The Route

This weekend I was lucky enough to head to Wisconsin to visit my grandparents’ lake home in Oconomowoc. It was fantastically beautiful up there, as you can see:

and I’m very excited to use it as one of the rest stops on my epic ride … which begins this coming weekend! My dad and I have been in fully fledged preparation mode this week, making last-minute emails and finalizing the route. 

Here is the plan thus far:

Saturday, July 26th: We’ll depart close to 8am from home and head the few blocks to our Courthouse Square and local Coffee Shop. We hope to see some friends there, so we may start the ride itself as late as 9am. 

Highlights of Day One: The first ten miles are a bit of a local tour, passing Franklin College (the first school on the jersey), using our local Greenway Trail to pass by my old elementary school, then doing a lap around Franklin Community High School (my current school), then heading north to Indianapolis. There we visit the University of Indianapolis (the second school on the jersey), which my older sister is about to attend this fall, then follow the Indianapolis Cultural Trail to the City Center, passing the State Capitol, and then heading up through Butler University (the third college on my jersey). Then we travel through the artsy community of Broad Ripple (most exciting part of the day of course, love the good bohemians) and pick up the Monon Trail through the rest of Indianapolis and Carmel. We then work our way up to the first stop, at Wesley Manor in Frankfort after about 102 miles. My great grandparents lived there until their deaths, and I still have memories of visiting the retirement home to listen to their stories and draw in their especially entertaining coloring books. At the home, I’ll be lucky enough to enjoy a reception hosted by my Great-Grand-Aunt, Nelle, who is 90 and still lives there.

Sunday, July 27th: Departing Wesley Manor/Frankfurt, and hoping to join up with a group of Lafayette area cyclists who have been following my blog, headed to Valparaiso University (Jersey college #4).

Highlights of Day Two: This day is pretty much rural Indiana, with a nice section along the Tippecanoe River in the middle. It’s a longish day, about 115 miles. In training I’ve done three 100+ mile days, but this will be the most miles I’ve done in a two-day period ever. This day will most likely involve a valiant struggle against boredom and some interesting conversations with dad. Maybe I’ll work on my singing. Sometime in the afternoon we will arrive for a visit at Valpo. For this day, sleeping arrangements have yet to be made but we’ll have it figured out soon.

Monday, July 28th: Departing Valpo and heading through Chicago.

Highlights of Day Three: This day we head west to Crown Point in order to pick up the Erie Lackawanna Trail which takes us through the rest of Indiana and into Chicagoland. About the halfway point of the day brings us to the University of Chicago (Jersey College #5), and from there it’s following the LakeShore Trail all the way through Chicago, passing all the great sites of the Skyline, Museums, etc. On the way through and out of Chicago, we pick up a couple of “bonus” colleges rolling through Loyola and Northwestern Universities, then we continue on along the Lake all the way to old Fort Sheridan, then west to Hawthorn Woods where an old friend will put us up for the night. This could well be the most challenging day for me; it’s 110 miles and my third consecutive 100 mile day. The bonuses are that the vast majority of the miles are on trails, and the midday stop at the University of Chicago can be extended if need be. Worst case scenario, we have lots of connections in Chicago from our days living in the Windy City so we can truncate the day if needed. 

Tuesday, July 29th: Departing northern Chicago suburbs to western Milwaukee suburbs. 

Highlights of Day Four: Assuming all is on track, we have an easier day of 82 miles and a possible rest day to look forward to at the aforementioned lakehouse with my grandparents. The path follows well-traveled cycling roads northwest toward McHenry where we pick up the Prairie Trail to the Wisconsin border. We do get to ride through the resort town of Lake Geneva (likely a lunch stop) and end at Oconomowoc. 

Wednesday, July 30th: Planned as a rest day, but available if we need to slow down the first half of the trip. By this time, we’ll have ridden close to 400 miles over 4 days, and ideally a full rest day will be in order. 

Thursday, July 31st: Mapping hasn’t been done yet, but the plan will be to go 100 miles through Madison, WI and a bit beyond. This will likely be a motel stay, and the route will be flexible based on how we’re doing. 

Friday, August 1st: The goal will be Lacrosse, WI. Again, probably a motel night and distance is flexible. 

Saturday, August 2nd: Cross the Mississippi and head to Rochester, MN where I’ll be staying with an old family friend who is President of Crossroads College, another bonus college visit.

Sunday, August 3rd: The goal will be to make it to Minneapolis and Macalester college. We’ll likely be staying with cousins who live in Minneapolis. 

Monday, August 4th: My official college visit at Macalester. We also have one day “in the bank” in that if I were to need to slow the second half of the trip we could delay the arrival to Monday, and do the visit Tuesday. 

Tuesday, August 5th: Return home in Mom’s van – she’ll be driving up to participate in the college visit and to bring us home. 

Wednesday, August 6th: First day of school for my senior year!

As we finalize the maps for the second half of the trip, I’ll detail them here on the blog. 

Sorry for the long post, but here is the route, in all its almost completely planned glory!!


Thanks for reading,




P.S. If you are interested in details, I'll post links to the daily route maps themselves in "The Route" page of this site.  Just head to the menu and look under "More," and dig in if you're interested.  Thanks!