Spooky history hits hard at happy hour. This Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl strings together old-school buildings and pub time, with stories tied to real local sites. Two things I like right away: the nearly 300-year-old Middleton Tavern stop and the added eerie detail about a staff-named spirit, Roland.

The format is social first and scary second. You get short, timed stops where you’ll hear tales and also have a chance to settle in with a drink, and that can be great for some nights while feeling a bit too pub-focused for others. My main caution is simple: if you’re after nonstop ghost lore, you may want a faster story-to-bar ratio.

Key Highlights You’ll Actually Notice

• Seven haunted stops in about two hours, with multiple 20-minute tavern visits
• Free admission ticket for each location, so you are not paying extra entry fees
• A guide-led mix of history and ghost stories, centered on Annapolis sites
• Cozy tavern pacing, where you can order a beverage while you listen
• A standout Middleton Tavern moment tied to the spirit called Roland
• Prohibition-era hauntings at Galway Bay, wrapping the crawl in a very Annapolis way

Boos & Booze in Annapolis: What This Ghost Pub Crawl Really Is

This is not a silent, candlelit walking tour where everyone keeps their voice down and stares at cobblestones. It’s an evening pub crawl built around history, local legends, and the kind of atmosphere you expect from old Annapolis taverns—where you can hear stories while you take in the setting.

You’ll start at 22 Market Space in Annapolis at 6:00 pm, then head from place to place. The tour ends back at the meeting spot, so you’re not stuck figuring out your own route home late in the evening. And because it caps at 25 travelers, you get that small-group feel that works better for story timing than giant groups do.

Most importantly, the tour is structured around quick hits. Some stops are 10 minutes, others are 20 minutes. That matters, because you’ll want to listen fast, order efficiently, and be ready to move when the guide signals it’s time.

Price and Value: Does $36 Feel Fair?

At $36 per person for about two hours, the value comes from what’s included. You’re not just paying for a guided walk. You’re paying for a guide, researched and accurate local history, and authentic local ghost stories, plus you get a mobile ticket and free admission tickets at each stop listed on the route.

Alcohol isn’t included—so you’ll still pay for drinks separately if you want them. But the $36 price covers the human part (guide + storytelling) and the event structure (entry/stop access). If you’ve ever done a history tour where the narration is good but the locations feel like mere backdrops, this format is different: you’re actually going inside places tied to the legends.

Also, the tour being booked about 10 days in advance on average tells you something practical: popular time slots do fill. If you want a certain day, don’t wait until the last second.

Timing and Logistics at 6:00 pm From 22 Market Space

Your night starts at 22 Market Space at 6:00 pm and runs roughly two hours. That timing is smart. You’re catching evening energy without it becoming a late-night shuffle. You also have enough time to visit several locations without the whole thing turning into a long slog.

Since it’s a mobile ticket experience, have your phone charged. You’ll also want to dress for Annapolis evening weather—especially if you’re walking between stops. The tour is described as near public transportation, which is handy if you don’t want to worry about parking.

One more thing that affects your experience: the tour is not recommended for people with mobility impairments. If mobility is a concern, it’s worth thinking carefully before booking, because it’s a multi-stop crawl with short visits and movement between sites.

Stop 1: Middleton Tavern and the Spirit Named Roland

The first stop is Middleton Tavern, a building described as nearly 300 years old. You get about 20 minutes here, and the structure is classic for a ghost pub crawl: listen first, look around second, and when the group settles, enjoy a drink.

What makes this stop feel special is the detail tied to the site. The story includes a spirit the staff has named Roland. I like when a tour does this kind of site-specific naming because it gives the legend a point of reference. Instead of vague hauntings, you’re hearing a story anchored in the place itself.

Possible drawback? Since it’s a tavern, it’s also a place where you might want to order something. If you’re one of those people who likes to sit still and absorb every word, try to order quickly so you’re not juggling the first drink with the start of the story.

Stop 2: 136 Dock St and the Old Annapolis Jail

Next you head to 136 Dock St, tied to the Old Annapolis Jail. Here you’re looking at about 20 minutes and a different mood from the tavern. The theme is life for an accused criminal awaiting trial, which adds a darker, more grounded edge to the ghost element.

This is a stop that works well if you enjoy the overlap between ordinary human history and haunting stories. The setting is not just spooky. It’s tied to how people lived, feared, and waited while their fate was decided.

The practical piece: this stop is shorter and more focused. You’ll probably want to stay attentive rather than spend that time scanning for menu boards. Think of it as your “story concentration” stop.

Stop 3: Reynolds Tavern and 1747 Pub (With a Spirit in the Mix)

Then it’s Reynolds Tavern and 1747 Pub, again for about 20 minutes. This stop leans into one of those classic haunted-house rules: stay on the right side of the resident spirit. The tour’s wording frames it like a legend you should respect, not a set of jump-scare surprises.

Why this stop is a good fit for a pub crawl? It’s built for atmosphere. You can feel the timeline through the architecture and the tavern layout, and the story theme stays tied to the location rather than floating off into generic folklore.

If you’re the type who prefers more haunting and less chatting, this is where you’ll want to settle in early. Once you’ve ordered, you can focus on listening without feeling rushed.

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

After the taverns, you switch gears at St. Anne’s Parish for about 10 minutes. This one is tight. You’re hearing about a church that survived a great fire in 1858, plus tales tied to a man rumored to have started the hauntings and the notable spirits said to lurk on the grounds.

Ten minutes sounds short, but that can work for a group tour if the guide keeps things focused. It’s a “quick hit” stop that gives you a sense of Annapolis as a lived-in historic town, not just a collection of bars and ghost corners.

