Montgomery boasts several arts and entertainment options close to home. Economically-minded theatre lovers can enjoy excellent student productions at Sycamore High School and Cincinnati Hills Christian Academy (better known as CHCA). The Village Tavern hosts live music on weekend evenings and Sycamore Township offers Sunday evening concerts in the warm weather months, featuring local and regional performers. The Blue Ash-Montgomery Symphony Orchestra also holds concerts year-round; many of the members, including conductor Michael Chertock, play with the Cincinnati Symphony Orchestra and other notable regional groups.

Montgomery is dedicated to family recreation, and supports a park system that consists of more than 96 acres, spread over eight parks. What makes these parks unique among Cincinnati communities is that they are connected by over 10 miles of bike paths and sidewalks, allowing easy access for all residents and providing a haven for cyclists.

Johnson Nature Preserve features a walking trail, where trees felled by a 1999 tornado biodegrade naturally to prevent erosion. Centrally-located Montgomery Park hosts the city's Fourth of July celebration in the summer, and sledding in the winter. Pioneer Park offers the broadest range of use areas, with everything from butterfly gardens to baseball diamonds, but even the smaller parks, such as Pfeiffer, feature tennis courts and tot lots. Those who like to swim can join the beautifully-kept Montgomery Community Pool on Hopewell Road, open every day during the summer (and also home to the Montgomery Makos Swim Team). Even their business district includes lovely benches and nooks to sit in.

Golf enthusiasts will enjoy the nearby Kenwood Country Club, which offers two championship courses, along with a youth swim team, tennis courts and recreation for the whole family.