Insurance
Acquiring Insurance is not a fun thing, especially if you start looking in the wrong places.
Places to start looking
The chances of finding an insurance company that is familiar with community bicycle organizations are slim, so finding one that is familiar with nonprofits in general is the better approach. Ask other local nonprofits who they use too.
Assuming your organization is a non-profit, you have certain resources at your disposal. One such resource is the National Council of Nonprofit Associations which different state-level Nonprofit Associations belong too. Ask them who they would recommend.
League of American Bicyclists
The LAB offers a discounted insurance program through American Specialty. A group must be an LAB member to get the discounted rate. Rates are based on your number of "members" (students and shop users, in our case) and cover regular activities only; extra coverage may be obtained for special outside-the-shop events and races on a fee-for-event basis.
What to Cover
Liability
At least a million dollars in coverage.
Child Molestation Coverage
Does your organization work with kids? You should have child molestation coverage. Sounds horrible, but the act of one rogue volunteer can sink your organization. This would cover you in such an event and require you to do background checks on all your volunteers.