Lace up a pair of comfy shoes and get ready to traverse this immensely walkable city, beginning with a stroll through America's oldest public park, the Boston Common(enter at Tremont St and Boylston St). The Great Elm Tree, located on the westerly side of the park, was a favorite spot for public hangings during the 17th and 18th centuries, and a plaque marks the place where the tree stood until 1876. Exit the Common onto Beacon Street and proceed into Beacon Hill, an affluent neighborhood with a grisly past. Here you'll find the former home of Dr. George Parkman (8 Walnut St), one of Boston's wealthiest men whose dismembered body parts were found in and under the laboratory of Harvard Medical College professor John Webster, who owed money to Parkman, in 1849. Webster's trial, conviction and subsequent hanging sparked a media storm, and some still debate his guilt (an audio walking tour of the crime is downloadable at parkmanmurder.com for $4.99). All this talk about death has probably made you hungry, so stroll over to The Paramount(44 Charles St; 617-720-1152, paramountboston.com), which has been dishing out grub since 1937. Long lines form for its cafeteria-style breakfast (served daily until 4:30pm) that includes no fewer than six types of pancakes ($5--$8.50). Directly above the restaurant is where the Boston Strangler's last "official" victim, Mary Sullivan, was found murdered in her apartment on January 4, 1964. "To this day, the identity of Sullivan's killer remains entirely unclear," says Dr. Jack Levin, a professor of criminology at Northeastern University. "Albert DeSalvo was originally thought to have murdered all 13 Strangler victims. Upon exhumation of Sullivan's body, however, none of DeSalvo's DNA was found, and the mystery continues." One thing is certain: DeSalvo spent time in the old Charles Street Jail, and so can you, by way of its transformation into The Liberty Hotel(215 Charles St; 617-224-4000, libertyhotel.com), which allows you to "live like the felons do—but with better room service," jokes Veronika McDonald King, program manager for walking-tour company Boston by Foot Inc. (bostonbyfoot.org). Sip a house cocktail like the Green Mile (a gin martini, $13) or a Jailbait (a pomegranate mojito, $12) as famous mug shots look down at you in the Liberty's Alibi Bar & Lounge(857-241-1144, alibiboston.com). "After having a drink or two, ask the concierge to let you look at one of the jail cells, which have been turned into luxurious guest rooms," suggests Levin. Just don't end up in the drunk tank.
Underneath Boston's blue-blood overcoat, things aren't always what they seem. Case in point: Harvey Parker, founder of the polished Omni Parker House(60 School St; 617-227-8600, omnihotels.com, $180-$239), is one former guest who refuses to leave: Since 1941, he's materialized in various rooms. We're all for personalized attention, but considering that Parker passed away in 1884, we'll skip the turndown service. Employees have also reported the elevator's penchant for traveling to the third floor—whether or not the button has been pushed—a location where not one, but three ghosts are suspected to be permanent residents (including the spirit of Henry Wadsworth Longfellow). Guess they can't get enough of the Parker House rolls and Boston cream pie, both of which were first served at this spooky inn.