→ Like an impatient child on a birthday, you can’t wait to unwrap summer. As the morning sun peeks over Lake Michigan on Memorial Day eve, you kick off the season with BIKE THE DRIVE (5/30), a carefree and car-free spin lakeside. Exhilarated, you mark other dates on Chicago’s cycling calendar:

• the BIKE TO WORK RALLY (6/18) in Daley Plaza, where you can get tips on two-wheel commuting;
• the all-night L.A.T.E. RIDE (7/10-11), a 25-mile circuit of city parks and neighborhoods;
• the three-day TOUR OF ELK GROVE (7/30-8/1);
• and the BOULEVARD LAKEFRONT TOUR (8/29), with three routes, ranging from 15 to 62 miles.
• Or grab a cowbell and cheer on the nation’s top pro cyclists in the USA CYCLING PROFESSIONAL NATIONAL CRITERIUM CHAMPIONSHIP (8/14) in Glencoe.

→ You’ve been so hard at play you could use some recovery time. On 6/8 you pick up a hot-off-the-press copy of THE ONLY GAME IN TOWN: SPORTSWRITING FROM THE NEW YORKER, make a date with your sofa, and devour timeless prose by a Murderer’s Row of talents—Roger Angell, John Updike, John McPhee, and Ring Lardner, among others—who paint with nouns and verbs the way Greg Maddux did with sinkers and cutters.

→ Your literary diversion was nice while it lasted, but it couldn’t mask the fact that your soccer-loving pals have headed to South Africa for the quadrennial WORLD CUP while you’re stuck in the wrong hemisphere. You seek the next best thing: a raucous setting in which to watch the hotly anticipated U.S.–ENGLAND MATCH on 6/12. The Globe Pub and Ginger’s Ale House are great soccer hangs but might be packed with smack-talking Brits, so you opt for the Ukrainian Village location of Small Bar (a member bar of the U.S. Soccer Federation), order a proper American pint (Two Brothers Bitter End, $5), and remind any Englishmen within earshot that when these teams last met in the World Cup 60 years ago, the Yanks shocked the world.

→ After a brief but heady fling with the beautiful game, you return like a repentant lover to the national pastime. Besotted with all things CUBS, you await visits to the Friendly Confines by the team’s cross-town rival (6/11-13) and that central division bully, the St. Louis Cardinals (7/23-25). In the interim, you take a GUIDED TOUR OF WRIGLEY FIELD, featuring a Piniella’s-eye view from the dugout and stops in both locker rooms. The original visitors’ clubhouse remains from the ballpark’s 1914 opening, meaning you stand in the cleat prints of Jackie Robinson, Willie Mays, and other greats.

OR

What’s that? Any day the Cubs get beat is sweet indeed? You can’t wait for the WHITE SOX to demolish the North Siders during part two of the Crosstown Classic on 6/25-27—same goes for their arch-rival, the Minnesota Twins, on 8/10-13. But you wonder why Wrigley’s bleacherites get to own the patent on barley-infused fun. Solution: a PREGAME PARTY ON THE PATIO near right-center field at U.S. Cellular Field; festivities include discounted game tickets and an unlimited buffet.

→ With some July days hot enough to smelt iron ore, you gravitate toward the water. Fortunately, you had the foresight to enter a team in the DRAGON BOAT RACE FOR LITERACY (7/24), in which crews of paddlers square off in two-boat heats on the Chicago River, just off Ping Tom Memorial Park, until a champion is crowned.

For a more pampered cruise, see Summer Hot List: Luxury & Pampering »

→ Stoked, you seek out more rowing. A CANOE TRIP on the scenic Lower Fox River—with its sandstone cliffs and gentle currents—fits the bill. C & M Canoe Rental, in Ottawa, is one of several outfitters that can equip your voyage, but C & M’s trips begin and end at a tavern. Score!

For kid-friendly and closer canoeing options, see Summer Hot List: Family Fun »

→ You’ve become so deft with a paddle that you’re ready to try the growing sport of STAND-UP PADDLE BOARDING—a cross between kayaking and surfing that’s popular in Hawaii but has gained a foothold in Glencoe, of all places. You sign on for a lesson with the Great Lakes Board Company, which also rents the boards for $20 per hour.

→ All this time on the water has rusted your golf game—but whacking balls to regain your stroke can get monotonous. TOPGOLF, a high-tech driving range in suburban Wood Dale, turns practice into play time for serious golfers and hackers alike. The object is to score points by hitting balls onto targetlike greens up to 250 yards away; a microchip embedded in each ball transmits stats on shot distance and location to a computer monitor in the hitting bay.

If a world in which golf balls communicate complex flight data leaves you seeking more scientific advancements, see Summer Hot List: Science Fun »

→ If, however, you find yourself craving a simple brush with nature, plot a course 25 miles north of the city. The OPENLANDS LAKESHORE PRESERVE (right)—long a part of Fort Sheridan but accessible to the public only since last September—offers just what the doctor ordered: a hike through Bartlett Ravine, one of the last remaining ravine and bluff ecosystems in the region, harboring rare plants and a profusion of birds, and leading to a mile-long stretch of beach backed by 60-foot bluffs left behind by the last glacier. As you sink your feet into the sand, with nary a volleyball player or Rollerblader in sight, you ooze ahhhs.

→ Spirit replenished, you’re ready for summer’s final challenge, the CHICAGO TRIATHLON (8/29), for which you’ve diligently trained between less competitive outings.

→ Up to this point, your focus on the race has kept your mind off Labor Day, but summer’s symbolic end arrives anyway. Good thing LEBOWSKI FEST, the traveling bowling-and-bashes tour devoted to the cult flick The Big Lebowski, hits town 9/17-18. A dose of ten-pin philosophizing provides perspective as you prep for an autumn equally well played.

CLICK HERE FOR MORE DETAILS ON ALL OF THE EVENTS »

Photography: (Cyclist) walik/istockphoto.com, (soccer player) AP Photo/Gus Ruelas  Opposite: (Fukudome) Chicago Tribune photo by Phil Velasquez, (Nix) Chicago Tribune photo by Nuccio Di Nuzzo, (oar) dny59/istockphoto.com, (golf ball) Diane39/istockphoto.com, (shoreline) Charlie Westerman/courtesy of Openlands, (icons) miteman/istockphoto.com, (The Big Lebowski) Polygram Filmed Entertainment