If you're in the mood for art, Red Tree Gallery always has something unique and interesting on its walls and Essencha occasionally features live music. However, the entertainment mainstay in Oakley is undoubtedly The 20th Century Theatre, which hosts both local and national talent on a weekly basis. Also of note is Oakley After Hours - during the summer, shops stay open late and live bands play on the streets on the last Friday of the month.

The entire neighborhood of Oakley is quite walkable, which makes for a popular form of recreation. If you would rather sit than stroll, there is a nice, little park at Oakley Square (at the intersection of Madison and Markbreit) called Geier Esplanade, which has a small green space and a few benches. Oakley also has a CRC recreation center with an outstanding after school day camp, lots of youth and adult activities and a very popular senior program.