The Date Day Diary

Chicago Area Date Day Ideas

Aliotta, Haynes and Jeremiah were on to something when they wrote about Lake Shore Drive.  On a sunny day, there may not be a more picturesque drive anywhere.  Today was sunny.  Rather than drive, however, we ditched the car and biked along the Chicago Lakefront Trail.

We parked just off 39th street, in Burnham Park, and headed south.  Yes, south.  We like this part of the trail because it’s rarely crowded, contains some interesting buildings and art work, and offers some of the best views of the city.  We made our first stop at 41st street beach, where you can always find clean restrooms, and then headed for Promontory Point.  “The Point”, built in the 1930s, is a man-made peninsula that juts out into Lake Michigan.  It’s a wonderful park with a nice promenade, beautiful landscaping and incredible views of the city.  Thanks to Alfred Caldwell, who designed the “council rings” along the water, it is also the only place on the lakefront where you can legally have a fire.

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Leaving Promontory Point, we continued south past the Museum of Science and Industry until we reached the 63rd St. Beach House.  We’ve never been inside, but we enjoy marveling at the opulence of the exterior of the building that was built in 1914.  Rumor has it that the place has become neglected and is starting to fall apart.  That would be a shame.

Turning around at 63rd street, we headed back north towards downtown.  On the way, we passed by Tom Friedman’s Looking Up.  This 33-foot stature resembles a giant tin foil man staring into the sky.  We christened him Reynold, took a quick picture and moved on.

The ride between 63rd street and downtown took quite a bit longer than we expected.  Part of it was a slight headwind, part of it was increased number of people on the trail once we reached McCormick Place and part of it was Theresa stopping every minute or two to take picture of the concrete mountains rearing up.

Every time we ride along the lake we come across something new and today was no exception.  We visited the 5-acre Gold Star Families Memorial and Park, which is dedicated to all Chicago police officers that have been killed in the line of duty.  the Chicago Firefighter and Paramedic Memorial and saw the waterfall on the east side of McCormick Place.  If you haven’t taken the time to see these, we highly recommend you do.

We also circled along the outside of the aquarium, skirted the edge of Grant Park and took in Buckingham Fountain.  The views are wonderful, and the vibe is great, but the trail does get a little crowded and many people don’t understand or follow the rules.  The city has invested millions of dollars over the past few years to separate the walking / jogging path from the biking path, unfortunately not everyone reads the signs and things are still pretty chaotic.

We navigated the terrible part of the path near Navy Pier, which should be fixed with the addition of a bridge soon, and rode along the lake to Oak Street Beach.  Our plan was to have lunch on the beach, but the restaurant was not yet open for the summer.  We backtracked a little to Café Olivia, which is in Olive Park.  We had a great meal of Kale and Brussels Sprout Salad and Falafel, washed down with a couple of beers.  The food was a little pricey, but the location on the beach and the views of the city more than made up for it.

After lunch, we biked our tired selves back down to 39th street and our car.  Our minds were feeling fine and we were able to smell the green.  We did a total of 20-miles and felt pretty good about it.  Next time, we will skip going south and head to the northern end of the trail at Ardmore Ave (5800 North).

“There ain’t no finer place to be, than running Lake Shore Drive …”

May 2018
Chicago Lakefront Trail
Free Admission
3 – 4 Hours
$8 for 4 hours Parking at 39th Street
Café Olivia
550 E Grand Ave, Chicago, IL
1 Hour
$60 including drinks and tip

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