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October in the Windy City? Yes, please!

We don’t often think about fall foliage in the city, but the colors add a subtle flavor, as if the buildings have dressed for autumn. This year’s Open House Chicago, a decade-old annual free festival, runs through Nov. 1.

The website — — showcases Chicago-area sites “from iconic locations to under-the-radar architectural gems.”

This year, the pandemic has given everyone the opportunity to become more creative in staying safe while learning new ways to gather, and the festival has turned into a walking tour augmented with an app. Pro tip: Check the weather and consider all possibilities, from sweater weather to T-shirt and shorts to raincoats to windbreakers to warm jackets.

An easy walk from the Wicker Park Hyatt is The 606 (, a raised trail repurposed from an old El train line for hiking, biking or jogging. It connects four Chicago neighborhoods above the traffic and noise of the city. All of the entry points on The 606 are accessible, employing gently curving sidewalks, spiraling up through a park or small green-space, easy on any type of wheels, or even aging knees.

The effect is natural, landscaped with tufts of native plantings and boulders that double as benches. The vibe is friendly, as children, couples, dogs and their people, skate, bike, walk and roll down the path. Occasionally the 2.7-mile trail widens to accommodate pathways through a thicket or pocket forest or artwork, like the giant, black telescope, and benches where groups gather to share music or conversation. Brass numbers embedded in the pavement mark how far you’ve walked and how far to the end. The 606 even hosts an interactive science project called Environmental Sentinel,, where participants can observe the changes of temperature-sensitive plants and record and share the data. It is a project of the Trust for Public Land,

The Chicago Riverwalk is a great place to begin a visit downtown. This mile-and-a-quarter path hugs the river from the Lakefront to the Confluence and features three accessible entries that gently incorporate ramps with stairways or gradually sloping paths from the street above down to the trail. Pro tip: For easy and affordable parking, try using an app like Spot Hero, which lets you reserve and prepay for parking (often for about half price).

The Riverwalk itself is wide enough for social distancing when it’s not too crowded. Most people mask, though not everyone — especially those in the large boats docked at the water’s edge. Grassy aprons of lawn make good spots for picnics, and the large sections of stadium-style benches let people enjoy a sack lunch or watch the boats sail up and down the river, from the tour boats and big yachts to police boats and kayaks clustering like schools of fish. But don’t worry if you didn’t pack a lunch, because the wide walk features a string of restaurants with plenty of outdoor seating. Artwork and natural plantings are featured throughout the path, including floating gardens in the river. Abundant public restrooms are conveniently located along the trail, which has a block-party ambiance. As dusk falls, the lights blink on in the buildings above and reflect in the water, sparkling. The kayaks bring out glowing sticks lashed fore and aft and headlamps to continue the fun. Music in old-fashioned techno-rhythms escapes from the docked powerboats and snatches of blues from restaurants float by.

Pro tip: Make an appointment for a 2-4 hour free tour with a Chicago Greeter,

Chicago Greeters are volunteers who love to share their enthusiasm and knowledge about specific areas of Chicago. A walk from St. Michael’s Square in Old Town meandering to the lake will take you past historical houses, many of them cottages built after the Great Chicago Fire, which burned for two days in October 1871. St. Michael’s, although gutted in the blaze, was rebuilt using the surviving walls. Open House Chicago is providing a free app that gives guided walking tours, photos, descriptions and narration from experts about the sites. The app is available for the duration of the festival.

The Open House Chicago tour of Bronzeville begins at the Harold Washington Cultural Center and stops at various sites intersecting music, religion and civil rights, including Lil Hardin Armstrong’s home, Ebenezer Missionary Baptist Church where Gospel music began, and The Roberts Temple Church of God in Christ, where Emmett Till’s funeral was held. According to a New York Times article, last month the Roberts Temple was designated as an “endangered historic site.” Let’s hope that the OHC tour sparks interest in saving this important heritage. Pro tip: Parking is easy on the wide, walkable boulevards where many of these sites are located. Trees lining the boulevards are turning, the locusts especially are shedding their golden leaflets, which look like elongated golden coins on the sidewalks.

While you are in the Chicago area, you may want to visit Oak Park, with enough Frank Lloyd Wright homes within a tight walking area to keep a Chicago Architecture Center docent and her guests happy for a few hours. Pro Tip: If a Chicago Greeter tour is like a neighborly walk with a friend, a CAC docent tour is like having a graduate course in the history of architecture — without the stress. With the app or with a docent, you’ll learn to recognize some of the elements of a Wright house and feel much smarter by the end of the tour. Use the Open House Chicago website or app to plan your visit now.

Mary Lucille Hays writes the Letter from Birdland column in the News Gazette and the Piatt County Journal Republican. You can see pictures of Chicago sites on Instagram @BirdlandLetters. Mary can be reached at or via snail mail care of the Journal Republican, 118 E. Washington St., Monticello, IL 61856.

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