The first token is what is called a "St. Louis part-incuse" token. The manufacturing technique was popular in St. Louis, MO for many years. They made up a bunch of "stock" planchets - in the case of this one it probably had something like "Good For / 5¢ / Loaf", or something similar, in the center part where the lettering was raised above the field. The reverse side often had a raised indication of the manufacturer, but that part often is worn away. Then, when a guy like George Darmstaedter ordered some tokens, they made a ring-shaped die which would then be used to stamp the incused lettering as you see on your piece. The vast majority of this type of token has no room for the town and state, so they are "mavericks".
George Darmstaedter was a baker in St. Louis from at least 1895 to 1920 at 7130 Virginia Ave. Typically these tokens were used in the following manner. A regular bread customer would buy and pay for a dozen loaves of bread in advance. The old term, "a baker's dozen", meant that for the purchase of 12 loaves, the customer would receive 13. So, after paying 60¢, the customer would get a loaf of bread and 12 of these tokens for subsequent purchases. That way, the customer got a bit of a discount and could avoid stale bread in the house. The baker only had to have one cash transaction, and if the customer happened to lose or otherwise not redeem any of the tokens, that was nearly pure profit for the business.
John in the Great 208