My Boston terrier, Turtle, likes to stick to routine. 8 AM: Breakfast and morning stroll. 8:30 AM to 1 PM: Snore loudly in his favorite chair. 1 PM: Light flailing of his favorite toy snake, Snakey. Snakey steps out of line a lot, and Turtle is happy to show him who’s boss.
The highlight of Turtle’s day takes place around 5:30 PM. At that point, I wrap up my deadlines for the day, he gives Snakey a celebratory flail, and then we’re off to canine utopia: the dog park.
As recent Chicago transplants, Turtle and I both underestimated the immensity of Chicago winters. Come mid-April, we shattered our cabin fever with a trip to the Logan Square Dog Park. It was there that I first discovered Turtle’s unique play style, which can only be described as that of a four-legged bowling ball. I decided that if Turtle could find his place in this city then so could I.
There are 25 official city dog parks, or dog friendly areas (DFAs), mostly clustered on the north side. There are also several other unofficial gathering places, particularly in underserved neighborhoods like the west side. Many dog owners go rogue, letting their pets play off-leash in public parks such as Bickerdike Park, Garfield Park, and Maplewood Park (the last of which recently banned dogs altogether). In Rogers Park, dogs and their owners have been known to scamper around the beach after the lifeguards clock out. But for the most part, residents of neighborhoods without official dog parks have three choices: commute to another DFA, like I did when I lived in Austin; join one of the many meetup groups, breed-specific or not; or risk going off-leash and getting a city ticket. (Fines start at $50.)
My Dog Terrorizes a Lumpy Dog
When Turtle and I were still on the west side, we played it safe, taking advantage of Logan Square Dog Park’s extensive concrete play space. There, Turtle took a particular liking to a lumpy 14-year-old dog named Ruby. He wanted to play, but Ruby wanted to snooze, so we moved on to find a more youthful playmate.
My Dog Terrorizes a Sporty Dog
Unlike other brachycephalic breeds—pugs, French bulldogs—Boston terriers like to run. That’s how I found myself barefoot and filthy, chasing Turtle across the vast expanse of the Montrose Dog Beach as he pursued a wild-eyed Australian shepherd. The Montrose Dog Beach gets crowded when the weather is nice, and Turtle bounced from potential playmate to potential playmate like a crazed speed dater. Unfortunately, the beach’s vastness made it hard to keep him in check. This might not be a problem for a more athletic dog owner, but my partner and I agreed to save further dog beach excursions for special occasions.
My Dog Terrorizes a Designer Dog
Despite my cautious child-rearing, we live in a culture rife with toxic masculinity—which, I assume, is why Turtle is extremely uncomfortable around intact male dogs. While Wiggly Field is well maintained, we encountered a record number of them during our visit. To a newcomer, this impressive display of dog genitalia seemed to reflect on the pedigree of its south Lakeview-north Lincoln Park location. My neutered and now slightly insecure dog and I trudged back to Andersonville, where Snakey got an especially aggressive flail.

My Dog Terrorizes a Giant Fire Hydrant
Jackson Bark, Chicago’s largest off-leash play space, boasts two enormous enclosures stuffed with agility equipment, a dog washing station, and even a six-foot-tall fire hydrant. Although not technically sanctioned as a Chicago Parks DFA—and currently threatened by development and undergoing federal review—Jackson Bark welcomes south-side dog owners. Up until May, Jackson Bark was the south side’s only dog park. Three more DFAs have broken ground across Oakland and Bronzeville since then, and Calumet Park’s first DFA opened in late July. Turtle loved Jackson Bark, scampering happily through agility equipment like rugged tires, doggy ladders, and hula hoops. Unfortunately, Jackson Bark is a solid half-hour drive from our place, which led us to our final destination.
My Dog Actually Does OK
Uptown remains one of Chicago’s most diverse neighborhoods, and that includes the Puptown Park crowd. Welcoming, laid-back, and attentive, Puptown’s diverse crew accepted Turtle’s antics. Regulars include a rotund pit bull named Ivan, a Pekingese named Coco that Turtle bats around like a furry mosquito, and a pair of Boston terriers who are rowdier than Turtle, which pleases me greatly. Now, Puptown is our go-to spot.
After we found our dog park, everything else seemed to fall into place. The daily exercise has eased Turtle’s separation anxiety, previously characterized by extended periods of barking. Although I still occasionally find myself lost on the Blue Line, we’re both feeling more at home. My only question: What are we going to do when winter strikes? v
Logan Square Dog Park
Sunrise-sunset, 2925 W. Logan, chicagoparkdistrict.com. F
Montrose Dog Beach
6 AM-9 PM, 601 W. Montrose, mondog.org. F
Wiggly Field
Sunrise-sunset, 2645 N. Sheffield, chicagoparkdistrict.com. F
Jackson Bark
6 AM-11 PM, 6000 S. Lake Shore Dr., jacksonbark.com. F
Puptown Park
4900 N. Marine, puptown.org. F
DFA admission is free, but all dogs require a $10 city permit and tag, available from a vet. More information at chicagoparkdistrict.com.