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.

Parks & Trails Council bicycle ride.

© Parks & Trails Council

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

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. Wisconsin, Michigan and Minnesota rank No. 1, 2 and 3 for miles of rails converted to trails, and Illinois and Iowa also are in the Top 10.

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 2012.

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.

Most day tours charge $25-$40, 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.

Mankato River Ramble.

© Bicycle Alliance

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

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

May 6, Minnesota Ironman from Lakeville, Minn. Hostelling International Minnesota sponsors this ride from the Twin Cities' southern suburbs to the Minnesota River Valley and back.

Routes are 17, 30, 68 or 100 miles, with the century ride going through Jordan, LeSueur, Montgomery and Lonsdale.

May 6, Hip Breaker from Trempealeau, Wis. The Trempealeau County Bike Club hosts this ride along the Mississippi River and into the bluffs, on routes of 10, 23 or 43 miles (the ride's name comes from the hill on the 43-mile route). Be sure to take time to see the spring wildflowers in Perrot State Park, which adjoins Trempealeau.

May 19, 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 27, 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 27, 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 2, Tour de Pepin from Lake City, Minn. This ride around Lake Pepin has three routes: 12 miles to Wabasha, with return by bus; 32 miles to Stockholm, Wis., with return by paddlewheeler; and 72 miles around Lake Pepin, a wide spot on the Mississippi River in southeast Minnesota.

Cost includes a Friday night pasta feed in Hok-Si-La Park (an excellent place to camp), admission to the National Eagle Center in Wabasha and an excursion on the Pearl of the Lake paddlewheeler.

For more, see A spin around Lake Pepin.

June 2, Tour of Lakes from Crosslake, Minn. This ride in the lakes country north of  Brainerd and on the Paul Bunyan State Trail, hosted by the Paul Bunyan Cyclists Bicycle Club, is known for the gourmet food served at its rest stops. 

Bicyclist on the Tour of Cuyuna.

© Beth Gauper

A bicyclists rides by a marsh on the Tour of Cuyuna in September.

Registration closes May 1 or at 1,200 riders. Routes are 35 or 68 miles.

For more about the trail, see Bicycling the Bunyan.

June 3, Ride for the Arts in Milwaukee. This ride along the Lake Michigan lakefront includes routes of 5, 12, 25, 50 and 75 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.

June 3, Ride the Drive in Madison. Ride, walk or skate a car-free six-mile loop along Lake Monona, around the State Capitol and through downtown. There are also family activities, parades, food and music.

June 8-10, 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. There’s an overnight in Hinckley. 

June 9, 2012, BRAMCO, the Bicycle Ride Around Madison County, Iowa. Bicyclists start in Winterset and see some of the famous bridges of Madison County on routes of 40 or 60 miles.

June 9, 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.

Riders can go out and back on different routes or can return on shuttles, cutting mileages in half.

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

June 9-10, Tour the Raccoon from Des Moines. This ride, sponsored by the Des Moines Cycle Club, follows the paved Raccoon River Valley Trail 65 miles northwest to Jefferson, which will be holding its Bell Tower Festival, then back.

Saint Paul Classic.

© Bicycle Alliance

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

June 9-10, Big Mac Shoreline Scenic Bike Tour from Mackinaw City, Mich. On Saturday, this tour heads west of town along Lake Michigan on routes of 25, 50, 75 and 100 miles.

On Sunday at 7 a.m., participants also get to ride across the Mackinac Bridge to St. Ignace, with bus transportation back. Enter by June 1. The tour is repeated Sept. 15-16.

June 15-16, Le Tour de Shore from Chicago to Warren Dunes State Park in Michigan. 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 16, Fat Tire Tour of Milwaukee. The original crawl through Milwaukee celebrates its 27th year with a ride on the Hank Aaron State Trail, starting from Best Place, the old Pabst Brewery hospitality room.

Costumes are encouraged. For details, contact Phil Van Valkenberg at ticycling@yahoo.com. It's a benefit for the Bicycle Federation of Wisconsin.

June 16, Bike Ride for Nature from Ridges Sanctuary in Baileys Harbor, Wis. Ride the bucolic county roads of Door County on routes of 25, 50 or 100 kilometers.

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

June 16, 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 or 200 kilometers and make a loop through Barneveld, Mazomanie and Black Earth.

Bicyclists on Lake Pepin.

© Beth Gauper

On a ride around Lake Pepin, bicyclists stop at a Maiden Rock bakery.

Only 1,300 riders are allowed on "the toughest one-day challenge ride in the Midwest.'' The ride fills by lottery; enter Jan. 16-18.

June 23, 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 4, Watermelon Ride from Shoreview, Minn. The Twin Cities Bicycling Club hosts this family ride around lakes in the northern suburbs of St. Paul, followed by a picnic at Snail Lake. Routes are 15, 25 or 55 miles.

July 14, Tour de Brew from Amana, Iowa. Millstream Brewing in the Amana Colonies sponsors this poker run, which features a microbrew and a poker card at each stop; the best hands win door prizes.

