If New York is the big, glamorous, in-your-face marathon, Boston is its wise old cousin. It's the oldest marathon in the country, first run in 1897, and it's typically considered the Holy Grail of races for distance runners. That's because of its storied past, but also because Boston has a challenging qualifying time of 3:05:00 for men ages 18-34 (it goes up by five minutes for each age group), which translates to seven-minute miles. Runners who want a crack at Boston will often try to qualify at relatively fast courses like Chicago, Portland, or Disney World. As with most races, another way in is by raising money for charity. So if a three hour marathon isn't in your future, apply to raise money for one of the 31 charities affiliated with Boston for a chance to get one of its guaranteed spots. [Third Monday in April; baa.org]