Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Boos & Booze makes a clever night of the city’s old buildings: you hear ghost stories, step inside historic pubs, and get a taste of local drinking lore along the way. The most memorable stops include the nearly 300-year-old Middleton Tavern, the Old Annapolis Jail, and Galway Bay, tied to the city’s Prohibition past.

I like the mix of real local history and supernatural tales, and I like that the route includes several places where you can order a drink instead of only listening on the sidewalk. The guide Ryan has earned special praise for being patient and engaging.

The main drawback is the pace. You spend about 20 minutes at several taverns, so the evening may feel more like a pub crawl with ghost stories than a full ghost-history walk. Alcohol costs extra, and the quality of the experience depends greatly on the guide and how smoothly each bar stop works out.

Key points to know before you book

• Seven downtown stops in about two hours: The route covers taverns, a former jail, a church, government grounds, and a pub tied to Prohibition.
• Drinks are not included: The $36 price covers the guided experience, but you pay separately for beer, wine, cocktails, or other beverages.
• Ryan received especially warm praise: His patient and engaging approach helped make the evening enjoyable for one group.
• Stories compete with bar time: Several stops last about 20 minutes, which suits a social evening but may disappoint anyone seeking nonstop ghost lore.
• The group can reach 25 people: That is small enough to feel organized, but not necessarily intimate.
• Mobility matters: The experience is not recommended for people with mobility impairments, and no private transportation is provided.

What this Annapolis ghost pub crawl is really like

This is less a theatrical scare show and more a guided evening through Annapolis buildings with old reputations. You meet at 6 pm at 22 Market Space, then move among seven locations, hearing stories about spirits, accused criminals, tragic workers, church hauntings, and Prohibition.

The route gives you two kinds of entertainment at once. You get local tales that connect ghost lore to actual places, and you get time inside several pubs. That combination works well for a first evening in Annapolis, especially if you want an easy introduction to the city after dinner or before a later night out.

The listed price is $36 per person. That is fair if you value a guide, organized access to several historic locations, and the social ease of a pub crawl. It is less appealing if you expect drinks, private attention, or a long series of elaborate paranormal investigations, since beverages and guide gratuity are extra.

The experience is offered in English, uses a mobile ticket, and ends back at the meeting point. Confirmation arrives within 48 hours, subject to availability. The group limit is 25, so this is not a private tour, but it is also not designed for a huge crowd.

Middleton Tavern and the spirit called Roland

The first stop is Middleton Tavern, a building nearly 300 years old. You go inside, hear about the people connected with its walls, and have the chance to order a drink while keeping watch for Roland, the spirit associated with the tavern.

This is a strong opening because the setting does much of the work. You are not hearing a ghost tale in a generic meeting room. You are in an old tavern with a long working life, and the drink gives you time to look around and settle into the mood.

Plan on about 20 minutes here. Since admission is included, your only extra cost is whatever you choose to order. If you want to keep the bill low, you do not need to buy alcohol, though the pub setting is clearly part of the experience.

The limitation is time. Twenty minutes allows for a story and a drink, but not much lingering. If Roland does not make an appearance, the stop still has value as an old Annapolis setting, but you should not book the tour expecting a guaranteed paranormal event.

The Old Annapolis Jail at 136 Dock Street

At 136 Dock Street, the focus shifts from tavern spirits to the Old Annapolis Jail. You hear what life was like for accused criminals waiting for trial, then learn about people connected with the site who are said to remain in the surrounding streets.

This stop adds useful weight to the crawl. Ghost stories can become vague when they are detached from place. A jail gives the guide a clear setting for discussing fear, confinement, accusation, and uncertain fate.

The visit lasts about 20 minutes, with no separate admission charge. It is a good point in the route for anyone who wants more than pub atmosphere, since the subject turns toward the justice system and the people who passed through it.

Still, keep your expectations measured. The information supplied for the tour does not promise an interior jail investigation or a long architectural visit. You are there to hear the story of the place and its dead, not to spend an hour examining jail cells.

Reynolds Tavern and the 1747 Pub

Reynolds Tavern and the 1747 Pub provide another drink stop, this time tied to one of Annapolis’s best-known legends. The warning to stay on the resident spirit’s good side gives this section a lighter, almost playful tone.

I like this stop for travelers who want the social part of a pub crawl. You can sit down, order something, and hear how a local legend has become part of the identity of the building. The experience does not treat the pubs as mere restrooms between stories. They are part of the story.

You get around 20 minutes here. That is enough to sample the atmosphere, but it can feel long if the guide has only a short tale prepared. One three-star assessment specifically found the bar time longer than expected and wished for more ghost stories instead.

That point matters when you choose this tour. If you enjoy stopping for a drink and chatting with a small group, the timing may feel relaxed. If you want a rapid sequence of haunted locations, the same schedule may seem padded.

St. Anne’s Parish and the fire of 1858

The stop at St. Anne’s Parish lasts about 10 minutes and brings the group to a church nearly 300 years old. You hear how it survived the great fire of 1858, along with stories about the person rumored to have started the hauntings and spirits associated with the grounds.

This is one of the route’s useful changes of pace. After taverns, a church gives the evening a quieter setting and a different kind of ghost story. The age of the building and the fire add a firm historical frame, while the rumored hauntings supply the supernatural angle.

Because the stop is short, expect an outdoor or brief site explanation rather than a full church tour. The material provided does not promise interior access, a service, or a long look at the building. You are there for the story and the atmosphere.

Rams Head Tavern and the petty spirits

Rams Head Tavern brings the group back indoors. Here, the guide tells tragic stories about people who lived and worked in the building during the early 18th and 19th centuries. The resident spirits are described as petty, which suggests a less solemn tone than the jail stop.

