Pinterest Tag

Annapolis Haunted Pub Crawl

Pub Crawl

Home » Haunted Pub Crawls » Annapolis

Try the new Crabtown Ghosts Boos and Booze Haunted Pub Crawl for some genuine scares, spirits, and spirits in Annapolis.

Pub Crawl
Tour Location Location

*Outside* of Middleton Tavern at 2 Market Space

Tour Duration Duration

Approximately 2 hours

Tour Info Info

Arrive 10 minutes early and allow time for parking.

Tour Order Admission

Press "Book Now" for availability.

Haunts of Annapolis


Welcome to the beautiful city of Annapolis, where ancient marshland meets the waters of the Severn River, and stately Georgian mansions coexist with extravagant Victorian homes and colonial buildings. Despite these enchanting visuals, Annapolis has a murky past lurking beneath the surface and carries a legacy of blood, death, and slavery that endures to this day.

Join us for a Crabtown Ghosts Boos and Booze Haunted Pub Crawl to discover just what makes Annapolis so haunted, washed down with a glass of liquid courage at some of the most exciting pubs the city has to offer. We’ll shine a spotlight on some of Annapolis’ most eerie and sordid tales…some of which originate in the very pubs we’ll be sharing a pint in!


Annapolis’ Haunted History


The settlement that later became Annapolis was originally on the northern shore of the Severn River, founded by Puritans that had been exiled from Virginia. 

Annapolis’ later prosperity came with a gruesome price. Annapolis had a profitable tobacco trade, and as such, tobacco plantations came shortly after. The need for cheap labor led to an increase in the population of enslaved people. By the 1750s, 40% of the population was made up of enslaved people.


Pirates’ Stomping Grounds


Up until 1780, when Baltimore was made an official port of entry, Annapolis was the busiest port in Maryland. The city was a transshipment point for a variety of goods, including rum from all around the world. From all sorts of people. Even those that would, on occasion, hoist the Jolly Roger.

Pirates ran rampant in the Chesapeake and eastern Atlantic. While the famous pirate captains sailed around in large ships with bands of fighters, most of the Chesapeake pirates would operate out of small ships that could easily surround the schooners moving towards Philadelphia or south to Yorktown. Many pirates frequented Annapolis, including Edward Teach, better known as Blackbeard. As well as Captain William Kidd and the female pirates Anne Bonny and Mary Read. There is even said to be pirate treasure buried on Gibson Island just north of the city.


Enjoy Spirits With Spirits


On our Crabtown Ghosts Boos and Booze Haunted Pub Crawl tour, we’ll share the city’s most haunted tales as we make our way through our spine-tingling locations and beloved watering holes. What better way to prepare yourself for terrifying ghost stories than with liquid courage?

Hear the tales of the unhappy spirits residing in the James Brice House, a luxurious Georgian mansion said to be the most haunted house in all of Annapolis. You’ll hear tales of the bride and groom that haunt the Maryland Inn, forever destined to play out the events of the tragic wedding day when they both lost their lives and the jealous husband who inhabits the Brooksby-Shaw House, still disbelieving that his wife remarried so soon after his own passing.



Locations on Tour

Middleton Tavern

A tidy colonial tavern that was once frequented by the likes of George Washington and Thomas Jefferson, Annapolis’ Middleton Tavern is now visited by another type of guest…one that will never leave. The tavern’s employees tell of a meddlesome Revolutionary-era spirit who puffs clouds of cigar smoke and throws plates when agitated.

As for other entities inhabiting the 266-year-old tavern, who can rightly say who they are? With so many years of history to parse through, the shadowy figures seen frequenting the bar could be anyone — and you could meet them yourselves on our tour.


Galway Bay Irish Restaurant and Pub

Galway Bay Irish Restaurant was formed by two separate buildings that were connected in the early 20th century. There are two ghosts that are said to haunt this building, one in the basement and the other in the second-floor storage rooms, each with their own tragic tale forever binding them to the pub.

What both spirits have in common is that both are audible to employees, whether they hear a sweet greeting or mournful tune of the girl in the basement or the terrifying scuffle of two men locked in an eternal struggle that only ends in doom.


Reynolds Tavern

Reynolds Tavern has been a fixture of Annapolis since the 1700s when it was opened by William Reynolds and run by himself and his wife Mary. In life and in death, Mary ran a tight ship at the tavern, ensuring total cleanliness both in physical appearance and in patrons’ language. 

Today, her spirit lingers over the tavern, making sure that it is running up to her standards with dire consequences if she is disobeyed. Mary’s rule enforcing isn’t just for the staff — tavern goers must make sure to watch their language during their time at Reynolds Tavern or Mary will be sure to admonish her in her signature style.

Albuquerque, NM
Duke City Ghosts
Alexandria, VA
Alexandria Ghosts
Annapolis, MD
Annapolis Ghosts
Asheville, NC
Asheville Terrors
Atlanta, GA
Atlanta Ghosts
Atlantic City, NJ
Atlantic Ghosts
Austin, TX
Austin Ghosts
Baltimore, MD
Baltimore Ghosts
Birmingham, AL
Birmingham Ghosts
Boston, MA
Boston Ghosts
Charleston, SC
Charleston Terrors
Charlotte, NC
Queen City Ghosts
Charlottesville, VA
Charlottesville Ghosts
Chattanooga, TN
Chattanooga Ghosts
Cheyenne, WY
Cheyenne Ghosts
Chicago, IL
Windy City Ghosts
Cincinnati, OH
Cincinnati Ghosts
Cleveland, OH
Cleveland Ghosts
Dallas, TX
Dallas Terrors
Deadwood, SD
Deadwood Ghosts