1000 miles sounds like a lot. But once you're comfortable on your bike, you will naturally find yourself wanting to go farther each time out. And you will pass that 1000-mile goal by so far that you'll be laughing at yourself. You may well end up shooting for 10,000 miles by Nov. 1st.

I have rides on my mountain bike that are easy at 40 miles per day. 10 days x 40 miles = 400 miles. Make that 20 days, if you prefer to give yourself a day off every other day.