Last year I started riding in May and had a goal of 1,500 miles. Didn't make it. Was close though. This year pretty much the same, started in May and set a goal of 2,000 miles for the year. Did a bike tour of 600 miles and some mountain bike riding over the summer and breezed right to the 2,000 mile goal. Was hesitant to set another goal for the remainder of the year because I didn't want to focus on miles and keep myself focused on having fun. The bike touring taught me that I can comfortable ride in the wind and rain so it didn't take me much longer to hit 2,500 miles. That's when I decided to reach for 3,000 miles. I'm almost there. Going to be close but I'm going to make it somehow.
My plan for next year is to start by riding all winter and have 1,000 miles before May 1st. Hit it harder after that and not let weather limit my riding as much.