The Black Bear was the first course at Woodland Valley. It was designed to be a nice median between the amateur and advanced players by including long holes through open fields and tight shots through the forest. Each section of the course is distinctly different by leveraging the natural elevation changes,  obstacles including both rocks and trees and in some areas deep forest. The Black Bear originally had water issues in the spring season but has since been remedied through a comprehensive drainage system allowing dry play through most of the year.

Additionally, a unique trait to Woodland Valley is that during the snowy winter months, the Black Bear's fairways are groomed and packed after each snowfall.