Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis keeps its ghost stories close to the waterfront, where old taverns, a former jail, and nearly 300-year-old buildings make a natural setting for a night walk. This Boos & Booze Haunted Pub Crawl mixes local history with stops for a drink, so you get more than a string of spooky tales.

I like the route’s variety and the chance to step inside several historic pubs, especially Middleton Tavern and Reynolds Tavern. I also like that the stories are tied to real buildings and local characters. The tradeoff is clear: you spend about 20 minutes in several bars, so this suits you best if you want a social pub walk, not a fast-moving ghost-story marathon.

Key points to know before you book

• Seven stops in about two hours: You move between pubs, an old jail site, a church, and Government House.
• Middleton Tavern’s Roland: Keep an eye out for the spirit staff have named Roland while you enjoy a drink.
• Ryan may lead your group: Ryan is praised for a patient, pleasant approach and strong storytelling.
• Drinks cost extra: The $36 tour price covers the guide and tour, not alcoholic beverages.
• A small group helps: The maximum group size is 25 people, large enough for atmosphere but still manageable.
• Walking matters: The tour is not recommended for people with mobility impairments.

Why this Annapolis ghost walk works

The best thing about this tour is its setting. Annapolis is compact, old, and full of buildings with stories attached to them. Instead of hearing ghost tales in a generic theater or bus, you hear them at the taverns, jail site, church, and government grounds connected to the tales.

The tour begins at 6 pm at 22 Market Space and ends back at the same meeting point. That makes it easy to fit into an evening downtown. You do not need private transportation, and the route is near public transportation.

The tone depends partly on your guide. Ryan has earned particular praise for being patient, pleasant, and informative. That matters on a ghost tour because the guide has to balance spooky mood with real facts. One poor experience described an underdressed guide, weak historical details, and confusion at the establishments, so I would keep expectations practical: this is a hosted walking experience, and guide quality can shape the night.

The tour is offered in English and allows service animals. Most people can take part, but the operator does not recommend it for people with mobility impairments. You will be walking between locations and standing during several story sections.

Middleton Tavern and the spirit called Roland

Middleton Tavern is the first major stop, and it gives the tour a strong opening. The building is nearly 300 years old, so the setting itself does much of the work before the guide begins the ghost stories.

You spend about 20 minutes here. You can come inside and order a drink while hearing about people who once lived within the building’s walls. The staff have given one resident spirit the name Roland, which gives you a simple mission for the stop: enjoy your beverage, listen closely, and keep watch.

Your drink is not included in the tour price. That is worth remembering before you arrive. The $36 admission pays for the guide and the walking experience, while alcoholic beverages are your responsibility.

I like this first stop because it sets the format quickly. You are not only standing outside and listening. You get a chance to enter a working historic tavern, settle in for a few minutes, and connect the story to the room around you. The drawback is that 20 minutes is not enough time for a long history lesson and a leisurely drink. Think of it as a short stop with atmosphere, not a full tavern visit.

The Old Annapolis Jail at 136 Dock Street

At 136 Dock Street, the tour turns from tavern lore to the grim side of Annapolis history. This is the site of the Old Annapolis Jail, where you learn what life was like for accused criminals waiting for trial.

The distinction matters. These were people awaiting judgment, not simply villains in a ghost story. That context gives the stop a more human edge. The guide also tells stories about people who met their fate there and are said to continue walking the surrounding streets.

You spend about 20 minutes at this stop. It is one of the more history-focused parts of the route, and it provides a useful change of pace after the first pub. I appreciate that the tour connects supernatural stories to the justice system and everyday fear of the past.

This is also where your expectations matter. The experience promises researched history and local ghost stories, but the amount of detail can vary with the guide. If you want a long discussion of Annapolis criminal justice, this short stop may feel brief. If you prefer a compact story with a strong setting, it fits the tour well.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub offer another chance to sit down with a drink and hear one of Annapolis’ best-known legends. The stop lasts about 20 minutes and centers on a resident spirit whose behavior, according to the tale, depends on how you treat the place.

That detail gives the stop a playful edge. The tour is not trying to frighten you every minute. It moves between tragedy, local legend, and pub humor, which keeps the night from becoming too grim.

The pub stops are also the most social part of the experience. You can order a beverage, listen to the guide, and enjoy a break from walking. A pleasant guide makes a real difference here. Ryan is especially well suited to this kind of stop, with a patient approach that lets the group settle in.

Still, you should know what you are buying. Some people want constant ghost stories and may feel that 20 minutes in a bar is too long. The tour is better for you if you like having time to absorb the setting and order a drink. If your main goal is to hear as many legends as possible, the pub pauses may feel like lost storytelling time.

St. Anne’s Parish and the fire of 1858

St. Anne’s Parish is a shorter stop, about 10 minutes, but it adds a different kind of atmosphere. The church is nearly 300 years old and survived a major fire in 1858. The guide discusses the man rumored to have started the hauntings, along with spirits said to linger on the grounds.

This stop is less about ordering a drink and more about hearing how a historic church became part of Annapolis’ ghost lore. The fire gives the story a clear historical anchor. You are not just hearing that a place is haunted. You are learning about an event that changed the building and helped shape the stories connected to it.

Ten minutes is enough for an introduction, but not for a full tour of the church or its grounds. You should treat this as a focused outdoor story stop. It works well as a pause between the pubs because the route briefly shifts from food and drink to religion, fire, and local memory.

