Dave from Kirkwood on 6/9/2021 8:55:39 AM:
You ask a lot of questions, so here are some general replies.
Not sure what you mean by not going so far and been a long time (since you rode a bike anywhere??), but it would be a good idea to do a long-ish day ride of 30-40 miles to make sure you and your bike are comfortable. Drive to Pleasant Hill and ride 20 miles out (and back) to make sure you feel ready.
As Kate says, the trail should be fine for road bikes unless there has been LOTS of rain. It drains very well, and plants suck up water during the summer to prevent excessive sogginess.
As for stops, it is best to call ahead (now) to make sure key stops for restaurants are going to be open, especially on weekdays. Some places have unusual hours or are still recovering from pandemic closures.
Finally, you should not be able to get lost - just stay on the obvious trail heading east (across numerous road crossings and avoiding side trails that are usually marked).