John Greenfield's Perimeter Ride. Nearly 100 mile miles, almost entirely within Chicago's city limits on a sunny summer Saturday. The pace is slow with plenty of stops. It takes you to parts in the city that you likely never visit on your own
A solor, do-it-yourself century is a good idea if you have all the skills and experience for repairs and feeding schedules. I cycled solo to St. Paul from Lake Geneva this last summer without incident, but was prepared for all breakdowns short of a cracked frame or bent rim, as much of it was out of my cell phone range.
Whether you join a group or go it alone, a training schedule is important as it will get you into shape and demonstrate if your bicycle (and saddle) is comfortable enough for 100 miles in a day. In a period of ten weeks ride everyday alternating easy days with more strenuous ones, increasing mileage each week until you reach 75 miles. Then you are ready. Most people who are in good cycling shape can do a century by just determining the number and duration of their rest stops, as well as avoiding over eating.
I like the Apple Cider Century because it is fun, festive, community based and well organized. The terrain is flat for the most part and they take care of your needs and disasters very well. Also they have a good layout of roads that allow for loops of various lengths, meaning you can bail out at 25, 50, or 75 miles if you are completely saddle sore and have to work the next day. It is however at the mercy of the weather, so it takes place, rain or shine, wind or calm, on the scheduled day. I did not have any trouble with cyclists unfamiliar with road etiquette. Yes, there are wandering kids from family units as well as Lance wannabes. Cycling etiquette is far, far worse on the Lakefront Bike Path. The traffic was not bothersome - any Chicago street is more challenging. The last advantage was my wife wanted to go only 25 miles, so the Apple Cider Century was a perfect site for both of us. She actually finished in time for the pancake breakfast. Tip: start early if you want an easier ride - but not before sunrise, as the town streets are not as good as the country roads.
The Apple Cider 2008 was my first century. I had a simple training routine set up for me by a very experienced ultra marathon runner and cyclist. He was not dismissive about the participants in large group affairs having survived the most recent Paris-Brest-Paris cycling event. Advice from others who race is colored by an annoyance by not having predictable, similarly skilled, participants around them. Good alert riding takes care of almost all of that. And in on organized centuries you are with hundreds of people happy to be doing what you are doing.
P.S. You can also do a century (or perhaps just a metric century-60miles) by just going up and down the Lakeshore Bike Path, which although familiar is just as scenic as any place else.
Within the city, I like a loop from Hyde Park up through the North Branch Trail and back again. A bit short of a century but it's easy enough to add on a few miles here and there if you like, and you hit the Botanic Gardens at the midpoint, which is nice.
Also, I wouldn't worry about training too much unless you have a goal in mind, like finishing a century in under six hours. The rule of thumb is just to ride a lot and increase the distance of your longest ride 10% each week, but you could leave your house and ride 100 miles right now and feel okay at the end if you kept drinking a lot of water and eating Cliff Bars, given a properly fitted bike.
Their are a couple that I have done that come to mind. Udder century is nice. It starts down in Union in Mchenry county. Good support, well marked routes, and a pasta dinner after the ride. Ramble ride put on BCLC out in Wilmot in Kenosha county. Good food, decent routes. Lots of hill work on some of the longer loops. Cream city century out in Waterford, WI is a great ride. It goes through southern Kettle Morraine by Whitewater, WI. Pasta dinner after ride, lots of hill work, homemade food, above average sag support. North Shore Century-one of the best rides of the year. I have done this one for the last 11 years. Great food this last year-Cliff bars,gels,shot bloks, pizza, and ice cream. Most riders are decent handlers on this ride. I rode with a fast group for most of the day. 8 of us made up the group-5 women and 3 guys. We kept the average around 24 mph going into a headwind! Food you can not beat and lots of nice towns and cities along the way.
My own rides I have done in the past have included riding from Kenosha out to Monroe. This goes through Lake Geneva, Delvan, Janesvile, along with all of the little towns in and around Monroe. Lots of bakeries, good restaurants, pubs, along with lots of sites to see. Note-Lots of hills on the way in to Monroe. The last thrity miles are past 13 percent grade and you must come well equipped with gear. Not many bike shops on the route if you have a break down. Kenosha to Madison. A decent ride. Lots of nice roads with not much traffic. Ride out through Whitewater and Kettle Morraine. Rest stop at Lagrange at the bike shop along with beer and great food. Lots of places to stop to eat, drink, several bike shops on route. Kenosha to Port Washington-A ride through Wisconsin's version of the North Shore. This takes you through a lot of nice areas along with plenty of places to eat and drink at. Port Washington has excellent places to eat at. Lots of outdoor areas, and plenty of bike shops to see and sites to see. I do alot of distance rides so I have lots of routes and places I have been to. Try a double century if a century starts to be too easy. Keep on riding
Interesting about the Apple Cider Century - hadn't heard of that before and may have to change my plans!
My original goal was to ride the Illinois and Michigan Canal Trail from Joliet to Lock 14 and back, solo. That's about 100 miles, albeit on limestone, not pavement. It's an incredibly scenic trail, in fairly good condition and not crowded at all. Occasional small towns along the way for water refills and Diet Cokes, but you have to be prepared for long stretches in the super-boonies.
I worked my way up to about 50 miles this summer on that path, and am keeping up the regimen on the Minoura trainer and at the gym this winter. Hope to celebrate my birthday in June with a new road bike and the Big C. Pavement and some company sounds good!
+1 on the Udder Century. I did my first 100 mile day on a supported ride. Rest stops, marked routes, sag wagons, and other riders helps. But I did it alone rather than with freinds, so I could do it at my own pace.
I rode from Hammond to my family's lake house in Monticello. 108(?) miles
My only recommendation is DO NOT TRUST GOOGLE MAPS. Gravel galore. Ugh. Haha, it was all good though. I will say that getting your brains beat out on 3 miles of gravel after already riding 70+ miles is not fun. =) Look out for loose dogs on the country roads!