The most difficult thing about dining in Oakley is deciding where to go. One could have samosas and curry at Baba India, or high English tea at Essencha tea house. For a step above common pub fare, there's Habits Café on Oakley Square, or for something completely different, Boca is a popular dinner spot for great Italian food. Dewey's Pizza and Skyline Chili are common favorites; however, if you are in the mood for something classy, there's four star Southern cuisine at Hugo. When it comes to snacks and desserts, Red Tree Gallery offers coffee and other goodies, while Aglamesis Brothers serves ice cream and gourmet hand-made candies. No matter what the occasion, Oakley has something tasty to put on the table.

Nightlife in Oakley is pretty calm, but there are still a few popular watering holes worth visiting. Many locals favor Habits Café, which serves food (and the best sweet potato fries around) and has a pool table. Oak Tavern also has a pool table, and more of a sports bar atmosphere. Oakley Pub and Grill is exactly what you’d expect, and famous for its ten-cent wings on Mondays. For live music, The 20th Century Theatre is the place to go – they regularly host both national and local groups, and the historic theatre is a classy place to take in a concert.