Racing Into The Weekend: Your Dog-Friendly Chicago To-Dos

Pup wants to make sure she’s squeezin’ every last bit of summer out of the final month and we couldn’t agree more! Luckily you don’t have to go crazy searching for bark-worthy events to make her yappy—we’ve got yer back. From a superhero-themed pawty to a dachshund derby (seriously, need we say more?!), check out our Chicago weekend to-do list. 

1. Dog Day at Gallagher Way

Gallagher Way, Chicago
Saturday, August 13, 11 a.m.–4 p.m.

Dog Day at Gallagher Way is back by pup-ular demand! Get your downward dog ready because the day kicks off with Dog Yoga at 11, then continues with an afternoon of socializing, lawn games for pups and peeps, drinks, local vendors, and a showing of “Best in Show.” Pets attending are required to be up-to-date on vaccinations and be leashed at all times.  

2. Dachshund Derby

Roosevelt Collection Shops, Chicago
Saturday, August 13, 1–4 p.m.; Registration for racers

What’s cuter than a bunch of low-riders dashing to the finish line on their pint-sized legs? Correct answer: Nothing. The 2022 Dachshund Derby benefitting Dachshund World Charities features food, vendors, and the cutest darn races for puppies, adults, seniors, and non-Dachshund wannabe’s (Dachshund mixes). Secure a spot in the race for $10 by August 12 to see if your weiner is a winner. Prefer to watch? There’s no charge for human and dog spectators.

3. Printer’s Row Art Fest

Dearborn Street from Harrison to Polk, Chicago
Saturday & Sunday, August 13–14, 10 a.m.–5 p.m. 

Art ruvers rejoice—the Printer’s Row Art Fest is bringing that creative vibe you need this weekend. Sniff out pieces from painters, street artists, jewelers, up-cycling artists, photographers, and mixed media artists. All that walkin’ got your stomach talkin’? Local restaurants will be serving up Chicago specialties. Just make sure Fido is on his best behavior—the festival welcomes dogs that are leashed and friendly. 

4. UltiMutt Superhero Pawty

Bucktown Pub, Chicago
Saturday, August 13, 2–5 p.m.; tickets required

Doggo’s been dyin’ to wear a cape so suit up and head to Ben’s 2nd Annual UltiMutt Superhero Pawty. Come for the dog-watching, and stay for the drinks, grub, and prizes. Tickets are $15 and proceeds benefit Be Fido’s Friend in honor of a special dog named Ben. Make sure your bestie doesn’t go home empty-pawed by springing for the $10 Super Snack Pack, a box of homemade goodies to fuel pup’s super-pawers!

5. Marty Fest 

Mart Anthony’s, Chicago
Sunday, August 14, 1 p.m.

Did somebody say meatball?! Okay, so pupper basically only cares about the food at this one, but Marty Fest is also bringing live music, drinks, games, and much more to this puppin’ fun street party. Admission is free, but make sure floof brings her wallet—she’s gonna wanna sample all the authentic Italian cuisine. 

6. Ice Cream Social

Two Bostons Pet Boutique, 6 store locations
Saturday, August 13, 12–3 p.m. 

If you and your sweet-toothed sidekick are anywhere near a Two Bostons location this Saturday, put the car in bark and stop in for their ice cream social. They’ll have dog ice cream and toppings for furry guests, and ice cream sandwiches for hoomans, too. Make sure pup’s looking his best because he’ll want to pose with his sundae in the ice cream photo booth. 

7. Saturday Pup Crawl

The SoFo Tap and Sidetrack, Chicago
Saturday, August 13, 12–3 p.m. at SoFo & 1–5 p.m. at Sidetrack

Puppo’s reminiscing about the excitement of Pride Weekend, so we’ve got a recipe for a mini make-your-own pup crawl that’ll take you and your fren to not one but TWO furbulous LGBTQIA+ bars. Start at The SoFo Tap where every Saturday is Doggy Days and they’ll be serving up free dog treats, half-priced drafts, and their “Cheap Drinks Everyday” specials. Keep the pawty going at Sidetrack for their monthly Dog Day where the drinks and treats will be flowing, and pup may even score some pawesome swag from Tito’s Handmade Vodka.

No pupper in your life yet? Get a heckin’ dog already!

If you live in a world without tail-wags—what a tragedy—check out this Chicago-area adoption event! 

PAWS Chicago

  • Need a little re-tail therapy? Your favorite downtown Barrington shops are opening their storefronts and windows to adoptable pets from PAWS Chicago from 12–4 p.m. on Sunday, August 14. Browse merch and mutts at the same time, and maybe you’ll find yourself bringing both home! A map will be posted prior to the event on their website so you can plan out your walking tour of furry frens! 

Sniff out more events on our calendar and submit your own events here. And don’t furget to tag us @SidewalkDog in pics of your tail-waggin’ weekend!

Featured photo: Kojirou Sasaki

Sidewalk Dog’s mission is to help dog parents spend more time with their puppers by discovering and sharing activities they can do and places they can go—together! Sniff out our award-winning newsletter and Instagram, and join our Dog-Friendly Chicago Facebook Group.

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