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The cartoon Popeye originated from the town of Chester. A six foot Popeye Statue is standing in Segar Memorial Park to honor the creator Elzie C. Segar. Every year the Popeye Picnic is held.

The City Chester and the Chester Chamber of Commerce can provide help finding local events and businesses in Chester.

The City of Chester has two very nice community parks. Cole Memorial Park is on Opdyke Street or Route 3 South. The large park is home to a public swimming pool along with a softball diamond, numerous shelter houses, trails and tennis courts.

The Cohen Recreational Complex, which is a large complex that contains two baseball diamonds and three softball fields, walking/exercise track, parking and picnic areas (still being completed in 2008) is located on Route 3 North. Soccer fields are next to the complex and this area is known as "soccer hill".

Next to the Chester High School is the "mini-park". This mini-park consists of three lighted outdoor basketball courts. Nearby is the Chester High School community track.

Chester Skateland is the happening place for children of all ages. Skateland is a roller rink but also offers free walking time every morning and various other activities.

Mt. Hope Bison Farm breeds quality plain bison for breeding stock.

Not far from Chester is the Randolph County State Recreation Area - Fishing, hiking, picnicking, boating, hunting and camping are just a few of the choices, keeping even the most outdoorsman content on 1,101 acres. Located five miles north east of Chester in Randolph County, it lies in the rolling hill country of Southern Illinois. Offering a cool retreat from hot summer days, well shaded picnic areas, hiking trails and scenic forest stands await park visitors.

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