A Kayakin' Kind of Town

Leading this seedy pack in the 1860s was Roger Plant, a diminutive gangster who ran a "vice resort" at the corner of Wells and Monroe streets that was known to police as the Barracks, but dubbed Under the Willow by Plant for a lone tree nearby. Plant stood 5 feet 1, weighed about 130 pounds and, Plascencia tells us, was feared by almost everyone in Chicago. "The only person who wasn't afraid of him was Mrs. Plant. She weighed about 300 pounds and, when they argued, she'd lift him by his collar with one hand and slap him with the other until he cried like a baby."

Lest we view Plant as an anomaly, Plascencia recounts the sordid tale of Mickey Finn, who owned the Lone Star Saloon and Palm Garden restaurant on South State Street. "He concocted a knockout drink that never failed and had all his bar girls slip it to unsuspecting strangers," Plascencia says. (You know where this is going, right?) "They woke up the next day in the alley behind the bar, naked and broke." The cops closed the saloon in 1903 -- the Chicago Public Library now stands on the site -- but, of course, the phrase survives.

As we mosey back upstream, passing Wolf Point, where the three branches of the Chicago River meet, we are met by Wateriders owner Charlie Portis, who pulls a small travel guitar out of his kayak. We raft up as he sings a tribute to Chicago to the melody of Bob Dylan's "Blowin' in the Wind."

Portis can barely carry a tune, but his lyrics are endearing:

How many buildings has the world put up

Reaching ever nearer the sky?

And how many stand as Chicago did it first,

Steel frames soaring to fly . . .

As tour epilogues go, this beats the heck out of "Please, watch your step as you disembark the boat."

Wateriders (312-953-9287,http://www.wateriders.com) offers kayak tours of Chicago generally at 10 a.m., 2:30 p.m. and 5:30 p.m. Saturdays and Sundays through autumn (weather permitting); call for exact times. Private groups of six to 20 people can arrange tours seven days a week. Reservations required for all outings. Tours run about three hours and depart from 900 N. Kingsbury Ave., just north of Chicago Avenue in the Domain building. Wateriders provides all equipment and drinking water. Price is $55 per person, $50 per person for groups of four or more.

John Briley last wrote for Travel about vacationing cheaply in Big Sur, Calif.