Chestnut Street historic downtown district is Seymour's walkable core — brick storefronts, cafes, the historic Seymour Theatre and John Mellencamp memorabilia at local restaurants. Mellencamp was born and raised in Seymour, and his hometown ties are marked around town for visiting fans.
Jackson County Historical Society Museum on Chestnut preserves county history from farming through the WWII Freeman Field era. Freeman Field was a WWII P-47 Thunderbolt training airfield famous for the 1945 Freeman Field Mutiny by Tuskegee Airmen officers protesting segregation — the story is one of the more significant civil-rights events in the U.S. Air Force's history.
Muscatatuck National Wildlife Refuge 15 minutes east is a 7,800-acre wetlands preserve for birding, wildflower walks and a summer auto tour. Jackson-Washington State Forest just south of Seymour has hiking, camping and quiet fall color.
More within easy reach — Columbus, IN 30 minutes north for the mid-century architecture tour (Saarinen churches, Miller House); Brown County State Park 60 minutes northwest for peak fall color hiking; Louisville, KY 75 minutes south for the Bourbon Trail; and French Lick Springs Hotel 90 minutes west for the historic dome-and-spring resort. Spring pulls Mellencamp fan-tourism and Chestnut Street Spring Fest, summer runs on the Jackson County Fair (July) and Muscatatuck wildlife-refuge visits, fall pairs with US-50 color drives and Colts football to the north, and winter drops to off-season I-65 corridor rates. Seasonal highlights include Jackson County Fair (July), John Mellencamp hometown events (year-round), and Brown County Fall Foliage (October, 60 min northwest).