Roadtripping Lake Pepin


One of the most beautiful stretches of Minnesota is found between Red Wing and Winona, along the Mississippi River. To be truthful, we owe a lot of credit to Wisconsin, as Lake Pepin is hard to enjoy wholly from only one of the two states. While I call this piece Roadtripping Lake Pepin, it’s somewhat of a misnomer. Feel free to end your trip when Lake Pepin does by crossing over to Wisconsin on Highway 25 at Wabasha, but I’d recommend seeing it through all the way down to Winona. This is a trip I’ve made each fall for many years and the adventure doesn’t feel complete without seeing a fair stretch of Bluff Country.


The most important facet of a roadtrip is settling on the parameters. Know your audience and your objectives. Coffee within the first hour is important, probably still within the Metro Area…perhaps while still within walking distance of home. Never go with more than one person per window, nobody wants to straddle the hump in the backseat without being able to see more than the trunks of the trees along the roadside. Music is key, let the persnickety one pick it. Never ever start with a wine tasting in Hastings as everyone will require naps before you even get to Lake Pepin. There’s living and learning and each year’s roadtrip is usually better than the last.

We’ve got about eight hours and many miles to go–very few places will make the cut; others will merit their own trips. For instance, we’re roadtripping–it’s not a day for hiking or biking Frontenac State Park. It could be a good reconnaissance mission for an overnighter in the future, but plan to be home by nightfall. And, depending upon your group of travelers, it could be all about food, art, window-shopping, antiquing, or all of the above. There are so very many options.

Because so much of the Minnesota side of the route is accessible for shorter day trips, I focus on how to do the whole loop in a day, most of the stops occurring on the Wisconsin side. This is not a slight to our fair state, but more a look at how a region is experienced. Given that much of the Minnesota side involves high-speed travel down Highway 61 with exits and turns into the river towns, I find the slower pace that takes me through the river towns that flank the Great River Road (Highway 35) in Wisconsin to be preferred. We’re driving the main drags and looking inside the storefronts of history; quaint and industrial, artistic and plain, bleak and optimistic. All of it, wonderful.

The Route

It begins in Hastings on Highway 61/63 and continues all the way down Winona to cross to Wisconsin on Winona Street (43) and turn north on the Great River Road (35) at the “T.” When all the way up to just north of Bay City, you can cross back over to Red Wing on 63 or wait until Prescott when 35 brings you to 10 that will cross you back to Hastings. Check out your maps, plot your course. My friend Matt went down in hysterical lore the year he told me to just “turn left” in Winona to get to Wisconsin. As his luck would have it, the exact place I “turned left” got us precisely where we needed to be. Still, I like to have a little better sense of where I’m going than that.


Once you’re clipping along on Highway 61 going south from Hastings, you’ll see signs for places that deserve a separate trip. Alexis Bailley Vineyards is toward the very start of the journey. Red Wing beckons the window-shoppers in the vehicle, but stopping too early might mean losing momentum for getting around the lake. It’s important to establish the taskmaster of the journey as sometimes there is navigational enforcement to be done…like when passing a store called the Uffda Shop. Also, be sure to look to your right as you leave Red Wing; an unexpected architectural delight is to be found in the Minnesota Correctional Facility there. On to Lake City, there are the sights of Lake Pepin to behold: sailboats, a marina, and the only lighthouse on the Mississippi River. Grab some apples at the Pepin Heights store, take some time to drink it in, but then keep on going…much of your destination lies ahead of you. Wabasha has a great shopping area as well as the National Eagle Center. Typically, I tour through the town with a stop for chocolate and coffee at The Chocolate Escape and a drive-by nod to the Eagle Center, right on the riverfront. Because Wabasha requires getting off the highway and finding your way through the town streets, it might be easily skipped in case you’re feeling hunger pains and want to get to the lunch destination in Wisconsin sooner than later.

