How to Spend a Weekend in Bluff Country
Comprised of a network of roadways that wander and wind along the Mississippi River from Minnesota to the Gulf of Mexico, the Great River Road stretches for 3,000 miles through 10 states. And you know what? We think Minnesota’s 565-mile section is the best part of the whole shebang.
That’s because it runs through Bluff Country, a very scenic and easy parkway-style drive that’s perfect for a weekend road trip. There’s plenty to see and do in Bluff Country any time of the year, but fall is the most popular time to go because of all the stunning leaf peeping available. (Check out the Department of Natural Resources’ Fall Color Finder to track when autumn colors peak each year.)
Regardless of when you visit, once you land at MSP and get in your rental car, your Bluff Country adventure begins by heading east!
Friday
Shop in Stillwater
Get going on a short and sweet 30-minute drive to your first stop, Minnesota’s beloved Stillwater. This small and scenic riverside town has a bustling downtown brimming with something for everyone, so start your weekend with some local shopping.
There are many local shops like Black Letter Books which carries everything from kids’ books to literature, poetry, first editions, and gently used paperbacks. All Things Sheard offers cute and crafty Alpaca-inspired and Alpaca fleece-based gifts and goodies that make great souvenirs, as does Art N Soul thanks to its many beads, rocks, fossils, and precious stones.
There’s also Candyland, Barbara Ann’s Fudge Shoppe, and Grandpa Joe’s for stocking up on sweets for the rest of your road trip as well as lots of vintage, antique, and clothes shopping options, too.
Once you’ve shopped and strolled until you’re ready to drop, fuel up for the rest of your day with lunch at Brick & Bourbon. This local spot focuses on fresh ingredients for its dishes and many, many cocktails and spirits to accompany them.
It’s also got a really great patio!
Seize the Season Outside
The best thing about Stillwater is that there’s something excellent to do outside any time of the year.
If you’re visiting during the spring or summer, the best thing to do with your late afternoon is to head to the nearby St. Croix Vineyards. It was started in 1992 and features a tasting room housed in a restored 100-year-old barn, wine tastings, winemaking tours, $15 wine flights, and plenty of live music on summer Saturdays. Be sure to check out their event page since there’s usually something special going on (think wine glass painting and cheese and chocolate weekends).
For visitors enjoying Stillwater in the fall, ‘tis the season for all things autumnal. Aamdot’s Apple Farm has all of the family-friendly fall activities you could want. There’s apple picking among their Honeycrisp, First Kiss, Pazzaz, Haralson, and Keepsake varieties as well as wagon rides, a hay bale maze, pony rides, and plenty of chances to enjoy the cute goats that live there all year long.
For those who like to adventure during the winter, you have to check to see if your trip aligns with the town’s annual World Snow Celebration each January. The best part of the celebration is the World Snow Sculpting Championship that hosts teams from around the world who compete to craft the best snow sculpture in exchange for prize money and a championship title.
If you’re visiting outside of the short window of the snow sculpture events, you’ve got to book a hot air balloon ride instead. The solitude and silence that comes with a winter flight can’t be beat, plus it’s one of the best ways to take in the beauty of the landscape.
Settle in at a Local Hotel
When the evening rolls around and you’re all adventured out, it’s time to settle in for the night at the 13-suite Hotel Crosby. This sweet little property comes complete with a rooftop hot tub and Matchstick Restaurant and Spirits on its ground level, a lovely spot that features farm-to-table sharable small plates and over 700 rare and unique spirits.
Don’t worry; there are lots of wine and beer choices, too.
Saturday
Ease on Down the Great River Road
Start your day with a quick and easy but also very tasty breakfast of coffee and pastries at Mon Petit Cheri, a French-ish bakery with a sprawling espresso offerings and a range of breakfast dishes, too. They don’t take reservations, so just head on in.
From there, it’s time to continue your drive down the bluff-filled, Mississippi River-adjacent Great River Road towards Red Wing, home of the famous boots of the same name. Be sure to take it slow and easy so you can take in the stunning landscape without rushing.
Shop for Red Wings in Red Wing
In just under an hour, you’ll be in Red Wing that’s home to the flagship Red Wing Shoe Store. Not only does it feature a giant boot and a company museum, the store’s lower level is home to an extensive selection of discounted boots and shoes that comprise an outlet.
If you’re a fan of Red Wings or just well-made leather footwear in general, this is the place to shop because the price is right.
Frolic in Frontenac and Swing by Wabasha
Next, scoot just 15 minutes further down the Great River Road to Frontenac State Park tucked along the tree-filled shores of the Mississippi River. Frontenac is home to 13 miles of hiking trails and just over seven miles of cross-country ski trails, but the best part is all the birds you’ll see here. From bald eagles to sedge wrens, Frontenac is home to a whopping 273 species — the highest of any park in the state.
Once you’ve stretched your legs and seen birds sail the skies, it’s time to get back in the car for another 30-ish minutes to the Wabasha Overlook, a roadside attraction that offers easily-accessible and super sweeping views of the river and beyond. Linger over the views, take scenic photos, or capture a selfie to remember the trip by.
Wind Things Down in Winona
Another half hour or so down the road lies Winona (after which Winona Ryder is named!), which is where you’ll want to spend the night so that you’re ready to explore it in the morning.
Rest your head at the Alexander Mansion Bed and Breakfast, a Victorian delight that offers breakfast in four or five courses.
Sunday
Take a Self-Guided Glass Tour
Once you’ve had an elaborate breakfast at the hotel, download the eATLAS app and take yourself on a stained glass tour of the town known as the stained glass capital of America — home to a whopping six stained glass studios. The self-guided tour includes 16 stops that encompass photo stops and exclusive discounts that get unlocked along the way.
Swing By Lake Park
This city park encircles Lake Winona is a family-friendly gem any time of the year. In the warmer months, rent canoes, kayaks, or paddleboards to hit the water and stop by Every Child’s Dream, an inclusive and accessible playground that clocks in at more than 16,000 square feet.
In the winter, opt for skate rentals to glide across the natural ice rink or go for shoe shoes for a trekking adventure instead.
Lunch at a Local Wine & Cocktail Bar
Before you get back in the car to head back to MSP and ultimately home, enjoy a super local lunch at Muddled Thyme. It serves up craft cocktails that incorporate extracts from the Winona-based Watkins company, as well as Neapolitan-style pizzas fresh out of a brick oven.
