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.

Bicycling around Crosby in fall.

Beth Gauper

The Tour of Cuyuna in September winds through Minnesota lakes country.

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, Minnesota and Wisconsin 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 2014.

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.

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.

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

April 27, Minnesota Ironman from Lake Elmo, Minn. Hostelling International Minnesota sponsors this ride from the Twin Cities' eastern suburbs to the St. Croix River Valley and back. Routes vary from family-length to 100 miles.

May 10, 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 17, 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 25, 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 25, 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, 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 1, 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 7, 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) and admission to the National Eagle Center in Wabasha.

For more, see A spin around Lake Pepin.

June 7, Tour of Lakes from Baxter, 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. 

Bicyclists on Lake Pepin.

Beth Gauper

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

Registration closes May 1 or at 1,200 riders. Routes are 35 or 65 miles.

For more about the trail, see Bicycling the Bunyan.

June 6-8, 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 7-8, Tour of the Mississippi River Valley from Bettendorf or Preston 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.

June 12-15, Cedar Valley Trails Festival in Cedar Falls/Waterloo, Iowa. There's a Candlelight Night Ride, a five-mile family ride, a 25-mile rec ride and a 40-mile explorer ride in this area, which has more than 100 miles of paved trails.

June 13-14, Le Tour de Shore from Chicago to New Buffalo 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 14, 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 45 or 60 miles.

June 14, 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 14-15, 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.

June 14-15, 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. 13-14.

Bicyclists on the Mesabi Trail.

Beth Gauper

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

June 14, 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 14, 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; enter by early February.

June 14, Fat Tire Tour of Milwaukee. The original crawl through Milwaukee celebrates its 30th 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.

Costumes are encouraged, and this year's theme is "Milwaukee (Napoleon) Dynamite.'' It's a benefit for the Bicycle Federation of Wisconsin.

June 20, 2015, 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, Bears to Pedal in White Bear Lake, Minn. This first-time family ride features routes of 4, 30 and 46 miles, partly on the Gateway State Trail, and includes food and entertainment.

June 28, BACoon Ride from Waukee, Iowa. This new 71-mile tour of the Raccoon River Valley Trail features bacon stops and a bacon-themed lunch.

June 28, 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.

June 29, MOST Tour from Montague, Mich. Four loops of 25, 50, 66 and 75 miles pass Lake Michigan beaches and orchards on the Muskegon Oceana Scenic Tour, hosted by the West Michigan Coast Riders.

July 4, Watermelon Ride from Shoreview, Minn. The Twin Cities Bicycling Club hosts this family ride around the Twin Cities, followed by a picnic.

A church on the Lake Wobegon Trail.

Beth Gauper

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

July 12, 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 12, Tour de Fat in Chicago. New Belgium Brewing's annual tour from Palmer Square is part ride, part party, with contests and a costumed bike parade.

July 19-20, 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. 

July 20, 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 26, Tour de Fat in Minneapolis. New Belgium Brewing's annual tour from Loring Park is part ride, part party, with contests and a costumed bike parade.

Aug. 2-3, 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.

Parks & Trails Council bicycle ride.

Parks & Trails Council

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

Aug. 2-4, 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. 2, Mesabi Trail Tour to Coleraine, 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. 2, Tour de Tonka in the western suburbs of Minneapolis. Ride one of five routes around Lake Minnetonka, from 16 to 100 miles.

Aug. 16, Tour de Pines in Minnesota's Itasca State Park, between Park Rapids and Bemidji. Routes are 25, 50 and 75 miles.

Aug. 16, 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. 16-17, 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. 24, Ride the Drive Eastside in Madison. This version of the downtown ride features the east neighborhoods. There are also family activities, parades, food and music.

Mankato River Ramble.

Bicycle Alliance

The Mankato River Ramble in October winds through southern Minnesota.

Aug. 29-Sept. 1, 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.

Aug. 29-Sept. 1, Bike Minnesota with Parks & Trails. This annual ride is hosted by retired Minnesota Court of Appeals Judge David Minge. It uses state trails and stops in state parks, nature areas and attractions, where local experts give talks. 

Cost of $190 (after July 31, $200) includes camping, meals, bicycle support and membership or renewal in the Parks & Trails Council of Minnesota. It fills, so sign up early.

Sept. 6, 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. 7, 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. 7, Four Star Bike & Chow in Chicago. Four street routes explore the South Side, and riders get punch cards good for samples at three restaurants (samosas, pierogies, Thai) and a Revolution beer.

Mankato River Ramble.

Bicycle Alliance

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


Sept. 7, 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. 13-14, 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 14-15.

Sept. 14, 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. 21, 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 35, 64 and 103 miles.

Sept. 27, 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.

Pastries on the Tour of Saints bike ride.

Jerry Hass

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

Oct. 4, Apple Affair from Galesville, Wis. This is ride is part of a fun festival in this pretty town up the bluff from Trempealeau. There are relatively 6- and 18-mile routes through orchards and hillier 35-, 55- and 72-mile routes.

Oct. 4, 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. 4, Caramel Apple Ride from Sauk Centre, Minn. There are three  out-and-back routes on the Lake Wobegon Trail.

Oct. 5, 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 28, 42, 63 and 103 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. 5, Mankato River Ramble from Mankato, Minn.This first-time 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 the League of Illinois Bicyclists.


Last updated on July 28, 2014
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