9 Prettiest Main Streetscapes In Wisconsin
Wisconsin has some stunning main streets and beautiful small towns with charm and charisma. Sheboygan, for example, with its stunning Lake Michigan shoreline, is affectionately called “the Malibu of the Midwest.” While some of these gems are incredibly rich in architectural elegance, others excel in charm, gasp-inducing backdrops, or simply lovely streets and storefronts. Many of these streetscapes are Rockwell-esque and hands-down paint-worthy. But which are the prettiest? Starting with Sturgeon Bay, discover below the 9 prettiest streetscapes in Wisconsin.
Sturgeon Bay
Downtown Sturgeon Bay, with its historic brick buildings that overlook the Sturgeon Bay Ship Canal and colorful storefronts that effortlessly draw the attention of passers-by, is a delightful stretch to feast your eyes on. Third Avenue, which serves as the commercial and cultural spine of the city, is a great place to stroll, shop for one-of-a-kind gifts, and explore local arts and crafts. If you want to start the day with a tongue-tingling meal, Door County Fire Company is a relaxed bar and grill serving decadent sandwiches and American comfort food in a former fire station.
From here, weave your way to Door County Maritime Museum, which offers immersive exhibits about the region’s maritime history and shipbuilding heritage. There's the Historic Sturgeon Bay Bridge, an iconic piece of architecture connecting both sides of Sturgeon Bay that was originally built in 1929 and is listed on the National Register of Historic Places. You can drive or walk across the bridge, as you take in the area's peaceful views. For some amazing glass art, Popelka Trenchard Gallery & Glass Studio simply has no peer.
Bayfield
The tiny harbor town of Bayfield, sitting nicely at the edge of the largest of the Great Lakes, forms a gateway to the northern wilderness of the Apostle Islands. Rittenhouse Avenue, the town's corridor of culture, bustles with eye-catching attractions and palpable charm. The street offers fabulous views of Lake Superior and Madeline Island, one-of-a-kind boutiques, and cool, beachy gift shops such as the Brownstone Centre, which keeps Bayfield tee shirts and sweatshirts, as well as the 5-star-rated Bloom, just across the street.
The painting activity at Bloom is ideal for those who simply want to sit, sip, and paint. Many visitors enjoy taking a ride to the Apostle Islands National Lakeshore, an expansive preserve (nearly 70,000 acres) covering 12 miles of cave-studded shoreline. For those who prefer to linger in town, Bayfield Maritime Museum has unique nautical artifacts and demonstrations telling the story of life on an inland sea.
New Glarus
America’s Little Switzerland is surrounded by woodland pastures and rolling hills, and is steeped in Swiss cultural heritage through events like polka festivals and harvest celebrations, as well as museums such as the Swiss Historical Village, which offers a glimpse into 19th-century immigrant life. Start your day at Fat Cat Coffee Works in the heart of downtown, a cozy space offering a diverse selection of homemade goods, including cinnamon rolls and coconut cream pie. The upstairs seating area is a cool spot to relax, while the outdoor patio is ideal for sunny days.
Alternatively, people rave about the charming, local vibe of New Glarus Bakery, a highly cherished gem that has been specializing in Swiss and American treats since 1910. For a breath of crisp air, especially now that you have the energy for some serious adventure, head out on the Sugar River State Trail, which follows an old railroad bed through rolling farmland and woods, or venture into nearby New Glarus Woods State Park, which offers bone-deep tranquility just minutes from the village.
Trempealeau
The signboard that welcomes visitors to Trempealeau is a giant catfish statue mounted near the main roadway. Even if you didn't know anything about the town, you would guess that it has water, and, therefore, some beautiful, rustic scenery to go with it. Trempealeau’s Main Street runs right down toward the Mississippi River, and the area is surrounded by meandering tributaries, inland lakes, and woodsy nature parks, all of which are prominent elements of mind-calming beauty. Start the day with some finely cooked pesto omelets at River Cafe, a small-town culinary gem known for its traditional English breakfasts, before exploring one of Wisconsin's most stunning outdoor gems: the 1,200-acre Perrot State Park.
More than 12 miles of trails here snake through prairie and afford sweeping views from bluffs, while bikers have the opportunity to sample the 24-mile Great River State Trail, which winds conveniently close to the campground. Meanwhile, the Trempealeau National Wildlife Refuge offers excellent bird-watching opportunities and is not to be missed, either.
Minocqua
Minocqua has an old, neat, but touristy downtown with photo-worthy features. It's certainly difficult to wrap your head around the fact that more than 2,000 lakes surround Minocqua. Therefore, for a water-themed adventure, you wouldn't find a town that comes close. Kobe Sushi, centrally located on Oneida Street, which serves as the main drag, is a low-key outpost serving an array of sushi rolls in an indoor environment with cute decor. Right next door is Dan's Minocqua Fudge, the go-to place for kick-ass taffy, super creamy ice cream, and some of the best candy in the world.
