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My favorite date of the whole year happens in the back half of October, when the bluffs along the Mississippi go copper and gold and the tourists of summer have mostly gone home. You get the river road nearly to yourselves, the air has that cider smell, and every stop feels like a discovery even if you’ve been there a dozen times.
This is the fall date I’d plan for you if you were staying with us in Prescott: a slow breakfast, a drive south on Highway 35, a bluff-top hike, a cider flight, pie, and dinner at a little café on the water that doesn’t take reservations. It works from mid-October into November, with a few timing notes at the end that matter more than usual this year.
Don’t rush the morning. Walk to The Kitchen Table on Broad Street and split the Hangover Hash and the Lobster and Asparagus Benny so you each get a bite of both. Or, if one of you isn’t a big-breakfast person, take two lattes up to the loft at the Twisted Oak Coffee House and sit by the window for a while.
Before you leave town, drive up to Freedom Park on the bluff. It’s the official start of Wisconsin’s Great River Road, and from the overlook you can see the blue St. Croix meet the brown Mississippi. In October the trees on the Minnesota side light up, and it’s the best first photo of your day.
From Prescott, Highway 35 runs south along the river through Diamond Bluff, Hager City and Bay City before the road climbs and dips along Lake Pepin, the wide stretch of the Mississippi between Bay City and Pepin. The bluffs rise right off the road here, and fall color usually peaks around the second or third week of October, though every year is a little different. Check the Travel Wisconsin Fall Color Report the week of your trip.
Insider tip: Use the scenic pull-offs. There’s one just outside Stockholm and another just north of Pepin, and they’re the safest way to get that photo of the river stretched out below the bluffs.
This is the part of the day you’ll talk about later. Maiden Rock Bluff State Natural Area is a 263-acre preserve owned by the Wisconsin DNR, and the bluff itself is a limestone wall that rises about 400 feet above the river and stretches nearly a mile. A 1.5-mile loop takes you through prairie and oak woods to a series of clearings and an overlook right at the edge of the cliff, with all of Lake Pepin spread out below you.
The bluff carries a legend about a young woman who leapt from the ledge rather than marry against her will, and standing up there, you’ll understand why the story stuck. Keep an eye on the sky: this is one of only a handful of natural bluffs in Wisconsin where peregrine falcons nest, and bald eagles ride the updrafts along the face.
Insider tip: There’s no fence at the edge and the rock can be slick with leaves, so wear real shoes and keep a hand on each other. To get there, take County J north from Highway 35 in Stockholm, then County E, then Long Lane to the small lot. It’s free.
Just down the hill, Maiden Rock Winery and Cidery sits in an orchard on the bluff between Maiden Rock and Stockholm. Order a cider flight and find a spot outside if the sun’s out. Their hard ciders are small-batch and gluten-free, and the Honeycrisp and Red Hawk are the ones I’d start with. They make fruit wines too, plus apple strudel, jams and jellies that make good souvenirs. It’s dog-friendly, there are lawn games, and on a sunny October afternoon it’s hard to leave.
Insider tip: They’re closed Tuesday and Wednesday, and late-season hours can change, so call ahead if you’re going in November.
Stockholm is a village of about 100 people, settled by Swedish families in 1854, and it’s home to what USA Today readers named the best pie shop in America two years running. Stockholm Pie and General Store makes more than 40 varieties over the year. Get two slices and share: the Kentucky Bourbon Chocolate Walnut and the Lingonberry Lemon are a perfect pair. If you can’t decide, ask about a pie flight. Then wander the general store for old-fashioned candy, Wisconsin cheese and a bottle of local wine for later.
While you’re in town, step into Indigo Swan, a jewelry and fine art gallery representing about 60 artists. It’s the kind of place where a little something becomes the souvenir of the trip.
Ten minutes farther, Pepin sits right on the water, and you have two great choices.
The Harbor View has been a river-road institution since 1980. There are no printed menus. Instead, the day’s dishes are written on the original chalkboard and updated through the evening. Their best-known plate is pan-fried halibut with black butter caper sauce, and I’ve never seen anyone regret ordering it. They don’t take reservations, so put your name in, grab a glass of wine and wait by the marina. That wait is part of the date.
If you’d rather feel like you flew to Italy, Villa Bellezza is built like a little hill town around a piazza with a fountain. Order a bottle of their wine and a wood-fired pizza from the brick oven at il Forno, and if it’s chilly, ask for a seat under the heated porticos. If your date falls on the third Thursday of November, that’s usually when they release their Pepin Nouveau, the first wine of the season.
Make downtown Prescott your home base and book direct with us: The Port of Prescott for boutique king suites steps from the river, Port After Dark for romantic suites made for couples, The Harbor Hotel for themed rooms and extended stays, and The Cove Guest House for downtown condos and group getaways.
Planning a romantic weekend? See our romantic getaways in Prescott.
