A ghost story comes with your first sip. This Annapolis pub crawl mixes classic haunted locations with locally researched tales in a tight 2-hour loop.

I especially like the way the tour builds atmosphere stop by stop, from taverns to jailhouse history, without turning into a long lecture. The main drawback to consider: the night can feel a bit bar-heavy, so if you want only the scariest stories and very little drink time, you may wish the pacing leaned more toward storytelling.

Key highlights you can count on

• Small group size (max 25) makes it easier to hear the guide and keep the vibe friendly
• Well-researched, history-forward ghost storytelling rather than pure camp
• Pub stops plus famous Annapolis sites keep it from feeling like a one-note haunt
• Spirit named Roland at Middleton Tavern adds a fun throughline
• Prohibition-era stop at Galway Bay ties hauntings to real local history
• Mobile ticket plus a clear meetup point at 22 Market Space

Ghosts and drinks: how this 2-hour crawl really feels

Annapolis does “evening stroll” well. This tour leans into that vibe with a simple format: walk to a haunted spot, hear the story, then take a quick drink break. At 2 hours total, it never feels like you’re committing your whole night to one theme. You get enough time to settle in, but not so much time that boredom has room to show up.

The other big strength is the blend of ghost talk and history. The tour is built around authentic local ghost stories and thoroughly researched, accurate history, which matters more than you’d think. In a lot of haunted tours, the facts are thin and the spooky bits do all the work. Here, the stories come with context, so the hauntings feel tied to real places, real periods, and real people—exactly how local lore is supposed to land.

Price-wise, $36 for about two hours is in the fair, not-fancy category for an experience like this, especially since the stops are run as part of the tour program. The alcohol is not included, so plan on buying your own drinks if you want them. Still, you’re paying mainly for a guide, the story thread, and access to the themed stops—not for a bar tab.

And yes, there can be a bit of “bar time.” One review highlighted the feeling that there’s limited stories and more time spent in each bar than they wanted. That doesn’t mean it’s a bad tour. It just means you should match your expectations to the format: this is a ghost pub crawl, not a dark-house-only haunt marathon.

Where you start: 22 Market Space at 6:00 pm

You meet at 22 Market Space, Annapolis, MD 21401, and the start time is 6:00 pm. That’s a smart slot because you hit the town when the light is starting to fade, but before late-night fatigue sets in. It also pairs well with a pub crawl: you can grab dinner earlier or come hungry and let the tour timing do the rest.

The tour ends back at the meeting point, so you’re not hunting for a ride at the end. It’s also near public transportation, which helps if you don’t want to think about parking or timing a car.

You’ll likely be in English, and the tour is designed so most people can participate. One note: it’s not recommended for people with mobility impairments, so if walking or uneven conditions are an issue for you, it’s worth considering another way to experience Annapolis.

Your guide makes or breaks the night

This tour leans on the guide. The included perks aren’t just a person who tells spooky lines; you’re getting a friendly guide with thoroughly researched and accurate history plus authentic local ghost stories. That structure gives the guide something solid to work with.

One thing that really comes through in feedback is how much guests enjoy when the guide keeps things patient and paced well. A guide named Ryan was singled out for being terrific and patient, and that kind of approach matters when a group of up to 25 people is moving together and settling in at each stop.

If you’re the type who likes to ask quick questions or you just need your guide to keep the tempo comfortable, prioritize that. You don’t need to be the loudest person on the tour. You just need a guide who can keep the story moving without steamrolling the group.

Stop 1: Middleton Tavern and the spirit named Roland

The first stop is Middleton Tavern, a building described as nearly 300 years old. This is where the tour sets its tone. The idea is simple: you step into a very old structure, learn the early-life context of the site, and listen for the haunting that staff have named Roland.

Why this works well as a starting point: early on, you’re still getting your bearings. A nearly 300-year-old tavern gives you immediate atmosphere, and the named spirit gives you a hook to remember as the night continues. You’re not just hearing random ghost facts; you’re following a storyline thread.

