There is a triathlon bike course in Pawling; at least one, anyway. According to the info I found, it's a 7.11-mile ride originating in Pawling and snaking its way up to Wingdale in Dover. There's also a maximum elevation shift of about 200 feet, so it looks reasonably challenging (not that I'd know from experience or anything). Looks like fun, so surely check it out.
There are others in the greater region, into Connecticut and on the other side of the river, but this is clearly a Pawling resident's best bet, and it's longer than a lot of those other trails.
