There’s something special about fall in Southern Minnesota—the crisp air, colorful bluffs, and small towns that make you slow down and soak it all in. Whether you’re chasing river views, local bites, or the perfect pumpkin photo op, this part of the state has it all. From train rides and vineyards to cozy cafés and apple orchards, here are a few of my favorite fall day trips and weekend getaways worth adding to your list.
No matter what you are looking for this fall, these southern Minnesota gems make it easy to slow down, take in the colors, and make the most of the season.
My must-see fall destinations in soutern Minnesota
Winona Minnesota
Best for: Seeing the fall colors
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Nestled in Southern Minnesota’s bluff country, Winona is one of the best spots to soak in fall colors. Start your day with a warm Bloedow’s donut, then hike or drive up Sugar Loaf Bluff or Garvin Heights for sweeping views of the river valley. Cross the border into Wisconsin for a glass of wine and live music at Elmaro Vineyards or wood-fired pizza at Winghaven Pizza Farm. Traveling with kids? Ferguson’s Orchard in Galesville WI is a fall wonderland with apple picking, gem mining, and a corn pit that’s sure to be a hit.
Red Wing Minnesota
Best for: Scenic river views and colorful bluffs
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Just a quick 50-minute train ride from St. Paul, Red Wing makes for the perfect fall day trip. Hop on the Amtrak and enjoy the colorful Mississippi River views along the way. Once you’re there, hike Barn Bluff for a postcard-worthy overlook, grab lunch at Scarlet Kitchen & Bar inside the historic St. James Hotel, then wander downtown to shop Red Wing Shoes, Phileo Style, and Forever Adored for local finds and cozy vibes.
La Crosse Wisconsin
Best for: Riverfront views and sunset hikes
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Just a couple hours from the Twin Cities (about 2.5 hours and you’re there), La Crosse offers the kind of crisp, colorful fall escape you’ve been looking for. Start your adventure on the La Crosse Queen riverboat, gliding past majestic bluffs and shimmering water as the leaves turn—all while you sit back and relax. Next up: head to the lookout at Grandad Bluff (hike or drive—your call) to catch that golden-hour glow spreading across the landscape. Then lean into the fun side of fall at the Hidden Trails Corn Maze—you’ll twist, turn, laugh, and maybe get a little lost (in the best way). Finally, wind down by wandering downtown La Crosse: explore the vintage-vibe finds at Drift Mercantile, sip at La Crosse Distilling Co., grab a cozy cup at Global Grounds Coffee Shop, treat yourself at The Pearl Ice Cream Parlor and finish the night with a retro cocktail at Starlite Lounge. If you’re craving fall color, good eats, and just-right relaxation, La Crosse checks all the boxes.
Montgomery Minnesota
Best for: Eating and drinking all things fall
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Just an hour south of the Twin Cities, Montgomery is one of Minnesota’s best-kept small-town secrets. Start your visit with a craft beer at Montgomery Brewing, then grab a slice (or two) at Pizzeria 201, a local favorite tucked in a historic building downtown. Next, unwind with a glass of wine at Next Chapter Winery before heading to Montgomery Orchard for classic fall fun—apple picking, cider flights, a corn maze, and cozy hayrides. With great food, friendly locals, and plenty of autumn charm, Montgomery proves you don’t have to go far to feel worlds away.
