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Bring the kids for fun-packed downtown adventures

June 23, 2021
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With its good schools, low crime rates and natural wonders, Wisconsin is a family-friendly place—but still, only a handful of downtowns have what it takes to entertain children and their parents for an afternoon.

These three destinations promise fun daylong outings for the whole family, including children of all ages.


In southwestern Wisconsin’s driftless region, Platteville is a walkable and outdoor adventure-friendly destination with plenty of arts and culture.

Following the signs to downtown, visitors arrive at the museum campus where they can visit both the Mining and Rollo Jamison Museums.

While a museum highlighting mining and cultural history may not seem like a child-friendly attraction, the Rollo Jamison museum features plenty of up-close exhibits highlighting every-day artifacts from pioneer life that will engage a child’s interest, including wagons, toys and instruments. Hands-on opportunities and understandable explanations lead to interesting family discussions. Capping off the visit is a train ride in the yard and a walking tour leading into the 1845 lead mine shaft itself.

Leaving the museum campus and crossing into the heart of the Main Street district, it’s time for a snack.

Depending on the weather and time of day, good options might include 3 Marias Ice Cream, offering a diverse array of traditional and Mexican ice cream flavors, or Badger Bros Coffee, featuring quality custom roasts and a full menu of drinks and snacks.

After your snack, continue walking up Main Street, visiting any shops that speak to you. You might decide to stop at the Rountree Gallery, a cooperatively run art gallery with regularly scheduled classes and speakers, try your hand at hatchet throwing at the Revolutionary War-themed and family-friendly Throwing Seven’s storefront, explore the newly built Platteville Public Library to check out its interactive children’s section and artwork, or walk around the 820-acre University of Wisconsin-Platteville campus with its numerous historic buildings and regularly scheduled activities.

Those up for additional activity might take a hike to the iconic giant M emblazoned on the hillside of the Platteville Mounds just outside town. The stairs to the M itself are well-maintained and fairly moderate for an uphill hike, or you can continue on the ridgetop trail for more views, about two miles round trip. The trailhead is located on West Mound Road off of County Road B east of town.

For an easier walk, or for those who brought bikes along, the Rountree Branch Trail parallels the Rountree Branch of the Little Platte River. It is paved and even lit on the areas closer to town. The trail can be accessed from either the Wisconsin Welcome Center at Highway 151 and Staley Avenue, or near the dog park east on Mineral Street. It extends along the Mound View State Trail eight miles to Belmont, home of the first Wisconsin State Capitol historic site and museum which itself is worth a visit, if you make it that far.

Returning to downtown Platteville, make time for dinner before hitting the road. Steve’s Pizza Palace offers made-from-scratch pizza, including gluten-free options, and a wide variety of craft beer, while Los Amigos offers a wide variety of traditional Mexican cuisine in a colorful and welcoming space. The attached general store offers the chance to take home traditional and hard-to-find food and craft items from Mexico, Central America and South America.


One of the larger Main Street communities, Kenosha offers a big footprint for exploration and its public transit options accommodate a park-once itinerary, which is great for families.

Kenosha has both a Lakefront Trolley and a historic streetcar system that are fun for kids and convenient for families.

By parking near the southern end of downtown, or even at Southport Park, riders (post-COVID, May through September) can hop on the trolley for a small fee per ride or $3.50 for an all-day pass, which also provides access to the historic streetcar. Trolleys can be boarded at any of the marked stops, or simply flag down the driver for pickup along the route. Before arriving at the museum campus, riders will receive a tour of the lakefront and Third Avenue Historic District.

Hop off the trolley once it veers right toward HarborPark and head for the museum campus, home to the Kenosha Public Museum, Dinosaur Discovery Museum and Civil War Museum. Depending on the interests of your family, any of them can be a great option to pass an entertaining few hours.

The Public Museum offers a wide variety of hands-on activities highlighting ecosystems and mammoth digs, featuring the discovery of wooly mammoth remains in the Kenosha area. The Civil War Museum offers life-size dioramas of the Civil War experience which, combined with the 360-degree movie-screen, bring the war to life. And the Dinosaur Discovery Museum provides the requisite collection of giant skeletons beloved by many children coupled with interactive sound and environmental experiences to transport users back to the Mesozoic Era.

After getting your fill of museums, kids can take a break in the lakefront splash pad or stroll the lakefront path along the HarborPark neighborhood to appreciate the giant sculptures on display in the sculpture walk. New sculptures are commissioned and installed every two years as part of the Community Foundation’s Arts Fund.

This is also a great time to take a ride on the two-mile loop of the electric streetcar system to see more of downtown. The ride takes less than half an hour and runs every 15 minutes. The streetcars themselves are painted in the style of a vintage streetcar system from a North American city.

