Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis gets especially atmospheric after dark, when this two-hour haunted pub crawl links old taverns, a former jail, a church, and government buildings through stories of spirits and tragedy. You will stop at seven places, with time to buy a drink at several of them.

I like the mix of local history and pub time, and I like that the group is capped at 25 people. The catch is that the tour spends about 20 minutes at several bars, so you may want more ghost stories and less drinking time. One guide, Ryan, received warm praise for patience and a friendly manner, though another guest found the guide’s presentation and historical detail lacking.

• Seven downtown stops: Taverns, a former jail, St. Anne’s Parish, and Maryland’s Government House all fit into one walk.
• Drinks are optional purchases: Your $36 ticket covers the guide and tour, but not alcoholic beverages.
• Roland at Middleton Tavern: Keep an eye out for the resident spirit named by the staff.
• A small group setting: The tour accepts no more than 25 people, which should make it easier to hear the guide.
• A 6:00 pm start: The evening timing suits visitors who want a story-filled walk before dinner or more nightlife.
• Free cancellation deadline: Cancel at least 24 hours before the start for a full refund.

Why this Annapolis ghost walk works

This is not a haunted house with actors, props, or sudden scares. It is a guided walk through old Annapolis, where the setting supplies most of the mood. You hear stories connected to real buildings, people, deaths, fires, jails, and Prohibition-era activity.

That approach suits me because the best ghost tours use the city itself as the stage. You begin at 22 Market Space and return there after visiting seven locations. The route keeps you in the central part of Annapolis, and the stops are short enough to give you variety without turning the evening into a single long lecture.

The $36 price is fair if you want a guided introduction to Annapolis after dark and plan to buy one or two drinks along the way. It is less attractive if you expect the ticket to include beverages, admission to special rooms, or a steady stream of dramatic hauntings. The pubs are part of the setting, but your food and alcohol are extra.

The tour is offered in English, with mobile tickets. Confirmation is sent within 48 hours of booking, subject to availability. Since the experience is limited to 25 people, booking around 10 days ahead is a sensible idea, especially if your Annapolis visit falls on a busy weekend.

Middleton Tavern and the spirit called Roland

The first stop is Middleton Tavern, a nearly 300-year-old building with a long connection to Annapolis dining and drinking. You enter, hear stories about people connected to the building, and have the chance to order a drink.

The most specific piece of atmosphere here is Roland, a mysterious spirit named by the tavern staff. That detail gives you something concrete to watch for instead of leaving the ghost story at the level of vague whispers. Keep your eyes open, but treat any strange movement as part of the fun rather than proof of the supernatural.

You spend about 20 minutes here. That is enough time for an introduction and a drink, but not enough for a full meal. If you want dinner, plan to eat before or after the tour rather than counting on a relaxed table service experience during the crawl.

The old jail at 136 Dock Street

At 136 Dock Street, the focus shifts from tavern spirits to the Old Annapolis Jail. You learn what life was like for an accused person waiting for trial, along with stories of people who met their fate there and are still said to walk the nearby streets.

This is one of the more valuable stops for anyone who wants history alongside the ghost tales. A jail gives the guide a chance to explain fear, uncertainty, and punishment in human terms. The stories gain weight because the location was tied to real legal hardship, not simply a building chosen for its age.

The stop lasts about 20 minutes. You should expect an explanation from outside or around the site rather than a long indoor jail tour, since no separate admission is included. The experience is strongest when you listen for the link between the building’s past and the legends attached to it.

Reynolds Tavern and the 1747 Pub

Next comes Reynolds Tavern and its 1747 Pub, another chance to buy a drink while hearing about a famous local legend. The warning here is playful but clear: stay on the resident spirit’s good side.

This stop shows the tour’s basic rhythm. You hear a story, spend time in an old drinking place, and decide for yourself if you want a beverage. The format works well for a relaxed evening, especially if you prefer conversation and atmosphere to a rapid march from one ghost site to the next.

It can also be the point where the tour feels slow for some people. You spend about 20 minutes at the stop, and a portion of that time may go toward ordering or sitting with a drink. If you want a dense history lesson, pay close attention during the guide’s introduction, then use the pub time to ask questions.

St. Anne’s Parish and the fire of 1858

St. Anne’s Parish brings a change of pace. The stop lasts about 10 minutes, and the subject is a church nearly 300 years old that survived a major fire in 1858.

You hear about the man rumored to have started the hauntings, as well as notable spirits said to linger on the grounds. The church setting adds a different kind of mood from the taverns. Here, the stories are tied to religious space, fire, memory, and the idea that certain events leave a mark on a place.

Because this is a short stop, do not expect a long architectural visit or time to explore every corner. It works as a compact story break between the longer pub visits. You may appreciate the change if you want the crawl to feel like a walking tour of Annapolis, not simply a bar route.

Rams Head Tavern and petty spirits

Rams Head Tavern returns you to the pub setting, with tales about people who lived and worked in the building during the early 18th and 19th centuries. The building is also said to house petty spirits, which gives this stop a lighter edge than the jail or church.

The word petty matters here. Not every ghost story needs to involve murder, tragedy, or a grand curse. Small disturbances and troublesome personalities can make the stories more amusing and easier to remember. This stop is a good fit if you enjoy folklore with a bit of humor.

