Words by Zach Moeller.

The trip started under the familiar circumstances of heading to the bar after a session, which almost always results in the usual one too many drinks and impulsive (poor?) decision making. All too often my boy Stasio and I end up spending our days off skating Tompkins Square Park, never actually going to any other of the spots that we half-heartedly suggest to each other before retiring down the street to our bar, The Library. Although it’s one of our favorite places, Tompkins can be like quicksand; if you fight it and try to escape, you will just become more trapped.

Maybe it was the frustration of hardly skating spots other than TF, or more likely it was that our bartender Stefania was being generous with her pours, but in a moment of genius inebriation we bought plane tickets to Chicago with the sole plan of skating all day and then flying back.

With only one day to spend in the Windy City, we thought it wise to get a good night’s rest before our 6am departure. Instead we ended up back at the Library Bar. The whole flight it was clear that we should’ve listened to our fatigued bodies the night before, but shortly after landing we gained some energy during a session at the completely empty Grant Skate Park. Even the strictest street skating purist wouldn’t be able to deny that this park is incredible, and it was crazy to have it to ourselves in a city with nearly 3 million residents.

For a business day we had surprisingly good luck cruising around The Loop, the city’s downtown area, recieving only glances and waves from Chicago’s finest as they drove by. In a weird crossover of what felt like the cityscape of Manhattan with plazas that almost mimic a late ’90s Philly, we pushed around finding whatever we could to skate.

Beyond the most well known spots, we really didn’t have any clue where else to skate, so we decided to go to Uprise skate shop to ask the locals. Tim and G hooked it up with some spots, but more importantly they shared their knowledge of nearby digs to get some beer and deep-dish pizza. Knowing that we would fall into food comas following brews and deep-dish, Stasio and I decided to check out a couple more spots before settling in at Pequod’s for a true taste of Chicago cuisine.

Sadly, the time came to return to the airport to head home to New York. We both felt like we could fall asleep standing up, but somehow made it to our gate and onto our flight.

In just under 16 hours we had successfully covered over 1,500 miles, skated some new spots, and somehow managed to stay awake for it all. As we learned that day, sometimes it pays to leave your local spot.