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Family Biking in Chicago

and a Bike Bar Hop for the grown-ups!

By Debra Flanagan, Macaroni Kid Chicago Northside September 22, 2021

Fall brings about some of the best biking weather, and we love to take advantage of it.  

It was only about three years ago, when we started biking as a family. My daughter was 11 and my son 9. We started by joining Chicago Family Biking on monthly Kidical Mass rides around local neighborhoods through the fall and into December.  Each ride has its own fun theme, but each teaches kids how to ride on city streets. It can be downright scary, so going with an organized group that manages traffic is ideal. The key is developing confidence.

Once we felt comfortable, we began biking on our own to school in the spring, and camp in the summer. Short one to two mile rides.  

When pandemic hit in 2020, we got our practice in riding around Graceland Cemetery.  No cars and no covid.  It was great.  It is also quite pretty and serene.  I highly recommend it for new riders.

Eventually, we ventured back onto roads and began increasing our distances.  We started biking to The Bloomingdale Trail at The 606, 2.7 miles of multi-use recreational path between Ashland (1600W) and Ridgeway (3750W).  There are 12 access points, approximately every quarter-mile.  The path is wide and a little hilly. We always make a point of taking a break at Parson's Chicken & Fish on this ride.

We started biking the North Shore Channel Trail up and around Skokie Northshore Sculpture Park, as well as the North Branch Trail through Forest Preserves that lead all the way up to the Chicago Botanic Garden in Glencoe.  The city's Shared Streets program, made it very safe for us to get to and from the trail heads.  Note, the city extended the Shared Streets program through the summer of 2021, and hopefully it will become a regular recurrence.   

Biking up to Evanston and Wilmette were a little trickier, but once we figured out our way to the Glenwood Greenway and the Greenview Greenway, it's pretty smooth sailing up to N. Rogers Avenue, where we head east until we are on the lakefront again.  The new greenway on Clark Street should make it even easier. We always split up our Evanston rides with lunch at the Firehouse Grill.

Above all, however, my favorite ride is simply along the Lakeshore.  There are so many ways to modify your trip.  You can bike down to Navy Pier or the Chicago Riverwalk.  You can bike down to Maggie Daley, or even the Museum Campus.  You can simply ride to the beach or one of the many lakeside restaurants, or make them a stop along your longer ride.  In fact, my husband and I have made it a date activity to ride round-trip from Lakeview down to the Museum Campus, stopping at all the bars/cafes along the way for food or a drink.  We call it the Bike Bar Hop.  Stops include: The Lakefront Restaurant, The Shore Club, Castaways, Whispers at Oak Street Beach, Caffe Oliva, and Pablo's Tiki Snack Shack.  I assure you at least one of these places, if not all, will have you feeling like you are on a tropical vacation. There is also a northbound version of the Bike Bar Hop with stops including, The Dock at Montrose Beach, LakeBreeze, and The Waterfront Cafe.

Now that the kids are very competent on their bikes, they are able to ride with friends and get around on their own a little bit.  If we lived in the suburbs this would be second-nature to all the neighborhood kids. For us city-dwellers, it takes a little investment, but I assure you it is well worth it.