Again, allow about 20 minutes. Drinks are not included, so you can order only if you want to. If you have already had enough by this point, you can still listen to the story and treat the pub as a historic setting rather than a required drinking stop.

Government House of Maryland

The Government House stop lasts about 10 minutes. The building you see is not the original government house, but the site has a long political past and its own ghostly inhabitants.

This stop adds a useful layer to the evening. Annapolis is not only old taverns and sailors. Government buildings also carry stories about the people who worked, lived, argued, and died around them. Even with limited time, the location helps show how hauntings are connected to many parts of city life.

Do not expect access to a private interior or a formal government tour. The value here is the story and the setting along the route. It is a brief pause that keeps the tour moving toward its final pub.

Galway Bay and Annapolis during Prohibition

The final stop is Galway Bay Irish Restaurant and Pub, where the subject turns to Annapolis during Prohibition. You can sit down, hear about one of the key sites in that local story, and order a drink if you choose.

This is a smart ending because it connects ghost-tour entertainment with a documented period of American history. The phrase have a drink where others could not captures the joke, but the stop also gives you a glimpse of how alcohol shaped local life when it was illegal.

You spend about 20 minutes here. Since the activity ends back at the original meeting point, you can return to Market Space afterward or continue your evening nearby. The tour does not include private transportation, so you walk between the stops and make your own plans once the guide says goodbye.

What the guide can make or break

A ghost tour depends heavily on delivery. The stories need clear timing, enough detail, and a guide who can read the mood of the group. Ryan received especially strong praise for patience, a pleasant manner, and an informative approach. If Ryan is leading your tour, you can expect a guide who has been described as easy to spend an evening with.

The feedback is not uniform. One account described a guide as too young and poorly dressed, with weak historical facts and poor coordination at the establishments. That is worth keeping in mind, since the experience relies on both the guide and the pubs being ready for the group.

Another person felt the guide was pleasant but wanted more ghost stories and less time in each bar. This is the clearest practical warning for booking. You should choose this crawl if you want a social night with history and drinks. Pick a more story-heavy walking tour if you want nonstop legends and little downtime.

The tour promises researched history and authentic local ghost stories. The key word for you is balance. Some stops are built around a story, while others give you time to sit and drink. The experience will feel better if you know that before you arrive.

Timing, walking, and group size

The 6:00 pm start gives you an evening setting without making the tour a late-night event. At roughly two hours, it fits neatly before or after dinner. You will return to the starting point, which keeps the night simple if you have a hotel or restaurant nearby.

The group limit is 25 people. That is not an intimate private tour, but it is small enough for the guide to address the group without a microphone in many situations. Arrive ready to walk between stops, and wear shoes that you can manage for two hours.

The activity is not recommended for people with mobility impairments. Service animals are allowed, and the meeting point is near public transportation. Most people can participate, but the route’s walking and the time spent entering and leaving pubs are worth considering before you book.

Who should book the Boos & Booze crawl

I would choose this tour for a first evening in Annapolis, a casual night with friends, or a date that needs a little structure. You get a guided look at old buildings, a former jail, a church, government history, and several pubs without having to plan the route yourself.

It also suits you if you like ghost stories but do not need theatrical scares. The tales are tied to local buildings and people, and the pubs give the night a social feel. The English-language format keeps the storytelling straightforward.

I would hesitate if you do not drink and dislike pub stops. You can skip the alcohol, but the tour still spends substantial time at bars. I would also hesitate if your main goal is an intense paranormal investigation. This is a history walk with ghost lore, not a specialized hunt for evidence.

The guide matters more than usual. Ryan has been praised for making the evening friendly and informative, but the mixed feedback shows that the standard can vary. If you book, keep expectations focused on a pleasant, story-based walk rather than a perfectly staged production.

Should you book this Annapolis ghost tour?

Book it if you want a moderately paced evening walk that mixes local legends, old buildings, and optional drinks. The $36 cost is reasonable for a two-hour guided experience, especially if you value the route planning and the chance to hear stories you would not find by simply walking past the buildings.

Skip it if you want a rapid series of frightening tales or if you would rather spend the whole evening inside historic sites. The long pub stops are either the tour’s best feature or its main weakness, depending on what you want.

Cancel at least 24 hours before the 6:00 pm start for a full refund. Changes or cancellations within 24 hours are not refunded. That simple rule gives you some flexibility, but you should make your decision before the final day.

FAQ

How much does the Annapolis Boos & Booze tour cost?

The tour costs $36 per person. Alcoholic beverages are not included, and you pay separately for any drinks you order.

How long does the haunted pub crawl last?

The experience lasts approximately two hours and ends back at the starting point in Market Space.

Where does the tour begin?

The tour begins at 22 Market Space, Annapolis, Maryland 21401.

What time does the tour start?

The scheduled start time is 6:00 pm.

How many people can join the tour?

The tour has a maximum group size of 25 people.

Can I cancel for a full refund?

Yes. You can receive a full refund if you cancel at least 24 hours before the experience start time. Cancellations or changes made within 24 hours are not refunded.