Jim Winkle - routes

Jim Winkle's Bike Routes from Madison, Wisconsin

Most of these popular routes start from the east Arboretum entrance. A few have a sustainability theme... organic/local food restaurants, solar/wind energy, a farm that grows food for people (these are surprisingly rare), a farm incubator, and certainly biking itself is an earth-friendly way to travel.

These use Ride With GPS; download the free client if you have a smart phone. Upgrade to their Basic level and it will speak the route to you (and more).

I've gotten a lot of positive feedback about these routes, and even thank-you gifts (which was totally unexpected, but I'm grateful)! Let me know what you think of these rides.

"More dramatic elsewhere, perhaps more strange, more thrilling, more grand, too, but nothing that picks you up in its arms and so gently, almost lovingly, cradles you as do these southwestern Wisconsin hills." -- Frank Lloyd Wright

Below you'll find:

LaCrosse to/from Madison, Wisconsin

Other Rides

A rare round barn, outside of Viroqua, WI

Day Trips

Many of these are lovely rides, especially the longer ones. There are generally restrooms and water at the halfway point. Some of these rides require a state trail pass to make it easier to get out of Madison.

Biking the Boardwalk Bridge, 28 miles (728 ft up). Possible lunch/coffee at The McFarland House Cafe on Exchange St. Route now clockwise for less time on busy Hwy B!
Paoli Pump, 29.4 miles (848 ft up), small hills. Possible lunch/coffee at Sow's Ear. The Paoli pump water tastes terrible, so fill up in Verona. Route.
The Oregon Outing, The Oregon Outing, 35.5 miles (916 ft up), few hills. Possible lunch/coffee at Firefly. Kickback Cafe, or elsewhere. Route.
Frenchtown Fling, Frenchtown Fling, 40 miles (1265 ft up), some moderate hills and then there's Observatory Hill. Great historic cemetery on Frenchtown! Possible lunch/coffee Sow's Ear. Route.
Mountainous Mt. Vernon, 50.6 miles (2074 ft up), quite possibly the hilliest half-century near Madison. For an extra hill, go up Observatory Hill Rd from Paoli Rd. Be careful coming back down to Paoli Rd... it's hard to see cars at the intersection and they can't see you, either. Possible lunch/coffee at Sow's Ear. Route.
Roll to the Trolls (Mt. Horeb), 52.7 miles (2099 ft up), hilly. Be careful going down the hill on Malone Rd; there's a curve in the road when you're going fast! Lunch at Donald Park, The Grumpy Troll, or elsewhere. Very fun gentle 2-4 mile downhill out of Mt. Horeb. Route.
Brooklyn Bop, 55.1 miles (1593 ft up), few hills. Possible lunch/coffee in Oregon at the Firefly. Route.
Swiss Biking Bliss (New Glarus), 56.9 miles (2080 ft up), some big hills around New Glarus. Possible lunch/coffee at Kristi's, Fat Cat Coffee Works (RR St), or elsewhere. Route.
Evansville Expedition, 59.5 miles (1874 ft up), some hills. Possible lunch at DeBroux House Cafe or elsewhere. Route.
Devil's Lake State Park, 63.3 miles (3618 ft up), long-ish hills; great ride! We'll drive to start at Pheasant Branch. Bring your suit/towel! Route.
Rock River Ramble, 69.8 miles (2157 ft up), some hills. Lunch on banks of the river or in Stoughton, maybe at the El Rio Grande. Route.

I lucked onto this road at just the right day of the year (Oct 20).

Great Blue Heron

Century Bike Rides

One hundred miles in one day... it's really not that hard; you just have to work up to it. A good bike helps, too... the longest I had ever ridden was 30 miles, but immediately went 70 on my new bike, and the next weekend did my first century ride. Here are a few century rides, give or take.