Winona is as much an active, working city as the ones you just left for the day. What surprised me the last time I went around Lake Pepin was the jewel in the crown of Minnesota’s art scene, the Minnesota Marine Art Museum, peacefully and quietly existing down in the riverfront college town of Winona. There are visiting collections (Norman Rockwell was particularly delightful last year) as well as a permanent collection that knocked me off my feet. Impressionist and Post-Impressionist paintings of international importance are contained within the attractive, weathered cedar-shake building on the Mississippi, including works by Bradford, Buttersworth, Cole, Homer, Monet, O’Keeffe, Picasso, Pissarro, Renoir and Van Gogh. Each time I turned a corner, I gasped at who and what I saw hanging on the wall. Delightful. If you choose to do the roadtrip in a clockwise fashion, instead of starting in Minnesota and going counterclockwise, I recommend stopping at the museum in the late afternoon before going to dinner at one of the fine restaurants in Red Wing.


Once you’ve crossed over from Winona to Highway 35 in Wisconsin, the first town you’ll encounter to the north is Fountain City. Set in the bluffs, my annual lunch destination is up the hill from the highway: The Monarch Public House. A quiet, historical place by day (but what looks to be a Packer bar by night), The Monarch has been serving travelers since 1894. A brewhouse and restaurant, it always sates us by the time we get there for a late lunch. I order the same burger every year, the “I Am Uncle Harry’s Burger,” a “big, juicy burger with a thrilling combination of cheddar, bistro mustard sauce, chopped green olives, and thinly sliced onion.” It never fails to please.

Fed and happy, we proceed north on the Great River Road. If someone needs to stretch a bit, checking out Lock and Dam 4 at Alma is fascinating…but we usually plod onward to Nelson for an ice cream cone at The Original Nelson Cheese Factory (more loosely known as the Nelson Creamery). The blueberry ice cream is divine and, even when you see the line stretching outside the door to get some, it’s worth the fleeting wait…whichever the flavor. Plenty of motorcycles line the road and the crowd is a mix and match of people looking for cheese, wine, ice cream, or a meal of sandwiches, soups, and pizza. We’re usually stuffed by then, and more so with the ice cream, so our stop is often short and sweet.

North of Nelson is the town of Pepin. Pepin hosts gorgeous and interesting art in its shops and is a required stop for anyone looking for a stroll along the water. My first destination is Great River Coffee Roasters on Highway 35 before heading down to the waterfront to park and browse through the shops. Antiques, garden gifts, art, and novelties await in Pepin. And, if you’re there for lunch or supper, The Harbor View Café is historically popular—with reason—and has pleasing coq au vin and Swedish meatballs.

Stockholm is the belle of the ball. I look forward to getting to Stockholm all year. It’s been the topic of foodie buzz recently due to the “Pizza Farm” at AtoZ Produce and Bakery (which only serves pizza on Tuesdays) but it also has events like a film festival and Christmas in Stockholm that draw people to its fine locale. What so appeals to me is the use of the historical buildings along Highway 35. A house has been turned into The Palate with aporch and lower level full of kitchen implements, gourmet ingredients, décor, and wine. Bogus Creek Café & Bakery and The Stockholm Pie Company keep us in our sweets. Ingebretsen’s (of Minneapolis) has a smaller, more genteel store which is oh-so-apropos in Stockholm. Gelly’s Pub & Eatery has proven itself invaluable as a place to send someone who’s not interested in window-shopping. OQ Quilts* has handmade treasures and quilting supplies. Stockholm General* stocks Wisconsin foods and wines with delicious samples to taste. A must-see, Abode,* is an artist gallery, an interior design studio, and a home and lifestyle showroom. (*GLBT-Owned.)

Up the hill from Stockholm (past a cemetery that can get pretty creepy as the sun gets lower) is the Maiden Rock Apples, which is where I usually end the formal portion of the tour and buy a sack of apples. Unlike other stops along the way, this location allows you to wander through the trees and pick your own apples or taste and take what they’ve already prepared for purchase. A little hay bale maze is available for the kids, but usually we just sit on it because we think we’re old and tired. The sun gets lower on the farmland of Wisconsin as we sip some cider and prepare for the return trip to the Cities.

A road well-tripped, a river well-traveled.

Check out more of this article on Lavender’s Digital Edition.

5100 Eden Ave, Suite 107 • Edina, MN 55436
©2023 Lavender Media, Inc.