Help Me Plan a Wisconsin-area Road Trip for a 10 Year Old

[vwwestyman]

I've mentioned the family here and there in the forums in the past. Two years ago, the dad was killed in a helicopter crash, leaving behind the wife and 4 kids.

Prior to his death, they had started what was to be a tradition of Dad taking each kid on a special trip for their 10th birthday. Now, kid #3 is turning 10 in mid-late August and I'm going to take him on his trip!

They live out in the boonies in far northwest Wisconsin.

This kid definitely fits the archetype of the forgotten middle child and deserves to have a great trip.

Here are the types of things I'm considering in weighing all this out:

Since they live in the boonies on 8 acres, he's definitely and outdoorsy kid. And pretty adventurous. Though he's backed down on it now, at one point he was talking about wanting to go skydiving. (He is, understandably, very nervous to fly.) He wants to go on a road trip in my Westy.

He also really likes parkour and skateboarding and has recently asked about finding "a skatepark with a drop in bowl or an indoor gym made for parkour."

His mom thought about maybe a day or two at Wisconsin Dells and an indoor skydiving place along with a cool skate park in one of the bigger cities.

We're also talking about trying to line things up with one of the pro sports teams in the region, such as a Twins, Brewers, White Sox or Cubs baseball game, or maybe a Vikings, Packers, or Bears preseason football game. I decided we needed to know if he had any interest in one of these and then plan the rest of the trip (timing and direction) around that, but I guess that gives an idea of the directions we might consider heading.

I think some combo of a little time in a cool nature area and in a big city would work well for him.

Time frame would be something like a "long weekend" trip for him. (Doesn't necessarily have to be over an actual weekend, I can get off work whenever like now that I'm my boss.) I think I'd drive up from Manhattan, we'd leave the next morning, and then do either three days and two nights or (I think my preference would be) four days and three nights. Then I'd probably stay there a night before heading back.

Anyway, I know there is a lot up in the air, but I was thinking if any of you knew of any gems or cool spots that lines up with some of these things, that may give me some more direction. I know nothing about parkour and skate parks, but am more than willing to go there and maybe even give it a bit of a try. I think if he is interested in a pro sports thing that would help with the "direction" portion of it.

I don't think I can quite say "money is no object" but Dad will be paying for the trip with his life insurance, so as long as things are somewhat reasonable there is a lot of flexibility.
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Dave Cook

President, Wild Westerner Club

1978 Champagne Edition Westy, repowered to '97 Jetta TDI
1973 Wild Westerner
My Thing

[Shanghai Paddles]

Driving along the North Shore of Lake Superior on MN 61 is an awesome time! Lots of great hiking and camping spots along the way, and Duluth is a bigger city, although no sports teams. If you end up heading more south, or for you on your way up to pick him up, driving along the Mississippi River on WI 35 is one of the best roads in the Midwest. Say from around Fountain City up to Prescott. It’s almost like driving along the PCH in Cali. Lots of fun twisty roads shoot off of it too, although you probably aren’t trying to carve corners in a westy haha. I’m just outside of Minneapolis if you want some ideas to do around here. Should be an epic trip for him! (And you!)
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1967 Beetle, 1915cc. ~Daily driver~
2004 Passat, 1.8t APR stage 2. ~Race car~
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2002 Audi S6 Avant, Manual Swap ~When you need groceries fast, but want to have fun~
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[kingkarmann]

The Door County Peninsula is very nice too.
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"Depression is a malfunction of the instrument we use to determine reality.”

Mike Gerson

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[Xevin]

Only you will know how to guide this trip. When the road trip gets going. Have a plan for wifi so little man can do what he’s comfortable doing at home. Remember, to him you are old and not dad. Plot a course for a sports game destination or what you and he have talked about. None of us have a feel for what he wants. Talk to him. However, along said road trip. You might find some magic deviating off course. Like an impromptu rafting trip. Or some other fun thing he didn’t expect. Only you will know when you hit the road.
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Keep on Busin'

[marklaken]

Madison is pretty fun city to explore and they have a public skate park with two drop in bowls: https://madison.com/ct/entertainment/city_life/pho...6c4.html#2

Devil's Lake north of Madison is a good camp spot on way to Madison.

Chicago would be a really cool destination, but maybe too far a drive for a long weekend in a bus.
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Mark Laken
Fort Collins, CO

[ach60]

[Abscate]

I think Dave has the Bentley manual for child interactions, it’s more the trip itinerary and locale where guidance is needed

Sent with love


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.ssS!