The Scene

Midwest road-trip destinations perfect for weekend getaways

Waterfront in Sheboygan, Wisconsin

This season, explore the rich tapestry of the Midwest with a road trip!

From relaxing along the lake in Wisconsin or Michigan to breathtaking natural wonders in Shawnee National Forest, these destinations offer something for every adventurer.

Whether you crave a weekend getaway or a week-long odyssey, buckle up and get ready to discover hidden gems, iconic landmarks and small-town charm, all less than a day’s drive from northern Illinois.

Let’s map out your perfect Midwest adventure with these top road-trip destinations!

Shawnee National Forest, Southern Illinois

This national forest, tucked between the Ohio and Mississippi rivers in southern Illinois, has so much to do and see. Explore the more than 289,000 acres of rolling hills, rugged bluffs and oak hickory forest. Shawnee has camping, horseback riding, hiking, biking, water activities, fishing, beaches, climbing, scenic driving and more. The forest is home to such attractions as the famed Garden of the Gods wilderness and recreation area, Bay Creek Lake, Jackson Falls and many more. The area is rich in Native American history, including the Trail of Tears National Historic Trail and forest sites used in the Underground Railroad. You can camp in one of many campgrounds in the forest, rent a cabin or stay in a hotel or Airbnb in a nearby town. Some towns located near the forest are Marion, Carbondale and Murphysboro; all have hotels if roughing it in the wilderness isn’t your cup of tea.

While you’re there, check out the Shawnee Hills Wine Trail, which has 11 award-winning wineries along a 35-mile scenic drive on Illinois Route 127 and U.S. Route 51.

Visit the nearby city of Metropolis and snap a selfie with the 15-foot-tall Superman statue.

Sheboygan, Wisconsin

A sailboat on Lake Michigan in Sheboygan, Wisconsin.

Located along Lake Michigan between Green Bay and Milwaukee, Sheboygan has it all, from world-class golf courses and spas to history, art and even surfing! According to the Sheboygan Visitor’s Center, the city has been dubbed the “Malibu of the Midwest” for its surfing scene.

Spend the day at the city’s sandy lakefront beaches for swimming, boating, kayaking or fishing. The charming city center has boutiques, many breweries and pubs, fine dining and fast-casual favorites. Hike through Indian Mound Park, which is listed on the National Register of Historic Places, and has 18 Indian burial mounds spread across 15 acres. If you’re looking for unique art, check out the John Michael Kohler Arts Center’s world-class art collection, and browse the city’s street murals or the Sheboygan Visual Artists’ work at EBCO ArtWorks.

If you’re traveling with kids, consider the Blue Harbor Resort, situated on the lakefront. It has an indoor water park, arcade and two indoor mini-golf courses. Relax with a massage or facial at the resort’s Reflections Spa.

For more information about Sheboygan, go to

Saugatuck/Holland, Michigan

Oval Beach in Saugatuck, Michigan

Known as the Art Coast of Michigan, Saugatuck is a one-of-a-kind small town located along the shores of Lake Michigan. The area has pristine beaches and waterways, lush forests and sand dunes. Enjoy an afternoon on a boat, take a ride on the dunes, explore the Saugatuck Harbor Natural Area with a hike, or climb Mt. Baldhead for a gorgeous view of the lake and coast. Stroll through the area’s art galleries and studios, and shop in the cozy downtown area, taking advantage of the many unique retailers. There’s a variety of lodging available, including B&Bs, historic inns, resorts, hotels and rental cabins and cottages.

Just over 10 miles north of Saugatuck is Holland, Michigan, where you’ll find a taste of the Netherlands along the lake coast.

The windmill and tulip fields in Holland, Michigan.

The city’s rich Dutch history is on full display in the city’s architecture in the downtown area, in the Dutch treats and goods in local shops and restaurants, and in the many Dutch-themed events throughout the year. Popular events include the Tulip Time Festival and Magic at the Mill. A trip to Holland wouldn’t be complete without a visit to the famed DeZwaan Windmill, Nelis’ Dutch Village or the Veldheer Tulip Farm. For a relaxing day, visit Holland State Park Beach and Tunnel Park Beach. Take a long bike ride or hike along the area’s many trails. For the golfers in your group, the area has several public courses. A variety of lodging abounds, from camping to cabins to luxury hotels and everything in between, so you’ll find something to suit your budget.


More than 125 storefronts line downtown Galena. (Photo provided by Galena Country Tourism)

Step back in time to the 1800s in this historic jewel of a town tucked in the rolling hills of northwest Illinois, where Iowa, Wisconsin and Illinois meet. The area boasts rolling hills and rugged bluffs, perfect for a variety of outdoor activities any time of year. The charming downtown is filled with 125 unique shops and historic sites. Visit the home of former President Ulysses S. Grant, and the Dowling House, the city’s oldest home, built in 1826. Visit nearby Apple River Canyon State Park and marvel at the limestone bluffs, deep ravines, springs, streams and wildlife. Lodging options include several guest houses, hotels and the nearby Chestnut Mountain Resort or Eagle Ridge Resort and Spa. Visit during one of Galena’s many special events, including the Galena Irish Fest in August, the Historical Society’s 30th Annual Cemetery Walk in September or the many holiday celebrations in and around the city in November and December.

Door County, Wisconsin

Door County, Wisconsin

A variety of unique communities dot the peninsula that is Door County. Some of them along the 300 miles of shoreline include Sturgeon Bay, Egg Harbor, Washington Island and Baileys Harbor. At just about any location, guests are close to the water for boating, fishing and water sports. Door County has five state parks, 19 county parks, dozens of beaches and acres upon acres of wilderness. Stroll through the quaint lakeside communities and charming downtown shopping and dining districts, visit local wineries and breweries and indulge in the vibrant arts scene. There are so many things to do and see in Door County, from historic sites, architectural wonders and museums to golf, live music and seasonal events and festivals.

For those interested in astronomy, Newport State Park on the tip of the Door Peninsula is recognized on the International Dark Sky Association’s list of 48 dark skies around the world. On a clear night, visitors can see thousands of stars and the Milky Way.

Aimee Barrows

Aimee Barrows

Aimee Barrows is the editor of The Scene, Shaw Local News Network's entertainment section. The Scene is your go-to destination for all things fun in Northern Illinois. Prior to The Scene, Aimee was the editor of the Kane County Chronicle for five years, and a freelance reporter for Shaw Media for four years.