Illinois' Historic 'Mother Of Chicago' Is A Route 66 Suburb With Walkable Downtown Charm And River Trails

If you're longing for a stunning and storied U.S. road trip, there are few routes that hold a candle to Route 66. Stretching from California to Chicago, the iconic "Mother Road" route delivers neon nostalgia and kitschy Americana in all its glory, showcasing the best of the U.S. and symbolizing the freedom of the open road.

To travel the route from east to west, starting at the "Begin Route 66" sign in downtown Chicago is the way to go. While the Windy City is full of sights (and tourist traps to avoid), the essence of Route 66 lives and breathes in its smaller stops along the way. Situated about 35 miles southwest of the route's starting point, one of these smaller destinations is Plainfield, Will County's oldest community. Known as the "Mother of Chicago," Plainfield earned the nickname in the 1800s when its lumber was used to build Chicago's first frame houses. Today, it's a vibrant suburb of Chicago with small-town charm, scenic river trails, and a rich history. If you want to get your kicks on Route 66, kick off your journey with a stop in Plainfield.

If you're planning to fly to the area, landing at Midway International Airport (MDW) will put you about 30 miles away from Plainfield. Alternatively, you can fly into Chicago O'Hare International Airport (ORD), though it's a bit farther out. Regardless of where you choose to land, since Route 66 is a classic road trip route, you'll want to rent a car for your journey. Although Route 66 was decommissioned in 1985, you can still travel portions of the historic route. Leaving from Chicago, you'll travel down I-55, which branches off to IL-126 (also marked as Old Rte 66 on GPS navigation apps), leading to Plainfield.

Dating back to the 1830s, Plainfield has a vibrant past, which is thriving in its Historic Downtown District, listed on the National Register of Historic Places. Wandering its walkable streets, you'll find a number of historic buildings, including the Opera Block House (also known as the Clock Tower Building), a stunning Queen Anne-style edifice built in 1899. One block over on 600 W. Lockport Road, you'll find the Historic Standard Oil Gas Station, which was built in 1928. The building has since been repurposed, but a vintage gas pump stands outside, effectively tying it to its Route 66-era past. 

Fun fact: Plainfield also claims to be the birthplace of the ice cream sundae back in the 1890s. So, if you want to bite into more local history, treat yourself to a delicious sundae at Hazel Marie's.

Beyond Plainfield's historic downtown, you'll find an outdoor wonderland of hiking trails, which are perfect for stretching your legs before getting back on the road. Before setting out, be sure to stop at the Lincoln Highway/Historic Route 66 alignment sign located at 15251 Lincoln Hwy. In the 1940s, these two highways were the longest in the world, and Plainfield was the only place where they intersected.

After a quick photo op, continue on to explore Plainfield's beautiful trails. Located in Settler's Park, the Plainfield Story Walk is a paved, half-mile trail with waterfront views and tree-lined beauty. If you're looking for a longer trek, try the Lake Renwick and Budde Lake Loop Trail. Comprising 3 miles, the idyllic trail passes by Turtle Lake, as well as the Lake Renwick Heron Rookery Nature Preserve, where you can see great blue herons nesting in their natural habitat. South of town, the Mather Woods Park Loop offers a peaceful 1.3-mile walk beneath canopies of lush trees.

If you wish to stay the night in Plainfield, check into The Plainfield Inn. Housed in a former 1800s schoolhouse, the historic inn boasts nine comfortably-appointed suites in the heart of downtown Plainfield, making for a sweet and storied retreat.