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$$$ Borgo Grondaie, Strada delle Grondaie, 53100 Siena, Italy ( 39/577/332539;www.www.borgogrondaie.com). $$ Hotel More Di Cuna, Via Cassia Nord, 53014 Monteroni d’Arbia, Siena, Italy ( 39/577/385166;www.hotelmoredicuna.it).

Bet or Not, Horse Races Take You for a Ride

If you like to bet on horse races, your adrenaline rush comes as your horse gallops closer to the finish line, hopefully in first place. Even if you’re not inclined to put money down on a horse, at these annual events there is so much activity around the races you’ll be entertained from early morning when the horses exercise on the track into the wee hours when owners of the winners celebrate. —LF

Kentucky Derby, U.S.A.: Aristides was the first to gallop across the finish line on May 17, 1875, the day the Kentucky Derby tradition began. Today, the annual race for 3-year-old thoroughbreds, always held the first Saturday in May, is the reason and excuse for the 2-week-long Kentucky Derby Festival in Louisville, Kentucky. If you can’t afford to sit in “Millionaire’s Row” at Churchill Downs, buy general admission tickets for the infield. Here you can party and watch many of the rich and well-connected. Kentucky Derby (www.kentuckyderby.com); Kentucky Derby Festival (www.kdf.org).

Racing at Churchill Downs, home of the Kentucky Derby.

Grand National, England: Competitors must face 16 challenging fences while riding around the course. The contenders must run almost two circuits of the course, make 30 jumps, and then there’s a long run to the finish line. Reportedly some 600 million viewers watch this annual steeplechase race, which is held in early April at Aintree Racecourse near Liverpool. 0151/523-2600. www.aintree.co.uk

Preakness, U.S.A.: Poet Ogden Nash wrote, “The Derby is a race of aristocratic sleekness, for horses of birth to prove their worth to run in the Preakness.” Held in Baltimore in mid-May, the Preakness is the second of the three famous races—the other two are the Kentucky Derby and the Belmont—that are called the Triple Crown series. www.preakness.com.

Emirates Melbourne Cup, Australia: The Emirates Melbourne Cup is billed as “the race that stops the nation,” and Australians say it’s true. This almost 2-mile race for 3-year-old thoroughbreds, which is always held the first Tuesday in November, is one of the richest in the world both in prizes and in the money passing among hands through bets. Reportedly, more than $140 million was bet on the Cup alone on tote throughout Australia. www.melbournecup.com.

The Prix de L’Arc de Triomphe, France: This annual race at Hippodrome de Longchamp racecourse, just minutes from Paris’s Eiffel Tower, attracts entries who have won flat races in other European countries. If you’re going to bet, choose a horse that has the speed and stamina for this 2,400m/2.4km (7,874 ft./11⁄2-mile) course. Viewers from 191 countries have watched this annual race, which happens the first weekend in October. www.prixarcdetriomphe.com/en/index.html.

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The Rat Race

Swinging Through the Urban Jungle

Edinburgh, Manchester, Newcastle & Birmingham, U.K.

Race across a freeway flyover, jog the stairwell up a 12-story high-rise, abseil down its red brick facade, cycle around a city park, then wade through a canal weir before assailing a rock wall into a derelict shipyard. Cut across the abandoned dockland and kayak along the seashore before stopping at a food stand for a compulsory gorge on a local delicacy such as jellied eels or deep fried Mars bars in batter. Then bungee jump over a motorway bridge before descending into a drainage system and emerging in a busy pedestrian street full of Saturday night shoppers and jeering drunks. The U.K. Rat Race is an adventure with a difference, foregoing the muddy paths and open fields of conventional endurance races and replacing them with all the urban obstacles that four historic cities can throw at you.

The Industrial Revolution took place in the British cities of Manchester, Birmingham, Edinburgh, and Newcastle and it is in each one that a series of 2-day