MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Tours on two wheels

On organized weekend bike trips, it's easy to go along for the ride.

Mankato River Ramble.

© Bicycle Alliance

On the Mankato River Ramble, cyclists stop in Rapidan for pie.

If you like to ride bikes and you live in the Upper Midwest, you've lucked out.

This is a bike-crazy part of the country. Michigan and Minnesota rank No. 1 and 2 for miles of rails converted to trails.

Wisconsin pioneered rail trails and for years was the top state, but it has slipped to fourth place, with No. 3 now taken by Pennsylvania. Illinois and Iowa once rounded out the Top 5 but have been supplanted by New York and Washington state.

Wisconsin's Elroy-Sparta State Trail sparked the boom in bicycle tourism in 1967; when surrounding towns and counties saw all the tourists who came to ride it, they built their own trails. We also can ride on thousands of miles of quiet country roads, built so dairy farmers could get their milk to market.

Now hundreds of bike tours show off the trails and the towns they go through. Nearly every tour ends with music and a picnic and offers non-stop goodies at rest stops.

On the Lake Wobegon Trail, the Caramel Roll Ride matches the calories in a freshly baked pastry to the calories burned in an hour of riding ("Coincidence? Think again'').

And some towns really take advantage of what they've got. On the Tour de Pepin, riders who only want to go halfway around Lake Pepin, a wide spot in the Mississippi, get to return by paddlewheeler.

The main attraction of these tours is not only that they're fun, but they're easy. Signs mark every turn, sag wagons pick up tired riders and mechanics fix flats. There's nothing to do but pedal, enjoy the scenery and chat with fellow riders.

Below are some of the best and most scenic weekend and day tours in 2019.

For longer rides, see Sightseeing by bike.

For more, see Bicycling in MinnesotaBicycling in Wisconsin and other Bicycling stories.

Sign up early to save. Most rides allow same-day registration, but some rides cut off registration a month or more in advance.

Saint Paul Classic.

© Bicycle Alliance

In Como Park, cyclists on the Saint Paul Classic pass the pavilion.

Most day tours charge $30-$45, which includes sag wagons, mechanical support, food and, often, a T-shirt. Weekend tours include camping and return by motorcoach.

They're all non-profit, and most raise money for good causes. Fees nearly always are discounted for advance registrations and for families, children and teams. 

Some rides limit the number of riders, and some benefit rides require fund-raising. Helmets are required.

May 18, Zoo-De-Mackinac from Harbor Springs, Mich. This 51-mile ride along Lake Michigan starts at Boyne Highlands Resort, stops for lunch at the famous Legs Inn in Cross Village, continues to Mackinaw City for a finish party, then goes on to Mackinac Island for more parties.

May 26, Leinenkugel's Chippewa Valley Century from Chippewa Falls, Wis. This ride from Irvine Park heads north along the Chippewa and Flambeau rivers, past lakes Wissota and Holcombe and across the Ice Age National Scenic Trail, ending with beer and a brat feed. Routes are 35, 50, 75 or 100 miles.

May 26, Bike the Drive in Chicago. This ride gives bicyclists a golden opportunity to ride on a car-free Lake Shore Drive. Routes are 15 or 30 miles, and there's a post-ride festival in Grant Park. This is a holiday weekend, so hotel rates should be fairly low.

For more about bicycling on Chicago's lakefront, see Spin City.

June 1, Tour de Pepin from Lake City, Minn. This ride around Lake Pepin, a wide spot on the Mississippi River in southeast Minnesota, has four routes: 32 miles to Stockholm, Wis., with return by paddlewheeler; 50 miles to Maiden Rock and back to Stockholm, with return by paddlewheeler; 72 miles around Lake Pepin; and 100 miles, Lake Pepin plus a countryside loop.

Cost includes a Friday night pasta feed in Hok-Si-La Park (a good place to camp). For more, see A spin around Lake Pepin.

June 2, Ride for the Arts in Milwaukee. This ride along the Lake Michigan lakefront includes routes of 5, 12, 25, 45 and 70 miles. The three longer routes will include the Hoan Bridge on I-794, which will be closed to cars for two hours, and the longest route goes as far north as Port Washington. 

The rides start and end at the Summerfest grounds, and there's a party afterward.

Pastries on the Tour of Saints bike ride.

© Jerry Hass

On the Tour of Saints, riders get pastries from Cold Spring Bakery.

June 2, Ride the Drive in Madison. Ride, walk or skate along Lake Monona to three parks for family activities, parades, food and music.

June 7-9, MS 150 from the Duluth area to the Twin Cities. Half of this ride, which benefits the Minnesota chapter of the National MS Society, is on the paved Willard Munger State Trail. Riders are bused from the finish in White Bear Lake to the start in Proctor. Thereís an overnight in Hinckley. 

