Cowboy Days, Pampered Nights

By Denice Ryan Martin

Grab your boots and your cowboy hat! Wisconsin is home to some of the prettiest horseback riding trails this side of the Mississippi. Combine that with a stay in a luxurious B&B and you’ve got one fun and romantic getaway. Here are some ideas to get you started.

Southeast Wisconsin Horseback Vacations

Close to Milwaukee, Madison and Chicago, Kettle Moraine Forest South Unit is a popular destination for horseback riders, with over 85 miles of equestrian trails through hardwood forests and with many vistas overlooking kettles, oak savanna prairies, and freshwater lakes.

Dream A Horse - Mukwonago

Dream A Horse stable is conveniently near the state forest trailhead. Options include a one-hour trail ride into the forest or the three-hour Eagle trail ride that includes a stop a local saloon and restaurant. There’s even a corral where you’ll tie up your horse.

Eagle Centre House Bed and Breakfast - Eagle

Soak your saddle-weary bones in an oversized tub at this replica of an 1846 Greek revival style stagecoach inn. Enjoy a full candlelight breakfast in the dining room. You’ll easily slip into a time gone by.

Nearby attractions: Old World WisconsinEast Troy Electric Railroad Museum

South Central Wisconsin Horseback Vacations

Columbus Carriage House Bed & Breakfast - Columbus

This grand B&B is on the National Registry of Historic Places, offering Victorian accommodations with modern conveniences. Horse owners appreciate the “Bed & Bale” option, offering boarding at the nearby Midwest Equestrian Center. A one-hour Clydesdale Horse Drawn Historic Carriage Tour provides a fascinating architectural tour of the city.

Nearby attractions: Antique Shoppes of Columbus-Kurth MansionColumbus Antique Mall & Museum

Southwest Wisconsin Horseback Vacations

Known as the Driftless Region or the “Land of the Hidden Valleys,” the area, untouched by the ice age glaciers, offers scenic rugged hills and incredible natural beauty.

Redrock Trail Rides - Sparta

Homesteaded in 1885, this four generation farm features 12+ miles of groomed horseback riding trails covering beautiful ridges and valleys. Riders choose from 26 gentle, well-trained horses and ponies.

Red Ridge Ranch - Mauston

One-hour trail rides through 250 acres of rolling farmland and wooded hills. Features breath-taking views of the Lemonwier River.

Franklin Victorian B&B - Sparta

Just two blocks from friendly downtown Sparta, the Bicycling Capital of America,
this historic brick-red home provides a signature multi-course healthy breakfast to get your riding day started. Large private bathrooms are a plus.

Nearby attractions: Deke Slayton Memorial Space & Bicycle Museum; Danzinger Vineyard; Down a Country Road Amish Tours & Shops

Northwest Wisconsin Horseback Vacations

The ancient Penokee Mountain Range and tranquil Chequamegon National Forest are waiting to be explored by horseback.

Big Spruce Stable - High Bridge

Take a glimpse into the past on trails set in the foothills of the Penokee Mountain Range. A friendly trail guide will lead you on completely wooded pathways and across the gentle Krause Creek, as you wind your way through the quiet forest.

Penokee Mountain Inn - Mason 

Rest, recoup and relax at this quiet sanctuary on nearly 80 acres of forested land. Each evening guests enjoy homemade desserts like the “ain’t no such thing as too much chocolate” served with wine or cordials.

Nearby attractions: St. Peter's Dome and Morgan Falls

This entry was posted in Horseback Riding, Bed & Breakfasts