Remember too that frequency is important.
There are 26 weeks between May 1 and November 1. To reach 1,000 miles in that time, it's a average of 38½ miles a week. If you ride only once a week, that's 38½ miles every ride. Twice a week, that's still nearly 20 miles a ride. But, if you ride five days a week, that's only 7¾ miles per ride.
If we can due 10 miles on most nights, this is doable...