Bicycling and shopping vacations

She likes to explore the shops and he likes to sweat? No problem.

bicyclists along Chicago's Lakefront Trail
Chicago's Lakefront Trail goes past Navy Pier and near the shops of Old Town, Oak Street and the Magnificent Mile.

As often as not, vacationing couples find they're in a mixed marriage: One likes to shop, one likes to bike or hike.

What to do? I've seen dozens of men patiently waiting on benches as their wives and girlfriends scour the shops.

But it needn't be an either/or proposition. Pick one of the destinations below, and you'll find both great shopping and great riding (or running, or skating) routes, plus great restaurants in which to relax afterward.


Where to ride : Chicago's 18-mile Lakefront Trail. For more, see Spin City.

Where to shop : The Magnificent Mile, Oak Street, the Loop, Old Town, Navy Pier. For more, see Chicago stories.


Where to ride : The 30-mile Grand Rounds, which can be extended on the Southwest LRT trails to Chanhassen and Victoria and the Luce Line to Winsted.

For more, see Bicycling around the Twin Cities.

Where to shop : Downtown, Uptown, Grand Avenue, the Mall of America. For more, see Twin Cities stories.


Where to ride : The Oak Leaf Trail in Milwaukee, with 48 miles of paved off-road paths, 31 miles of parkway drives and 27 miles of connecting streets. For more, see Bicycling along Lake Michigan.

Where to shop : Milwaukee's Historic Third Ward. For more, see Milwaukee stories.


Where to ride : The paved 17-mile Capital City State Trail, which connects Madison to the 40-mile Military Ridge Trail to Dodgeville. * *

Where to shop : State Street and Monroe Street. For more, see Shopping in Madison and Power shopping in Wisconsin.


Where to ride : The 30-mile Interurban Trail along Lake Michigan from just north of Milwaukee to Belgium. For more, see Bicycling along Lake Michigan. * *

Bicyclists on Minneapolis' Cedar Lake Trail.
The Cedar Lake Commuter Trail takes bicyclists to Target Field and downtown Minneapolis.

Where to shop : Cedarburg, a Yankee mill town with a winery, galleries and shops in antebellum buildings. For more, see Jolly Cedarburg.


Where to ride : The 42-mile Root River State Trail and 18-mile Harmony-Preston Valley State Trail in southeast Minnesota, which connects to the Root River trail five miles west of Lanesboro.

For more, see Bicycling in bluff country.

Where to shop : Lanesboro and on Amish tours. For more, see The belle of bluff country and Amish country.


Where to ride : 130 miles of the Paul Bunyan State Trail from Baxter to Akeley, the Heartland State Trail between Park Rapids and Cass Lake and the Migizi Trail around Cass Lake in Minnesota lakes country.

For more, see Bicycling the Bunyan.

Where to shop and stay : Nisswa. For more, see Fast times in Nisswa.

New Glarus

Where to ride : The 32 miles of the Badger State Trail from the Madison exurb of Fitchburg to the Illinois border, 13 miles on the Jane Addams Trail to Freeport, Ill.; and 23 miles on the Sugar River State Trail from New Glarus to Brodhead.

Where to shop : New Glarus and Paoli. For more, see A slice of cheese country.

Sturgeon Bay

Where to ride : The 31-mile Ahnapee State Trail from Casco to Sturgeon Bay, trails in Peninsula State Park and county roads around Door County.

Where to shop : Algoma, Sturgeon Bay, Egg Harbor and Fish Creek. For more, see The door to Door County and Outdoors in Door County.

Red Wing

Where to ride : The 19½-mile Cannon Valley Trail between Cannon Falls and Red Wing on the Mississippi River in Minnesota.

Where to shop : Pottery Place and downtown in Red Wing. For more, see Roaming in Red Wing.


Where to ride : Minnesota's 55-mile Central Lakes Trail, which connects with the Lake Wobegon Trail and spurs into Morrison County for a 127-mile system.

For more, see Bicycling the Central Lakes.

Where to shop : Alexandria. For more, see Alexandria's enigma.

Last updated on June 6, 2016

Your browser does not support our events calendar page. Please consider an update.