Featured Stories
Adventures worth sharing, from the Wayward Community, published periodically
A Holiday Weekend in Kankakee County
Kankakee County has something for everybody during the holiday season. Over this 48-hour kid-friendly adventure we package up Kankakee County’s holiday lights, Christkindl markets, architectural history, children's museum, nature, food and drinks, and even sightings of Santa Claus and reindeer.
Trails and Taprooms Adventure in Verona, Wisconsin
One of the best parts of adventuring around Verona is its access to an abundance of trails. From biking and hiking to straight-up exploring, you can make your way along paved pathways and gravel greenways through rolling farmland, vast woodlands, and boundless prairie. Especially during peak fall season, an adventure in this nature-surrounded slice of Wisconsin doesn’t disappoint. And beyond the region’s pristine trails, travelers can also find their fair share of watering holes for craft beer and local wine, book shops and boutique stores, and cozy coffee shops with homemade pastries.
A Perfect Fall Family Adventure on Blue Hill Peninsula
From coffee shops to candy shops, the Blue Hill region and Deer Isle have everything you need to slow down for a weekend and enjoy time together. Making the trip in the Fall, as the leaves begin to turn, gives visitors a picturesque backdrop for the weekend while the tourist crowds remain notably absent. The Blue Hill Peninsula is the ideal locale for a family retreat, one that even the youngest travelers can savor through manageable hikes and peaceful moments.
Pedaling Port: A Weekend on the Interurban Trail
The Ozaukee Interurban Trail is the centerpiece of this biking adventure, offering a picturesque route both north and south of Port Washington. The trail is paved and car-free, which makes it perfect for biking and a stark contrast to biking the city streets of Chicago or Milwaukee.
Arts and Culture Road Trip on Two Wheels
Verona, Wisconsin is an ideal launching point to explore the rich arts, culture, and landscape of the Sugar River Valley, and what better way than via motorcycle? On this long weekend trip we explore the Swiss immigrant heritage of New Glarus, the Scandinavian traditions in Mount Horeb, performing arts at American Players Theatre, the UNESCO World Heritage Site of Taliesin, and more.
Venetian Weekend in Port Washington
Port Washington, a charming lakeside town, is a rare gem of a destination that balances kid-friendly excitement with a bona fide vacation experience for adults. This weekend getaway was a captivating blend of outdoor adventures and relaxation, from a bustling farmers market and playful playgrounds to serene beach strolls and great food for every taste. Port, as the locals call it, is a truly special weekend destination that checks all the right boxes for kids and adults alike.
Quintessential Maine Paddling in the Grand Lakes Region
If you were to close your eyes and picture the Maine wilderness, I’d bet you picture a burly guide navigating the rapids of the Allagash or that same guide sitting at the local haunt telling tales of the bear they hunted last season. Happily, you wouldn’t be so far off describing parts of the Downeast Lakes Region, a swath of land about a four-hour drive from Portland.
A Locavore’s Weekend in Kankakee County, IL
To travel well means to slow down and indulge in a place with a locavore’s mindset. This comes naturally in a place like Kankakee County where the locally grown food, drinks and culture of the small towns make up the fabric of the region.
The Ultimate Summer Adventure Weekend in Kankakee County
What do you get when you pack in paddling, music, scuba diving, and state park camping into one weekend? A whole lot of adventure. Exploring Kankakee County looks and feels different than your average weekend trip from Chicago. Just 50 minutes from The Windy City, the Kankakee River Valley brims with lush nature, great food, interesting history, and a community that’s passionate about sharing its uniqueness with anyone who visits. Here’s how to explore this nature-filled gem of the Midwest.
Paddling, Pints and Swiss Delights
The small community of Paoli, Wisconsin boasts an outsized personality with Midwestern humbleness. Located just 12 miles from downtown Madison, this sweet and savory town is situated in the heart of the Sugar River Valley. Combine this with the rich Swiss heritage of nearby New Glarus and you’ve got yourself a one-of-a-kind Summer weekend that is enough to satisfy adults while also being kid friendly. This section of Sugar River Valley is the perfect playground for a weekend of outdoor adventure that pulls in history, Swiss culture, Wisconsin traditions, incredible paddling, hiking, and a healthy dose of ice cream, because… this is America’s Dairyland after all.
Heritage Days in Unforgettable Forgottonia
The drive to Unforgettable Forgottonia from Chicago is a comfortable and nostalgic one for me. I hadn’t been back since attending Western Illinois University years ago; in the years since I’ve adventured through nearly all 50 states and over 43 countries around the globe. Macomb and Western Illinois dubbed themselves “Forgottonia” after a satirical political movement in the 1970s…
A Different Side of Downeast: A Weekend in Machias, ME
All of Maine’s Vacationland delights with none of the crowds, visit Machias, a quaint and classic riverside town 3.5 hours north of Portland. It would be easy to spend a whole week or more exploring the natural beauty of “downeast” with Machias as your homebase, but for those with only a weekend at their disposal, don’t worry: we’ll cover how to make the most of your time.
48 Hours of Adventure in Lockport and Lemont, IL
“Totally unexpected experiences so close to home. From being pushed out of my comfort zone at The Forge to playing some disc golf at Dellwood, I was surprised about how much we did (and how much history we learned) in such a short period of time.”
48 Hours of Adventure in Kankakee County
Kankakee County serves up endless bike trails, calm river kayaking, and great vibes all summer long. With just an hour(ish) drive southwest of Chicago, you can trade in the brick buildings and city traffic for a weekend of clear-your-head adventure in the open air of Kankakee County.
SUP, Summer?! Adventures in Port Washington, WI
Surfing without the lineup? Biking without the traffic? Port Washington, Wisconsin offers up serious outdoor adventures centered around a delightfully walkable town. Just a 40 minute drive from Milwaukee or 2 hours north of Chicago, this charming harbor town features speakeasies, gastropubs, and fine dining alongside waterfront parks.
Train and Bike Adventure to Unforgettable Forgottonia
This small town on the west side of Illinois, also known as Forgottonia, is the perfect escape for any Chicagoan (or any Midwesterner, really) with an adventurous spirit who wants to explore a quiet town with no shortage of things to do.
Literally Outside: Five Siblings, One Getaway
Not all families grow up escaping into nature on the regular. The Anees family – five siblings and all – spent more time traveling in smaller packs in their younger years, as it was expensive to gear up and get out with that many kids. As they got older, the siblings (now ages 30 to 19) would plan trips together, but typically, just a few of them at a time.
Introducing: Supply Run
Supply Run is a new high-stakes international travel reality show by the team at Uncharted Spirits. Concocted by brothers, Jake and Chad Vanags, the first season of Supply Run starts in late March 2023. You’ll be able to follow it live as a featured trip on Wayward. In the meantime, you can get involved by supporting Supply Run on Kickstarter.
The Wisconsin Winter Experience
Verona, WI sits on the edge of the Driftless Region, allowing easy access to fat tire biking, world-class cross country skiing, snowshoeing, downhill skiing and snowboarding, ice skating, hockey and more. “Hometown, USA” offers all of the amenities of a city with the warmth of a small town.
Trips We Love: Best Wayward Adventures of the Year
Our Wayward community has some of the boldest, most creative adventurers out there, and we always love to show them off! That’s why we gathered some of the best journeys shared on Wayward throughout the year for your vicarious viewing pleasure. See what these crazy kids have been up to in 2022!