Best places near Chicago to see the leaves change in the fall

It’s that time of year when the green leaves of summer take on the fall glories of reds, yellows and vivid oranges. Within driving range from Chicago are some of the best places to see the leaves change, grab a pumpkin, and pick some apples. Consider this your tip sheet for the Midwest’s best spots for leaf views.

WISCONSIN
Kettle Moraine, Northern and Southern Units
Distance from Chicago: 133 miles to Kewaskum; 150 miles to Elkhart Lake.
Peak Season: Mid October.

This 25-mile drive through Wisconsin’s tree-dense Kettle Moraine State Park begins in Kewaskum and meanders north to Greenbush. The scenic trail is easily marked with green and white “Acorn” signs and must stops include the Mauthe Lake Recreation Area with its Tamarack trees; Parnell Observation Tower on State Highway U, one quarter miles west of Highway A, with views from the forest’s highest elevation point; and the historic Wade House in Greenbush built in 1860 as a stagecoach inn. From Greenbush head about 10 miles north to Elkhart Lake where the leaves get even more spectacular over the lake. Rent a canoe or kayak from The Osthoff Resort, or enjoy the view from one of the resort’s lake-facing rooms with private balconies.

The Bayfield Peninsula/Apostle Islands
Distance from Chicago: 440 miles to Ashland.
Peak Season: Mid October.

This fall tour in northern Wisconsin begins in Ashland and follows State Highway 13 along Lake Superior to Bayfield. From Bayfield you can take a car ferry to Madeline Island, one of 22 Apostle Islands that are national parks. (You can also kayak along the islands and their coastlines of sea caves.) Must-sees on Madeline Island include the La Pointe Indian Cemetery, Big Bay State Park, and Lotta’s Lakeside Café for dinner or Sunday brunch. From Bayfield, the fall tour continues west on 13 to the Brule River State Forest. Head back to Ashland and spend the night in your own historic cabin at the tree-filled, 20-acre Inn at Timber Cove bed and breakfast with on-site hiking and apple picking.

IOWA
Southeast Portion of the Great River Road, Burlington to Keokuk
Distance from Chicago: 245 miles to Burlington; 281 miles to Keokuk.
Peak Season: Beginning to mid October.

This historic and scenic drive that follows the Mississippi River roughly 40 miles from Burlington to Keokuk delivers a stunning landscape of limestone bluffs, quaint river towns, and oak, walnut, and maple trees. Points of interest along the route include “Snake Alley” in Burlington dubbed, “Crookedest Street in the World” by Ripley’s Believe it or Not; the Old Fort Madison on the banks of the Mississippi in Fort Madison; the Observation Deck in Keokuk – an historic swing bridge built in the late 1800s that is now a lighted observation deck with views of the Mississippi River; and the Keokuk National Cemetery, Iowa’s only national cemetery with graves for Union and Confederate Civil War soldiers.

Ohio River Scenic Route in Southern Indiana
Distance from Chicago: 315 miles to Corydon.
Peak Season: Middle Two Weeks of October.

This scenic route along the Ohio River in southern Indiana showcases brilliant colors of reds, yellows, and oranges from the sycamores, maples, tulip poplars, and red and white oaks that lined the roads between Corydon and Tell City. West of Beechwood, the drive will take you through the Hoosier National Forest most of the way to Derby. The 200,000-acre forest is almost a destination within itself with more than 200 miles of hiking, horseback, and mountain bike trails, five lakes, and one of the best photo spot on the drive: Buzzard Roost recreation area on the bluffs of the Ohio River along State Route 37 south of Interstate Highway 64. Another leaf hotspot is The Overlook Restaurant along the Ohio River in Leavenworth. The Blue Heron Vineyard & Winery in Cannelton is a nice detour (and also has a bed and breakfast on its grounds), as are O’Bannon Woods State Park in Crawford County and the Squire Boone Caverns south of Corydon discovered by Daniel Boone’s brother in 1790.

Tip: If you want to make a leaf stop in Indianapolis (183 miles from Chicago), check out Fort Harrison State Park, Eagle Creek Park, or Crown Hill Cemetery, which has tree tours that cover the 50 trees of Indiana.

For more fall drives near Chicago, check out these two stories I wrote for the Chicago Tribune for the Midwest’s best places for the fall colors:

2009 Best Fall Drives

2007 Best Fall Drives