Know what you're getting into: "You need to feel inspired on a deep and intrinsic level, because it's going to take a lot of your time," says Chris Fickel, co-organizer of the CT Jamboree, a two-day Colorado Trail ride that benefits multiple-sclerosis research. "I've spent about 300 hours a year on this race."
Partner with a charitable organization: This will allow donors to write off gifts, which makes fundraising easier. Charity Navigator (charitynavigator.org) independently evaluates charities for their health, effectiveness, and expense ratios.
Get permission: Landowners, cities, counties, and public-land agencies are often open to allowing a nonprofit event on their turf. Chart your course, find out what agencies manage the land, trails, or roads, and get a permit.
Snag sponsors: Hit up a local restaurant for food or a gear shop to provide prizes for the participants who raise the most money.
Having an online fundraising portal is key: Sites like Active.com and JustGiving.com offer online giving modules for charity events. "For the inaugural ride, donations were all cash and checks, and we made $15,000," says Fickel. "The following year, we put up our Web site, and we bumped up to $30,000."