July 21-22, 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. 4-5, 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 62.5, 75 or 100 miles. It benefits the Wisconsin chapter of the National MS Society.

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.

Aug. 4-6, CowaLUNGa from Gurnee, Ill.  This ride heads from the northern Chicago suburb of Gurnee to Hubertus through Wisconsin’s 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. 4, Mesabi Trail Tour to Hibbing, Minn. The ride on this beautiful paved trail through the Iron Range ends in Virginia and includes transportation to the starts of 15-, 27- and 51-mile routes.

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

Aug. 4, Tour de Tonka in the western suburbs of Minneapolis. Ride one of five routes around Lake Minnetonka, from 17 to 100 miles.

Aug. 18-19, 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 new Historic Hills Scenic Byway.

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

Aug. 19, Top of the World from Whitehall, Wis. This ride on the ridges and valleys of Trempealeau County in southwest Wisconsin has includes 15 miles in  river valley and increasingly harder routes of 23, 40 and 60 miles.

Aug. 19, MOST Tour from Montague, Mich. Four loops of 25, 50, 62 and 75 miles pass Lake Michigan beaches and orchards on the Muskegon Oceana Scenic Tour, hosted by the West Michigan Coast Riders.

Aug. 26, Four Star Bike Tour in Chicago. Formerly the Boulevard Lakefront Tour, this ride includes the 12-mile Chicago Ramble, 21-mile South Side Jaunt, 35-mile Boulevards & Beyond and 66-mile Ultimate Neighborhood Ride.

Riders on the Mesabi Trail Tour.

© Beth Gauper

Riders on Minnesota's Mesabi Trail Tour roll into Keewatin.


There's a festival afterward in the West Loop at the University of Illinois-Chicago, the start and finish.

Aug. 31-Sept. 3, La Crosse Area Bicycle Festival. 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.

Sept. 1-3, Bike Minnesota with Parks & Trails. This annual ride is hosted by Minnesota Court of Appeals Judge David Minge. It uses state trails and stops in state parks and nature areas.

Cost includes camping, meals, bicycle support and membership or renewal in the Parks & Trails Council of Minnesota. It fills, so sign up early.

Sept. 8, Tour of Cuyuna from Crosby, Minn. This ride in this low-profile lakes area, on the eastern edge of the Brainerd Lakes, includes routes of 30 and 60 miles.

For more, see Autumn at the lake.

Sept. 8, 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 10, 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. 9, 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. 9, Door County Century from Sturgeon Bay, Wis. This ride from John Miles Park/Door County Fairgrounds through the picturesque Door Peninsula includes routes of 30, 62, 76 and 100 miles.

Sept. 15-16, Big Mac Shoreline Scenic Bike Tour from Mackinaw City, Mich. On Saturday, this tour heads west of town along Lake Michigan on routes of 25, 50, 75 and 100 miles.

On Sunday at 7 a.m., participants also get to ride across the Mackinac Bridge to St. Ignace, with bus transportation back. Enter by Sept. 1. The tour also is held June 11-12. 888-455-8100.

Sept. 16, Minneapolis Bike Tour. Ride a 14- or 27-mile route on parkways along the Mississippi and the Chain of Lakes. Start and finish is Parade Field, across from the Walker Art Center; there's a party afterward.

The Lake Wobegon Trail through central Minnesota.

© Beth Gauper

On the Caramel Roll Ride in June, riders go through Melrose on the Lake Wobegon Trail.

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

Sept. 16, Pedal the Kettle west of Milwaukee. Ride through the rolling kettle moraine landscape on this ride sponsored by the Spring City Spinners Bicycle Club of Waukesha, Wis. Routes are 30, 60 and 100 miles.

Sept. 22, 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. 22, Potosi Brewery Bicycle Tour from Potosi, Wis. Ride 24, 45, 65 or 100 miles in the very scenic coulees of southwest Wisconsin, along the Mississippi River north of Dubuque.

Sept. 29, Sugar River Bike Tour from Brodhead, Wis. The ride, on the 23-mile Sugar River State Trail and surrounding countryside, is part of the southern Wisconsin town's AutumnFest.

Oct. 6, Apple Affair from Galesville, Wis. This is ride is part of a fun festival in this pretty town up the bluff from Trempealeau. There's a relatively flat 20-mile route through orchards and hillier 35- and 60-mile routes.

Oct. 6, Tyranena Oktoberfest from Lake Mills, Wis. This ride from Tyranena Brewery, east of Madison, has routes of 18, 26, 46 and 66 miles. The fee includes beer, dinner, music and brewery tours, and it benefits Tomorrow's Hope. This ride fills quickly.

Oct. 7, 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 25, 62 and 100 miles and mountain-bike routes of 15, 20, 30 and 45 miles on the flat, crushed-limestone I&M Canal Towpath along the Illinois River.

Oct. 7, Mankato River Ramble from Mankato, Minn.This first-time ride from Land of Memories Park has separate loops of 14 and 42 miles, which can be combined into a 56-mile route. 

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 and the League of Michigan Cyclists.


Last updated on February 1, 2012
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