Rams Head Tavern and its petty spirits

Rams Head Tavern brings the group back indoors for another 20-minute stop. Here, the stories focus on people who lived and worked in the building during the early 18th and 19th centuries.

The tour describes several petty spirits connected with the building. That wording suggests a less grand, more mischievous style of haunting. You might hear tales that feel closer to troublesome household encounters than to a single dramatic apparition.

I like the contrast with the Old Annapolis Jail. The jail stop deals with accused criminals and people who met tragic ends. Rams Head shifts attention to workers and residents, which helps the tour show how ghost lore grows from ordinary buildings and ordinary lives.

Again, drinks are optional and separate from the ticket. If you decide to order at each pub, your final cost will be much higher than the $36 admission. You can also focus on the stories and keep your spending down. The tour does not require you to buy alcohol.

Government House of Maryland

The Government House stop lasts about 10 minutes. The building you see here is not the original government house, but the site remains tied to Maryland’s political past and has its own ghostly inhabitants.

This is an interesting reminder that ghost tours are often about places, not only structures. Even when the present building is not the original one, the location can carry layers of memory and rumor.

The stop is brief, so do not expect an extended architectural visit. You will hear about the site and its reported spirits before moving on. I find this kind of stop useful because it widens the tour beyond taverns and tragedies. Annapolis’ ghost stories reach into civic spaces, too.

Galway Bay and Annapolis Prohibition history

The final pub stop is Galway Bay Irish Restaurant and Pub, where you sit down and hear about one of the important sites in Annapolis’ Prohibition history. The tour frames the visit around a simple challenge: have a drink in a place where others once could not legally do so.

That gives the ending a lighter, more social mood. After stories involving jails, fires, and tragic lives, Prohibition history brings the group back to drinking culture and the city’s more colorful past.

You spend about 20 minutes here. This is a good place to ask your guide questions if time allows, especially if you want to connect the ghost stories with the city’s broader past. The tour returns to the original meeting point after this stop, so you are not left searching for a final pickup point.

What $36 buys you

At $36 per person, the tour sits in a reasonable range for a two-hour guided walk with seven locations and several indoor stops. You are paying for the guide, the route, the storytelling, and access to the organized experience. You are not paying for drinks, private transportation, or a tip.

The value is strongest if you plan to spend the evening downtown anyway. You get a ready-made route through notable old buildings, plus a guide who supplies the historical background and local legends. The tour can also save you the trouble of choosing which pubs to visit and how to connect them.

The value drops if you dislike stopping for drinks or if you want a lecture packed with ghost accounts. One three-star experience found the guide pleasant but felt that the tour spent too much time in bars and not enough time on stories. That is a fair concern.

You can control some of the cost by ordering fewer drinks. You can also treat each pub as a setting rather than a required purchase. The guide tip is not included, so plan for that separately if you feel the service deserves it.

Group size, timing, and practical fit

The maximum group size is 25 people. That is not a private walk, but it is small enough that you should be able to hear a guide who manages the group well. Ryan’s patient style is especially useful in a group setting, where people may be ordering drinks, finding seats, or catching up after the walk between stops.

The tour lasts about two hours, though the exact pace can depend on the group and the establishments. The seven stops add up to roughly two hours of planned time, with the longest pauses at the pubs. Wear shoes suitable for walking and expect to stand during at least some sections.

Confirmation arrives within 48 hours of booking, subject to availability. The experience is often booked about 10 days ahead, so I would not leave it until the last evening of a short Annapolis visit.

You can cancel for a full refund up to 24 hours before the start time. Changes or cancellations made within 24 hours are not refunded. The cutoff uses local time, which is worth checking if you are booking from another time zone.

Who should book this ghost pub crawl?

I would choose this tour if you want a relaxed evening of local stories, historic buildings, and pub stops. It fits couples, friends, and small groups who enjoy hearing a tale and then sitting down with a drink. It also works well as an introduction to Annapolis after you arrive, since the route brings together several central sites.

You should think twice if you want a serious paranormal investigation, a fast-paced walk, or a detailed account at every stop. The tour is built around short visits and changing moods. Some stories are tragic, some are playful, and some are tied to old buildings more than to dramatic sightings.

The experience is also less suitable if walking or standing is difficult. Service animals are allowed, and most people can participate, but the operator does not recommend the tour for people with mobility impairments.

Should you book the Annapolis Boos & Booze crawl?

Book it if the mix of historic pubs and local ghost lore sounds better than a pure sightseeing walk. Middleton Tavern, the Old Annapolis Jail, St. Anne’s Parish, and the other stops give the evening a clear sense of place. Ryan is a promising guide choice, and the $36 price is fair when you value the route and the storytelling.

Skip it if you want nonstop legends or if spending time inside bars does not appeal to you. The best way to approach this tour is as a social history walk with ghosts, not as a two-hour scare show. Order only what you want, listen for the details tied to each building, and let the old streets provide the atmosphere.

FAQ

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

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

What time does the tour start?

The tour starts at 6 pm.

How long does the tour last?

The experience lasts approximately two hours.

Where does the tour end?

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

Are drinks included in the $36 ticket?

No. Alcoholic beverages are not included in the tour price.

Is the tour offered in English?

Yes. The tour is offered in English.

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 refunded.