What’s it like in Winchester, Indiana?

The History of Randolph County and Winchester, Indiana

Randolph County was authorized by the Indiana General Assembly in 1818 and named after Randolph County, North Carolina, where prominent settler Benjamin Cox and many other Quaker settlers were natives of. Five of those settlers donated land to make Winchester the county seat that year, and it was named for Winchester, Virginia.

In the mid-1800s, Randolph County was an important part of the Underground Railroad and was home to three distinct settlements of free African-Americans. In the 1880s and 1890s, oil and natural gas were discovered in the county, and Winchester became dominated by the glass industry.

One notable Hoosier from Winchester is James P. Goodrich, who was Indiana’s 29th governor from 1917-21. His term generally focused on the state’s contributions to World War I.

More recently, Winchester was hit by a quarter-mile-wide EF-3 tornado in March 2024 that left 40 injured, 22 homes destroyed and over 100 others damaged. The local Taco Bell and other structures were leveled, but the community rallied together and has rebuilt much of what was lost. 

As of the 2024 census, Winchester’s population is 4,800, making it the largest of nine incorporated towns/cities in Randolph County. Union City is second with 3,435 residents. Winchester is the 138th-largest city in Indiana.

Things to Do In or Near Winchester, Indiana

Head to downtown Winchester and check out the Randolph County square grounds, which features a 73-foot-tall Soldiers & Sailors Monument – the second-tallest such monument in Indiana – honoring Union soldiers who fought in the Civil War. It was dedicated in 1892. There is also a World War I “Doughboy” statue dedicated in 1928 that commemorates World War I soldiers from Randolph County who paid the ultimate sacrifice, and a tank memorial dedicated in 1958 to commemorate World War II and the Korean War.

From the first weekend in May into mid-September, Hummel Drive-In Theatre is an iconic spot to catch a flick on Friday and Saturday nights. Located three miles east of Winchester, Hummel has a playground for kids, concessions and two screens that show two movies apiece, with the first showtimes starting at 8 p.m. Adult tickets are $10, children are $5 and kids 4 and under get in free!

Staying outdoors, Winchester Speedway is known as the “World’s Fastest ½ Mile” – a half-mile paved oval racetrack that seats 5,000 spectators. Starting in May and ending in mid-October with the Winchester 400 Weekend, enjoy watching USAC Silver Crown cars, Thunder Roadsters, Monster Truck throwdowns, and the ASA STARS National Series in action.

For golfers, get your fix at Winchester Golf Club, which features three 9-hole courses called Beeson, Pony and Willow. Beeson has more bunkers to navigate, while Pony and Willow are filled with water hazards.

Places to Eat or Drink in Winchester, Indiana

Start your day at Mrs. Wick’s Restaurant, a full-service bakery cafe that is open Tuesday through Saturday. They make 36 varieties of pie each day, and breakfast is served all day. You can also take home legendary Mrs. Wick’s pot pies, pie shells or unbaked frozen pies.

A quick history lesson before we dive into Winchester’s food menu any further. Mrs. Wick’s Restaurant opened in the mid-1980s in honor of Duane “Wick” Wickersham’s supportive wife, Ruby. The entire Wick’s pies operation, however, goes back to Duane’s opening of The Rainbow Restaurant in downtown Winchester in the mid-1940s. There, he used his grandmother’s recipes to sell pies, and they were such a hit that he was producing and selling 300 pies per day after just four years. Then in 1961, he purchased a building in town that today is home to the production of 10,000 pies and over 30,000 pie shells in an 8-hour shift. Mr. Wickersham was a highly successful entrepreneur, to say the least.

Now, back to restaurants in Winchester. Another good morning spot is Northblock Coffee Co. where you can grab your favorite seasonal morning beverage and muffins or donut holes in a relaxing atmosphere. Visitors give them 4.9 stars on Google. 

For pizza lovers, Our Pizza House was established in 1960 and has been a local favorite ever since. Breadsticks and ‘zas are menu staples, but its 21 varieties of super sub sandwiches are sneaky good, too. There’s also Chicago’s Pizza Winchester, one of 24 Chicago’s Pizza locations across central and southern Indiana. Founded by Ron Epple and Bob McDonald in 1979, Chicago’s Pizza has 4.5 stars on Google with many reviews praising its breadsticks, salad bar and deep-dish pizza.

If you like Mexican food, there are a couple spots in town to hit up. Grab street tacos, fajitas or a chimichanga from Cuervo’s Tacos, which was established in 2020 and has 4.8 stars on Google. Then there’s the family-owned El Carreton Mexican Restaurant with over 1,200 Google reviews, many praising the service and atmosphere plus menu favorites like fajitas, enchiladas, and chimichangas.

Amazing Joe’s Steakhouse is a great dinner spot and has over 130 Google reviews and 4.7 stars. It’s one of three Amazing Joe’s locations, with the others in Muncie and Columbus, Ind. The ribeye is a favorite among visitors.

For dessert in Winchester, there are two places to check out. Established in 1987, Bogie’s Ice Cream has become a summer staple for sweet treats. Open seasonally from the first Monday in March through Labor Day, Bogie’s has drive-thru and walk-up services for a menu that includes everything from ice cream cones to the best milkshakes in Randolph County.

House of Flavors is another local spot to grab ice cream. It has 50 flavors of hand-dipped ice cream, monster size sundaes, burgers, a massive tenderloin sandwich and more on its menu. Service is known to be fast and friendly, and guests give ‘em 4.6 stars on Google.

Winchester Community High School

Winchester Community High School is the home of the Golden Falcons. The school has not won any IHSAA team state championships in its history, but Payton Sparks, who went on to play at Ball State and Indiana, did posterize our video editor and designated Get Indiana foodie Robert Porter in high school back in 2021.

Winchester does have eight Indiana State School Music Association marching band titles on its resume, winning Class B championships in 1974, 1975, 1977, 1978, 1979 and 1980 along with Class C championships in 1986 and 1987. The marching band also took home runner-up finishes in 1973, 1976, 1981, 1982, 1983, 1988, 1996, 1997 and 1998.

That’s it for small town breakdown No. 40 of 2025. Where should we head next?