Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Old Annapolis gets livelier after dark. This two-hour haunted pub crawl links historic taverns, a former jail, a church, and government grounds through local ghost stories and carefully chosen stops. I like the mix of folklore and real Annapolis history, and I like that you can settle into several old pubs instead of rushing from one outdoor stop to the next. The main drawback is that some people may want more ghost tales and less time sitting in bars.

The route is easy to follow, the starting point is central, and the $36 price is fair if you want both a guided walk and a chance to visit several atmospheric places. Still, your drinks cost extra, and the experience depends heavily on the guide and on each pub being ready for the group. Ryan has earned especially warm praise for being patient, informative, and pleasant.

Key points before you book

• Seven stops in about two hours: The route covers Middleton Tavern, the Old Annapolis Jail, Reynolds Tavern, St. Anne’s Parish, Rams Head Tavern, Government House, and Galway Bay.
• Drinks are extra: Admission to the stops is included, but alcoholic beverages are not.
• A strong setting for ghost stories: You move through buildings and places tied to nearly 300 years of Annapolis history.
• Small enough to feel manageable: The group limit is 25 people, which helps the guide keep the walk together.
• The guide matters: Ryan received especially strong praise, while one low rating raised concerns about presentation, historical accuracy, and coordination with the pubs.
• Best for walkers who enjoy folklore: The tour is not recommended for people with mobility impairments.

Why this Annapolis ghost walk works

Annapolis is a good city for a ghost tour because the old center is compact and full of buildings with long memories. Here, the stories are not placed in a generic haunted attraction. They unfold at taverns, a former jail, a churchyard, and government grounds.

I like that the experience uses real places as its stage. Middleton Tavern is nearly 300 years old. St. Anne’s Parish also reaches back nearly three centuries and survived a major fire in 1858. The Old Annapolis Jail adds a harder edge, since its stories center on accused criminals waiting for trial and people who met grim ends.

The tone is social rather than frightening. You are not signing up for jump scares or theatrical effects. You are walking through Annapolis at night, hearing local tales, and having the chance to order a drink along the way. That makes the tour a good evening option for adults who want a little mystery without giving up comfort.

The balance may not suit everyone. A three-star experience found the guide pleasant but felt the group spent too much time in bars and not enough time hearing ghost stories. If you prefer a fast-moving historical walk with constant storytelling, that is a real concern. If you enjoy pausing in old pubs, it may feel like part of the appeal.

Meeting at 22 Market Space at 6 pm

The tour begins at 22 Market Space, Annapolis, Maryland 21401, at 6 pm. It also ends back at the same meeting point, so you do not need to arrange a ride between the start and finish.

The central meeting point matters. You can treat this as an evening introduction to Annapolis, then remain in the old center after the tour. The route uses several downtown locations, and the experience includes no private transportation. You will walk between stops.

The group can reach a maximum of 25 people. That is not an intimate private tour, but it is a reasonable size for an urban walk. A smaller group usually makes it easier to hear stories and keep track of the guide at crossings and entrances.

You should wear comfortable shoes and expect a mix of outdoor walking and indoor pub visits. The tour is not recommended for people with mobility impairments, so consider the walking demands before booking. Service animals are allowed, and the area is near public transportation.

Confirmation arrives within 48 hours of booking, subject to availability. The tour is offered in English, and mobile tickets make entry and check-in simple.

Middleton Tavern and the spirit called Roland

The first stop is Middleton Tavern, a nearly 300-year-old building with stories tied to the people who lived within its walls. It gives the tour a fitting opening: you enter an old Annapolis tavern, hear about its past, and have the chance to order a drink.

The staff have given one reported spirit the name Roland. That detail adds a personal touch. Instead of hearing only about an unnamed presence, you have a figure to watch for as you take in the room.

Admission to the stop is included, but drinks are not. That distinction is important because the title may suggest that beverages are part of the $36 price. They are not. You can buy a drink, but you are not required to turn every stop into a full round.

Middleton Tavern also sets the pace for the night. You may spend around 20 minutes here, enough time for a story, a look around, and perhaps a beverage. If you prefer a steady flow of folklore, the time can feel generous. If your priority is visiting many different sites, the indoor pauses may seem long.

