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My favorite Wisconsin memory was going out on the lakes in the northwoods for the first time. The drives past the dairy farms near the Rice Lake area was a treat (reminded me of rural Vermont with the big red barns and large silos). Door County was a memorable trip with a detour over to Egg Harbor. The scenery was awesome, the people friendly, and the experience was very nice.
I grew up in a rather large family in Madison (I don't live in Wisconsin anymore) ...but like others - vacations up north - at a lake, any lake. We'd stay in cabins....and if a kid got noisy - they'd be banished (with dad, of course) to sleeping in the car.... hah!~
There'd always be a dog at the lake (we couldn't have dogs because of allergies) and we'd spend time fishing and boating.
Heck - I remember trips across town (from the far west side of Madison to the east) to Grandma's house. Seemed like a million miles away back then - while it was probably less than 15 miles.
We had a great childhood. Madison was a wonderful place to grow up.