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This red pressed-brick theater, one of Chicago's oldest, is where John Dillinger—dubbed Public Enemy No. 1 in 1934—saw his last film, Manhattan Melodrama. One of Dillinger's female companions, known thenceforth as "the Lady in Red," betrayed him to federal agents in exchange for dropping outstanding deportation charges against her. Upon spotting her vibrant dress as the pair exited the theater one evening, authorities fatally shot Dillinger. Last year, new ownership transformed the city landmark into a space to present live theater in addition to films, restoring the Lincoln Avenue façade and interior grand staircase to their early-20th-century glory. Despite recent efforts to downplay the theater's past, locals and tourists alike simply can't stay away. (2433 N. Lincoln Ave., Chicago, Ill.; 773/871-3000).
After robbing a Telluride bank in 1889, Butch Cassidy fled 30 miles southwest to the settlement of Dunton Hot Springs, deep in the San Juan Range of the Colorado Rockies. While there, the "Robin Hood of the West" carved his name into the wooden bar of the local saloon. In 1994, business partners Bernt Kuhlman and Christoph Henkel turned Dunton Hot Springs, then a tiny ghost town, into a luxury resort comprising 11 cabins with authentic exteriors and wood-burning stoves, a library, two spa treatment rooms, and the saloon, where the inscribed bar remains untouched—a cherished reminder of the West's most romantic outlaw. (52068 W. Fork Rd., Dolores, Colo.; 970/882-4800; cabins from $300 per person).
Hotel staff has long suspected that Al "Scarface" Capone owned this historic 137-room inn for 18 months during the prohibition era (records don't show his real name), but one thing's certain: the mob boss used to retreat to Room 222 when his affairs became too intense in Chicago. The building was a convenient getaway for Capone. From the upper floors, his henchmen could monitor the Dubuque Bridge for threats—from both sides of the law—crossing the Mississippi, and the underground garage neatly concealed his cars. Quirky structural details, like the cubbyhole at the top of the staircase with a hard-to-spot door (perfect for watchful bodyguards), make for an intriguing stay. (200 Main St., Dubuque, Iowa; 563/556-4200; julieninn.com; doubles from $85).
James' fellow gang member Robert Ford fatally shot an unsuspecting (and unusually unarmed) James from behind at this house in 1882. Ford had secretly been in negotiations with the Missouri governor to bring James in, but the governor's swift pardon of Ford after the murder left many speculating that James' assassination had been the real plan. Today, the bandit's former four-room residence draws over 20,000 visitors a year, and contains relics such as a diamond pin James was wearing when he was killed, a bullet from his right lung, and a cast (created in 1995 when the body was temporarily exhumed) of his skull showing where the bullet entered behind his right ear. (1202 Penn St., Saint Joseph, Mo.; 816/232-8206; $2 per person).
Chosen by F. Scott Fitzgerald as the background for Tom and Daisy Buchanan's wedding in The Great Gatsby, this elegant hotel was also a favorite of the 1920's most infamous gangsters. Charles "Lucky" Luciano, credited with reinventing the mafia, Dutch Schultz, the "Beer Baron of the Bronx," George Remus, a Cincinnati bootlegger, and Al Capone all went to the Seelbach to gamble and bootleg. The lovely Oakroom, formerly a billiards hall where Capone once played cards, has a strategically placed mirror, two hidden doors leading to underground tunnels, and spring-loaded tip-off doors, all to ensure a quick getaway in case of a police raid. (500 Fourth St., Louisville, Ky.; 502/585-3200; seelbachhilton.com; doubles from $159).
Boston's fugitive Irish crime boss, James "Whitey" Bulger, supposedly collected unpaid loans at the shabby Triple O's pub, now a sleek bar and grill called the 6 House. In the heart of insular South Boston, the 6 House is a far cry from its former self: a neon sign announces the pub to the street and flat-screen televisions line the spacious bar area. On the run since the FBI dropped him as an informant in the 1990's, Whitey has reportedly returned to Southie on occasion, a fact that draws curious Bostonians to his former haunt. (28 W. Broadway, South Boston, Mass.; 617/268-6697).
The filet mignon may be among the best in town, but the real appeal of this midtown classic is its edgy past: in December 1985, mob boss Paul Castellano was gunned down outside on the busy 46th Street sidewalk on the orders of the infamously captivating John Gotti. Tensions ran high between "Big Paul," then head of the notorious Gambino family, and his ambitious cousin, "Dapper Don," as questions of succession arose. Weeks after the highly public shooting, Gotti became boss of the Gambino family, a position he held long after his imprisonment. To this day, no trip to the restaurant—a renowned power-lunch spot—is complete without a whisper about its villainous affiliation. (210 E. 46th St., New York, N.Y.; 212/687-4855; dinner for two from $140).
One evening in April 1972, during a birthday meal of linguini with clam sauce, the ruthless New York gangster "Crazy Joe" Gallo was fatally shot in this kitschy seafood joint, whose nautical atmosphere is anything but sinister. Despite moving from its original location on Mulberry Street, Umberto's littleneck clams and late hours (they're open until 4 a.m. each day) consistently draw celebrities like Robert De Niro and Martin Scorsese, as well as hungry after-party hordes on the weekends. (386 Broome St., New York, N.Y.; 212/431-7545; dinner for two from $50).
—Bree Sposato
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