The Old Annapolis Jail at 136 Dock Street

At 136 Dock Street, the tour turns toward the Old Annapolis Jail. This stop focuses on what life was like for accused criminals waiting for trial. That subject gives the ghost stories more weight than a simple tale about a wandering spirit.

You hear about people connected to the jail and about those said to still walk the streets after meeting their fate there. The setting lets the guide connect legal history, confinement, fear, and local legend.

The visit lasts about 20 minutes. It is one of the route’s more distinctive stops because it moves beyond tavern folklore. You are not only hearing about an old building. You are considering the people who passed through it and the uncertainty of waiting for judgment.

The jail stop may appeal most to you if you enjoy historical context with your supernatural stories. It may be less appealing if you want a direct haunted-house style experience. The focus is on tales and atmosphere, not special effects.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub bring the tour back to the social side of old Annapolis. This is another place where you can sit down and order a beverage while hearing about one of the city’s best-known legends.

The warning to stay on the resident spirit’s good side gives the stop a playful tone. It is less grim than the jail and more focused on the relationship between an old drinking place and the stories that have grown around it.

You spend about 20 minutes here. That repeated format, a story followed by time in a pub, is central to the experience. I like it because you get to see historic interiors instead of only looking at facades. You also get a natural pause in the walk.

Still, this is where the pacing question becomes important. The tour includes several stops of roughly 20 minutes, and the time inside the bars can compete with time for additional stories. If your ideal evening includes a drink and conversation, this rhythm works well. If you want a dense stream of legends, you may wish the guide moved on sooner.

St. Anne’s Parish and the fire of 1858

St. Anne’s Parish offers a short outdoor or grounds-based stop of about 10 minutes. The church is nearly 300 years old and survived a major fire in 1858, giving the guide a clear historical event to work with.

You hear about the person rumored to have started the hauntings and about notable spirits said to linger around the grounds. The church adds variety to the route. After taverns and a jail, you get a religious site with its own stories and a different mood.

Because the stop is brief, expect an overview rather than a long examination of the church. That can be a welcome change in pace. You get a compact story, a chance to take in the setting, and then move on.

This is also a reminder that the tour is not only about buildings where people drank or were confined. Sacred spaces and public landmarks are part of the city’s supernatural map too.

Rams Head Tavern and its petty spirits

Rams Head Tavern brings you into stories about people who lived and worked in the building during the early 18th and 19th centuries. The tales are described as tragic, with a few petty spirits said to remain in the walls.

The word petty suggests a different type of haunting. You may hear about spirits associated with small annoyances or troublesome behavior rather than a single grand tragedy. That can give the tour some humor after the darker material at the jail.

This stop lasts about 20 minutes. As at the other taverns, you can order a drink at your own cost. The value here comes from combining a historic interior, a local story, and a short break from walking.

I would use this stop to judge your own preference for the tour’s tone. Annapolis Ghost Tours Boos & Booze is not trying to make every story terrifying. It mixes sadness, curiosity, humor, and pub culture. That broad range is part of its charm, but it may feel too light for someone seeking a serious paranormal investigation.

Government House and a changing seat of power

The Government House of Maryland adds a civic chapter to the route. The current building is not the original government house, but the site and building still carry a long political past and their own ghostly inhabitants.

This stop lasts about 10 minutes. It is shorter than the tavern visits, but it helps widen the subject beyond private buildings. You hear that public power and government life also have their lingering stories.

The stop works best as a quick outdoor explanation rather than a major tour highlight. You are not visiting the original government house, and that distinction matters. The appeal lies in the site’s connection to Maryland government and in the legends attached to the building that now occupies it.

Galway Bay and Annapolis Prohibition history

The final stop is Galway Bay Irish Restaurant and Pub, where you can sit down and order a drink at a place tied to Annapolis Prohibition history. The guide frames it as one of the important local sites from that period.

This is a clever closing stop. The tour begins with an old tavern, moves through crime, religion, government, and tragedy, then ends with a story about a time when drinking itself was restricted. It brings the evening back to the pub setting while adding a specific historical theme.

