Tasty Tomato Festival

September in the Driftless is full of fun activities and events.  One that is quite unique is the Tasty Tomato Festival in Westby.  The event is put on by Deeply Rooted, a certified organic farm serving the Driftless Region with tasty, fresh, and local tomatoes.  The Festival includes tomato tastings, workshops, live music and local vendors.

Where to begin?  Bring along some lawn chairs or a blanket.  Find a comfy spot to listen to the live music that plays throughout the day.

Tasty Tomato Festival
2019 date:  September 1

Villa Louis Carriage Classic

Each year, the weekend after Labor Day, brings the Villa Louis Carriage Classic in Prairie du Chien.  An event like you may have never seen before.  Dressed in turn of the century garb, horsemen and women compete by driving their open air carriages pulled by ponies, single horses, or teams of horses.  The event is judged and prizes awarded, bringing in carriage enthusiasts from all over.

Where to begin?  The event goes on rain or shine.  Though lightning might postpone some events, so be sure to be prepared for weather.  One thing you can’t miss is the Sunday end of show Concours d’Elegance. By invitation only, the most elegant of the show are featured.

Villa Louis Carriage Classic
2019 date:  September 6-8

Vernon County Fair

One of the longest running county fairs in the state can be found in Viroqua.  This is a quintessential Wisconsin county fair.  You can expect a midway of rides, carnival games, and food (possibly on a stick!).  You’ll see a tractor pull, horse shows, livestock sale, demolition derby and more. Five fun filled days packed with activities.

Where to begin?   Get a taste of growing up in the Driftless by checking out the 4-H and FFA kids’ contributions to the fair.  From their home grown garden goods, to the animals they helped raise.

Vernon County Fair Save & Exit
2019 date:  September 11-15

Driftless Area Art Festival

On the third week in September the small town of Soldiers Grove plays host to the Driftless Area Art Festival.  The visual arts are well represented with artists showcasing their painting, photography, jewelry, pottery and much more. Plus this art festival aims to showcase culinary and performing arts as well.  Walk through the tents and take some time to talk with the artists about their creations.

Where to begin?  Not often is the family dog allowed to come along.  But if they’re well behaved and socialized. Your dog is welcome to attend.  Just be sure they’re leashed.

Driftless Area Art Festival
2019 date:  September 21-22

Gays Mills Apple Festival

The town of Gays Mills is well known for their apple orchards, so it’s no surprise they’d want to celebrate the apple harvest.  And boy do they ever! A flea market, a carnival, downtown vendors, and a parade. The festivities aren’t just confined to one area.  You’ll find live music and activities at multiple venues. By the time the Apple Festival is over, you’ll know this Driftless town like your own.

Where to begin?  Head out of town and into the ridges to check out an apple orchard or three.  Pick up some apples, or cider, or maybe a pie.

Gays Mills Apple Festival
2019 date:  September 27-29

Driftless WisconsinThere is simply no better place to explore, by car, by bike, or by boat. The scenery when you explore the Driftless Wisconsin Area is unmatched. The history is fascinating. The people and communities are diverse. Around every bend of the road, every twist of the river, something interesting awaits.