Jay, where are you located?
In 2006 a buddy and I started a small for-profit LLC called Raven Singletrack. The objective was to "unite the clans" so to speak and bind the community behind two things. 1) Having fun on bikes. Not just rides, but we rubbed some rock'n'roll on our gatherings making them too fun to pass up. 2) To give that community a collective voice for trail advocacy. We found people who would show up for the BBQs and fun events couldn't then wiggle out of the hard work of building trails without a bunch of guilt. We later transformed that community into a community-guided club: The Prescott Mountain Bike Alliance. They in turn have helped get thousands of man-hours of trail built through IMBA. They have a pretty powerful voice now and it all started with me on the phone with the local riders, a bunch of small rides, cases of cheap beers, and a few shovels. Our first ride in 2007 had 7 riders. Our first trail work day with the forest service had 6 people. By the time we handed everything over to the club we helped form, rides would have over 75 people and people had to reserve a spot on a trail day as we didn't have enough equipment. It has been so successful, IMBA relocated a representative here PERMANENTLY! Not gonna lie, I'm very proud it all started with two of us chatting over burritos.
So, long story, but sometimes the first step is uniting your user group. Without that audience all behind new trails, there's not a chance it will happen. Unite your group. Initiate dialog with the land managers to feel out the challenges. Call IMBA for advice, and get ready to herd the cats (your local riders).
My personal advice - aligning any group with a "good citizen" foundation is tough. Creating something organic and fun they will want to be a part of is much harder to do, but the results are far more successful.