If you visit on a Saturday, don’t miss an opportunity to visit one of two weekly farmer’s markets. From May to October the Kenosha HarborMarket takes over the streets of HarborPark from 9 a.m. -2 p.m. with more than 100 vendors, while the year-round Kenosha Public Market operates on the same schedule out of The Vault Banquet Hall, 625 57th St.

Having worked up an appetite, there are numerous options for lunch.

Some of the most family-friendly and unique-to-Kenosha offerings include the iconic Franks Diner, which occupies a historic train car and serves up traditional diner staples; Trolley Dogs with its kid-friendly menu and colorful décor; or Rustic Road Brewing Company with its large upstairs loft and outdoor patio space.

Once you’re fueled up, either hop back on the streetcar, or visit Total Cyclery, 5039 Sixth Ave., to rent bikes and explore the lakeshore bike trail. Along the trolley, you’ll pass Veterans Park and along the Sixth Avenue corridor, travel by bike provides great views of the marina and lakeshore.

Several of the fishing charters leave from here, if you want to plan for a future trip. Around the bend, you’ll reach Simmons Island and its iconic Southport Light Station, with yet another museum, and expanse of sandy beach.

At the end of the pier at the south end of the island is the North Pier Lighthouse, which is now an art studio and gallery – Kenosha Lighthouse Studio – offering regular shows and events.

After getting your fill of beach time, you can either finish the streetcar loop or continue the bike trail, which both travel north to the Carthage College campus about two miles north or ride back to downtown.

After returning your bikes or reaching downtown, you might want to grab a snack for the road. Sandy’s Popper offers sweet and savory treat options, while The Buzz Café offers caffeinated options for adults. End the day back at Southport Park and say goodbye to Lake Michigan with a walk along the Kenosha Sand Dunes before heading home.


A self-proclaimed “Cool Little River Town,” Polk County’s Osceola delivers on its promise. Its small size makes everything walkable, and there’s plenty to see and do in this scenic town for an afternoon or a day.

To make a day of it, plan ahead and book tickets on the Osceola & St. Croix Valley Railway, which runs weekend 90-minute scenic train tours with fully restored 1916 vintage Soo Line passenger cars.

Alternatively, or if you have more time, you can also rent canoes or kayaks and arrange for a shuttle service from Riverwood Canoe & Kayak to make the seven-mile paddle from Interstate State Park to Osceola. The water trail passes through the deep canyon of the St. Croix Dalles as well as Close’s Slough, a wetland bird habitat along this designated wild and scenic river. The paddle is downstream and takes two to three hours, with plenty of sandbars offering rest and snacking opportunities.

If you arrive in town a bit early for your outing, children will enjoy exploring the new Osceola Discovery Center and Wilberg Memorial Library, walking around Mill Pond Park and along the Osceola Creek, and my children vouch for the quality playground at Oakey Park just north of downtown.

When you’re ready to take a break for lunch or dinner, don’t miss out on one of Osceola’s many outdoor patios. The Watershed Café offers locally-sourced farm-fresh food on their back deck overlooking Geiger Falls, while PY’s Saloon offers a shaded outdoor patio to enjoy fresh fries and pub food menu.

Osceola Lane’s Little Lambeau has a Green Bay Packers-themed outdoor dining ambiance. Visitors have the option of taking their meals to go from any local restaurant and exploring the many picnic areas around town, which can be found on this map.

Once you’ve enjoyed a leisurely meal, it’s time to visit Osceola’s crown jewel and tackle the 156 steps down to Cascade Falls.

Spend some time walking around, behind or even through the falls, and then wander down Wilkie Glen or up the Eagle Bluff Trail to find the best panoramic views of the St. Croix River Valley and downtown from a variety of perspectives.

The trails make it possible to make a loop of less than one and a half miles to experience the best of the falls, bluffs, a natural spring and the river, arriving back at downtown. While short (allow 45 minutes), some sections are steep, so wear good shoes. Insider tip – if you’re still in town in the evening, be sure to stop back at the falls overlook to view the changing colored lighting that provide a completely new perspective.

Once you’ve caught your breath after the climb back up to downtown, take some time to walk along historic North Cascade Street, visiting a variety of local shops offering an eclectic mix of fashion, home goods, gifts, local art and crafts.

Don’t forget to stop and grab an ice cream cone to wrap up a perfect day, either at The Looking Glass, which serves up Cedar Crest scoops and shakes or at Dairy Queen for your traditional favorites.

Depending on which way you leave town, or if you’re staying overnight in the area, you could also schedule a quick side trip to Trollhaugen Outdoor Recreation Area in nearby Dresser, Franconia Sculpture Park just across the river, or Interstate State Park to the north.

Trollhaugen offers skiing in the winter and ziplines and aerial adventures in summer and Interstate offers miles of hiking trails and ferry tours highlighting the area’s glacial past while the sculpture park sits on 50 acres and has a rotating collection of 120 outdoor sculptures, some of which are interactive.

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