Vintage Hilly Hundred Cycling Shirt Bloomington Indiana 90s

A heather gray Screen Stars Best shirt from 1992, single-stitched and made in the USA, printed to mark the 25th running of the Hilly Hundred — the beloved Indiana cycling tour that rolls through the hills around Bloomington. The back carries the event map with its “First Day” and “Second Day” routes; the sleeve reads “25th Anniversary” beside a little bicycle. The front leans into the joke every rider knows, billing it the “Chilly Hundred.”

That wordplay is earned. The Hilly Hundred started in 1968 and long ago settled into an October slot, which means two days of climbing steep southern-Indiana grades through the turning leaves — and mornings cold enough to make “Chilly” the truest word on the shirt. It’s a tour, never a race: thousands of cyclists, rest stops with live music and free food, and a friendly, unhurried spirit that’s kept the ride going for decades. By its 25th year it was already a Midwest institution.

The blank tells its own story. Screen Stars Best was the heavyweight sibling in the Fruit of the Loom family, the tag serious tee collectors chase for its softer hand and better drape. Single-stitch construction and domestic manufacture put this squarely in the golden age of the American event tee.

Twenty-five years of Indiana hills, printed on a blank that climbs just as well as the riders did.