A haunted night in Annapolis with a drink plan. This Boos & Booze crawl strings together historic places for about two hours, with you getting stories right where they happened and time to settle in for a beverage. I like the cozy pub-stop pacing and the way the tour keeps you moving through landmark buildings instead of parking you in one spot.

Two other things I really value: the tour’s locally grounded ghost storytelling and the emphasis on researched, accurate history as part of the hauntings. One possible drawback: if you want nonstop chills, some guests may feel the focus can lean more toward bar time than extra ghost detail during each stop.

Key highlights you’ll feel in the first 20 minutes

• Seven historic stops in roughly two hours, timed so you can hear stories and still enjoy the atmosphere
• Free admission tickets at each venue stop, so you’re not paying extra to enter
• A guide-led walk with small-group energy (up to 25 people)
• Old Annapolis Jail, Middleton Tavern, and St. Anne’s Parish built into the route
• Prohibition-era Annapolis context ending at an Irish pub with that theme
• English mobile ticket format that’s convenient for last-minute logistics

A 6:00 pm Ghost Pub Crawl in Annapolis: what you’re actually buying

This is a classic walking pub crawl, but with an intentional story spine. You start at 22 Market Space in Annapolis at 6:00 pm, and the experience ends back at the same meeting point. The price is $36 per person for about two hours, and that matters because you’re not only paying for a walk—you’re paying for someone to stitch the places together with story and context.

A key value point: the tour includes friendly, well-presearched guidance and authentic local ghost stories, and the stops each have admission tickets marked free for the tour. In plain terms, you’re paying for guided access and interpretation, not for random bar-hopping.

Also plan for drinks. Alcoholic beverages are not included in the tour price, so you’ll want to budget for at least one drink if you plan to follow along with the “have a beverage at the stop” vibe. The tour is set up so you can participate with what each venue offers, but you won’t get handed a free drink.

Meeting at 22 Market Space: how the route feels in real time

The starting location is easy to find, and the format is simple: meet at 22 Market Space and follow the guide from there. Since it ends where it begins, you’re not stuck guessing how you’ll get back to your car after a story-heavy evening.

The group size is capped at 25 travelers, which helps the guide keep momentum. You’re also in English, and you’ll get a mobile ticket. If you like smooth check-ins, this setup is usually low-stress—just make sure your phone battery isn’t living dangerously.

One practical note: the tour is not recommended for people with mobility impairments. That doesn’t mean it’s unsafe; it just means you’ll be walking and navigating uneven old-town streets while stopping often enough that slow pacing can get difficult.

Middleton Tavern and the spirit named Roland

The crawl begins at Middleton Tavern, a building that’s nearly 300 years old. The hook here is that you’re not just hearing general ghost lore—you’re stepping into a specific place and hearing about the people who lived around and through it.

What I like about starting at Middleton is the atmosphere. You get a character-driven ghost story setup, including a spirit the staff has named Roland. Then you get to do the most useful thing on a pub crawl: reset your senses. You’ll have about 20 minutes at this first stop, and that’s long enough to listen, take a breath, and decide how you want the rest of the night to feel.

Possible downside: if you’re hoping for a lot of stop-to-stop escalation, you may find that the first location sets the tone more than it shocks you. Still, it’s a strong opener because it frames how the guide handles the balance between history and haunting.

Old Annapolis Jail at 136 Dock St: accused criminals and waiting for fate

Next is 136 Dock St, the Old Annapolis Jail. This is a different kind of ghost story stop. Instead of focusing mainly on spirits, the tone shifts toward what it meant to be accused and waiting for trial—an atmosphere that fits the building.

The time here is about 20 minutes, which is ideal for this kind of story. Jail settings work best when you can slow down and let details land. You’re walking away with more than just a spooky punchline; you’re getting a sense of how fear and uncertainty shaped daily life for people who ended up here.

This stop is also great if you like hauntings with moral weight. The ghost component isn’t just jump-scare vibes; it’s tied to human stories, and that tends to make the whole crawl stick in your mind after you leave the pubs.

Reynolds Tavern and 1747 Pub: legends plus the challenge of staying on a spirit’s good side

After the jail, you move to Reynolds Tavern and 1747 Pub, where you’re directed toward one of Annapolis’ well-known legends. The ghost angle here comes with a friendly warning: you’ll hear about a resident spirit and the idea that you should keep on its good side.

This is one of those stops where the pub setting matters. It’s easier to enjoy a story like this when you can order a drink and settle in without feeling like you’re rushing. You’re there for about 20 minutes, which is enough to hear the story clearly and still feel like part of the venue rather than a quick photo stop.

One consideration: pub crawl pacing can mean you spend more time inside than you expected, especially if you like “more haunting, less chatting.” If you tend to want a nonstop stream of stories, this stop—and the crawl overall—may feel more relaxed than you hoped.

St. Anne’s Parish: 1858 fire survival and rumors about who started the haunting

Then you reach St. Anne’s Parish, a nearly 300-year-old church that survived a major fire in 1858. This stop stands out because it pulls you into the endurance story of the building itself. Fires are dramatic events, and when you combine that with centuries of local memory, the ghost lore has a sturdy foundation.

