Travel Destinations - United States

Popeye’s Playground: The Best Things to Do in Chester, Illinois

Welcome to Chester, Illinois- home of Popeye the Sailor. Join us as explore this historic town nestled along the Mississippi River. Our guide to Things to Do in Chester, Illinois will give you a blueprint for your journey. You’ll encounter not only iconic Popeye sights, but also the history and architecture of this charming small town. Oh, and we’ll let you in on an amazing hidden lunch spot nearby!

Mural of Popeye creator in Chester

The First Thing to Do in Chester: The Welcome Center

10 By-Pass Road

Start your visit to Chester at the Welcome Center in Segar Park. The Welcome Center is staffed by volunteers Monday-Friday 9am-4pm, but the bathrooms and brochure racks are available in off hours. There are displays about the history of the town and things to do in Chester, and tons and tons of brochures and maps you can take. Outside the Welcome Center, take a minute to stop at the overlook to appreciate the Mississippi River.

Chester Bridge

Chester Bridge

From the Welcome Center overlook, you can see the nearby Chester Bridge. This bridge connects Illinois and Missouri and is one of the only bridges in the area. Officials in Chester thought of the idea for the bridge in the late 1930s, but since it would be crossing states they needed federal permission. They finally began construction in 1941 and the bridge opened the next year. However, it didn’t last too long because a 1944 tornado severely damaged it. It reopened in 1946, and has been in continuous use. You might also be happy to know that it used to be a toll bridge- but now it’s free! The bridge also had its Hollywood moment when it was used in the movie In the Heat of the Night.

Popeye the Sailor Statue

Statue of Popeye in Chester, Illinois

Out front of the Welcome Center, say hello to the star of Chester- Popeye the Sailor. This bronze statue was erected in 1977 to celebrate creator Elzie Segar. Segar was born in Chester in 1894 and worked at the local Opera House. While working there, he started taking classes which led to creating the Thimble Theatre comic strip. Originally Popeye was actually a side character in the strip, but eventually stole the show and is now known worldwide.

Discover the Popeye Character Trail

Decades after the original Popeye statue was created, the town of Chester decided to capitalize even more on the cartoon connection. They began a multi-year project of creating the Popeye Character Trail. Currently there are 18 statues throughout town featuring different characters. Visiting the characters along the Popeye Character Trail is one of the most popular things to do in Chester.

We’ve put together a free download checklist to help you make sure you find all the characters!

The Most Popular Thing to Do in Chester: Spinach Can Collectibles & Museum

Mural of Popeye characters in Chester

1001 State Street

Located in the former Opera House, where Segar worked as a young man, is Spinach Can Collectibles store and museum. This shop is filled with Popeye comics, toys, collectibles, and more for sale. There is also a section in the back with display cases of items not for sale, which serves as a small museum. On the walls of the shop there are newspaper articles with more Popeye history. It also highlights some of the real-life Chester residents that inspired characters in Segar’s comics.

Merchandise for sale at Spinach Can Collectibles
Display of Popeye items at Spinach Can Collectibles
Display of Popeye items at Spinach Can Collectibles
Closeup of Popeye collectibles
Display of Popeye items at Spinach Can Collectibles in Chester Illinois
Popeye museum in Chester

Architectural Heritage in Chester, IL

If you’re a historic building enthusiast looking for things to do, Chester is a town that celebrates its architectural history. One of the brochures you can pick up at the Welcome Center is the Chester Heritage Trail. We visited the Cohen House, which is known for its unique blue storm windows. This house was built in 1855 and the town claims that Mark Twain had remarked on the windows when seeing it from the Mississippi. Today it’s owned by the city and used as a community center. Other highlights on the Heritage Trail are the Stone Cottage, Chester Public Library, and Randolph County Courthouse.

Visiting the Mary’s River Covered Bridge

1200 State Route 150

Located outside of downtown Chester, Mary’s River Covered Bridge is a historic red covered bridge. It was built in 1854 by Wilhelm Misselhorn from Germany. It was in continuous service from 1854-1930. The bridge has a 90 foot span and the original timbers have been preserved. The state renovated the bridge in 2005, but when we arrived at the bridge we were surprised to see it missing most of its roof. Apparently, last year a major storm damaged the bridge and it has not been fixed yet. We really hope the state makes it a priority to repair and preserve the bridge!

Illinois’s Smallest State Park

Historic marker for Governor Shadrach Bond
Governor Bond Memorial State Historic Site

Chester, IL is also home to what’s considered Illinois’s smallest state park! Governor Bond State Historic Site is the burial site and monument to the first governor, Shadrach Bond. Governor Bond is buried in Evergreen Cemetery and the monument was erected in 1882. The original obelisk was damaged in a 2008 storm, but has since been repaired. Part of the original stone is now a bench in front of the memorial. Governor Bond is in good company, he’s neighbors with the first Illinois Secretary of State, Elias Kane, and many of the founders of the town of Chester.

The Best Hidden Barbecue- Wally’s in Ellis Grove

Wally's barbecue in Ellis Grove
barbecue platter
smoked caramel creme brulee
Inside Wally's barbecue in Ellis Grove Illinois

On our way out of Chester, we stopped in nearby Ellis Grove for a late lunch at Wally’s barbecue restaurant. Josh found Wally’s while searching online for restaurants near Chester and said it had good reviews online. When we pulled up we had to double-check that we were in the right spot because it looked very unassuming. It’s a tiny chef-owned restaurant that feels like you’re eating in someone’s kitchen- and wow was it great barbecue! We split the combo platter and a smoked caramel creme brulee. Everything was amazing, it was very reasonably priced, and the owner and his wife were very friendly.

Other Things to Do Near Chester, IL

We combined our trip to Chester with visiting Fort Kaskaskia and its satellite historic sites. Check out our Fort Kaskaskia Guide here: Fort Kaskaskia and More: Historic Sites and Campground Guide

Josh exploring Fort Kaskaskia

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