Tom and Marna's Bike Blog (Posts about Leg 1)

Leg 2, Ride 1: Chicago (northside) to Chicago (southside)

Tom Walsh — Tue, 12 May 2026 22:27:05 GMT

A quick easy day today, just 17 miles across the city from the north side to the south side. This is the second of hopefully three very short rides (next one is Detroit to Windsor). This generally has the do with the spacing of acceptable places to stay -- in this case, we preferred to do a short day then a medium day, rather than a long day.

Thunderstorms are moving through the area from the northwest today. So, we were watching the radar map, and we tried to time our ride so that we arrived at our hotel after checkin time, but before the storms caught up to us. We just barely succeeded -- rain started a few minutes after we checked in.

Leg 1 Epilogue: Chicago

Tom Walsh — Tue, 12 May 2026 02:34:09 GMT

We took a couple of days off here in Chicago to visit family and explore the city. We're staying with Peter (Marna's brother), Jill, and Malcolm.

On Saturday, Peter and Malcolm met us partway along our route, and we rode together for the last bit. We mostly spent the evening catching up with P&J, and being taught (by Malcolm) how to play various board games.

Leg 1, Ride 7: Lake Bluff to Chicago

Tom Walsh — Sun, 10 May 2026 02:29:40 GMT

We made it to Chicago, and to the end of the first leg! We are still in good spirits and we're feeling pretty good. I think we made the right call by keeping the mileages low early in the trip, to try to work ourselves into shape gradually.

Today's ride was smooth and uneventful. Beautiful weather all day, and for a change, we were not fighting a headwind today.

Leg 1, Ride 6: Kenosha to Lake Bluff

Tom Walsh — Sat, 09 May 2026 01:16:37 GMT

State #2! A short ride today: just 26 miles to Lake Bluff, Illinois.

There's not much at all in Lake Bluff, at least not near our motel, so we spent the entire morning lingering in Kenosha.

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Leg 1, Ride 5: Milwaukee to Kenosha

Tom Walsh — Thu, 07 May 2026 23:35:51 GMT

Well, today was our first tough weather day of the trip. We awoke to a frost advisory and a temperature of 38F. We started from Downtown Milwaukee with a whipping headwind coming from the south. Then the rain started. Near the end of the day, as we approached Kenosha, the same story: cold, brisk headwind with rain.

But, the cold was no match for my secret weapon: dish gloves. The gloves, sadly, prevented me from taking pictures for the foul weather parts.

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Leg 1 Interlude: Milwaukee

Tom Walsh — Thu, 07 May 2026 03:31:57 GMT

We took a day off from riding today. A chance to rest our legs, and also to spend some time in Milwaukee. Tomorrow, we're off to Kenosha.

Milwaukee is a super cool, quirky, hugely-underrated city. Easily one of the top 20 places in the USA, probably top 10. If you've never been here, you should come.

Leg 1, Ride 4: Waukesha to Milwaukee

Tom Walsh — Tue, 05 May 2026 19:12:09 GMT

Huge breakfast today, and a short ride. But, it doesn't matter -- I'm hungry the second I step off the bike.

Some minor issues on the ride today. The New Berlin Trail was "closed" until November. As is custom for bike trail construction, "closed" means "there's zero active work being done, and you can totally get through, but we put up closed signs anyhow which everybody will ignore".

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Leg 1, Ride 3: Jefferson to Waukesha

Tom Walsh — Tue, 05 May 2026 01:27:23 GMT

We started today with some minor hills, then we had an unpaved rural trail, which changed to a paved suburban trail, and we finished on city streets. Basically, the same thing as yesterday, but in reverse order.

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Leg 1, Ride 2: Madison to Jefferson

Tom Walsh — Sun, 03 May 2026 23:33:56 GMT

Today was our first "real" ride, long enough that we broke a sweat and stopped to rest a few times. 36 miles in 3 hours and 22 minutes. Which is certainly not fast, but not awful considering that we were on a dirt path most of the day.

We rode this same path in 2011 when we did a Minneapolis-to-Milwaukee ride. On that trip, we learned that biting horseflies can fly about 13 miles per hour. This year, no horseflies.

Although it started off a bit chilly, this ended up being a beautiful day for riding. We just barely avoided some rain that passed a couple miles south of us, and then it was sunny and mild the rest of the day.

Leg 1, Ride 1: Madison to Madison

Tom Walsh — Sun, 03 May 2026 00:38:18 GMT

Hey, it's our first riding day of the trip! A real arduous slog today: almost 14 whole miles!

We kept today's ride really short because it's our first road bike ride of the entire year, and because we wanted to have plenty of time to deal with any problems we might discover once we actually started pedalling.