You also learn about a man rumored to have started the hauntings, plus notable spirits said to lurk on the grounds. Time here is shorter—about 10 minutes—but that doesn’t mean it’s less important. A quick stop at a church can hit hard because the building context carries weight, and you don’t need a long block of time for the setting to do its job.

If you like lore that’s tied to specific landmarks and dates—rather than generic spook tales—this is the stop where you’ll likely feel the most “okay, this place makes sense for haunting.”

Rams Head Tavern and the mix of tragedy and petty spirits

Next up is Rams Head Tavern, another venue with layered stories. You’ll hear about tragic tales of people who lived and worked in the building during the early 18th and 19th centuries, along with the suggestion that you might have an experience with petty spirits.

The word petty matters. This is the kind of haunting concept that feels more like everyday oddities than grand supernatural drama. That can be fun, especially in a tavern setting where small eerie moments tend to feel more plausible and less like a movie script.

You’ll get about 20 minutes at this stop, so it’s a solid mid-to-late evening listen. By now, you should have a feel for how your guide paces the story—how much time is for explanation, how much is for room ambiance, and when they move you along.

Government House of Maryland: history building, not the original seat

The crawl continues to the Government House of Maryland, where you learn that this is not the original government house, but the current building still carries history and its own share of ghostly inhabitants. This is a smart inclusion because it widens the ghost lens beyond taverns and churches.

Time here is about 10 minutes, which works for an overview stop. You don’t want to overload your evening with “and then history happened” lectures. A shorter stop helps keep the emotional arc of the crawl intact while still adding variety.

If you like variety—one stop heavy on jail atmosphere, another on church lore, another on civic history—this one is your palate cleanser before the final pub stop.

Galway Bay Irish Restaurant and Pub: prohibition history as a closing mood

The final stop is Galway Bay Irish Restaurant and Pub, where you get to sit down and do what others couldn’t during Annapolis prohibition history—have a drink. It’s a playful way to end: you’re not just hearing ghosts, you’re finishing with a story about laws, enforcement, and what it means to break rules.

Time here is about 20 minutes, giving you space to wind down, order one more drink if you want, and let the whole night settle. A crawl ending in this kind of social setting usually feels right because you finish with conversation rather than the need to pack up and leave immediately.

Price, drinks, and getting the most from your guide

For $36 and about two hours, you’re paying for three things: a planned route, researched storytelling, and a built-in schedule for when you’re at each location. The stops have free admission tickets (so you’re not paying entry fees on top), and the guide is included.

The guide quality can make or break this kind of tour. One name that comes up is Ryan, described as patient and enthusiastic, and that’s exactly what you want on a story-heavy pub crawl. Even when the route is set, a patient guide helps you follow the narrative and enjoy each venue rather than feeling rushed.

Here’s how you’ll get better value regardless of who leads:

• Listen first, then order. If you wait until after the story starts, you can catch the key details before the bar noise ramps up.
• Set expectations about bar time. Some stops may feel longer than your ideal if you’re craving constant ghost intensity.
• Ask your guide to connect the dots. If the stories feel separate, it often helps to focus on how the guide links the building’s past to the hauntings.

And remember: alcohol isn’t included, and guide tips aren’t included. Budget for your drink choices so the night stays fun rather than stressful.

Who should book this ghost pub crawl (and who might want to rethink it)

I think this tour is a strong match if you:

• want historic Annapolis stops with storytelling instead of a generic nightlife walk
• like the mix of history plus local ghost lore
• enjoy a small group vibe (up to 25 people) where you can hear the guide at each stop

You might rethink it if you:

• strongly prefer more ghost detail per stop over time spent inside the pubs
• need a perfectly polished guide performance every minute of the night (there’s enough variation in style that one guest flagged professionalism issues)

Also, if you have mobility challenges, this one may be tough due to the walking and stop frequency, even though service animals are allowed.

Should you book Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl?

Yes, if you want a fun, story-led way to experience Annapolis after hours. The route covers big local anchors—Middleton Tavern, Old Annapolis Jail, St. Anne’s Parish, Rams Head Tavern, Government House of Maryland, and Galway Bay—and it does it in a single evening without making you coordinate anything. The price feels fair for two hours of guided storytelling plus free admission tickets at the stops, as long as you budget separately for drinks.

If your ideal ghost tour is pure supernatural intensity with minimal downtime, you may want to adjust expectations. This is a pub crawl first and a haunted lecture second. For the right mood, though, it’s an entertaining way to let history and hauntings share the same room.

FAQ

How much does the tour cost?

The price is $36.00 per person.

How long is the tour?

It runs for about 2 hours.

What time does it start?

It starts at 6:00 pm.

Where do I meet the tour?

You meet at 22 Market Space, Annapolis, MD 21401, USA.

Is alcohol included in the price?

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

Is the tour in English?

Yes, the tour is offered in English.

Do I need to pay anything extra at the stops?

Admission tickets are listed as free for each stop, and the tour includes the guide and storytelling, but you should still expect to pay for any drinks you choose.

How many people are on the tour?

The tour has a maximum of 25 travelers.

What is the cancellation window for a full refund?

You can cancel up to 24 hours in advance for a full refund.

What should I know about accessibility?

This tour is not recommended for people with mobility impairments. Service animals are allowed.

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