What's Happening in the Driftless

Our picks for getting out and exploring this month

There’s something special about October here. The bluffs start showing off, the little river towns are buzzing, and there always seems to be something happening just down the road.

We pulled together a few events we think are worth checking out during your stay. Pick an event, take the scenic route, stop somewhere you’ve never been—and don’t worry about rushing back. That’s kind of the point around here.

— Tina & Bryan

🍎Gays Mills Apple Festival

September 25–27 • Gays Mills, Wisconsin

We couldn't leave this one off our first monthly guide! Head into the hills around Gays Mills for one of the area's classic fall traditions. It's also a beautiful time of year for the drive through orchard country.

Our tip: Don't be in a hurry. This is one of those drives where taking the long way is part of the fun.

🎨Art in the Park

October 3–4 • Elkader, Iowa

Art, fall weather and a beautiful small town make this an easy addition to an October weekend. Browse the artists, explore Elkader and grab something to eat while you're there.

Flea Market Under the Bridge

October 3–4 • Marquette, Iowa

This one's practically in DD's backyard. Browse the vendors under the bridge, then spend some time exploring Marquette and neighboring McGregor.

🛍️ Fall Arts & Crafts Festival

October 10–11 • McGregor, Iowa

This is one we'd especially recommend to our guests. Downtown McGregor is already fun to wander, and during the festival you'll find artists, makers and plenty of reasons to linger.

Flea Market Under the Bridge

October 10–11 • Marquette, Iowa

Missed it the first weekend? You get another chance! Pair the flea market with the Arts & Crafts Festival and you've got an easy full day without traveling far from DD.

DD idea: Start in Marquette, wander McGregor afterward, grab dinner, then head back to the house for a game night. ❤️

🍺 Witches Night Out

October 15 • Decorah, Iowa

Grab the girls and head to Decorah for an evening downtown. Shops, specials and Halloween fun make this one especially good for a girls' getaway.

Oktoberfest

October 15–18 • Prairie du Chien, Wisconsin

Cross the river for Oktoberfest fun in Prairie du Chien. Add downtown shopping, dinner or a stop along the Mississippi and make a whole afternoon or evening of it.

🎃 Halloween Parade & Festival

October 24 • McGregor, Iowa

Costumes, a parade and Halloween fun in downtown McGregor make this a great one for families—and you're only a short drive from home base at DD.

Our suggestion: Make a day of it. Explore downtown, find somewhere local to eat, and then come back to DD for a cozy night in.

🐾 You don't have to fit everything in.

Choose something that sounds fun, take the scenic route and leave yourself a little time to do absolutely nothing, too.

That's what we hope a stay at Driftless Destinations feels like—time to explore, but also time to reconnect.

From Tina & Bryan ❤️

Have a favorite event, shop, restaurant or hidden gem we should include next month? We'd love to hear about it. We're always finding new things to share with our guests.