The timing here is about 20 minutes, with admission ticket free for the tour stop itself. You can expect the guide to use that window to get you oriented and establish what kind of ghost lore style this tour prefers—grounded, local, and tied to place.

Possible drawback: starting with a tavern also signals that you’ll be in a bar setting fairly quickly. If you’re not a drink-at-the-bar type, you can still enjoy it, but you’ll want to treat the drink as optional, not required.

Stop 2: 136 Dock St and what a jailhouse meant

Next up is 136 Dock St, the Old Annapolis Jail. This stop shifts the mood from tavern folklore to something darker and more grounded: what it was like for someone accused of a crime while awaiting trial.

Even if you don’t consider yourself a “history person,” a jailhouse perspective tends to hit differently. It’s not just ghosts moving through walls; it’s people under pressure, fear, uncertainty, and the weight of a community’s judgment. That’s the kind of setting where haunting stories often make emotional sense.

This stop is about 20 minutes, again with admission ticket free. The format likely stays consistent: the guide sets the scene, then you hear what locals believe still happens on those streets.

A practical note: jail history can be heavy. If you prefer your haunted tours on the lighter side, keep that in mind and make sure you’re mentally ready for the shift.

Stop 3: Reynolds Tavern and 1747 Pub with a resident spirit vibe

Then you move to Reynolds Tavern and 1747 Pub. This is positioned as one of Annapolis’s renowned legends, and the framing is clear: enjoy a beverage, but pay attention to the fact that there’s a resident spirit who may not care about your casual attitude.

This is a fun stop if you like playful scare energy. It also keeps the theme consistent with the idea of a pub crawl: you’re not just visiting buildings; you’re visiting buildings where people actually went to drink, socialize, and—according to local legend—stumble into supernatural trouble.

Timing is about 20 minutes. Like the others, admission is ticket-free as part of the tour experience.

If you want a tip for enjoying this kind of stop: use the story as your focus, not the drink. I’m not saying skip it. I’m saying let the guide’s thread pull you along so the time in the bar doesn’t feel like dead time.

Stop 4: St. Anne’s Parish and the 1858 fire

St. Anne’s Parish comes next, and it’s the shortest stop at about 10 minutes. You’ll hear about a church that’s described as nearly 300 years old and the fact it survived a major fire in 1858.

That fire detail matters. Stories about hauntings often cluster around events that were traumatic, sudden, and communal. A surviving church after a major fire gives you a natural anchor for the rumor mill—and for any “not all spirits left” type of lore.

You’ll also hear about the man rumored to have started the hauntings, plus notable spirits said to lurk around the grounds. Even with a shorter time slot, this kind of stop can deliver a concentrated payoff: one historic event, one place, and a few legends tied to it.

If you’re the type who likes photos, watch your timing here. A 10-minute stop means you’ll get less slack for wandering or checking your phone. Pay attention first; snap pictures after you’ve heard the key details.

Stop 5: Rams Head Tavern and the tragic tales you can feel

The crawl continues at Rams Head Tavern, where you’ll hear tragic tales from the early 18th and 19th centuries. The setting here is framed as full of people and work life from that earlier era, with the possibility of running into a petty spirit that resides in the walls.

This stop is about 20 minutes. It’s also a place where the tour likely blends character sketches with place-based legend: who worked there, what the atmosphere was like, and how those stories turned into ghost lore over time.

Why I think this is a highlight: taverns are social hubs. That means the stories have more variety than a courthouse or a church alone. Even when the tales are tragic, the tavern setting gives the legend a human scale.

One thing to consider: if you’re already feeling a little “story fatigue” from previous stops, Rams Head might feel a bit intense. The trick is to stay mentally flexible. Treat each location as a different chapter, not one long conversation.

Stop 6: Government House of Maryland and the haunting after the real building

After Rams Head, you hit Government House of Maryland. Here’s an important framing detail: it’s not the original government house, but the building on the grounds still carries history and is said to have ghostly inhabitants of its own.

This is a short stop at about 10 minutes, which makes it more of a quick thematic landing than a full deep-story session. But it still works because it gives you a shift from tavern-and-jail energy to civic history. That variety is part of why pub crawls like this can feel more interesting than straight walking tours.