The value of this section lies in its human scale. Rather than treating the building as an old shell, the guide connects it to workers and residents. Tragedy, routine, and everyday conflict give ghost stories more shape than a simple claim that a place is haunted.

You have about 20 minutes at the tavern. A drink can make this a comfortable pause, but remember that your beverage is not part of the $36 fee. If you are watching your budget, account for the cost of several optional drinks across the evening.

The tour can work perfectly well without ordering alcohol. Still, the pub setting is central, so someone who dislikes bars may find the format less appealing than a standard historical walking tour.

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 carries its own history and ghost stories.

This stop shows how the tour uses Annapolis itself as the setting. Not every location is presented as a surviving colonial interior. Some are places where layers of civic history and local legend have gathered over time.

It is also a short stop, so you should expect a concise explanation rather than an extended visit inside the building. The information provided does not say that the group enters the Government House or receives a formal interior tour.

For me, this kind of stop works best when you want variety. It breaks up the tavern visits and gives the guide a chance to talk about government, public life, and the spirits attached to important places.

Galway Bay and Annapolis Prohibition history

The final scheduled stop is Galway Bay Irish Restaurant and Pub. The guide connects this location with one of the most important sites in Annapolis’s Prohibition history, then invites you to sit down and have a drink.

That makes a fitting ending. The route begins with an old tavern and finishes with a place tied to secret or restricted drinking. The evening closes not with a dramatic haunted-house finale, but with a social stop where you can reflect on the stories and continue your night if you wish.

You spend about 20 minutes here. Again, the drink is your responsibility, and the tour ends back at the original meeting point. That makes the route convenient for planning dinner or another activity afterward, though you should allow a little flexibility if the group runs behind.

The Prohibition angle also gives the crawl a useful local focus. You are not hearing only generic tales about restless spirits. The evening connects ghosts with taverns, jails, churches, government, and the city’s drinking past.

How much history and how much haunting?

The tour promises researched history and local ghost stories. Those are important strengths, but the balance can vary. One highly positive account praised Ryan’s informative style and patient manner, while another found the stories too limited and wanted more time hearing about ghosts instead of sitting in bars.

You should read that as a useful warning, not a reason to dismiss the tour. The format itself explains the difference. A two-hour crawl with seven stops leaves only a short time at each location, and several stops are built around sitting down for a beverage.

If your ideal evening includes conversation, old buildings, and a few spooky stories, this format should suit you. If you want dense historical detail at every stop, ask yourself if you would rather take a dedicated walking history tour. The strongest version of this experience depends on a guide who keeps the stories focused and uses the bar time well.

Guide Ryan has received particularly warm praise for being patient and enjoyable company. That is worth noting because the guide is the main link between the buildings. You are not simply visiting pubs on your own. The person leading the group shapes how much history you hear and how lively the night feels.

Value, group size, and practical limits

At $36, the tour offers a reasonably priced evening activity, especially if you treat it as guided entertainment plus a route through historic Annapolis. The fee covers the guide and tour content, but not alcoholic drinks, transportation, or a tip.

The cost can rise quickly if you buy a beverage at every bar. You do not have to drink, but if you plan to join the pub side of the crawl, set aside extra money. The price also does not include private transportation, so the experience is best suited to people comfortable getting between the downtown stops without a vehicle supplied by the operator.

The maximum group size is 25. That allows a guide to address the whole group, though it may feel less personal than a small private walk. Since the tour runs in English, you should be comfortable following spoken stories in English for two hours.

It is not recommended for people with mobility impairments. Service animals are allowed, and the meeting area is near public transportation. Most people can participate, but you should consider the movement between several city locations and the time spent in pub settings before booking.

Free cancellation is available if you cancel at least 24 hours before the 6 pm start. Canceling within 24 hours does not qualify for a refund, and changes during that period are not accepted.

Who should book the Annapolis Boos & Booze crawl?

I would choose this tour for a first evening in Annapolis, a casual night with friends, or anyone who likes local legends better when paired with a historic tavern. It also suits visitors who want a planned route rather than researching seven old places on their own.

You will get the most from it if you enjoy a mix of storytelling and social stops. Come ready to listen, but do not expect a nonstop scare show. The ghost stories are the thread connecting the evening, while the pubs provide much of the comfort and character.

I would hesitate to recommend it to someone seeking a serious paranormal investigation, a quiet architectural tour, or a detailed lecture at every stop. The short visits and optional drinks make the evening relaxed, but they also limit the amount of material the guide can cover.

Should you book it?

Book the Annapolis Boos & Booze Haunted Pub Crawl if you want historic pubs, local ghost lore, and an easy two-hour evening for $36 before drinks and tip. The seven-stop route gives you more variety than a single haunted tavern visit, and Ryan’s praised guiding style shows how much a good leader can add.

Skip it if your priority is maximum historical detail or a tightly packed series of supernatural stories. The best fit is a curious, social visitor who enjoys old buildings, a little mystery, and the chance to order a drink along the way.

FAQ

How much does the Annapolis Boos & Booze Haunted Pub Crawl cost?

The tour costs $36 per person. Alcoholic beverages and guide gratuity are not included.

How long does the tour last?

The experience lasts approximately two hours.

What time does the tour begin?

The tour starts at 6 pm.

Where does the tour meet?

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

Where does the tour end?

The activity ends back at the meeting point.

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, if you cancel at least 24 hours before the experience start time. Cancellations within 24 hours are not refunded, and changes during that period are not accepted.