Without a tangible goal, ercise can start to feel like a grueling, pointless slog. (Abstract concepts like "feeling better" and "living longer" make for poor motivators.) What you need is an organized race, something to stoke your competitive instincts, push your regimen forward, and test just how fit you really are. Seeing that race date on the calendar will keep you honest about working out in dreary-ass winter. And if you plan it right, the big day won't be something to dread—it'll be a launching pad into a vacation.—NICK MARINO

An Empire State of Burn

New York City

**

February 4

**

Once a year, the Empire State Building opens its stairwells for a footrace to the top. Thomas Dold, the German who won seven consecutive races from 2006 to 2012, explains the appeal of running those 1,576 steps.

"The Empire State Building is an iconic building, that's the first thing. The second thing is that you have a really, really cool view above New York when you're on the top. And the feeling is completely different from what you get if you take the elevator. Because you look down on the street and you know: 'I have done it by myself. It's just me.' And to get this very exciting feeling, you only have to wait eighty-six floors! The whole way up, you're looking forward to this moment when you get to the finish."

POST-RACE MEALDinner at Cosme, the first U.S. restaurant by Mexican superchef Enrique Olvera.

WHERE YOU'RE STAYINGThe NoMad Hotel, the best bed (and bar) in limping distance from the race site.

Leave Your Heart (and Lungs) in San Francisco

Northern California

**

June 7 and 14

**

The Bay Area hosts two spectacular races just one week apart. Completing either is a triumph, but the truly badass can book a full week in Northern California and pull off both. Here's your itinerary.

SUNDAY (June 7)

** **Kick things off with the Escape from Alcatraz triathlon. That's a once-in-a-lifetime 1.5-mile swim from The Rock through the Bay, followed by an eighteen-mile bike ride through city parks and an eight-mile run through Baker Beach to the grassy finish line of Marina Green. Now check into the waterfront Hotel Vitale and pass out.

MONDAY

** **Crawl to the hotel elevator and press "penthouse." That's where the spa is, and where you'll get the soreness soaked, massaged, and aromatherapied right out of your body.

TUESDAY

** **Time to get moving again. Rent a bike at Bike and Roll and pedal gingerly across the Golden Gate Bridge.

WEDNESDAY

** **Today's really the only day you want a hard workout. Hit the Embarcadero jogging path, which runs from your hotel doorstep along the water to Fisherman's Wharf.

THURSDAY

** **Raid the legendary Ferry Building farmers' market. Then picnic in the Insta-worthy Marin Headlands.

FRIDAY

** **Dinner at Nopa. Think rabbit pappardelle, wood-baked butter beans, grilled broccoli, and olive-oil cake with strawberry ice cream.

SATURDAY

** **Take it easy. Maybe buy some boots at Unionmade. See a Giants game. The only thing that should elevate your heart rate today is a Hunter Pence home run.

SUNDAY (June 14)

** **Finish with The Dipsea, a 111-year-old trail race that romps 7.5 miles through the woods, ravines, and horse-ranch country of Marin County. The quirky course (shortcuts are allowed!) ends at Stinson Beach, and an unusual age-handicap system means that anyone at any age has a fighting chance of winning. So watch out for Granny in the Reeboks.

A Road Trip on Two Wheels

_The Florida Keys

_September 12

Don't think of the Key West Cycle Challenge as a bike race. Think of it as a bike jaunt—a postcard-ready tour of one hundred sun-kissed miles from Key Largo on down. The whole spirit of the event is mellow: If you're not up for riding the entire century on your own, you can bring some buddies and do it as a relay. Either way, your course is the Overseas Heritage Trail, a railroad track turned bike path with turquoise water on all sides and a tropical tailwind at your back.

POST-RACE MEALEat dockside at Hogfish Bar and Grill, and order the namesake fish sandwich on Cuban bread. (If you stick around town and go fishing tomorrow, come back and they'll cook your catch for you.)

WHERE YOU'RE STAYINGCasa Marina, a 311-room Key West luxury lodge that dates from 1920, with two oceanfront swimming pools and the island's biggest private beach.

Run Like a Bear

Chicago

**

May 23

**

Pro football players and lunatic streakers shouldn't be the only ones to frolic on NFL grass. Which is why, every Memorial Day weekend, 15,000 runners (many wearing Ditka mustaches and sweater-vests) line up for the Soldier Field 10 Mile road race. The race starts outside the stadium and heads south along Lake Michigan, an out-and-back course delivering panoramic skyline views. There's only one hill, and it's at the end: the players' tunnel that pours onto the Bears' landmark field as you sprint to the fifty-yard-line finish. You'll be done before most people have breakfast and ready to move on to the important stuff: hot sausage, the lakeshore, and cold pitchers of midwestern pilsner.**—**BILL BRADLEY

POST-RACE MEALA charred Polish sausage with sport peppers at Wiener's Circle.

WHERE YOU'RE STAYINGThe new Godfrey Hotel, a Cubist marvel with a 15,000-square-foot rooftop.

You Really Need to Tri this Place

Traverse City, Michigan

**

June 13

**

The M22 Challenge is a funky triathlon near the top of the Michigan mitten. You run 2.5 miles, starting from Sleeping Bear Dunes National Lakeshore, then bike seventeen miles around Big and Little Glen lakes. And then, instead of swimming, you kayak or stand-up paddleboard for 2.5 miles on the little lake. Traverse City is blessed with fresh water, clean air, cherries you'll scarf by the pound, and a sky so starry you'll actually recognize some constellations, so rent yourself a lake house and make this your post-race vacation circuit.

THE LITTLE FLEET

** **Thirsty? Try this indoor-outdoor bar. Hungry? Eight food trucks are parked outside.

STATE THEATRE

** **Michael Moore programs this grand old one-screen movie theater on the main drag.

THE COOKS' HOUSE

** **The seven-course tasting menu costs just $60 and lets you rub elbows with Mario Batali. He summers in TC and loves this place.

INTERLOCHEN

** **Hit this famed arts center for alfresco shows by acts like Willie Nelson.

MISSION POINT LIGHTHOUSE

** **At the end of Old Mission Peninsula, you can tackle miles of scenic hiking trails and crack a bottle of wine on the beach.

Just Do It: Book Your Ticket Now

** **Many of these races sell out months in advance. See one you like? Lock it in today, so you don't get passed on your way to the starting line.

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