What's the most scenic route from Chicago to Door County?Taking a motorcycle trip from Chicago to Door County . . . what is the most scenic route? - Melissa, Chicago, and others
You'll want to follow the Lake Michigan Circle Tour signs — basically, keep the lake on your right as much as possible. I did part of it in July, between Kenosha and Milwaukee, and it'll take you past some gorgeous beaches and lighthouses.
At the border, Illinois 137 turns into Wisconsin 32. Take that all the way to Milwaukee, with a detour in Racine to see Wind Point Lighthouse, a classic Poe tower just north of downtown (from North Main Street, take Lighthouse Drive to Wind Point, then return to 32 on Four Mile Road).
You can hug the lake all the way through Milwaukee, a very scenic stretch. In Fox Point, you'll have to get onto I-43. At Grafton, Wisconsin 32 separates from I-43 to go through Port Washington (you could also peel left on County Road T to visit Cedarburg).
Then you have to get back on I-43 to Sheboygan. Take Wisconsin 28 into town.
The official route returns you to I-43, but you could also take County Road LS to Manitowoc, then 42 to Two Rivers. From there, take County Road O to Point Beach State Forest and its lighthouse (for more, see Two trails from Two Rivers).
Keep going until you hit Wisconsin 42 and take it to Algoma.
From there, you can continue to Sturgeon Bay on 42 or hug the lake on county roads S and U. From Sturgeon Bay (see Door to the Door), County Road B hugs the Green Bay side of the peninsula and county roads TT and T the Lake Michigan side, to Whitefish Dunes State Park and Cave Point County Park (see Outdoors in Door County).
I like to plan routes with a Wisconsin DeLorme Atlas & Gazetteer, which will show you all the scenic little roads and also state parks and attractions. You can buy one at Target, bookstores or sporting goods stores.