Jay,
I've started two over the years and am getting ready to launch a cigar club now. The best thing I ever did was to visit an active club before starting my own. I learned how a properly run one is operated. You'll need a venue or course, a president, a tresurer and a small core of loyal participants that will actually show up once a month. You'll then have to decide about dues and weather you'll collect them or not and then what you'll do with them after they're collected.
I've found that the biggest road block are folks schedules. Thanks to this crappy economy folks are working more than ever, have less free time and generally wanna rest when they're off duty. A loyal group of enthusiastic members will inspire more to join and so on and so forth.
Also, a monthly newsletter sent to members serves as a reminder of the meeting date and place and it's also a way for non active members to catch up on the club.
Check out the SHPC's newsletter: http://www.shpcboston.org It's done by secretary Nelson Pidgeon and will give you a great look into a successful and active club. All back newsletters are archieved at the bottom of it...
If you have any questions drop me a pm and I'll try to help if possible...