
Photos by Caitlin Abrams
Small town store front
It’s always a relaxing wait for scratch cooking from the iconic Harbor View Café.
Harbor View Café
For 40 seasons, this scratch kitchen has been cooking fresh food made with all the bright and vibrant ingredients of the region. By working with local produce farmers, butchers, dairy farmers, cheesemakers, and others from its community, it’s cultivated a unique and comforting small-town, big-flavored taste of the valley. 314 1st St., Pepin, WI, 715-442-3893, harborviewpepin.com
Stockholm Pie and General Store
The original pie shop (there’s a newer outpost in Red Wing) is a must-stop destination. You will regret it the whole ride home if you skip. You’ll understand when you have to make the choice between an apple blackberry pie touched with cardamom or a lingonberry lemon that remains a sweet/tart classic. Note that a whole banana cream pie needs a 48-hour notice, it’s that special, but you can get the upper Midwest favorite raisin sour cream pie most of the time. If you are planning for an October trip, the pumpkin pecan combo pie is clearly the move. N2030 Spring St., Stockholm, WI, 715-442-5505, stockholmpieandgeneralstore.com

Assortment of pies
Good luck picking a favorite at Stockholm Pie and General Store.
Reads Landing Brewing Company
River watching reaches an art form here. Mainly because you can work your way through the list of seasonal housemade beers while you watch the kayakers and barges flow by. This part in the river never freezes over during the colder months, making it an eagle-watching hot spot. Spying on mighty birds while digging into fish fry, hefty sandwiches, and other tavern fare is a great way to spend an afternoon. 70555 202nd Ave., Reads Landing, 651-560-4777, rlbrewingco.com
Hager Heights Drive-In
This family-run drive-in usually closes at the end of September, so get a jump on it if you’re seeking its famous “broasted” chicken. The crisp bird is light and crunchy with a full shake of seasoning. Grab a bucket of chicken only, or go for the full dinner option with coleslaw and fries (or mashed potatoes if there’s a nip in the air). 7866 170th Ave., Hager City, WI, 715-792-2118, facebook.com, Hager-Heights-Drive-In
Nelson Cheese Factory
Picnic people in the know head straight to Nelson. In this former cheese factory turned foodist paradise, you can find cheeses from all over, artisan breads, locally cured meats, and other goodies to pack a basket. Or grab one of its pizzas if it’s Thursday through Sunday, and take some time on the flagstone patio with beer and wine. S237 WI-35, Nelson, WI, 715-673-4725, nelsoncheese.com
Penguin Zesto East
Do not leave town without a stop at this ice cream shop. Serving since 1949, this red-and-white-striped barn churns out serious banana-split-and-hot-fudge sundaes, frozen Zingers, toasted coconut–dipped cones, and so much more. 602 E. 3rd St., Winona, 507-452-9444
Plus Three More:
Flowing water means good beer and ciders.
Turning Waters Brewing Co.
When bed & breakfast owners get into craft brewing, they turn their garage into a brewery and taproom. At least they do in Wabasha, where Turning Waters Brewing was created as an outdoor gathering space for guests of the inn. Of course, it’s grown and now makes Hoppy Girl beers while serving pub pizzas and Cedar Crest ice cream and even hosting beer dinners from time to time. 136 Bridge Ave., Wabasha, turningwatersbrewing.com
Spiral Brewery
Hastings was a rich brewing town until Prohibition cleared it out. Spiral Brewery, the first to open there since that dark time, is now flying the flag for craft brewing. With 2nd Street in front of the brewery closed off to create more outdoor drinking space and live music scheduled on Friday nights through September, it feels almost normal to be sipping a Mississippi Fog Hazy IPA or a Töwnie Kölsch on a warm autumn night. 111 E. 2nd St., Hastings, spiralbrewery.com
Maiden Rock Winery & Cidery
The best evolution happens when orchards start pressing and fermenting fruits. Maiden Rock’s premium ciders are a great result of that development, from the semi-dry sparkling Scrumpy cider to the new Kingston Black semi-sweet still cider. Head out for typical apple orchard fun, but don’t forget to sample the ciders and fruit wines before heading out on any wagon rides. W12266 King Ln., Stockholm, WI, maidenrockapples winerycidery.com

Bottles of cider
Find Local Wine
Great River Road Wine Trail
Maybe you didn’t know there was wine country in Minnesota and Wisconsin. OK, it’s no Napa Valley, but the Great River Road Wine Trail, winding and curling through the Upper Mississippi River Valley, is worth a meander. No fewer than 10 wineries populate the trail, which stretches on both sides of the region from Cannon Falls down to La Crosse before dipping down for a stop at Eagles Landing Winery in Marquette, Iowa.
Starting at Cannon River Winery, grab a map and a passport, which can be stamped in each tasting room as you make your way. Some stops, like Falconer Vineyards and Maiden Rock, also have hard cider for sampling and purchase. And others, like Villa Bellezza Winery, in Pepin, offer restaurant seating (you’ll need some of its chewy-crust pizzas).
Be prepared: Some of these wineries nestled in bluff country will surprise you and may shift your thinking about locally grown wine. greatriverroad winetrail.org
Please check online or call ahead for updates and current hours.