After a hearty breakfast, head down to Bearskin Trailhead Park, one of the most scenic trails in the region with killer views on every side. It begins in Minocqua and concludes in Tomahawk, spanning 18 miles along the serene Bearskin Creek. You can rent a sturdy two-wheeler at Z-Best Bikes, about 3 miles away in Woodruff. Alternatively, Torpy Park is a lakefront beauty with a sandy beach, shallow water, and decent picnic areas.
Marinette
Located on the south bank of the Menominee River at its mouth on Green Bay, part of Lake Michigan, Marinette always steals the show with its beautiful shoreline. The area has lakes brimming with trophy fish, stunning ATV and snowmobile trails, and inviting restaurants on Main Street, such as Cafe Green, the go-to place for black bean burgers along with specialty salads and sandwiches. Across the street is Main Street Antique Mall, which offers a great variety of antiques from jewelry to furniture. Marinette County, you may already know, is the Waterfall Capital of Wisconsin.
At some point, you will want to explore the more than a dozen sparkling beauties, typically sampled via a self-guided waterfall tour. But before that, Stephenson Island Park is just around the corner and can serve as an awesome curtain raiser. Expect a pretty waterfront, a museum, a lovely footbridge, and a beautiful Wisconsin welcome sign. There's Mariner Theatre, if you want to catch a show, and enJOY Gifts & Gathering, a gift shop and coffee shop, where you can relax all day in a comfy chair, sipping coffee and reading an interesting book.
Hurley
Hurley is another Wisconsin gem with a beautiful streetscape. You will love its old main strip, interesting gangster history, and low-set two-story buildings. Silver Street, which once boasted 87 saloons and clubs, is today speckled with family-owned restaurants and other business establishments selling a wide variety of items. The Montreal River, which flows through the town, lends the entire stretch a mist of rustic beauty and countryside allure.
Kickstart your trip at Sharon's Coffee Company, a Silver Street joint offering delicious skillets, cinnamon rolls, and avocado toast. With enough energy to walk around, zigzag your way to the Iron County Historical Museum, where you will admire pictures of President John F. Kennedy when he visited Hurley. Of course, many exhibits focus on the area's mining history. Interstate Falls Park, a must-see attraction just a heartbeat from downtown Hurley, features an impressive waterfall with fabulous views.
Sheboygan
About 10 years ago, Sheboygan Squared launched new beautification and streetscaping efforts throughout the District, making the whole area bright and inviting, especially with the added abundance of flowers showing up in the traditional corner planters, mid-street baskets anchored to light poles, and large individual planter boxes. The districts, including Riverfront and South Pier, have noticeable architectural elegance, outstanding restaurants, and a bit of art. The John Michael Kohler Arts Center, which boasts 12 art galleries in 99,000 square feet of space, is one of Sheboygan's most adorable cultural landmarks.
Trattoria Stefano, a well-established culinary gem with excellent reviews, serves upscale Italian cuisine in a casual, rustic setting. It is a real taste of Italy right by Lake Michigan. Meanwhile, City Green is often the site of live music every weekend through the summer. Another unmissable green space is Rotary Riverview Park, a swoon-worthy space with dreamy views of Lake Michigan and a great boardwalk along the Sheboygan River.
Baraboo
Baraboo’s neatly laid downtown teems with late 19th and early 20th-century commercial buildings, most of which are arranged in a cluster around the central Sauk County Courthouse Square. Unlike many towns, Baraboo does not have a single main drag; instead, several key streets serve as its main thoroughfares, including Broadway Street and Water Street. On the Square, the AL. Ringling Theatre, touted as “America’s Prettiest Playhouse,” often runs live events and arthouse films. It is a gift from circus founder Al Ringling and has been an ornate fixture in downtown Baraboo for over 100 years. Coffee Bean Connection, a red brick storefront on 3rd Avenue, roasts on-site and is an idolized name on the local café scene. There's the Carnegie-Schadde Memorial Public Library, a lovely place to curl up with a gripping read. Meanwhile, Driftless Glen Distillery, on a scenic spot along the Baraboo River, offers guided tours of its bourbon and gin operations.
So, what every vacationer should know is that Wisconsin's small towns are not just jumping-off points to some hyper-local outdoor landmark with epic recreational opportunities. Some of these neat, compact spots, whether vibrant or laid-back, have Main Streets that one can spend an entire weekend drooling over. From colorful flower planters to catchy storefronts and sentimental murals, a few of Wisconsin's Main Streets are actually stand-alone attractions.
