So my CEO (who is normally in Santa Cruz, CA) is visiting the office this week, and he has a bike at his disposal, and would like to head out for a ride. Given that the office and corporate apartment are in the South Side, I thought we could head to the south, rather than heading through town and riding roads north of the city (where I’m more familiar with the lay of the land). So I’m looking for ride suggestions, in the neighborhood of 20-30 miles. He’s a cyclist, and currently in reasonable shape, so some moderate hills are okay.
Some vague options I’ve been considering are heading to South Park via Streets Run, or Carnegie via 50. Any other suggestions?