Arlington Heights, Ill.--I spent the weekend in Illinois attending Arlington Million Day at Arlington Park for the eighth year in a row; it’s become a tradition to attend the races with a large group of friends and family, and it’s always a grand--albeit expensive--time.

It also now acts as a bit of a homecoming for me, since I lived in Chicago--not terribly far from Arlington Heights--for a couple years when I was in graduate school at DePaul.

I spent Friday in my former stomping grounds, traipsing about Chicago with my best friend, who came in from Cleveland for the weekend’s bacchanalia. We caught a train from our hotel in Arlington Heights into Chicago, and there’s not a better city in this country to be in on a Friday during the summer than Chicago.

On a sunkist afternoon, we waltzed around the heart of the city, ambled down Michigan Avenue’s Magnificent Mile, took in the art (like Cloud Gate, aka “The Bean,” and the Crown Fountain) in Millenium Park, watched boats sail picturesquely on a Lake Michigan so blue it looked like it should’ve been hanging in the art museum just a few blocks away, and, of course, stopped often for, ahem, refreshments.

One of my (many) goals of the weekend was to buy a new pair of shoes, and as we meandered up State Street, we alighted upon shoe Xanadu and felt compelled to stop. Once inside, I felt I’d stumbled into Imelda Marcos’ closet--I can’t recall the last time I’d been in the presence of that many shoes.

I settled upon a pair of Clarks Desert boots, which had been in my mind since I saw them recommended by the style consultant of Esquire, Nick Sullivan, a few months ago. Not only did they look divine, they felt delightful. I don’t want to sound like Carrie Bradshaw here, waxing poetic about footwear, but I must admit I loved them, and--wearing them for the first time at the track the next day--they performed admirably. Though my friend wasn’t planning to buy anything, he got sucked in, as well, and also bought a pair of Clarks.

We ran into a bit of a hiccup when trying to catch our train back to the hotel, however. We were locked out of the station, couldn’t gain entry, and missed our train. Thankfully, there was an establishment with a neon light nearby, so we went there to drown our sorrows and plan our strategy. Our waitress explained there are actually two buildings, and the one we were attempting to enter was locked because of the late hour, but the other one is always open, naturally, due to the trains.

Now, I know what you’re thinking, How did I--someone who lived in the city for years--botch this? Well, granted, my friend and I were operating at less than peak capacity by this time of night, but I refuse to blame that, as--later--about a dozen other people were running for trains just like we were, so they must’ve experienced the same confusion. Moreover, this station was not one I’d ever used before during my time in the city.

Anyway, about two minutes before our train’s scheduled departure, we still had yet to gain entry, and I figured our cause was lost. But, we followed the other scamperers to the correct entrance--running with our shoe boxes as if we’d stolen them--then skipped up an escalator toward the tracks. I had no idea which train we needed, so, while running by, I shouted to one of the workers, “Which train to Arlington Heights?” He pointed, we jumped on like a couple boxcar hobos, and the train started moving before we could even sit down.

Perhaps the most propitious thing to happen all weekend was, when we got back to the hotel, they were overbooked, evidently due to a wedding party, so they upgraded us to a suite for free--and that suite was sweet!

Saturday is always an electric atmosphere, because Million Day is the biggest day of racing the entire year for Arlington Park. The Million remains one of the premier turf routes in America, and the supporting stakes--the Secretariat and the Beverly D--are none too shabby, either. All are grade 1 races, the highest designation a race can receive in America. They usually draw strong and bulky fields (although this year the Million drew a pitiful field of seven, and, adding to the indignity, it was then won by likely the worst horse to ever capture that prestigious race), and they’re often filled with European shippers--the Euros don’t invade America often, but when they do, it’s strictly for this sort of big-game hunting.

Many revelers get quite dressed up--men in suits and ladies in divine sundresses and baroque hats--and the whole day is one long party (which usually becomes a wake when the races are done and your wallet looks like an elephant sat on it). In fact, that’s part of the reason I always dress up--even when you’ve lost all your money, you at least still look like you have money. The adorables in sundresses--still the greatest invention in the history of mankind--and hats really got to show off this year in the “Strut your Stuff” best-dressed contest, held in the paddock area on the opposite side from the track. Did I have more interest in the contest than in some of the races? Yes, yes I did.

The races were a debacle for everyone in my group; none of us were in the black, so it was more a question of how deep your shade of red was. Fortunately, I was able to hit the Beverly D--thank you, Ryan Moore, the best jockey in the world, for bringing home that winner--and the finale at Saratoga, and those two triumphs halved my losses for the day.

Overall, I’ll be handling my American Express bill as if it were filled with Ricin when it shows up in a couple weeks, but I at least made it back here alive, and I got a lovely new pair of shoes, so I can’t complain (too much).

Ryan Anderson can be reached at and followed on Twitter @randerson_ryan