I know these are both road tandem events, but, there is some very good off-road tandem riding nearby.
The road events, first weekend is the Southern Tandem Rally 2012 (aka STR 2012) in St Augustine Florida.
Second weekend is the Florida Tandem Rally.
Southern Tandem Rally 2012
Florida PANTHERS* Tandem Club
Nearby is a trail system call San Felasco. These trails are great on a Tandem MTB. They are about 2 hours away from St Augustine, but an easy diversion on the way to Ocala and the Florida Tandem Rally, hosted by the Panthers Tandem Club.
San Felasco Hammock Preserve State Park CSO
Assuming you stay the entire week of tandem riding, you cane hit STR, stop by San Felasco, then head south to the Villages for more road riding.
About 20 minutes North of the Villages, in Belleview, is the Santos Trail system. This place is a great tandem off-road location. Some trails are impossible on a tandem, while the other 99% are flowing and relatively flat. We have hundreds of miles and smiles riding this place.
Ocala Mountain Bike Association - Home
If you are real adventurous, you can go further south to Alafia and Balm Boyette. About 2 hours away from the Villages, these two trail systems will be plenty of technical challenge. Also in a similar area is Croom, like San Felasco, a true XC riding trail.
SWAMP - Florida Mountain Bike Trails
So if you are heading South in October, consider getting dirty too.
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Thread: Florida October Tandem Events