The Midwest’s Best Fall Road Trip

.

A place that really has it all

As the leaf tips start to turn, a pilgrimage begins that brings people from across the Midwest to the river city of Winona. 
Winona bluffs with fall colors rise above clouds

The dramatic bluffs of the Driftless Region are unlike anywhere in the Midwest

Jaw-dropping beauty and an insanely good entertainment scene make Winona one of the Midwest’s most beloved destinations year-round, but the autumn months cloak the city in a special kind of beauty that leaves you breathless. Moreover, with a blend of incredible recreation, world-class arts and old-world charm, it’s a must-see destination that you’ll talk about moving to at least once before you leave. 

Perched on the Mississippi River just off of Interstate 90 in Southeastern Minnesota, the beauty of Winona is that it is an easy road trip from everywhere. And for those who have never ventured from the interstate down into our stretch of the river valley, prepare to be dazzled. 

Below is the shortlist of things we love to do in fall. It’s just a taste – check out our event calendar to design your own perfect getaway and please, bring someone from Vermont with you when you come. 

Hike & Bike Pretty Trails

Giant maple trees glow yellow over Winonas hiking trails in the fall.

A hundred miles of hiking and biking trails offer plenty of spots for a picnic

When leaves start to turn, our bluffs are transformed into a symphony of color, and when the rest of Minnesota is done, we are still going strong down here in the southeastern corner of the state.

Bonus: The bluffs and river valley that cradle Winona are crisscrossed with more than 100 miles of trails made for meandering. Bring a picnic, a camera, and someone to hold hands with. You’re going to want to stay awhile and wander. 

Pick your new favorite trail HERE or make a week out of it and hike them all.

 

Paddle with Pelicans

Canoers paddle by flock of pelicans

Huge flocks of pelicans and swans grace the river at Winona each fall

Or swans, or any of the other hundred species of birds that travel through the Mississippi River Valley each spring and fall. Don’t have a boat? No problem. Prairie Island Campground has canoes, kayaks and standup paddleboards available for rent, and you can put into the backwaters of the Mississippi River right there.

Bonus: Virtually every island and sandbar you see on our stretch of river is public land and you are welcome to pull up and sit for a spell or even pitch a tent and camp if you want to. You can thank John Latsch for that one – he bought it all up a century ago and gave it to us. Now THAT is a gift that keeps on giving. 

You can paddle our pretty Lake Winona too with a watercraft from Lake Park Lodge, situated right on East Lake Winona. 

Get Above it All

If you think the Mississippi River Valley is beautiful from down below, wait until you see it from the top of the bluffs. There are a few different routes up, depending on how adventurous you’re feeling, but each of them offers a spectacular vista of river and bluffs that stretches as far as the eye can see.

An aerial view of Winona shows Sugar Loaf rising high above the city

The view from the top of Sugar Loaf is hard to beat. 

Winona’s easiest choice is Garvin Heights, a park and lookout above the city that has a large parking area and handicap-accessible paved trail to the overlook.

Great River Bluffs State Park south of Winona is also easy to access and offers several vantage points for viewing the river valley.

Just north of Winona, John Latsch State Park has got a 450-foot-tall bluff peak where you can gaze at the river if you are willing to brave the half-mile of stairs that will take you there.

And for the most adventurous, rock climbing our city pinnacle, Sugar Loaf, to the top provides the most exhilarating view of all. Bonus: There is an outfitter in town that will help you do it. 

Soak Up Live Music

A national bluegrass band performs under big stage lights at Boats and Bluegrass

Multiple stages and a top-notch lineup make Boats and Bluegrass the region’s favorite festival.

Winona’s annual Boats & Bluegrass Festival kicks off at the end of September with another huge lineup of regional and national acts that will draw more than 1,500 people to the shores of the Mississippi River. The three-day event, now in its 16th year, is legendary for its chill, family-friendly vibe and it routinely sells out. But camping packages and single-day tickets are still available, so grab them now. 

Bonus: If you don’t make it to the festival, Winona is still chockfull of live music every weekend at coffeehouses, bars, and concert venues around town. Whether you like folksy singer-songwriters or pounding indie rock, it’s here and it’s amazing. 

 

Discover Local Flavors

Beer taps at Island City Brewing Company pour unique microbrews

Local brews and lots of events make Island City Brewing Co. a favorite Winona spot.

It’s fun to taste new things, and Winona delivers a hefty dose of delicious local fare. New and long-standing eateries and drinkeries dot our fine city, each with its own unique goodness, and you’re going to find some new favorites here. From mouthwatering burgers to gourmet specialties, Winona’s food scene has blossomed during the last decade with venues that food critics call out by name. 

Bonus: A downtown brewery and a collection of local wineries add eclectic flavors to our landscape. And pick up a Winona Visitor Guide when you come because a coupon page inside will get you into some of our favorite spots for a steal.