Closer to Indianapolis:
Here's some of my favorite rides in SW Indiana, off of I-74 near Cincinnati. It's still 100 miles from Indianapolis, though.
like your tag line says: Indiana: "It's Not As Flat As You Think!™"
from Harrison OH, with a stop at Brookville IN. The ride starts from the Harrison High School parking lot, easy to get to from I-74, and lots of parking. On the ridewithgps route link, pull down the Map list and checkmark Terrain
. The Whitewater River has cut deep valleys here.
The route map uses an abandoned road bridge in Cedar Grove IN at the 20 mile mark, but it's been permanently blocked
this year. So riders need to go north on US52 and cross the new Route 1 bridge.
Mile 1-20: easy climbing through farms and woods, then a short downhill to Johnson Fork Road, a stead 2% grade through a scenic creek valley, then up onto the plateau on English Hill Road, which has a great valley view, then 12% downhill into Cedar Grove. We stop at the gas station there.
Mile 20-28 follows the Whitewater River valley, on a sometimes rough road, but very little traffic and very scenic.
The return starts with a 450 foot, 6 mile climb up Blue Rock Road, then straight across farmland to a fast downhill on St Peters Road, to more Whitewater river roads. Very interesting and scenic.
Passing through Harrison OH has more traffic, but bikes do okay there. Then it's just a couple of miles to the end of the ride.
A similar route's outbound leg photo album is here.
47 miles, Fernald Park to Cedar Grove.
Fernald Park is the site of the Fernald uranium processing plants. After a huge cleanup, it's now a wildlife reserve.
This route is similar to the one above, with the same detour needed at Cedar Grove. But it returns up the very steep Gobblers Knob Road, at mile 23. The climb is 300 feet in .6 miles, an average 10% with two pitches at 15-18%. An alternative is to climb up the new Route 1, a steady 5-7%, but boring.
36 mile Harrison - Cedar Grove
is a shorter mixture of the above two rides.