If you’re a fan of linking old stories to modern streets, you’ll likely appreciate this one. If you prefer more time at each location, you might wish this stop were longer, but the tour overall keeps things moving for a reason.

Stop 7: Galway Bay and prohibition-era hauntings

The last stop is Galway Bay Irish Restaurant and Pub. This stop is tied to Annapolis prohibition history, and the story is built around the idea that you can do what others couldn’t: have a drink at one of the important prohibition sites.

That’s a clever close because it blends humor with historical context. Prohibition is already the kind of theme that makes ghosts feel plausible. Not because we need more drama in our drinking history, but because it was a time when people hid, adapted, and broke rules—exactly the backdrop that fuels local legend.

This stop is about 20 minutes, with admission ticket free as part of the program.

As a final chapter, it helps you leave with a feeling that the night was more than just spooky vibes. You finish with a local historical thread you can talk about on the walk back to your hotel or next dinner spot.

Price and what you get for $36

At $36 per person for about 2 hours, this tour lands in the reasonable range for an organized evening experience with multiple stops. You’re paying for several things bundled together:

• A friendly guide who delivers the story through authentic local ghost tales
• Thoroughly researched and accurate history (not just spooky sound effects)
• A guided flow that takes you to multiple known locations, ending back at the start

What’s not included: alcoholic beverages. That’s important for value. If you buy drinks at each stop, your total night cost will climb fast. If you treat drinks as occasional purchases and focus on the stories, $36 can feel like a smart deal.

Also, because the stops are admission ticket-free as part of the tour, you don’t have to add extra entry costs to your budget. That can matter on a short trip when you want your schedule to stay predictable.

Best times and timing tricks for a smoother night

This tour starts at 6:00 pm, which is good if you like your hauntings in early evening light. It also gives you a buffer after work or a day of walking. The tour is booked on average about 10 days in advance, so if you’re traveling during a busy season, don’t wait too long.

You’ll get a mobile ticket, and confirmation is typically sent within 48 hours of booking, depending on availability. That means you can plan without obsessively checking.

One more timing reality: the tour is designed with multiple stops averaging 10 to 20 minutes each. That means the pacing depends on you and your group settling quickly at each location. You’ll enjoy it more if you keep small stuff simple: arrive early enough to meet the group, and be ready to listen when the guide starts talking.

Is it worth your time? Who should book

This is a great fit if you want:

• An evening activity that mixes local stories with places you’d actually walk past anyway
• A guided format that keeps the night fun instead of uncertain
• A ghost experience that feels rooted in Annapolis life, not just generic horror tropes

It may not be your best choice if:

• You want nonstop scare-focused storytelling with very little time at bars
• You need a tour designed for mobility impairments (it’s not recommended for that)
• You hate the idea of being in pubs as part of the format

If you’re pairing this with dinner, do the planning in your head: eat first, then use the tour stops for atmosphere and maybe one or two drinks, not a full meal replacement.

Should you book this Annapolis Ghost Pub Crawl?

If you like haunted towns with real anchors—taverns, a jailhouse, a church after a major fire, and a prohibition-era angle—then yes, this is a fun booking. The price is fair for a two-hour guided experience, and the included focus on researched history plus local legends is a strong combo.

My decision rule is simple: book it if you’ll enjoy being part of a small group at cozy places for about two hours. Skip it if your ideal ghost tour is all story and no bar time. If you get the kind of guide who keeps the pace patient—like the Ryan experience people highlighted—you’re likely to have a night you’ll actually remember.

FAQ

What time does the tour start?

The tour starts at 6:00 pm.

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

It’s listed as approximately 2 hours.

Where is the meeting point?

The tour meets at 22 Market Space, Annapolis, MD 21401, USA.

Is the tour offered in English?

Yes, it is offered in English.

Do I get a mobile ticket?

Yes, the tour provides a mobile ticket.

Is alcohol included in the price?

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

What is the maximum group size?

The tour has a maximum of 25 travelers.

Is this tour recommended for people with mobility impairments?

No, it is not recommended for people with mobility impairments.