Adventure in the State’s Deep South
Head to the rolling, tree-topped hills of southern Illinois for a memorable mash-up of still-temperate weather and crimson leaves, pumpkin patches and wine trails, hiking and rock climbing. Build your trip around the region’s crown jewel, the 290,000-acre Shawnee National Forest. Nestled between the Mississippi and Ohio Rivers, the forest is home to 400 miles of horseback and hiking trails and ample opportunities for climbing, paddling, and fishing. Hike to Camel Rock in Garden of the Gods (pictured above) — a spectacular wilderness area of stark sandstone formations — or make your way to Crow Knob, once a beacon for travelers on the Underground Railroad. Sip fresh apple cider and pick your own pumpkins at Rendleman Orchards, or do an outdoor tasting at one of the Shawnee Hills Wine Trail’s 11 wineries.
▶ Drive time 5 hours
▶ Where to stay The three units at Rocky Comfort Cabins (from $189 for two nights) offer upscale comfort along the wine trail. (Be advised: Two of the cabins are Hobbit-themed.)
Rural Solitude on a Working Farm
The aptly named Has Bin is a 1950s grain bin in Vermilion County that’s been converted into a well-appointed guesthouse (from $115, including breakfast). Nearly everything inside — from the clawfoot bathtub rescued from a nearby farmhouse to the sink that was once a Singer sewing machine — has a cool salvage story. Get a from-scratch breakfast of baked French toast and bacon delivered to your door, then explore the adjacent family farm, situated along the North Fork River. You can fish in the farm’s pond, see the fall harvest in action, even ride on a combine. Finish the day with a book and a glass of wine on the guesthouse porch.
▶ Drive time 2 hours 30 minutes
▶ Things to do nearby Bike the Kickapoo State Recreation Area; gaze at the heavens at the Middle Fork River Forest Preserve, Illinois’s first designated International Dark Sky Park.
A State Park Trifecta
Matthiessen, Starved Rock, Buffalo Rock: These three state parks along the Illinois River, all within 20 minutes of one another, offer an incredible variety of day-trip options well into fall. Let the weather be your guide. Crisp and cool? Hike above, or into, the canyons at Starved Rock or Matthiessen, or commune with the three resident bison at Buffalo Rock. Sunny and summer-like? Cruise past Buffalo Rock along the river in a pontoon boat from Heritage Harbor in Ottawa ($300 for two hours; visitheritageharbor.com), or take a guided kayaking tour (pictured below) to see Buffalo Rock from a unique perspective (from $55; kayakmorris.com). You can even coast the historic I&M Canal on a mule-pulled boat (above; $18; iandmcanal.org).
▶ Drive time 1 hour 45 minutes
▶ Where to stay Go rustic at the Kishauwau Cabins (from $120) at Starved Rock, or rent one of the pretty, pet-friendly cottages on the river at Heritage Harbor (from $109).