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 western Great Lakes, 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, with Ohio close behind.

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 2021

The TOMRV bike tour in Iowa.

©

The Tour of the Mississippi River Valley, or TOMRV, is in June.

For longer rides, see Sightseeing by bike.

For trails on which you can organize your own trips, 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.

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 22, 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, 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 about the Grand Rounds, see Biking in Minneapolis.

May 30, 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.

Riding the Gitchi-Gami Trail.

© Debra Gagner

On Minnesota's North Shore, bicyclists follow Lake Superior on the Gitchi-Gami Trail Ride in August.

June 5, 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 6, Ride for the Arts in Milwaukee. This ride along the Lake Michigan lakefront from Veterans Park is the first in a series. There's also a ride June 13 from Brookfield and one June 27 from Port Washington.

June 6, Ride the Drive in Madison. Ride, walk or skate along Lake Monona to multiple parks for family activities, parades, food and music.

June 11-13, Tour of the Mississippi River Valley from Bettendorf, Iowa. Hosted by the Quad Cities Bicycle Club since 1978, TOMRV includes two rides from and back to Bettendorf. 

Mankato River Ramble.

© Bicycle Alliance

The Mankato River Ramble in October winds through southern Minnesota.

June 12, 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 12, MS 150 from White Bear Lake. This ride, which benefits the Minnesota chapter of the National MS Society, starts in White Bear Lake and goes to Grand Casino Hinkley. 

June 18-19, 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 19, Minnesota Ironman from Shakopee, Minn. Minnesota's oldest bike ride follows the Minnesota River, with routes of 37, 65 or 100 miles in the southwest corner of the metro area. It benefits Free Bikes 4 Kidz.

June 19, 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 19, 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.

June 19, Shooting Star Trail Ride from LeRoy, Minn. This southern Minnesota ride will cross the border and include Iowa's Wapsi-Great Western Trail on routes of 35, 55 and 72 miles.

June 20, Fat Tire Tour of Milwaukee. The original crawl through Milwaukee celebrates its 37th year with a meandering, 25-mile-max ride. Usually, it starts at Best Place, the old Pabst Brewery hospitality room, and includes stops at Lakefront Brewery and Wolski's Tavern. 

Costumes are encouraged. It's a benefit for the Wisconsin Bike Fed. 

Pastries on the Tour of Saints bike ride.

© Jerry Hass

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

June 19, 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, 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 11, 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.

July 31, Great River Energy-Mesabi Trail Tour from Chisholm, Minn. Out-and-back rides of 24 or 52 miles will start from the Minnesota Discovery Center. Other rides on the paved trail will start from Grand Rapids Aug. 28 and from Virginia Sept. 18.

Saint Paul Classic.

© Bicycle Alliance

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

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

July 31-Aug. 2, 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 18, 65, 130 or 190 miles. It benefits the Respiratory Health Association of Metropolitan Chicago.

July 30-Aug. 2, Ride Across Wisconsin. This 225-mile ride, a fundraiser for the Wisconsin Bicycle Fed, goes from La Crosse on the Mississippi to Green Bay on Lake Michigan, with an overnight in Plover.

Aug. 7, Tour de Tonka in the western suburbs of Minneapolis. Ride one of five routes around Lake Minnetonka, from 16 to 100 miles. 

Bicyclists on Lake Pepin.

© Beth Gauper

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

Aug. 21, 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, and 37 and and 55 miles on the trail and hilly county roads.

Aug. 14, The Courage Ride from Iowa City, Iowa. This ride starts at Big Grove Brewery and goes through the Amish and Mennonite countryside south of Iowa City on routes of 5, 18, 36, 70 and 100 miles.

Aug. 15, 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.

For more, see Wright in Oak Park.

Aug. 21-22, 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.

A church on the Lake Wobegon Trail.

© Beth Gauper

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

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

Aug. 22, Fat Tire Tour in Green Bay. This offshoot of the famously unconventional Milwaukee tour starts at Ned Kelly's Pub and meanders through town, stopping at bars and breweries.

Aug. 28, Great River Energy-Mesabi Trail Tour from Grand Rapids, Minn. Out-and-back rides of 24 or 48 miles will start from the Itasca County Fairgrounds. Another ride on the paved trail will start from Virginia on Sept. 18.

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

Aug. 28, 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.

Parks & Trails Council bicycle ride.

© Parks & Trails Council

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

Sept. 11, 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. 11, 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. 11, SepTimber Ride from Eagle River, Wis. In northern Wisconsin lakes country, routes of 28, 37 and 60 miles start at Tribute Brewing in Eagle River and stop at Three Lakes Winery at roughly the halfway point.

Sept. 12, 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. 12, 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.

Bicyclists on the Mesabi Trail.

© Beth Gauper

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

Sept. 18, Great River Energy-Mesabi Trail Tour from Virginia, Minn. Out-and-back rides of 26 or 50 miles will start from Olcott Park.

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

Sept. 18-19, 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. 

Fall, 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, see Chicago by bicycle.

Sept. 18, Tyranena Oktoberfest from Lake Mills, Wis. This benefit ride from Tyranena Brewery, east of Madison, has routes of 25, 46 or 66 miles. The fee includes beer, dinner, music and brewery tours. This ride fills quickly.

Sept. 25, 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.

Oct. 2, Apple Affair Bike Tour 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. 3, 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. 10, 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 BikeIowa, the Bicycle Federation of Wisconsin, the League of Michigan Cyclists and Ride Illinois.


Last updated on August 26, 2021