Headingley provides a multiplicity of recreational and cultural spots for residents and visitors alike. The John Blumberg Sports Complex is a world class softball and golf complex that has hosted many numerous International events.

Located on the Trans Canada Highway, the beautiful park offers 18 and 9 hole golfing, a driving range and five baseball diamonds with backstops. Kids will surely enjoy Thunder Rapids go carts and batting cages, located just east of the Village of Headingley.

The Odeon Drive In and Assiniboine Downs are popular facilities for both residents of the city and community during Manitoba's warm summer and fresh autumn months. Fine dining at Green Gates Restaurant is also a must for all fine dining connoisseurs. The Breezy Bend Private Golf and County Club is located just south of the river, along Roblin Blvd. (Provincial Road 241.)