Folklore Village, 99.4 miles (4864 ft up), some nice roller-coaster hills. See their website to see if there's anything going on and make it an overnight. Check with them if you want to camp. Route.
Jim's (Half-Century) Century Ride, 105 miles (4841 ft up). A spectacular ride that I did for my half-century birthday, this century covers some of my favorite roads and has everything. There are nice roller-coaster hills, cool valleys, ridges with great vistas, some beautiful old stone houses, country churches and schoolhouses, historic cemeteries, meandering creeks, assorted farm critters, rock outcroppings, and even a UFO! It's really quite nice. Route.
Mineral Point Century, 107.9 miles (5322 ft up). Hilly, but beautiful ride! Route.

If you do the full century, you might need to stop here and say a prayer :)

Weekend Bike Tours

Weekend rides (2-4 days).

Blue Mounds, 66.2 miles (two days, 2902 ft up) with overnight at Blue Mounds State Park. Hardly any gear is needed (mostly a sleeping bag and tent). Be careful going down the hill on Malone Rd; there's a curve in the road when you're going fast! Very fun gentle 2-4 mile downhill out of Mt. Horeb. Route.
The Brew Tour, 88.7 miles (three days, 27-32 each day, 3351 ft up) with overnights at New Glarus and Blue Mounds. Yes, there are a couple of big hills, so you deserve a brew at New Glarus Brewing and The Grumpy Troll! Route.
Pedal and Prance, 124.2 miles (three days, 30-50 miles per day, 6354 ft up) with overnights at Yellowstone Lake and Folklore Village. Check with them about camping, and save energy for the dance Saturday night! Route.

1-2 Week Bike Tours

The new Google maps broke many of these routes, but the cue sheets are still good. I now use ridewithgps.com, which allows infinite customizations to a route (Google allows ten). I'll try to redo the older routes as time permits.

These are mostly in the Driftless region of Wisconsin, which has quiet roads (a few cars per hour) and decent scenery. Do you know of other places in the US like this? Please contact me with your favorite places to tour!

