Jim Winkle's Bike Routes from Madison, Wisconsin

Most of the bike routes below start from the east Arboretum entrance. A few of these 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.

I organize small group rides using these routes; contact me early in the season if you know me and you're interested in biking on weekends. The rides get progressively longer throughout the season and culminate in a century ride.

Please read my short overview if you haven't already seen it. Below you'll find:

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.

  • Paoli Pump, 28.2 miles (786 ft up), small hills. Possible lunch/coffee at Tuvalu or Sow's Ear. The Paoli pump water tastes terrible, so fill up in Verona. Route and cue sheet.

  • Biking the Boardwalk Bridge, 28.4 miles (732 ft up). Possible coffee/lunch at The McFarland House Cafe (@8.5 turn left onto Exchange St). Route and cue sheet.

  • The Oregon Outing, 35 miles (1085 ft up), few hills. Possible lunch/coffee at Firefly. Route and cue sheet.

  • Frenchtown Fling, 39.6 miles (1250 ft up), some moderate hills and then there's Observatory Hill. Great historic cemetery on Frenchtown! Possible lunch/coffee at Tuvalu or Sow's Ear. Route and cue sheet.

  • Mountainous Mt. Vernon, 50.6 miles (2073 ft up), quite possibly the hilliest half-century near Madison. Possible lunch/coffee at Tuvalu or Sow's Ear. Route and cue sheet.

  • Roll to the Trolls (Mt. Horeb), 53 miles (2103 ft up), hilly. Lunch at Donald Park (@22.9), The Grumpy Troll, or elsewhere.52.4 miles (2085 ft up), hilly. Lunch at Donald Park (@22.9), The Grumpy Troll, or elsewhere. Very fun gentle 3.5 mile downhill out of Mt. Horeb. Route and cue sheet.

  • Brooklyn Bop, 53.3 miles (1578 ft up), few hills. Possible lunch/coffee in Oregon at the Firefly. Route and cue sheet.

  • Swiss Biking Bliss (New Glarus), 56 miles (2060 ft up), some big hills around New Glarus. Possible lunch/coffee at Kristi's, Fat Cat Coffee Works (RR St), or elsewhere. Route and cue sheet.

  • Evansville Expedition, 60.2 miles (1782 ft up), some hills. Possible lunch at DeBroux House Cafe or elsewhere. Route and cue sheet.

  • Devil's Lake State Park, 64.6 miles (2979 ft up), long-ish hills; great ride! We'll drive to start at Pheasant Branch. If Crystal Lake road is closed @14.9, go straight on Gluth Rd., turn left at Hwy 60, and then follow the cue sheet @19.6 (O'connor). Bring your suit/towel! Route (by Steve Toth) and cue sheet.

  • Rock River Ramble, 69.8 miles (2134 ft up), some hills. Lunch on banks of the river or in Stoughton, maybe at the El Rio Grande. Route and cue sheet.

I lucked onto this road at just the right day of the year (Oct 20). Can't wait to go back sometime to retake a better quality image.






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, 97.3 miles (4832 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 and cue sheet.

  • Jim's (Half-Century) Century Ride, 105 miles (4841 ft up). A spectacular ride, this century covers some of my favorite roads and has everything. There are nice roller-coaster hills (nothing huge), 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 and cue sheet.

  • Mineral Point Century, 105.7 miles (5287 ft up). Hilly, but beautiful ride! Route and cue sheet.

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, 63.7 miles (two days, 31.7+32, 2400 ft up) with overnight at Blue Mounds State Park. Hardly any gear is needed (mostly a sleeping bag and tent). Route and cue sheet.

  • The Brew Tour, 87.9 miles (three days, 27-32 each day, 3566 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 and cue sheet.

  • Pedal and Prance, 124.3 miles (three days, 49+30+45, 6279 ft up) with overnights at Yellowstone Lake and Folklore Village. Check with them about camping, and save energy for the dance Saturday night! Route and cue sheet.


1-2 Week Bike Tours

The new Google maps broke many of these routes, but the cue sheets are still good. I've started using ridewithgps.com, which allows infinite customizations to a route (Google allows ten). I'll be redoing 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!

  • Jim and Bonnie's 2020 tour, SW Missouri and NW Arkansas, 362 miles (19269 ft up). Route.

  • Jim and Bonnie's June 2018 tour, 360.4 miles (13108 ft up), 10? days. Route.

  • Jim and Bonnie's 2017 tour, 333.6 miles (16,501 ft up). Route.

  • Jim and Bonnie's 2015 bike 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 bike 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 bike 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 bike 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 bike 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

Other Rides

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