June 8-9, Tour of the Mississippi River Valley from Bettendorf or Goose Lake, Iowa. Hosted by the Quad Cities Bicycle Club since 1978, TOMRV gives riders a choice of distances, both scenic and hilly, to and from Dubuque.

Riders stay in dorms at Clarke University in Dubuque and return to their starting points on different routes.

June 8, Caramel Roll Ride from Albany, Minn. This ride on the paved Lake Wobegon Trail in central Minnesota features freshly baked caramel rolls that have 360 calories, which is what the trail association estimates is what a 170-pound adult burns in an hour of riding.

For more about the trail, see Bicycling to Lake Wobegon.

June 14-15, Le Tour de Shore from Chicago to New Buffalo, Mich. This ride from Millennium Park follows the Lake Michigan shoreline for 96 miles, with an overnight at Indiana Dunes State Park. Riders are bused back to Chicago. It benefits Maywood Fine Arts in Illinois.

June 15, Minnesota Ironman from Shakopee, Minn. Minnesota's oldest bike ride returns at a warmer time of year, with routes of 15, 30, 62 or 100 miles in the southwest corner of the metro area. It benefits Free Bikes 4 Kidz.

June 15, BACooN Ride from Waukee, Iowa. This bacon-themed 72-mile ride starts just west of Des Moines and follows the paved Raccoon River Valley Trail.

June 15, Fat Tire Tour of Milwaukee. The original crawl through Milwaukee celebrates its 35th year with a 25-mile ride that starts at Best Place, the old Pabst Brewery hospitality room, and includes stops at Lakefront Brewery and Wolski's Tavern. This year's theme is "Wizard of Oz."

Costumes are encouraged. It's a benefit for the Bicycle Federation of Wisconsin.

June 15, Peninsula Century Spring Classic from Baileys Harbor, Wis. Ride the bucolic county roads of Door County on routes of 25, 50, 62 or 100 miles.

In the sanctuary, orchids should be blooming; for more, see Spring in Door County.

Mankato River Ramble.

© Bicycle Alliance

The Mankato River Ramble in October winds through southern Minnesota.

June 15, Horribly Hilly Hundreds from Blue Mounds, Wis. This ride through the unglaciated Wisconsin River valley west of Madison isn't for novices. Routes are 100, 150 or 200 kilometers and make a loop through Barneveld, Mazomanie and Black Earth.

Only 1,300 riders are allowed on "the toughest one-day challenge ride in the Midwest.'' The ride fills by lottery; registration opens Feb. 1.

June 15, Bike Bemidji: Loop the Lake Festival. This 17-mile ride around Lake Bemidji in northern Minnesota includes music and food at five or six rest stops. Nice Ride bikes are available for rental.

June 22, Superior Vistas from Washburn, Wis. A family-friendly ride through the Bayfield Peninsula of Wisconsin, with vistas of Lake Superior.

There are loops of 13, 19, 34, 52, or 70 miles plus a century and a 40-mile route to Cornucopia and back. It benefits the Friends of Lake Superior Nordic Trails and the Washburn Cultural Center.

July 14, Tour of Saints from St. Joseph, Minn. This loop through the St. Cloud area west of the Twin Cities starts at the College of St. Benedict and winds past St. John's University. Routes are 18, 35 and 50 miles.

Parks & Trails Council bicycle ride.

© Parks & Trails Council

Riders tour Minnesota on the Parks & Trails Council's annual Labor Day weekend ride.

July 20-21, Scenic Shore 150 from Mequon, Wis. This ride follows Lake Michigan from Mequon, just north of Milwaukee, to Potowatomi State Park in Sturgeon Bay, with an overnight in Manitowoc.

The route includes three trails, the Interurban from Mequon to Belgium and the Mariners and Rawley Point trails between Manitowoc and Point Beach State Forest. The ride benefits the Leukemia & Lymphoma Society. 

Aug. 3-5, CowaLUNGa from Gurnee, Ill.  This ride heads from the northern Chicago suburb of Gurnee to Hubertus through Wisconsinís kettle moraine, with overnights in Williams Bay on Geneva Lake and Whitewater. 

Riders can bicycle one, two or three days, with mileages of 65, 130 or 190 miles. It benefits the Respiratory Health Association of Metropolitan Chicago.

Aug. 3-4, Best Dam Bike Ride from Pewaukee, Wis. This ride in southeast Wisconsin heads from the western Milwaukee suburb of Pewaukee through kettle moraine to Madison, with an overnight in Whitewater. 

Riders can choose to ride one or two days, with routes of 50, 75 or 100 miles. It benefits the Wisconsin chapter of the National MS Society.

A church on the Lake Wobegon Trail.

© Beth Gauper

The Caramel Ride in June uses Minnesota's Lake Wobegon Trail.

Aug. 3, Mesabi Trail Tour from Gilbert to Grand Rapids, Minn. The ride on this beautiful paved trail through the Iron Range includes transportation to the starts of four routes. 

For more about the trail, see Rolling through the Iron Range.