My suggestion: treat this stop like a briefing, not a deep lecture. If you want to research more later, note any names or themes you hear so you can look them up after the crawl ends.

Stop 5: Rams Head Tavern and the Tragic Thread

Your next stop is Rams Head Tavern for about 20 minutes. The tour theme here is tragic stories from the early 18th and 19th centuries, tied to the people who lived and worked in the building. As with the other sites, the ghost element comes as a follow-on: there may be petty spirits in the walls.

This is the stop that often decides whether you feel the crawl as playful or unsettling. Rams Head has the kind of tavern identity that can carry a haunting story well. It’s also long enough to let the guide set up the tale and let you sit with it rather than rushing past.

If you’re sensitive to darker story themes, this is the one to listen carefully rather than tune out. You’ll likely feel the emotional weight more here than at the “lighter” pub stops.

Stop 6: Government House of Maryland (The One That Is Still Historic)

At around 10 minutes, you visit the Government House of Maryland. The tour notes that this isn’t the original government house, but the building here still has history—and its own ghostly inhabitants.

I like stops like this for a reason: it keeps the crawl from turning into only tavern legends. You get a more civic, old-town feeling for Annapolis. Even if the architecture doesn’t do the full “haunted house” thing for you, the story framing can.

Because the time is short, you should come ready to absorb the highlights. If you’re the kind of person who needs time to wander and take photos, you might feel slightly rushed here.

Stop 7: Galway Bay Irish Restaurant and Pub, Plus Prohibition-Era Spirits

The final stop is Galway Bay Irish Restaurant and Pub, about 20 minutes. The theme is Annapolis prohibition history, with a story framed around what other people couldn’t do—have a drink at one of the key sites of that era.

This ending has a nice “wrap it up” energy. You can take in the Irish pub setting, hear the last major story, and end the tour on something very Annapolis-specific. It’s a good mental bookend: earlier stops give you tavern legends and jail stories, and the finale pulls it toward prohibition-era local lore.

Also, since it’s near the end, you can decide what kind of drink plan you want for the last half hour. Just keep an eye on the group timing so you’re not scrambling at the last moment.

Your Guide Can Make or Break the Night

The tour experience depends heavily on the guide’s rhythm and how well they keep stories moving across stops. The included promise is a friendly guide with thoroughly researched and accurate history and authentic local ghost stories.

In the feedback I’ve seen, Ryan gets called out as a terrific guide—patient, informative, and genuinely enjoyable. That matters on this kind of tour because the best guides know when to keep things tight and when to let the group settle into the mood.

One caution: if you’re hoping for pure history delivery, you should know this is also a crawl. Some people have felt that certain nights spend more time in bars than they expected for storytelling. So your best bet is to lean in with the right mindset: you’re doing a social route with structured stories, not a museum-style lecture.

Drink Strategy: How to Enjoy It Without Missing the Stories

Alcoholic beverages are not included in the $36. That’s actually helpful, because you control how much you buy and when. For a tour like this, your biggest enemy is not the ghost stuff—it’s losing track of the guide because you ordered slowly or got distracted.

Here’s what I’d do:

• Plan to order quickly at each stop so you can listen while the story is happening.
• If you want less blur, choose a non-alcoholic option or pace your drink.
• Bring patience for the stop timing. Ten-minute stops are where you should focus on listening over browsing.

You’ll still enjoy the atmosphere even without alcohol, especially because the sites themselves are the point.

Who Should Book This Tour (And Who Might Skip It)

This tour is a good match if you:

• Like ghost stories that stay rooted in real locations
• Want a 2-hour night plan that mixes history and pub time
• Enjoy group storytelling with an experienced local guide
• Want a slightly social pace, not a quiet, formal museum tour

You might want to skip or choose another option if:

• You only want the scariest ghost stories and would rather skip the bar time
• You need longer narration at each location (some stops are only 10 minutes)
• You have mobility concerns, since the tour is not recommended for people with mobility impairments

If you’re a first-timer to Annapolis, this is also a smart orientation night. You’ll hit recognizable local names, learn the themes behind them, and finish right where you started.

Should You Book the Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl?

I’d book it if you want an easy, fun way to see Annapolis after dark—while learning a thread of local history that connects taverns, jail life, church legends, and even prohibition-era lore. The $36 price feels reasonable because the tour includes the guide and free admission tickets for the listed stops, and it runs long enough to feel like a real outing.

My final decision tip: go in expecting a story-led crawl, not a nonstop ghost lecture. If that fits your style, you’ll likely have a memorable, very Annapolis kind of night. And if you end up with Ryan as your guide, you’ll probably feel like the tour is running at full speed.

FAQ

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?

The tour is approximately 2 hours.

Where do I meet for the tour, and what time does it start?

You meet at 22 Market Space, Annapolis, MD 21401, USA. The start time is 6:00 pm.

How many stops are included?

The route includes 7 stops: Middleton Tavern; 136 Dock St; Reynolds Tavern and 1747 Pub; St. Anne’s Parish; Rams Head Tavern; Government House of Maryland; and Galway Bay Irish Restaurant and Pub.

Are alcoholic beverages included in the ticket price?

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

Are entrance or admission tickets included?

Yes. Each stop lists admission ticket free, and the tour includes admission ticket access for the locations on the itinerary.

Is the tour offered in English?

Yes, the tour is offered in English.

What is the maximum group size?

The tour has a maximum of 25 travelers.

Is free cancellation available?

Yes. You can cancel for a full refund up to 24 hours before the experience starts. If you cancel less than 24 hours before, the amount paid will not be refunded.