, about 10 days ahead, which is useful to know if you are planning around a particular evening. Confirmation is issued 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 less than 24 hours before the tour are not accepted for a refund.

Who should book this crawl?

This tour suits you if you enjoy local ghost lore, historic pubs and a relaxed evening with several short stops. It can also work well as a first look at old Annapolis, especially if you want a guide to connect taverns, a jail, a church and civic history through stories.

It is less suited to you if you want a lecture packed with dates and detail, dislike spending time in bars, or need a route designed for limited mobility. The best reason to book is the combination: a little history, a little local legend and the chance to step inside several long-running establishments.

Book it if you want a sociable ghost walk with pub time built in. If your priority is deep historical analysis or nonstop storytelling, choose a tour designed around that instead.

FAQ

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

The tour lasts about two hours.

What time does the tour start?

It starts at 6 pm.

Where does the tour begin?

The meeting point is 22 Market Space, Annapolis, MD 21401.

Where does the tour end?

It ends back at the meeting point at 22 Market Space.

How much does the tour cost?

The listed price is $36 per person.

Are drinks included in the ticket price?

No. Alcoholic beverages and other beverages are not included.

How many people can join the tour?

The tour has a maximum group size of 25 people.

Is the tour offered in English?

Yes. The tour is offered in English.

Is the tour suitable for people with mobility impairments?

It is not recommended for people with mobility impairments.

How late can I cancel for a full refund?

You can cancel up to 24 hours before the tour’s start time for a full refund. Cancellation within 24 hours is not refundable.