I boldly crossed the Cheddar Curtain and went to Milwaukee with some friends last summer. We were on trails most of the way... it was really pleasant (except when we got lost and ended up going by a nuclear power plant...) but hot.

I also did John Greenfield's Perimeter Ride this year. After hearing so much about it for so long I just had to join in the fun. I plotted the route here:


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I did the Perimeter Ride too! But I cut out with about 8 miles to go, since the ride went right by my house. I've done two centuries: the North Shore Century this year, and as part of the CA AIDS ride there was a 105-mile day. :)
I hadn't done 100 miles since I was was in my teens. But this year, Chucko and I rode from the beginning of the Lakefront Path to the start of the Boulevard Lakefront Tour, did the metric century, then rode home. It put us at around 100 miles, if not a bit more.
Do the North Shore Century every year since 1999 along with the Ramble ride put on by the Bike Club of Lake County. Evanston Bike Club put out the most food which most of is homemade. Cream City Century also is a nice century and have rode this now for 4 years. The Udder Century is another nice event since you get an all you can eat pasta dinner plus fresh bread, meatballs, sausage, ice tea, and lemonade. The Mchenry County bike club puts this one on. Harmony 100 is also a excellent ride. Wheeling Wheelmen do this ride. Rode this one a few years ago.
The best in my opion are both the NSC, The Ramble ride and the Udder. Find lots of nice people to ride with, hot looking rides, great food. The real ass kicker is the Ramble in terms of hill climbs and technical ability. Ramble has lots of fast decents and always a killer head wind. Also since you are out in the county, loose dogs, farm equipment, rednecks in pick up trucks, turtles on the road along with road kill. This century has average sag support. Need to know how to change a flat.
As for my rides, their are several I did by myself that come to mind. Rode out to Monroe, WI. and back. This was 205 miles total. It was an excellent ride. Lots of eating, beer drinking. Had a headwind coming back which sucks. Took me 15 hours with only 4 stops. Refilled the Camalbak 4 times. I run a duel bladder system so that is 8 bladders at 102 oz. each. Seams like a lot but is is used up in no time. Lots of roller coaster hills. Speeds going down are past 40 mph. Rode up to Port Washington. This was a nice ride since Superweek was going on at the time. Stopped in Whitefish bay and watched several of the races. Rode out to Rockford and back. I got chased by a farm dog, rained on twice, witnessed a car accident, saw a cute red fox chasing a chipmunk, and got stopped by a cop in Barrington for failing to signal. I was turning right and did not bother to signal. He lit me up and told me to pull over. He gave me a warning. This was at 4:30 in the morning! Rode down to Navy Pier. This was a unique ride in the fact I left Chicago having more money than I started with. Someone lost a 2 $50 bills. Found them sitting in the street. Ate for free. Also got to see a bike thief get a asswhipping in Wilmette. Stupid bastard was trying to steal a Rat Fink Chopper bike from the train station. The theif was trying to get it moving but was not quick enough. The gal hit the piece of shit with a 1" thick Kryptonite chain. He hit the ground and she than precede to stomp him along with her boyfriend. Looks like we know who wears the pants in that situation. I rode up on them to see if they needed any help. Turns out they were out for a night ride and she had to stop and wait for her boyfriend who was taking a leak. She walk over to the bushes and waited for him. She did not bother to lock up her ride and caught the prick in action. This serves as a warning: Don't mess with a gal and her bike! HAHAHAHA!!!!!!!!!
perimeter ride twice, frozen snot once(the year it was 20 degrees and had a tailwind both ways!), lakeshore century in NW indiana once, various dayrides on my own, including one 130ish mile day where i ride to portage indiana(from hammond) for court, turned around and made my way up to daley plaza for CCM, ended up north somewheres and rode back home to indiana with a nap break in the bushes by the shedd..
oh also, i attempted the rotary ride in naperville one year, and after about 2 hours i ended up on the assend of a 30mph paceline, did that for about an hour then flatted out, after fixing the tire i found i was unable to really move, so i got a ride back to my car.. but hey, a 3 hour metric aint so bad.

i mean, do metrics count?
nwi hospice hustle one year if they do.
I did Lake Tahoe and the Century day on RAGBRAI. I think this year should be a big one!

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