To find a nearby race, go to the event calendar at USA Triathlon. Most sprints are in the summer, when cycling and swimming are palatable even in heat that makes running a chore.
Bonus: Giving your running muscles a partial break means they'll be fresh for harder road-race training in the fall.
Degree of Difficulty: 8
This Year I Will: Win a Medal
Finisher T-shirts are great, but the award that sets you apart from the finishing hordes is the coveted age-group medal. This is the prize you'll proudly display in a prominent spot in your home (if your spouse allows it, that is). But how do you win one—other than, you know, training harder and racing faster? A few "cherry-picking" tactics can be deployed.
Make It Happen: Choose a race that puts you in a five-year rather than a 10-year age division, which doubles the odds of winning something. Compete on weekends when there are multiple races in your area, which scatters the competition. And pick events that aren't well publicized. Peter Cini, a runner in Fairfax, Virginia, also suggests: "Low-turnout races, inaugural races and races put on by churches or schools often have easy competition and good prizes." See last year's times online.
More: Best Race-Day Medals
Cini notes that sometimes these strategies backfire: A slow age-group field with great awards one year is often followed by a stacked field the next year because the word gets out. There is no cakewalk. Just ask Apollo Creed (Rocky) or Goliath how their matches turned out. The only sure way to up your odds of taking home a den-worthy award is to train hard and consistently.
Degree of Difficulty: 9
This Year I Will: Try Real Trail Running
Melody Fairchild had success on the track as America's first high-school girl to break 10 minutes in the two-mile, and then on the roads as a frequent race champion. But one of her favorite surfaces is the trail—twisting, turning, undulating paths, not smooth rail-trails or dirt roads.
"Constantly adjusting your stride to maneuver over rocks and roots forces you to run more on your midfoot and forefoot, which teaches you to run more efficiently," she says. "After a trail run, your muscles feel completely worked because you're going up, down and sideways. It's the fast track to gaining fitness. Plus, driving to a scenic trail makes it an outing."
Make It Happen: Find nearby trails at trailrunner.com, or ask at a running shop. Fairchild, who leads trail-running camps in Colorado, says to gauge your workout by elapsed time, not distance—otherwise you'll get frustrated because you'll compare your pace to road runs.
Spend enough time off-road and you may want to consider buying trail-specific running shoes, which have better traction and are made of protective material that shields the feet from sharp objects.