Taking advantage of the miles of green space lovingly curated by the Chicago Park District along the lakefront bike path, it is possible to head south from Buckingham Fountain in Grant Park to the Indiana Border, cut across the South Suburbs to the Tinley Creek and Cal-Sag watersheds, then north dozens of miles along the Des Plaines River into Lake County. Again cutting across the northern suburbs on a Rockland Road bike path, one can descend via the Green Bay Trail
and North Branch of the Chicago River, traveling some 200 miles around Greater Chicago on an (almost) unbroken green ribbon of parks, Forest Preserves, and pedestrian or bike-walk infrastructure. While camping is available at several locations on this route, there is currently not enough camping to thru-hike the entire route without ridesharing back and forth from the trailheads. Below is a suggested route breakdown for thru-hiking. There are many other ways to segment this hike, but here is what we did.
Grant Park to Steelworkers Park (~16 mi)
Camping: Rideshare to Camp Shabbona Woods or look for lodging service/hotel in South Chicago area.
Highlights: Museum Campus, Burnham Wildlife Corridor, 63rd St. Beach, Jackson Park Harbor, South Shore Nature Center and Sanctuary, Rainbow Beach, Steelworkers Park & Climbing Wall.
Steelworkers to Camp Shabbona Woods (~ 15 mi)
Camping: Camp Shabbona Woods
Highlights: Calumet Park, Eggers Grove, William Powers State Recreation area, Green Lake Family Aquatic Center, Shabbona Woods.
Camp Shabbona Woods to Old Plank Trail Eastern Trailhead (~20 mi)
Camping: Rideshare to Camp Shabbona Woods (or reverse hike this section if you'd prefer to hike into camp)
Highlights: Brownwell Woods, Wilson Woods, Halsted Woods, Joe Orr Woods and Glenwood Woods. Be sure to grab a bite to eat at Gabe's Place in Glenwood.
Old Plank Trail to Flossmoor Road after Bartel Grassland (~ 12 mi)
Flossmoor Road to Camp Sullivan (~12 mi)
Camping: Camp Sullivan
Highlights: Bartel Grassland, Bachelor Woods, Camp Sullivan
Camp Sullivan to Camp Bullfrog Lake (~15 mi)
Camping: Camp Bullfrog Lake
Highlights: Sag Valley & Palos Forest Preserves, numerous side jaunts and trails, Swallow Cliff Stairs, REI Boathouse at Saganashkee Slough.
Camp Bullfrog Lake to LaGrange Park Woods (~ 15 mi)
Camping: Rideshare to Camp Bullfrog Lake or look for lodging service/hotel in LaGrange/Brookfield area.
Highlights: Little Red Schoolhouse, I&M Canal, Metropolitan Water Reclamation area, Chicago Portage National Historic Site
LaGrange Park Woods to Brookfield Zoo, then north to Schiller Woods (approx 15 mi)
Camping: Rideshare to Camp Dan Beard or look for lodging service/hotel in Schiller Park/Franklin Park area
Highlights: Brookfield Zoo, Trailside Museum of Natural History, Russell's Barbecue in Elmwood Park,
Schiller Woods to Alison Woods (~ 18 mi)
Camping: Rideshare to Camp Dan Beard or look for lodging service/hotel in Northbrook/Glenview area
Highlights: Des Plaines River Trail
, River Trail Nature Center
Alison Woods north to Old School Forest Preserve (~ 20 mi)
Camping: Rideshare to Camp Dan Beard or look for lodging service/hotel in Libertyville/Vernon Hills
Highlights: Half Day Forest Preserve, Captain Daniel Wright Woods, REI Vernon Hills, MacArthur Woods
Old School Forest Preserve to east Park Ave Libertyville, east to North Branch, South to Melody Farm Nature Preserve, east to Deerpath Road and Lake Forest College ,south past Fort Sheridan and into downtown Highland Park (~ 15 mi)
Camping: Rideshare to Camp Dan Beard or look for lodging service/hotel in Highland Park
Highlights: Middlefork Oak Savanna & the Openlands Conservation area, Fort Sheridan
Highland Park south to Skokie Lagoons via Green Bay Trail
, Chicago Botanic Garden and Skokie Lagoons (~16 mi)
Camping: Rideshare to Camp Dan Beard or look for lodging service
The trails have been around for a while, but this particular route was piloted in 2018 by members of the Chicago Outerbelt Alliance, a NFP organization with the mission of promoting eco-recreation in a metropolitan environment and engaging diverse communities in outdoor experience.