I'm planning a trip from SE Oklahoma to the UP of Michigan maybe this next summer.
Would like to ride the River Road during this trip. But wondering if there was a choice, which way/side would be the best?
I don't know that both sides are an option because of time and such. But would like to know if riding it north to south or south to north would be better and which side of the river would be best. Or maybe even one side is better on one end and the other side is better for the other end.

Any and all suggestions for this and things to do or places to stay would be greatly appreciated.

 

North of Dubuque I would ride the Illinois/Wisconsin side up to Prarie Du Chein, than the Iowa side past LaCrosse. Than move back over to the Wisconsin side at Winona

 

I have spent several days in Dubuque IA. An inexpensive, but quite satisfactory motel is the Econo Lodge 2090 Southpark Ct. Lots of things to do in Dubuque, too. Lots of old historic buildings with fascinating architecture. Go east on HW 20 about 15 miles to Galena IL. A smaller town that has one brazillion little shops and stores. OK...maybe not a brazillion. I'd say only half a bazillion. Anyway, kind of a neat place to visit. Lots of "cute boutique" kinda stores, but they also have some stores for men. I recall a knife store or sumpin' like that. Can't remember for sure. (I have a good memory...it's just short!)

Galena IL

 

If your are going to be on it as far south as St. Louis, stop for lunch or dinner at Fast Eddie's Bonair in Afton, Illinois.

 

By UP what area are you headed to? Copper Harbor? What general route and timeframe are you looking at?

Riding upriver will drift you slowly west....If I had a choice, go up the WI side- its more quaint- great overlooks, small towns w/ bars and pubs for a bloody or food. Put a night in LaCrosse, WI on the list.
at Prescott, WI you could start working northeast towards the UP. (No Name Saloon and Monkey Bar in Prescott is a good bike stop for a drink. )

Galena....is a Civil War town. It used to be a small farmtown....but now the downtown is a bit of a circus (shops, crowds). We avoid it on runs now as a result.

Dubuque has a similar old flavor, cool town.

Poopys in Savanna, IL is a good stop. Its about bikes- food is excellent. Maybe try to organize your trip to correlate w/ one of their events.

PM me if you have more detailed questions.

 

Wasn't really thinking about Copper Harbor. But if it is something I should hit, I could possibly add that in.
Figured I would hit Munising and then east. Cross the Mac bridge and down to Petoskey, Mi. Have a friend that lives there.
Also have a friend in New Holstein, Wi. (just south of Green Bay), so figure that will be on the agenda.
Plan to hit the HD stuff in Milwaukie on this trip as well.

 

there's quite a few MI threads on here w/ good input from locals....IMO if you're going all that way, I'd put Copper Harbor on the list. Really, when will you be back that way again?

Munising and the Hurricane Highway are typical suggestions.

Personally (and this is just my opinion) but if you're in it for the riding I'd skip Milwaukee.
Unless you're ferrying back over and will be 'right there'- then sure, hit it. Far better riding in the other areas you're looking at IMO versus heading into a City then getting caught up in Chicago (or suburbs) to get home.

Riding the peninsula around Traverse City is cool (they're known for cherries).

Door County by Green Bay can be touristy but has an old history, many folks like to visit there.

 

Got to hit the HD Museum. Just a bucket list thing I guess.

I will stay away from Chicago. Meet some guys on the south side of chicago every year anyway.

Again, thanks for your help/suggestions.

 

Mike, If you're going to hit Milwaukee, that's going to be well out of your way from the river. As mentioned offline, The GRR south of Galena isn't great. If you want to include the Harley Davidson Museum in Milwaukee, I would slab it directly there. Time it for a Thursday bike night if you can to get the most out of it. Then run west to Galena IL. As mentioned above, it's a bit touristy, but we actually like it. It's sort of like Eureka Springs. You could base there for a day and explore or head to Dubuque and run the river up as I described offline. If you're visiting a friend in New Holstein you would take the route I suggested - hwy 29, in which case you could make the stop at Doc's easily enough.

From New Holstein you would probably be best off just running 41 north to 35 then 2 to get to the Mac. The Wisconsin side of the lake isn't all that great. I would spend more time on the Michigan side. Petoski and Charlevoix are great.