Northwest Quarterly Getaway Guide, Annual 2022

A weekend’s journey is closer than you might think. Check out these fun destinations that are close to home but still feel so far away.

Freeport: Be a Trailblazer in Stephenson County

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Midwest towns may be easy to overlook, especially when you’re mindlessly driving past exits on the interstate and only paying attention to the GPS and notifications that pop up in your travel app. So, what unique stops might you be missing along the way? Be a trailblazer and forge your own path to places off the normal monotony of the highway routine and be enchanted by the beauty and opportunity of Stephenson County.

Visitors rave about the more than 50 miles of hiking and biking trails throughout the countryside. Pick your path and your challenge level and enjoy the views. The Jane Addams Trail offers a relatively flat, 17-mile, paved and compact-aggregate surface perfect for low-intensity, high-volume walking and biking excursions. If you want to take your performance to the next level, continue north into Wisconsin on the Badger State Trail, which is accessible from the Jane Addams Trail. Trailheads at Tutty’s Crossing, in downtown Freeport, Wes Block along the frontage of Highway 20, and in Orangeville, Ill., offer maps and mileage locations to plan your route.

Visitors are invited to rediscover Lake Le-Aqua-Na State Park just north of Lena with equine and hiking trails that are mowed and maintained for easy access. The trails offer gorgeous views of the park’s on-site lake, adjacent farm fields and varying topography. Take full advantage of the amenities offered in the park and book a campsite for your tent or RV to make a weekend of outdoor splendor.

Oakdale Nature Preserve offers year-round opportunities for those seeking leisurely or more-intense exercise. Located just 3 miles south of Freeport on Baileyville Road, Oakdale Nature Preserve offers 133 acres and more than 4 miles of trails that wind through forests, pass streams and cut across restored prairies. This wooded wonderland has many new amenities, including a spacious picnic shelter, a nature-based playground, trail enhancements and wayfinding signage. Fat-tire bikes handle the varied terrain well, and cross-country skis and snowshoes are great in the winter.

Krape Park in Freeport, Hideaway Park in rural Pearl City, Evangeline Forest Walk in Davis, and Dakota Nature Trail in Dakota also offer trails up to 1 mile in length for a short stroll or low-impact outing.

If water trails are more your style, Freeport and Stephenson County can accommodate. Yellow Creek is accessible from Krape Park with shaded scenery and limestone caves to watch and wonder. From the park, launch your own vessel or rent a paddle boat from park staff for a family adventure or quiet rendezvous. The Pecatonica River meanders for 30 miles through Stephenson County from Winslow through downtown Freeport at Tutty’s Crossing, before heading east to Atten’s Landing. New ramps were installed in late 2021 with a kayak launch at the Wes Block Trailhead, accessible from Heine Road. This is the perfect berth for your trail voyage by boat, pedal or foot.

A trailblazer is more than a trail-user. A trailblazer takes the time to adventure, make their own memories and find ingenuity in each experience.

A trailblazer knows how to find all there is to offer in Stephenson County.

Monroe, WI: The Art of Main Street Monroe

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Whether it’s your first visit or your 100th, it’s quite likely that your favorite aspect of downtown Monroe, Wis., is the Square.

The Green County Courthouse, built in 1891 and now open for self-guided tours, stands tall in the middle of the Square. Proper squares are rare in Wisconsin, yet the four blocks that comprise it have beautifully preserved buildings in different styles dating back to the middle to late 1800s.

The bustle of downtown Monroe owes thanks, in large part, to its popular retail environment. Main Street Monroe Inc., the nonprofit that handles community development, has been behind the creative spark that has fired up the community.

The retail environment has continued to grow over the past two years. A series of LIVE! shopping nights on social media allowed residents and would-be visitors from around the country to explore the Square’s more than 30 locally owned shops. Participating stores included women’s and men’s clothing boutiques, a toy store owned by a couple who started the business with their autistic son in mind, a jewelry store that celebrated 100 years in 2021, and a third-generation gift and framing shop that’s owned by a father and his son.

Main Street Monroe has a multi-year program called Project Pop Up, and multiple pop-up shops have not only opened but established long-term leases through this program. Four new businesses, ranging from a protein and shake spot to a doughnut cafe, have opened downtown in the past year.

The creative spark has also led to a downtown with synergy between businesses as once- empty niches fill up with attractions like chocolate and candy shops, breakfast spots and restaurants with cuisine ranging from locally inspired to classic Wisconsin.

Keeping a historical district thriving takes creative thinking – in the buildings and outside. Main Street Monroe has a reputation statewide for using public art installations to provide a family-friendly event that lasts a day or a weekend. This year, the 11th annual Cheese Glorious Cheese, a nod to Green County Cheese Days, is held in September for the first time in four years. It’s a celebration of all things loved in Monroe, the region and Wisconsin.

Twenty local artists will be creating pieces this year, and that’s also contributing to the buzz. 
“We never want to take it too seriously,” says Jordan Nordby, executive director of Main Street Monroe. “We always want it to be fun, because it’s family-friendly. We think about an elementary school student and how they’ll react as much as we think about their parents and grandparents.”

Nordby enjoys watching kids lead their family members to one piece after another with carefree, youthful excitement.

“It’s pure joy,” he says. 

This year will also include larger-than-life wood carvings. The pieces from local artists will be 5.5 feet tall and include parts in the shape of cheese wedges.

The art installation, restaurants and shops mean there’s more than enough to occupy a weekend. Throw in a popular summer block party concert series, classic car show, producers-only farmers market and a summer kickoff event, and you may just be saying your favorite part of visiting Monroe is the actual Square – and all that it offers.

To start planning a getaway trip to Monroe, head over to