Winchester has a vibrant small business scene and a laid-back vibe
Surrounded by farmland and intersected by forks of the White River, Winchester is a rural community of about 5,000 people and the seat of Randolph County. “I was born and raised in Winchester and found myself back in 2013 doing real estate. I try to sell people on the vision of why I live here, and for me, it’s a small, safe, quiet community,” says Brody Tarter, a broker with Re/Max Evolve. “At the same time, for the size of the community that we are, we really have everything you’d need. From shopping to entertainment and restaurants, all those things are still here. I think that’s what made me come back home.” In addition to a laid-back atmosphere and a vibrant downtown district, Winchester has a thriving manufacturing industry with several factories in town.
Small businesses thrive in downtown Winchester
While many rural communities struggle to retain and attract businesses, Winchester has a thriving downtown district packed with local shops, restaurants and services. “It is a vibrant downtown that’s lasted,” Tarter says. “There’s a demand for businesses and people to be downtown, and there are no empty storefronts.” Anchored by the Randolph County Courthouse, the central town square has a butcher, boutiques, restaurants and essential county services. U.S. Route 27 has casual franchise eateries and a Walmart for groceries. Wick’s Pies, a regional institution that makes more than 10,000 pies a day, is known for sugar cream pie, a custard-based treat as Hoosier as basketball and breaded tenderloins. Wick’s iteration is so famous that Winchester has been dubbed the “sugar cream pie capital.” The pie purveyor has a bakery and café that serves 36 varieties and all-day breakfast.
Relaxation at Goodrich Park, high-speed thrills at Winchester Speedway
Winchester has nearly 100 acres of green space, the majority of which is occupied by Goodrich Park. The sprawling, shady park features walking trails, playground equipment and a skate park. It’s also home to the village swimming pool, splash pad, dog park and amphitheater. “It has all kinds of sports and Little League games,” Tarter says. “It’s definitely a highlight.” The Winchester Speedway has been thrilling visitors since its inception in 1916. “It’s the fastest half-mile in the world,” Tarter says. “Winchester also has a nice library, and they do a lot of events over the summer when the kids get out of school.” Golfers can hit the links at the public Winchester Golf Club, and folks of all ages come to town for the Randolph County YMCA.
Winchester has 20th-century homes and new builds
Winchester’s housing stock mainly consists of existing structures built between the early 1900s and the midcentury, but some homes date back to the mid-1800s. Common housing styles include National, bungalow and ranch-style. The town has also seen more residential development in the past few years with new subdivisions like Lakeview Park. The median single-family price is about $150,000, which is on par with Portland and slightly higher than Union City’s median of roughly $130,000. “It’s been a pretty consistent market for us over the past 13 years. There still seems to be a demand for people who live in this area,” Tarter says. “Inventory has always been low, and I think that’s been a driver of demand. Another big driver for this area is USDA loans. The entire county qualifies for it, so we do a lot of no-money-down USDA loans.”
College credit at Randolph Central School Corporation
Kids can attend Randolph Central School Corporation, which receives a B rating from Niche. The district serves about 1,500 students and has three elementary schools, two middle schools and one high school, all within Winchester. Students can participate in academic, career and technical education dual credit programs through Ivy Tech Community College and earn up to 30 credit hours, which is the equivalent of a full year of college.
Less than two hours from Fort Wayne and Indianapolis
Winchester is about 15 minutes from the Ohio border and less than 30 minutes from Greenville, Ohio. Drivers are about 20 miles from Interstate 70 and 35 miles from I-69, two of the state’s primary highways. Many people commute to Winchester for work in factories and manufacturing plants. Medical care is available in town at Ascension St. Vincent Randolph. Drivers can get to Indianapolis or Fort Wayne within an hour and a half. Winchester is a horse-friendly community, and residents are allowed to ride their steeds within city limits.
Tornadoes can occur in the area; a 2024 tornado in Winchester caused one death, 37 injuries and significant damage to several businesses.
Celebrations for every season
Residents enjoy a slate of events year-round, including summertime events like free concerts in Goodrich Park and a weekly farmers market downtown. Winchester Main Street Festival, formerly known as Mardi Gras, is one of the town’s biggest events of the year. The fall street festival features vendors, food, carnival rides and entertainment. The holiday season kicks off with the Soldiers and Sailors Monument lighting in early November, followed by Majestic Christmas in early December, a holiday event with Santa, a parade, food and activities.
Written By
Leslie Klosterman
