Driving I-65 between Indianapolis and Louisville? Get off at the “Crossroads of Southern Indiana” for a plate at Larrison's Diner, a bite and pour at Brooklyn Pizza & Seymour Brewing Company, a drink at Rails Craft Brew & Eatery, a walk through Muscatatuck National Wildlife Refuge, the annual Seymour Oktoberfest downtown, and a photo op at the painted mural of John Mellencamp.
Small Town Breakdown No. 79: Seymour, Indiana
For this week's small town breakdown we're going from the booming town of Whitestown in Boone County to Seymour in Jackson County. Seymour is about an hour south of Indianapolis and an hour north of Louisville.
The History of Jackson County and Seymour, Indiana
Jackson County was established on Jan. 1, 1816, from pieces of Clark, Jefferson, and Washington counties. It was named for Andrew Jackson, who defeated the British at the Battle of New Orleans during the War of 1812 and would later become the seventh president of the United States from 1829–37. Vallonia served as the first temporary county seat starting in June 1816, but by November the seat had moved to Brownstown.
Seymour was platted in 1852 and grew up at the point where two railroads crossed: the north-south Jeffersonville, Madison and Indianapolis Railroad connecting Indy to the Ohio River at Jeffersonville and the east-west Ohio and Mississippi Railroad connecting St. Louis and Cincinnati. It became known as the “Crossroads of Southern Indiana” and was named for Hezekiah C. Seymour, a railroad man remembered simply as "the chief contractor and civil engineer. The first train rolled through in June 1854.
Seymour is the largest incorporated town/city in Jackson County with a population of 22,371 as of February 2026, making it the 47th largest city in Indiana.
The Reno Gang
Seymour's railroad crossroads made it not only a hub but a target. In October 1866, the local Reno Gang robbed an Ohio and Mississippi Railroad train just east of town, making off with thousands of dollars. Historians consider it the first robbery of a moving train in U.S. history.
Things to Do In or Near Seymour, Indiana
Seymour's downtown pays tribute to John Mellencamp with a mural of the musician painted by Indianapolis artist Pamela Bliss in 2019. The mural draws visitors from all over the country.
If you're visiting in early October (Oct. 1-3, 2026), plan around the Seymour Oktoberfest in downtown Seymour. It's grown into one of the region's bigger fall festivals, with a biergarten, food vendors, a parade, a 5K, carnival rides, hot air balloons, arts and crafts vendors, and competitions ranging from a brat-eating contest to a stein hoist.
Just a few miles east of town, Muscatatuck National Wildlife Refuge offers hiking and birding across acres of wetlands, forest, and grassland.
History buffs can also visit the Freeman Army Airfield Museum, on the site of the World War II-era Freeman Field where cadets trained. It's open from 10 a.m. to 2 p.m. on Saturdays.
For golfers, Shadowood Golf Course is an 18-hole public course that's been open since 1976. The tee boxes, fairways, and greens are always in great condition, making it a must-play in Jackson County.
Places to Eat or Drink in Seymour, Indiana
Start at Larrison's Diner, a Seymour institution since 1974. It's packed with decades of memorabilia. Pro tip: Order a bison burger and milkshake while you're there. They have a 4.7-star rating and nearly 1,000 Google reviews.
Rails Craft Brew & Eatery is another hot spot downtown, open daily except on Sundays. Guests love the cod dinner, salmon spinach berry salad, pretzel and beer cheese, and 50/50 burger, best enjoyed on its seasonal patio. Rails leans on local partners like Darlage Custom Meats and Marion Kay Spices for their ingredients.
Brooklyn Pizza & Seymour Brewing Company has been Seymour's home-grown pizza place since 2006, followed by the founding of the brewery in 2017. Microbrews, nanobrews, pizza, wings, and live music on the patio. You can't beat it.
Lola's Modern Kitchen is a trendy spot with 4.8 stars on Google. They have free-play arcade games for all ages, and the food is top notch as well. Fried cheese drizzled with smoked honey for starters, tacos and burritos for the main course, and cheesecake chimichangas for dessert.
Schwatzer's German Restaurant is a great place to dive into some Jagerschnitzel, bratwurst, and German beer, all while learning German for free on its website.
Poplar Street Tavern & Restaurant has draft beers from breweries across Indiana along with a selection of wines like Salt Creek, Purple Toad, and 19 Crimes. There's a family room and bar area for patrons 21 and older, and in the summer there's a large open patio that seats over 200 people.
High School History
Seymour High School is home of the Owls and has the second-largest gym in the country. They have captured three IHSAA state championships in school history, first in baseball in 1988, followed by girls golf in 1990 and boys golf in 1991.
Trinity Lutheran High School is a private school in town and is home of the Cougars. They've become a 1A juggernaut in volleyball, winning back-to-back state titles in 2025 and 2026.
That's it for small town breakdown No. 79. Where should we head next?
