The Kickapoo Valley—Hills, Streams, Amish, Antiques & Much More

canoeing in Kicakpoo Valley in Southwest Wisconsin
biking in Kickapoo Valley, WIsconsin
Wildcat Mountain state park, Wisconsin
Vernon Vineyards Winery in Wisconsin
Southwest Wisconsin
Southwest Wisconsin
apple orchards in Southwest Wisconsin Photo by Scott Bauer, USDA ARS [Public domain], via Wikimedia Commons
In the middle of the Driftless Area, the unglaciated rough landscape so unique in the upper Midwest, lies a wandering, scenic river, the largest tributary of the Wisconsin River, the Kickapoo. The Kickapoo Valley includes hundreds of miles of winding rural roads. Around each corner you can almost pick out a Norman Rockwell painting. You will find small dairy farms, tobacco sheds now empty and void of their precious old cargo, dozens of communities each with its own character, descendants of Norwegian immigrants, and newly arrived Amish who find this area perfect for their simple lifestyle. The Kickapoo Valley is almost a region to itself, a part of the Hidden Valleys that refuses to “grow up” and proudly hangs on to its history and its heritage.

The Kickapoo Valley may be enjoyed in one fully packed day trip, or it can be explored more thoroughly over several days. This trip starts at the north end of the valley, just south of I-90 and just south of Tomah, WI. The villages of Kendall, Wilton, and Norwalk lie across the top of the valley and all three are on the famous Elroy-Sparta bike trail, one of the oldest and nicest of the rails-to-trails in the state of Wisconsin. The Elroy-Sparta Trail connects to the La Crosse Trail to the west and together they constitute more than 100 miles of well-groomed bike trail.

Canoe Adventures

Going south from Wilton on Hwy 131 brings you to the village of Ontario, the center for three very active canoe livery services. Canoeists head south on the Kickapoo River from Ontario and can schedule pick-ups at a variety of points downstream – spending as little as two hours or as much a full day on the water. The north end of the Kickapoo is interspersed with limestone outcroppings. The water is typically shallow (except after spring melts or heavy summer rains) and suitable for safe family canoeing. A little further south on Hwy 131, at Rockton, the Kickapoo Yacht Club also rents many canoes from which to explore the river.

Putting in at either Ontario or Rockton will take you through two great natural areas – Wildcat Mountain State Park and the Kickapoo Reserve. These two public areas together engulf more than twenty river miles along the Kickapoo, ensuring that your trip will be private and scenic. Weekend summer canoeing can get more crowded – weekdays offer more quieter, more private canoeing and drifting. The Kickapoo Reserve itself offers 8500 acres of wooded hills and valley. There are separate hiking, biking, and equestrian trails and a new visitor's center that offers a peek at the history of the Valley and the notorious story of Lake La Farge.

The north end of the Kickapoo Valley is conveniently accessed by these Wisconsin-Inns B&Bs: 
  • Amil’s Inn - Wilton
  • Franklin Victorian Bed and Breakfast

Cashton Amish Settlements

Heading west from Ontario to Cashton would take you through the Cashton Amish Settlement, a well-established settlement in which Amish woodworkers, quilters, and craftsmen offer superior wares at very modest prices. The Amish are a peace-loving people who thrive in the rural Kickapoo Valley. They value the peace and serenity of the valley and see this as a place worthy of their hard work.

Several horse stables in the north end of the valley offer trail rides through some of the most interesting horse country in the mid-west.

Heading south from Cashton brings you to Westby, then Viroqua. These villages form the western edge of the Kickapoo Valley and are larger than the very small hamlets that lie along the Kickapoo itself. Westby celebrates its Norwegian heritage each year with Syttende Mai (the seventeenth of May) or Norway’s Independence Day. Great food, a parade, music, and traditional Norwegian arts and crafts abound on this weekend in mid-May. Westby is also home to some great antique shops, a first class cheese plant, and a beautiful Scandinavian gift shop. For a truly unique Wisconsin experience, visit on the second weekend of February to attend the Snowflake Ski Jumping Tournament and watch an international competition of Nordic Ski Jumping (don’t try this unless you are a professional!).

You will find these Wisconsin-Inns B&B's just minutes from the Amish settlements:
  • Westby House Inn - Westby

To the West of Westby and just off of Highway 14/61 is Branches Winery.
The charming boutique winery features delicious wines produced from estate-grown grapes. Surrounded by vineyard views, the tasting room offers wine by the glass and bottle as well as selection of appetizers featuring local artisan cheeses.  The outdoor patio is the perfect spot to take in the rolling hills.

Travel four miles south on Highway 14/61 out of Westby and turn west on to County Y for the Vernon Vineyards Winery.  This 15 acres in Vernon County offers lovely vineyard views and a beautiful new Tasting Room.  Part of the Driftless Region of Wisconsin, between the Wisconsin, Mississippi and Chippewa Rivers, this area, with its many rivers, valley and western-facing slopes, is able to grow more traditional wine grapes than other areas of Wisconsin.

In Viroqua you can make a mid-August stop to enjoy Wild West Days, and then in September enjoy Wisconsin’s last county fair of the year; the Vernon County Fair is held two weekends after Labor Day. Check out the live music and entertainment at the beautifully restored Temple Theater. Shop along a great main street that includes a first rate fly fishing shop, a unique rock (jewelry) shop, and a couple of cute cafes. In Viroqua you can also schedule 18 holes of wonderful golf.

Heading east from Viroqua will take you to Viola, at the heart of the Kickapoo Valley again. The annual Viola Horse and Colt Show is famous state-wide. Continuing south to Readstown gives you the opportunity to pick up with another canoe outfitter whose regular livery service extends south from Readstown to Soldiers Grove and Gays Mills. Soldiers Grove is America’s First Solar Village, with a unique history of old time floods solved only by moving the commercial buildings to higher ground. Stop at Soldiers Grove Dairy Days on Father's Day weekend, then the Driftless Area Art Festival is the third weekend in September.

Be sure to check out these Wisconsin-Inns when in the surrounding areas:
  • Country Pleasures B&B - Cashton
  • Westby House Inn - Westby

Gays Mills - The Apple Capitol of Wisconsin

Gays Mills is the Apple Capital of Wisconsin with many orchards that go back almost 100 years in time. Gays Mills has an active calendar of events with Music Fest (celebrated on Mother’s Day weekend) Crawford County Fair (mid July), and then Applefest (on the last full weekend of September). The five Gays Mills orchards are a beehive of activity from late August through October selling many varieties of the fruit that will keep the doctor away.

The mid and south ends of the Kickapoo Valley can be easily accessed by these Wisconsin-Inns B&Bs:
  • The Westby House - Westby
  • Country Pleasures B&B - Cashton
From Wilton to Gays Mills – beautiful scenery and a lot of activities are offered. Traveling south of Gays Mills you can drive along an almost unused 25 miles of the Kickapoo. Dairy Farms, cattle ranches, and small farm fields are the rule from Gays Mills to Wauzeka, an incredible drive with one beautiful landscape after another. At Wauzeka, the journey of the Kickapoo comes to an end as it empties into a broad and powerful Wisconsin River. A couple of canoe outfitters operate out of Wauzeka and Boscobel and offer trips southwest on the Wisconsin, ending eventually at Wyalusing State Park where the Wisconsin meets the Mississippi.

A dedicated canoe or kayak enthusiast could put in at Ontario, and take out at Wyalusing having had his boat touching the waters of the Kickapoo, the Wisconsin, and the Mississippi Rivers. A great natural experience.
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