A ghost story with a drink sounds like a fun plan. This Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl mixes short hauntings with real stops around the historic waterfront. You start at 22 Market Space and finish right back where you began, with the whole thing running about 2 hours.

I especially like the format: each stop is timed so you get both atmosphere and momentum. I also like the way the best guide sessions combine thoroughly researched history with local ghost legends, and the guide Ryan has a strong reputation for being patient and keeping the group engaged.

The main thing to consider is that it is still a pub crawl. If you’re expecting long, in-depth ghost storytelling at every location, you might find the stories feel a bit short, and the pace can sometimes mean more time inside than you wanted.

Key Highlights You Should Know

• 7 themed stops in about 2 hours, starting and ending at 22 Market Space
• Ghost stories tied to specific buildings, from taverns to a church and jail
• A guide style that can feel calm and patient, with room for questions when the group is responsive
• Named spirits like Roland at Middleton Tavern help the stories feel more personal
• You can choose your own pace with drinks on-site since alcohol isn’t included in the ticket price

A 6:00 pm Ghost Pub Crawl with 7 Historic Stops

This tour starts at 6:00 pm and moves at an easy evening pace. You meet at 22 Market Space, Annapolis, MD 21401, then head from stop to stop. The full circuit is roughly two hours, and the group is kept to a maximum of 25 travelers, which makes it easier to hear the guide without feeling lost in a crowd.

What I like about this setup is how it treats the night like a sequence, not a lecture. You get short story time, a change of scenery, and then a chance to grab a drink and reset before the next location. That is ideal if you want something fun to do after dinner, or you’re visiting Annapolis for a quick stop and want a concentrated taste of the spooky side of the city.

One practical note: this tour isn’t marketed as a sit-down theater show. It is more of a walk-and-enter-in-a-group experience, and it’s not recommended for people with mobility impairments. If you do go, wear shoes you’re comfortable in, because you’ll be moving around while the guide keeps the story thread going.

Middleton Tavern: Roland and the Nearly 300-Year-Old Setting

Stop one is Middleton Tavern, a nearly 300-year-old building where the tour focuses on haunting tales tied to the walls. The story centers on a spirit the staff has named Roland, and the vibe here is part tavern-casual, part old-building weirdness.

You’ll typically spend about 20 minutes at this stop, which is long enough for the guide to set the scene and share the legend without rushing you out immediately. It also gives you a chance to order a drink and settle in before the group continues.

Why this stop works: you’re getting a supernatural hook early, and you’re doing it in a place that already feels lived-in. It’s also a good place to decide your strategy for the rest of the crawl. If you enjoy the story style here, the rest of the night will likely feel like the same rhythm: short hauntings, then a breather, then another location.

Potential drawback: if you’re sensitive to noise levels inside bars, plan for it. Tavern stops tend to be lively, and that can make it harder to catch every line of the story unless you position yourself well.

136 Dock St: The Old Annapolis Jail and Life Awaiting Trial

At 136 Dock St, you shift from tavern ghosts to darker stakes. This stop focuses on the Old Annapolis Jail, with the tour exploring what life may have been like for someone accused and waiting for trial.

The stop runs about 20 minutes, and it matters because the mood changes here. The guide is still telling ghost stories, but the setting is more serious, so the entire tone of the crawl tightens.

I like this stop because it broadens the theme. A ghost tour can turn into the same spooky pattern over and over. The jail setting helps keep it from feeling repetitive, and it gives you a different kind of thrill that doesn’t rely only on bar atmosphere.

What to watch for: jail stories can hit a heavier nerve than playful pub-crawl hauntings. If you want purely light, spooky fun, you might prefer to treat this stop as a brief mood shift rather than the emotional peak of the night.

Reynolds Tavern and 1747 Pub: Legends, Beverages, and a Caution

Next up is Reynolds Tavern and 1747 Pub, where you get the tour’s take on one of Annapolis’ renowned legends. You’ll also hear how the spirit linked to the place wants you to behave, which is classic ghost-tour energy: playful, spooky, and slightly theatrical.

This stop is also about 20 minutes. That timing works well because it gives the guide enough space to tie the legend to the location while letting you enjoy your drink and take in the setting without feeling like you’re stuck waiting for the next move.

This is one of those stops where the pub-crawl element is clear. The story is there, but so is the social side. If you’re traveling with friends and want a night that mixes spooky with casual fun, this is a good place to relax.

Possible drawback: since each bar stop has a set time, if you’re hoping for more ghost lore at every stop, you may feel the stories come in bursts. The best tours keep the pace lively, but the structure means you’re not going to get a deep, hour-long sitdown narrative at one location.

St. Anne’s Parish: Fire, Survival, and Grounds with Spirits

At St. Anne’s Parish, the tour leans into a church setting tied to survival after a great fire in 1858. This stop feels different from the taverns because the focus shifts to a nearly 300-year-old church and the legends tied to the grounds.

Plan on about 10 minutes here. That short stop can be perfect if you like variety, because it breaks up the pub rhythm. You’ll hear about rumored origins behind the hauntings as well as notable spirits connected to the church grounds.

I like short stops like this when I’m booking a walking-and-story tour, because it keeps the night from dragging. If your group is staying sharp and the guide is speaking clearly, ten minutes can feel like a satisfying hit of spooky atmosphere.