You spend about 20 minutes here. If you have been buying drinks, this may be your last chance to settle in before returning to the starting point. Again, the beverage is your responsibility.

The Prohibition connection may be especially interesting if you prefer social history to ghost lore. It gives you a reason to remember the stop even if supernatural stories are not your main interest.

What the $36 price really buys you

At $36 per person, the cost is reasonable for a two-hour guided experience with seven stops, provided you value the guide and the access to historic pub interiors. You are paying for the route, storytelling, local research, and organization, not for drinks or transportation.

The stop admission is listed as free, so your main extra expense is whatever you choose to order. You can keep the evening affordable by buying only one drink, or spend more if you want a beverage at several pubs. The tour price itself does not cover alcoholic drinks.

The value is strongest for someone who would otherwise spend the evening wandering downtown without knowing the stories behind the buildings. You get a ready-made route and historical context. The value is weaker if you plan to visit the same pubs independently and mainly want a long list of ghost accounts.

The quality of the guide is a major part of the equation. Ryan received high praise for being patient, pleasant, and informative. One low rating raised concerns about a young guide’s clothing, historical accuracy, and whether the pubs were expecting the group. That is a serious warning, even though it appears to be an isolated poor experience among the available ratings.

Who should book this haunted pub crawl?

I would recommend it to adults who enjoy old buildings, local legends, and a relaxed evening with several chances to sit down. It also suits first-time visitors who want a quick introduction to Annapolis after dark without committing to a long ghost investigation.

You are likely to enjoy it if you appreciate stories that connect folklore to real places. The jail, church, government site, and Prohibition stop give the route more range than a simple bar-to-bar crawl.

I would think twice if you have limited mobility, dislike walking, or want a fright-focused attraction. I would also hesitate if you do not want to pay extra for drinks, since beverages are not included.

The tour has an average rating of 4.3 from nine ratings, so the overall response is positive but based on a small pool. Book with sensible expectations: this is a guided history-and-ghost walk with pub stops, not a guaranteed paranormal encounter.

Practical details that can shape your night

The start time is 6 pm, and the experience lasts about two hours. It ends where it begins at 22 Market Space, which makes it easy to continue your evening nearby.

Free cancellation is available if you cancel at least 24 hours before the start time. Cancelling within 24 hours does not qualify for a refund, and changes made inside that window are not accepted.

The tour runs in English. Most people can participate, but it is not recommended for people with mobility impairments. Service animals are allowed, and the route is near public transportation.

Since the group can reach 25 people, arrive ready to stay with the guide and listen in busy indoor spaces. If a specific guide matters to you, you may want to ask about availability when booking, since the guide can shape the experience considerably.

Should you book Annapolis Ghost Tours Boos & Booze?

Book it if you want a social evening that blends local ghost stories, old pubs, and Annapolis history. The route is varied, the central meeting point is convenient, and the $36 fee is fair when you consider the guide and seven stops.

Skip it if you want nonstop supernatural stories, a highly theatrical scare tour, or a fully inclusive price with drinks. For the best match, think of this as a walking history tour with haunted themes and pub breaks. With a strong guide such as Ryan, it can be a relaxed and memorable way to see Annapolis after sunset.

FAQ

Where does the Annapolis haunted pub crawl begin?

It begins at 22 Market Space, Annapolis, MD 21401, USA.

What time does the tour start?

The tour starts at 6 pm.

How long does the experience last?

The tour lasts approximately two hours.

Where does the tour end?

The tour ends back at the meeting point at 22 Market Space.

Are drinks included in the $36 price?

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

How many stops are included?

The route includes seven stops: Middleton Tavern, the Old Annapolis Jail, Reynolds Tavern and the 1747 Pub, St. Anne’s Parish, Rams Head Tavern, Government House of Maryland, and Galway Bay Irish Restaurant and Pub.

Is the tour offered in English?

Yes. The tour is offered in English.

What is the maximum group size?

The tour can include a maximum of 25 people.

Is the tour suitable for people with mobility impairments?

The experience is not recommended for people with mobility impairments.

Can I cancel for a full refund?

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