Aug. 3, Tour de Tonka in the western suburbs of Minneapolis. Ride one of five routes around Lake Minnetonka, from 16 to 100 miles. 

Aug. 17, Tour de Pines in Minnesota's Itasca State Park, between Park Rapids and Bemidji. Routes are 25, 50, 60 and 70 miles.

Aug. 17, Gitchi-Gami Trail Ride from Gooseberry Falls State Park north of Two Harbors, Minn. This ride on the scenic North Shore includes three routes, 28 and 37 miles mostly on the paved Gitchi-Gami State Trail and back, 37 and and 55 miles on the trail and county roads.

Aug. 17, The Courage Ride from Kalona, Iowa. This ride in the Amish and Mennonite countryside south of Iowa City includes paved routes of 16, 24, 39, 59, 81 and 100 miles, plus four gravel routes.

Bicyclists on Lake Pepin.

© Beth Gauper

On the Tour de Pepin in June, bicyclists stop at a Maiden Rock bakery.

Aug. 17-18, Bike Van Buren from Keosauqua, Iowa. In the southeast tip of the state, this ride takes two loops through the 11 historic Villages of Van Buren, along the Historic Hills Scenic Byway.

Riders can do the 64-mile Saturday loop, the 49-mile Sunday loop or both.

Aug. 18, The Wright Ride in Oak Park, Ill. Ride through Frank Lloyd Wright's old stomping grounds on routes of 10, 30, 50 or 68 miles.

Aug. 30-Sept. 2, La Crosse Area Bicycle Festival in La Crosse, Wis. Rides are planned each day in the coulees east of town and along the Mississippi River, as well as architecture tours, ice-cream rides and parties downtown and in Cameron Park.

Bicyclists on the Mesabi Trail.

© Beth Gauper

The Mesabi Trail Tour in August crosses Minnesota's Iron Range.

Sept. 7, Jesse James Bike Tour in Northfield, Minn. This ride, part of Northfield's deservedly famous Defeat of Jesse James Days festival, traverses the rolling countryside south of town on routes of 12, 30, 45, 60 and 100 miles; the century uses part of the Sakatah State Trail from Faribault. 

It benefits the Mill Towns Trail, which will link the Cannon Valley and Sakatah trails.

Sept. 7, Caramel Apple Ride from Sauk Centre, Minn. There are three  out-and-back routes of 18, 27 and 38 miles on the Lake Wobegon Trail.

Sept. 8, St. Paul Classic Bike Tour in St. Paul. Ride a 15-, 30- or 45-mile route along the Mississippi, lakes Como and Phalen and St. Paul parkways, starting and ending at the University of St. Thomas and punctuated by food and live music. Most of the route is car-free.

Register early for discounts.

Sept. 8, Door County Century from Sturgeon Bay, Wis. This ride from John Miles Park/Door County Fairgrounds through the picturesque Door Peninsula includes routes of 28, 50, 70 and 100 miles.

Mariners Trail on Lake Michigan.

© Beth Gauper

In July, the Scenic Shore 150 follows Lake Michigan on three bicycle trails, including the Mariners between Manitowoc and Three Rivers.

Sept. 15, Minneapolis Bike Tour. Ride 16, 25 or 32 miles along the Mississippi and the Chain of Lakes. Start and finish is Boom Island, in northeast Minneapolis along the river; there's a party afterward with food, music and beer.

For more on the Grand Rounds bicycle route, see Biking in Minneapolis.

Sept. 28, Headwaters 100 from Park Rapids, Minn. There are routes of 45, 75 and 100 miles; the last two reach Itasca State Park and return partly on the Heartland State Trail.

Sept. 28, Tyranena Oktoberfest from Lake Mills, Wis. This benefit ride from Tyranena Brewery, east of Madison, has routes of 25 or 50 miles. The fee includes beer, dinner, music and brewery tours. This ride fills quickly.

Oct. 5, Apple Affair from Galesville, Wis. This ride is part of a fun festival in this pretty town up the bluff from Trempealeau. There are relatively easy 6- and 18-mile routes through orchards and hillier 37-, 55- and 75-mile routes.

Oct. 6, Pumpkin Pie Ride from Ottawa, Ill. This ride near Starved Rock State Park in northern Illinois, sponsored by the Starved Rock Cycling Association, has road routes of 27, 42, 63 and 103 miles. 

Oct. 6, Mankato River Ramble from Mankato, Minn.This ride from Land of Memories Park has separate loops of 12, 26 and 42 miles. The 26-mile route is the Pie Run, with a pie stop at the Rapidan Dam Cafe.

Rest stops at Minneopa State Park, Rapidan Dam and Minnemishinona Falls include treats and live music. Register early for discounts.

More rides

For details on other rides, see the calendars at Minnesota Trails magazine, BikeIowa, the Bicycle Federation of Wisconsin, the League of Michigan Cyclists and Ride Illinois.

Last updated on June 13, 2019