MN Loop, 414 miles (10,500 ft up), mostly a loop. This route pieces together several bike paths in southern MN, most of which we've been on in the past. However, we haven't ridden this route yet and are looking for input. Route.
Lake Superior North Shore Tour (aka Jim and Bonnie's 2021 Tour), 299.8 miles (11521 ft up), some hills, out-and-back. Pix! This route avoids gravel roads. Roughly half of the whole route is on the Gitchi-Gami trail or decently quiet roads (in particular, from Duluth to Two Harbors and from Judge Magney SP onward). See route for more notes. Route.
Ozarks in October Tour (aka Jim and Bonnie's 2020 Tour, aka The Pandemic Pedal), 275 miles (13.5k ft up). Pix! See route for more notes. Route.
Iowa/Minnesota Mississippi River Tour (aka Jim and Bonnie's June 2018 Tour), 360.4 miles (13108 ft up), 10? days. Our approximate route. The Minnesota part was not pleasant -- many cars going fast. However, Winona is a sweet town! Route.
Driftless Tour to LaCrosse (aka Jim & Bonnie's 2017 Tour), 333.6 miles (16,501 ft up). Route.
Driftless Tour to Viroqua (aka Jim & Bonnie's 2015 Tour), 305.1 miles (14,838 ft up), 8 days. Day 1, 44.3 miles: Folklore Village (food in Verona @9.4). Day 2, 18.4 miles: Yellowstone. Day 3, 29.2 miles: Governor Dodge State Park (food in Mineral Point @16.8, Dodgeville @24). Day 4, 45.6 miles: Richland Center (food in Spring Green @13.4, Plain @23, @end). Day 5, 40.2 miles: Viroqua (food @end). Day 6, 17.3 miles: La Farge. Day 7, 41.1 miles: White Mound County Park. Day 8, 55.5 miles: Madison (food in Plain @8.1, Prairie du Sac @26.7, Roxbury @30, @end). Route.
Jim and Bonnie's 2014 Tour, 275 miles, shortish days (the longest day is 41.2 miles, unless we combine the last two days, then 55.3). Note that there are several overnights at Warm Showers sites. Food on day 1@19 (Spring Green), day2@18 (Muscoda), day3@end (Viroqua), day4@20 (Chaseburg: the Hideaway, open Thurs-Sun), day4@end (La Crosse: don't miss local food restaurants the Root Note and the Mint!), day5@12.5 (St Josephs), day5@end (Coon Valley), day6@11 (Westby), day6@end (La Farge), day8@8.4 (Plain), day8@end (Sauk City), day9@3.5 (Roxbury). Slightly old cue sheet.
Jim and Bonnie's 2013 Tour, 260 miles, shortish days (the longest day is 43 miles). Hightlights are Galena, Dubuque (esp the river museum), Pike's Peak and nearby Effigy Mounds National Monument, and Wyalusing SP. Possible food on day 2@17 (Gratiot), 24 (Warren); day 3 near end (Galena); day 4@end (Dubuque); day 5@20 (Balltown), near end (Guttenberg, not much); day 6@end (McGregor); day 7@5 (Prairie du Chien), day 8@33 (Fenimore), day 9@27 (Dodgeville). Cue sheet.
Jim and Bonnie's 2011 Tour, 450 miles. A really beautiful ride. Lots of medium-size hills, and also some big ones that we walked. Lots of Amish farms in Part I. Changes I would make for next time: Look for better roads in Minnesota (busy roads, NO shoulder at times). Try to stay in Lancaster instead of Klondyke Secluded Acres (which I can't recommend). Cue sheet for all parts.
- Part I, days 1-5 (177 miles): Devil's Lake, Wildcat Mountain, La Crosse. Non-mobile route.
- Part II, days 6-8 (151 miles): La Crosse, Decorah, Pike's Peak/McGregor, Lancaster. Non-mobile route.
- Part III, days 9-10 (100 miles): Lancaster, Folklore Village, home
Jim and Bonnie's 2009 Tour. We didn't ride all of this, so some is untested.
- Part I: The Crawford County Climb, 86 miles, days 1 - 3. A gorgeous ride, especially day 1. Morovits Hollow Rd is gravel (so is Walker)... they're working on getting it paved, and it has a dreadful uphill at the end. Hwy 35 along the Mississippi and Ferryville were a bit of a disappointment... few businesses open (perhaps because of the recession). Next time we'd go a different way, perhaps Hwy 27 (which is a ridge road). Make sure you get the wonderful biking map of Crawford County.
- Part II: Vernon Vistas and Valleys, 105 miles, days 4 & 5. We never made it to Wildcat Mountain, stopping instead in Viroqua. We took Cty Hwy J back to Soldier's Grove, and River Road into Gays Mills (contrary to the map, it goes all the way).

I love how this road looks almost like a bike path

LaCrosse to/from Madison, Wisconsin

There are many ways to get between LaCrosse and Madison, Wisconsin. Historically, most people on tour took the packed gravel trails since they're impressed they can make it the whole way without going on roads. That's cool, but I find the flat terrain becomes boring and the constant grind on gravel gets old. Plus Wisconsin has *great* back roads, so the off-road trails are not needed by anyone with experience biking.

If you haven't biked in SW Wisconsin before, you're in for a treat! Most back roads are paved and lightly travelled (especially the non-numbered roads). They're hilly, because this is the unglaciated "Driftless" area of Wisconsin which adds to their beauty. I love zipping down a hill and am willing to pay the price of going up a hill.

I have two routes: one from LaCrosse to Madison, and the other from Madison to LaCrosse. They are slightly different to take advantage of conditions that are better in one direction.

While I've probably biked on all of these roads, I haven't done it in one fell swoop nor recently. But the routes should be fine... there are very few bad roads in SW Wisconsin. Note that there is camping in Viroqua and LaCrosse, but the icons may be hidden by the grocery store icons.

Please let me know if you take one of these routes!

Madison to LaCrosse, Wisconsin, 162 miles, 7800 ft up. Route.
LaCrosse to Madison, Wisconsin, 161 miles, 8150 ft up. Route.

Other Rides

You'll generally need to drive to the start of these rides.

Wednesday "night" bike rides, quite hilly and fun rides through scenic rural Dane County. "Night" is in quotes because starting in 2026 people depart at any time (often 10 am).
Bombay Bicycle Club, many, many rides, starting in and out of town.

Thanks for reading; please let me know if it was helpful or if you have corrections.

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