Middleton Tavern's Cigar-Smoking Ghost and Three More Annapolis Bars
A two-hour pub crawl from Market Space, with Annapolis ghost stories told between rounds at four downtown bars.
This crawl spends about two hours walking between four Annapolis bars, with ghost stories told inside each one and on the streets in between. The booking page lists Middleton Tavern on Market Space, Reynolds Tavern on Church Circle, Rams Head Tavern on West Street and Galway Bay on Maryland Avenue, plus short story stops at St. Anne's Church, Government House and a Dock Street address. The operator says the exact lineup depends on the day of the week and the season, and that if a bar is unavailable the guide will try to find another. Reynolds Tavern's own site says it is closed on Mondays, so a Monday crawl will not stop there for a drink. Look for a guide in a black US Ghost Adventures T-shirt carrying a lantern.
The ticket covers the guide and the stories. Drinks are ordered and paid for at each bar, and the guide's tip is extra too. One booking takes up to 25 travelers, all of them 21 or older, and cancelling at least 24 hours before departure gets a full refund.
Annapolis Ghost Tours Boos & Booze Haunted Pub CrawlAbout two hours · Four bars · 21 and up with ID · Drinks extrawww.viator.comPlan Around the Earlier 5:45 PM Start
The booking slot reads 6:00 PM and asks travelers to arrive fifteen minutes early. The operator's own tour page and its booking notes give a 5:45 PM departure with the same fifteen-minute request, so be outside the meeting point by 5:30 PM. The booking page and the operator's booking system both name the Federal House Bar and Grill on Market Space as that meeting point. The operator's tour page names a different door on the same street, Middleton Tavern, which is also the first bar on the booking page's list. If there is no lantern outside Federal House, look outside Middleton Tavern. Tours run rain or shine, and the operator says it will contact you if a night has to be cancelled.
Three Tavern Ghost Stories on the Usual Route
The operator's tour page gives three of the bars a story each. At Middleton Tavern, the operator says, staff tell of a Revolutionary-era spirit who puffs cigar smoke and throws plates when agitated, and the booking page adds that staff call him Roland. The operator dates Reynolds Tavern to the 1700s, opened by William Reynolds and run with his wife, Mary; in its telling, Mary still keeps the room in order and admonishes guests who swear. Galway Bay was formed from two buildings joined in the early 20th century, and the operator says one ghost is heard in the basement and another in the second-floor storage rooms. On the booking page's timing each bar gets about twenty minutes, while the operator's notes allow anywhere from fifteen minutes to an hour per stop.
ID, Your Own Rounds and the House Rules
Every guest has to be 21 or older and carry ID, and drinks cannot be carried from one bar to the next. The operator refuses service to anyone who arrives intoxicated, cuts off guests who become severely intoxicated, and removes anyone who disrupts the tour. Pets stay home, though the listing allows service animals. The operator suggests bringing a water bottle and a snack. The listing marks the tour not wheelchair accessible, says most travelers can participate, and does not recommend it for travelers with mobility impairments or for pregnant travelers. The evening moves between bars on foot.
What Recent Guests Say About the Balance
Guests mostly write about their guide, describing someone friendly and knowledgeable about the town's history. Small groups happen. A guest on a quiet Monday in April 2026 called it "very much like a personal tour," and a traveler in December 2024 who turned out to be the only booking still got the full night. The complaint that repeats is the balance between bar time and stories: a guest in October 2024 felt the group spent a lot of time in each bar, and one in June 2026 wished there had been more to the ghost stories. In August 2026 a guest wrote that the guide arrived late and kept to the basics.
📍 The night begins on Market Space, and the operator says it wraps by 8:00 PM. That leaves the rest of the evening for dinner downtown; one guest in May 2026 left with a restaurant recommendation from the guide.