so I've never done any long distance riding before I commute every day about 19 miles round trip and if anyone is familiar with the San Mateo County, I live in Belmont on the top of a hill, so I have experience with some hill climbing. The farthest I've ridden at once was about 20 some odd miles and I wasn't tired. I'm planning this ride for tomorrow, friday 7/4, and I'm not worried about getting down to santa cruz, I'm more worried about riding back with the head wind. Anyone that has done it before, how hard is it? I was thinking about bringing a tent and sleeping bag and camping somewhere overnight and getting up in the morning and riding before the winds. Really how fast do the winds get? Would it be a miserable first experience or should I just go for the full century or do 50 miles each day?

Thanks

any advice is more than welcome especially since I'm planning on doing this tomorrow.

Don't try the century. Even if you manage to finish, it won't be fun. 20 miles is nowhere close to getting the feel of long riding.

I'm probably suggest doing a few longer rides before tackling a century. I'd also be worried that the huge increase in car traffic due to the holiday weekend might make the ride less than enjoyable. When I lived in Belmont, I used to ride Canada road down to Sand Hill Road, do the Portola Valley Loop, and then add distance/climbs as necessary. The basic ride is about 30 miles, I think, and there's a decent amount of climbing. There are several stores along the route, so you can stop to rest or buy drinks/food as necessary. PM me if you want more details on the route...