2016 (Updating to 2017)
Route 66: The Mother Road Eastward — This seven-week van tour takes route 66 from Santa Monica all the way to Chicago. Offered by the Adventure Cycling Association. Dates: Apr. 15 – June 4, 2017.
Route 66: The Mother Road Westward — An eight-week self-contained bike tour from Chicago to Santa Monica. Offered by the Adventure Cycling Association. Dates: Sept. 10-Nov. 3, 2017.
Grand Illinois Trails and Parks (GITAP 2016) — Six-day supported ride with a choice of camping or motels. 250 to 400 miles, depending on options. Sponsored by Ride Illinois, a bike advocacy organization. Dates: June 12-17 2016. (Limited to 225 cyclists, first-come, first-served)
Bicycle Illinois (formerly Bicycllinois) routes cyclists over about 550 miles of road. The ride leaves from Cairo and ends in Chicago, with overnight stops in Carbondale, Centralia, Effingham, Champaign and Kankanee. Dates: July 9 – 16, 2016.
Other Illinois bike rides —
Tri-State Bike Tour visits Indiana, Illinois and Wisconsin in one day of riding 85 miles, with a century option. Begins in Hammond, Indiana, and travels along Lake Michigan to Kenosha, Wisconsin. Presented by Bicycle Illinois. Date: July 16 and Aug. 14, 2016.
Tour de Stooges offers five routes of 15, 22, 31, 42 and 64 miles in southwestern Illinois. Lunch and slapstick comedy following the ride. Meets at Lindendale Park, Highland, Ill. Date: May 2, 2015
Also see Missouri: Cycle Across Missouri …
Touring Ride in Rural Indiana (TRIRI) June Bicycle Rally This long-running bike tour underwent a big change in 2011. Instead of a linear route, TRIRI established a base camp and hosted loop rides from that location. The tour is on hiatus in 2016.. Dates: (returns in 2017).
Rainstorm 2016– Ride Across Indiana — Same Thing Only Ride More Returns for its eighth year in 2015. Cyclists will ride five centuries in five days on hard-surfaced backroads of Indiana. Starting in Richmond, overnights at Brown County State Park, Clifty Falls State Park, Spring Mills State Park, and Bloomington. On the final day, cyclists join the 160-mile RAIN bike ride from Terra Haute to Richmond. Dates: July 11-16, 2016
Touring Ride in Rural Indiana (TRIRI) September Escapade This fall ride explores southeastern Indiana. Overnights at Brown County State Park, Spring Mill State Park, and Clifty Falls State Park. Different mileage options most days. Dates: September 11-16, 2016.
The Register’s Annual Great Bicycle Ride Across Iowa 2016 (RAGBRAI XLIV) The longest running cross-state bicycle tour celebrates its 44rd year in 2016. Registration to enter the RAGBRAI lottery opens Nov. 15, 2015; route announcement is Jan. 23, 2016.. Dates: July 24-30, 2016.
Ride Across Iowa This one-day Iowa crossing can either be ridden as a race or an extreme recreational bike ride. It’s 300 miles, but there’s also a 150-mile version. Council Bluffs to Muscatine. Date: Oct. 3, 2015 (check back to website or Facebook page)