Best August Road Trips: Fairs & Festivals

At the peak of summer, August is the time for spending lazy quality time with family and friends, slumping on a beach or floating on a lake or river. It’s also the time for aimless summer drives through the back roads of the rural heartland, hoping to come across a County Fair, a small town festival, or even a farmstand selling fresh corn or peaches. All over the country—in the Berkshires of Massachusetts, in the Finger Lakes of New York, or in the bluesy Mississippi Delta—people come together in beautiful places to celebrate different aspects of what makes America what it is.

August Road Trips: US-2 through Wisconsin and Michigan’s UP

One of the many great summer festivals is held way up north on the shores of Lake Superior: Big Top Chautauqua has been drawing visitors to a giant tent south of Bayfield, Wisconsin, for over 20 years. A non-profit throwback to the traveling tent shows and chautauquas that a century or more ago used to bring culture to rural America, Big Top Chautauqua shows include big-name performers, musicals, lectures, concerts, and circuses. Best of all, the festival is located within a quick boat ride of the gorgeous Apostle Islands, one of many unexpected wonders of the upper Midwest.

The rocky edge of the Apostle Islands National Lakeshore in Lake Superior
Apostle Islands National Lakeshore in northern Wisconsin. Photo © dpenn/iStock/

From Bayfield, the drive along two-lane US-2 heads west through scenic Duluth (birthplace of Bob Dylan), Grand Rapids (birthplace of Judy Garland), and on to the headwaters of the Mississippi River near Bemidji (birthplace of Paul Bunyan). Heading east, the road continues along the lake across the rugged Upper Peninsula, through places like Mackinac Island, Marquette, and Escanaba, where the lively UP State Fair takes place in the middle of August (August 13-19th in 2018).

Great Northern Road Trip Route - US-2 Through Wisconsin

For more on following US-2, check out The Great Northern Road Trip.

Other August Road Trips

August road trips: Winding road through South Dakota's Badlands National Park is perfect.
South Dakota’s Badlands National Park is a popular destination for riders attending the Sturgis Motorcycle Rally.

Aficionados of classic American motor cars come together at the end of August through Labor Day for the Auburn Cord Duesenberg Festival in Auburn, Indiana, where many of these great cars were produced. Northern Indiana abounds with roadside Americana, and a drive along sections of the historic Lincoln Highway, will bring you across rural farmlands, past Amish farm stands (popcorn is a prime local product) and numerous small towns and post-industrial cities like Elkhart and South Bend, home to the “Fighting Irish” of Notre Dame.

The Hoosier State’s northern tier also has an unexpected chunk of natural splendor: the Indiana Dunes National Lakeshore, where miles of tall sand dunes front onto Lake Michigan, less than an hour from Chicago.

Who loves the American road better: drivers, or motorcyclists? One place you don’t want to have that argument is in Sturgis, South Dakota, where every August (August 3-12 2018), some 100,000 Harley riders and their friends come together for a giant rally. Before and after the big event, bikers can be seen riding all over the nearby Black Hills, enjoying the curving S-turns as the make their way to pay respects at such national landmarks as Mount Rushmore, the Crazy Horse Memorial, and Wall Drug.

Recommended Travel Guides

Best August Road Trip - US-2 Through Wisconsin & Michigan's UP text over photo of the Apostle Islands and route map