While Chicago is full of fun activities for Labor Day weekend, it can be refreshing to plan a quick getaway to a nearby midwestern oasis. Lucky for us Chicagoans, there is no shortage of beautiful destinations that are the perfect distance for a weekend away from the city hustle and bustle. We are surrounded by quaint, charming towns and stunning nature! Here is a list of some of the most popular places to road trip to for an exciting weekend excursion:
This stretch of the Lake Michigan coastline is a great place to visit with its wide sandy beaches, towering dunes, excellent birding, and historical landmarks. Head to neighboring Chesterton for creative burgers at the Octave Grill and a pleasant night at Dunes Walk Inn, a restored 1881 mansion.
Lake Geneva offers the perfect activities for visitors of any age! From family getaways to golf outings – Lake Geneva has many activities for all! Whether you seek adventure, the arts, or want to connect with nature, the list of things to do in Lake Geneva is endless!
Michigan is the best place for you to explore. Take a spin on the carousel at St. Joe, tour a working windmill in Holland or stretch out on a beach – preferably with a lighthouse view. Towns like New Buffalo, St. Joseph, and Benton Harbor provide pristine beaches, great shopping, lakeside restaurants, and gorgeous views of sunsets over Lake Michigan.
This western Illinois town offers visitors a unique glimpse of history. In addition to its shops and restaurants, Galena is home to the most extensive collection of Victorian architecture. Soak in local flavor and do everything from hiking and boating along the Galena River to exploring antique shops, wine tastings, and more.
Cedarburg is home to both shoppers and history buffs, with a Main Street lined with boutiques and plenty of sights to see. Visit museums and indulge in local ice cream at the General Store Museum, Kuhefuss House Museum, and Wisconsin Museum of Quilts and Fiber Arts.
Visitors to Madison are always pleasantly surprised by its small-town vibe. Embracing the quirky and classy, Madison is an arts and culture hub with a unique collection of museums, shops, dining venues, and outdoor activities. You can wander the paths and trails at Olbrich Botanical Gardens, explore the University of Wisconsin Arboretum, or admire the art at Chazen Museum of Art. Another activity could be to take a leisurely cruise around Lake Mendota or Menona, and be sure to work up an appetite-Madison’s 600-plus restaurants offer something for every taste.
Starved Rock State Park is a fantastic pocket of land along the Illinois River, featuring 18 sandstone canyons, 14 waterfalls, and breathtaking hiking trails. Spend the night in rooms or cabins at Starved Rock Lodge, built in the 1930s by the Civilian Conservation Corps. If you’re up for more exploration, also visit neighboring Matthiessen State Park, where 5 miles of trails carve into a mile-long canyon, passing rocks, waterfalls, and beautiful vantage points.
Popular art, music, and food festivals fill the calendar in Milwaukee, along with a range of cultural attractions. You can watch the Milwaukee Art Museum’s striking Quadracci Pavilion open and close its wings, catch the Milwaukee Brewers in Miller Park, or take a simulated motorcycle ride at the Harley-Davidson Museum.
Elkhart Lake allows for quiet weekends of swimming, sunning, boating, and water-skiing in the crystal-clear lake.
Labor Day weekend trips and traditions are a big deal here in the Chicagoland area, especially due to our close proximity to a variety of beautiful lake towns and popular cities. With that said, Chicago is the perfect home base if you’re looking for big-city living with the option of a brief, fun weekend escape! Where is your favorite long weekend destination?