Consideration: because this is brief, it helps to listen closely right at the start. If you drift or step aside, you might miss the most important story beats of the stop.

Rams Head Tavern and Government House: Two More Stops, Two More Moods

The Rams Head Tavern stop is about 20 minutes and focuses on tragic tales tied to people who lived and worked there in the early 18th and 19th centuries. The vibe here is classic Annapolis: old building energy, pub comfort, and the sense that the walls hold on to stories.

Then the tour moves to the Government House of Maryland, where the guide explains that it is not the original government house but the building here still carries history and its own ghostly inhabitants. That stop is about 10 minutes.

I think the pairing works. Rams Head gives you a longer storytelling window, then Government House gives you a quick “one more haunting” punctuation mark before you head toward the final stop.

Where this can go wrong: timing is tight across multiple venues. If you’re hoping to linger, these stops may feel like a sprint. Still, that’s the trade for packing seven locations into two hours without exhausting people.

Galway Bay: Irish Pub Atmosphere and Prohibition History

The final stop is Galway Bay Irish Restaurant and Pub. This is where the tour taps into prohibition history, and it also keeps the crawl grounded in a modern, comfortable pub setting.

You’ll typically spend about 20 minutes here. That makes it a nice ending window because it gives you time to finish your drink, talk quietly with friends, and let the stories settle in rather than rushing out immediately.

What makes this stop a smart closer: the theme connects to real-world history (prohibition) while still keeping the tone fun and pub-friendly. If you want your last stop to feel less intense than the jail and more social than the church, Galway Bay fits.

Price and Value: Is $36 Fair for a Two-Hour Night?

At $36 per person for about two hours, this tour is priced like a focused, guided experience rather than a generic walking tour. And you do get a lot for that money: a friendly guide, stories built around specific local locations, and a set of stops designed to keep you moving.

Alcohol isn’t included in the ticket price, so you should expect to buy your own drink(s) if you want one. That matters for value because the total cost can rise depending on what you order. The upside is that you’re not locked into a drink package, which is useful if you’re pacing yourself or you’re with people who don’t want alcohol.

Also, the tour includes admission-ticket coverage at the stops, so you’re not paying extra on top of the $36 just to get into the locations while the guide is working through each location’s story.

My honest take: if you’re the type who likes guided stories with a social setting, this price is fair. If you only want ghost lore and would rather sit and listen, you might decide the pub structure is more than you need.

Who This Tour Fits Best (and Who Might Be Disappointed)

This tour fits best if you want a blend of atmosphere and story, and you’re open to the idea that some stops will feel darker and others more playful. It is also a good fit for couples, small groups, and visitors who want an easy plan that does not require reservations for each individual venue.

It may not be ideal if you are someone who needs long explanations and lots of detail at every stop. The shorter time windows at each location can make the stories feel limited, especially if you were hoping for more ghost storytelling and less time in each bar.

There’s also the reality of guide-to-guide variation. Some sessions seem to hit strongly on professionalism and historical accuracy, while others may feel off in pacing or detail. The positive pattern, including the strong reputation of Ryan as a patient guide, suggests that when the group clicks, the experience can feel like you’d happily spend the rest of your evening with the guide.

Quick Tips to Get More Fright per Minute

First, show up with the right mindset. This isn’t a silent, sit-and-listen museum experience. It’s an evening of short hauntings, location changes, and a pub-crawl rhythm.

Second, pick a spot near the guide at each stop so you catch the story details. Many of the stops are only 10 to 20 minutes, so missing the opening can mean missing the best lines.

Third, plan your drink order early. If you want to keep things moving, ordering promptly helps avoid pauses right when the next story starts. Since alcoholic beverages aren’t included, you’re in control of what you buy and how much you spend.

Finally, come ready for a mix. You’ll hear about named spirits like Roland, learn about an accused-criminal waiting-trial scenario at the jail, and get prohibition-themed ghost lore at the end. Variety is part of the value.

Should You Book Annapolis Ghost Tours Boos & Booze?

I’d book it if you want a fun, guided way to see multiple iconic Annapolis locations in one evening, and you like ghost stories delivered with a real tavern backdrop. The structure keeps it from feeling too heavy, and when the guide is in sync with the group, you get a night that feels both informative and easygoing.

I would hesitate if you’re expecting deep, long ghost monologues at every stop. Because each location is time-boxed and alcohol is not included, the experience can feel more social than scholarly.

If you do book, you can also take comfort that it runs on a straightforward plan: meet at 22 Market Space at 6:00 pm, enjoy about two hours of stops, then end back where you started. If you need flexibility, the tour is set up for easy changes if you cancel far enough ahead.

FAQ

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

It costs $36.00 per person.

How long is the tour and what time does it start?

The tour lasts about 2 hours and starts at 6:00 pm.

Where do I meet for the tour?

You meet at 22 Market Space, Annapolis, MD 21401, USA. The tour ends back at the same meeting point.

Are alcoholic beverages included in the ticket price?

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

What is included with the tour?

Your ticket includes a friendly, knowledgeable guide, thoroughly researched and accurate history, and authentic local ghost stories.

How big is the group, and is the tour in English?

The tour is offered in English and has a maximum of 25 travelers.

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