Annapolis Ghost Tours: Haunted Pub Crawl with Drinks

Spirits and spirits: you'll drink at the sites where Annapolis' ghosts are said to linger.

A 2-hour haunted pub crawl through Annapolis' historic district led by a live guide who shares authentic local ghost stories at seven stops, including a nearly 300-year-old building where staff have named the resident spirit "Roland," the Old Annapolis Jail, a church that survived an 1858 fire, and bars tied to the city's prohibition history. Minimum age is 21. Beverages are not included in the tour price.

Step-by-step itinerary

Haunted Pub Crawl in Annapolis

• Visit nearly 300-year-old haunted building
• Hear tales at Old Annapolis Jail
• Enjoy a drink at haunted legend site
• Learn about haunted 300-year-old church
• Hear tragic tales in historic building
• Explore ghostly government house
• Drink at historic prohibition site

The experience

What makes this different from a standard ghost tour is the drinking component woven through the route. You'll move through Annapolis' most haunted sites: a nearly 300-year-old building where a spirit called "Roland" is said to reside, the Old Annapolis Jail where accused criminals awaited trial, a church that survived a great fire in 1858, and several bars with their own ghostly histories, and at each stop you can order a drink while hearing the stories. The guide handles the history. You handle the liquid courage.

The route covers seven locations across the historic district, each one tied to a specific haunting or legend. You'll learn what life was like for those who faced trial at the jail, hear about the man rumored to have started the hauntings at the church, and visit the site of one of Annapolis' most important prohibition-era establishments. The guide is knowledgeable and researched, so the stories carry weight even when they're unsettling. Service animals are welcome on the tour.

Two hours is enough time to hit all seven stops without rushing, though you'll be moving between them steadily. The tour runs in the evening, which is when ghost tours typically operate, and public transportation options are available nearby if you need to get to the starting point. Bring cash or a card for drinks at each location. Those aren't included in the tour price, and neither is a tip for the guide if you choose to leave one.

What’s included

• Live guide in English.
• thoroughly researched and accurate history of each site.
• authentic local ghost stories.
• visits to seven historic locations including a nearly 300-year-old building, the Old Annapolis Jail, a church that survived an 1858 fire, and prohibition-era bars.

Before you book

Days and timesEvery dayDeparts at 18:00

AgesAdult (21 and older) · Under 21: can't be booked

GroupUp to 25

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

ConfirmationConfirmation within 48 h

Prices and times updated 3 days ago

Good to know

Low physical effortPets welcomePublic transport nearbyNot recommended during pregnancy

Operated by Annapolis Ghost Tours and Haunted Pub Crawls

Is this one for you?At 2 hours, the tour fits into an evening without consuming your whole night, so you can grab dinner before or after and still have time to explore other parts of Annapolis. The minimum age is 21 because drinks are part of the experience, so this is built for adults looking to combine history with a social outing in the historic district.

Traveler reviews

4.47★★★★★★★★★★

17 verified traveler reviews

Read all the reviews ›

Top questions

What is the Old Annapolis Jail like, and what stories does the guide tell there?

The Old Annapolis Jail is one of seven stops on the tour. The guide shares stories of accused criminals who awaited trial there and the spirits said to still walk those streets after meeting their fate at the site.

Can I order drinks at every stop, or just some of them?

You can order a beverage at multiple stops throughout the tour, including at bars and historic buildings. Drinks are not included in the tour price, so you'll pay separately at each location.

How long does the tour actually take, and will I have time to finish a drink at each stop?

The tour runs for 2 hours total across seven stops in the historic district. The pace is steady enough to cover all the sites and hear the stories, though how long you spend with a drink at each location is up to you.

Is this tour suitable if I'm not in great physical shape?

The tour is suitable for all physical fitness levels, so fitness is not a barrier. However, it is not recommended for people with mobility impairments, since you'll be walking between seven different historic sites.

What's the deal with the spirit named "Roland" that the guide mentions?

Roland is the name staff have given to the resident spirit in a nearly 300-year-old building that is one of the tour stops. You'll visit inside, hear the haunting tales of those who lived in its walls, and can enjoy a drink while keeping an eye out for any mysterious activity.