That's not Road America! 
Wife and I are going to Blue Harbor Resort for our 5th Wedding Anniversary in October. It seems that there is several things to do around Sheboygan itself, but is there anything else nearby that would be interesting or fun?
With the leaves turning, October should be beautiful up there!
I'd check out Elkhart Lake--- quaint little Midwestern resort town. There are a few nice restaurants, and Siebken's pub is a legendary place for racers/ fans who have been to the track.
Kohler--- Upscale resort area with golf courses / nice restaurants
Schwartz's Supper Club--- 8 miles from track in a tiny town called St. Anns (New Holstein mailing address) Great food, super friendly people, fun atmosphere.
Old Road Course-- You can still find most of the remaining circuit they used to race on. Taking a "lap" would be fun, and beautiful.
I'm sure there are also plenty of trails / hiking / fishing nearby.....it is Wisconsin!
if you are driving up.....hit these too
Like Jelly Beans? Pleasant Prairie http://www.jellybelly.com/visit_jelly_belly/wisconsin_warehouse.aspx
Mars Cheese Castle - Kenosha http://marscheese.com/
The Brat Stop - Kenosha http://www.bratstop.com/Default.asp?Redirected=Y
Great Lakes Dragaway - Union Grove - http://www.greatlakesdragaway.com/ (I am sure the wife will enjoy this)
The EAA's Museum in Oshkosh is worth a stop. I think it's of and by the EAA...but anyway, it's the aircraft museum there.
Duke of Devon pub on the riverfront
Al & Al's - Octoberfest
Kohler Arts Center
Charter Fishing on Lake Michigan
Sheboygan Falls
Random Lake Brat Fry
Harley has a museum in Milwaukee.
The Milwaukee Zoo is outstanding even if I haven't been there since my 8th grade trip back in 1976.
I also toured the Miller Beer plant on this same field trip and watched a few nuns kick back some cold Miller samples after the tour was over. Who planned this for a bunch of 1970's drug-era 8th graders?
Door County. Beautiful in October. A nice day-trip.
Golf. Sheboygan has several world-class golf courses nearby. Black Wolf Run, The Bog, Whistling Straits to name a few.
Take a night at Siebkins in Elkhart Lake for a round of drinks. A legendary race bar.
...also, if you happen to be there on the 14th, there is a PDX at RA. http://www.scca-milwaukee.org/pdx/pdx.html
Its for charity (March of Dimes), so I believe that your entry fee is tax-deductible too.
I don't think that the Gobbler is near Sheboygan, but you might pass by it.
In reply to pilotbraden:
Haha that site is awesome. Unfortunately it says its been torn down. 
Looks like according to google maps, the supper club is still there, but the has been torn down
Whitefish Sand Dunes is a nice day trip. Lots of walking trails and a nice beach to look at in October 
.
http://dnr.wi.gov/org/land/parks/specific/whitefish/
High Cliff State Park is on the shores of Lake Winnebago and it has some neat trails and views. http://dnr.wi.gov/org/land/parks/specific/highcliff/
Maritime Museum in Manitowoc has a WWII sub you can tour. http://www.wisconsinmaritime.org/index.php
Kettle Moraine has all sorts of geological features from Wisconsin's glacial past. http://dnr.wi.gov/org/land/parks/specific/kmn/
What type of activities are you looking for?
In reply to RossD:
I'm just looking for stuff that my wife will enjoy along with myself. I haven't gone anywhere but Road America and the EAA Air Show in that area.
There is a giant indoor train museum in Green Bay that I have wanted to see for a long time, but my wife shows no interest.
We really want a weekend to relax, but I feel that we will want to go somewhere and do something.
