It’s the most wonderful time of the year…

Okay, I know. That’s a Christmas song, but as the cooler winds started to blow this Labor Day weekend I knew we were rounding the bend into autumn and those words kept sing-songing through my head.

Winona is pretty all the time, but fall is when Winona is at its most beautiful, in my humble opinion. Starting in a week or two, shades of gold and crimson will creep across the bluffs, casting a warm glow on our hiking and biking trails and the very city that sits beneath them. By the end of the month it will be postcard gorgeous here and travelers from north and south will be heading this way to soak it in.

Indeed, if you’ve never been on the Great River Road in autumn you have no idea what you are missing, because even all my fancy words about it being pretty can’t describe it well enough.

But I’ll try. Picture this: On one side of the road you are hugged by the bright blue Mississippi River, on the other side, a symphony of color rises up hundreds of feet. The best stretch is from Lake City to La Crescent, with colors so brilliant they make you catch your breath, and Winona sits right in the middle of that route.

Bonus, at the base of our bluffs, unlike other towns along the way, are hiking and biking trails that will get you off the road and under the canopy trees for some of the most stunning paths I’ve ever seen anywhere. My hands-down favorite are the trails that start behind Holzinger Lodge, a building at the base of the bluff owned by the city.

There, trails snake back and forth up the side of the bluff, and at their peak every inch of it is bathed in brilliant yellow. Every so often crimson or orange leaves flutter down from a giant maple along the way, and this place feels like a dream filled with beauty and solitude. I go here a lot to walk and think and take pictures, and every time I am taken aback by this place like it’s the first time I saw it.

It’s hard to say exactly when those trails are at their most perfect because Mother Nature is hard to pin on a calendar, but I’d say between the the third week in September and the second week in October is when our colors usually peak here.

Take a look at the pictures below to get an idea of what I’m talking about, but trust me, you will be sad if you don’t come see for yourself.

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