Picnic, Paint, and Show Your Pride: Your Weekend To-Dos

Who has furry legs and is ready to pawty this weekend? Your dog! Whether you’re looking for a new dog park, brunch spot, or dog-friendly festival, we sniffed out the best activities in Chicago this weekend for you and your woofer.

P.S. Don’t miss a single weekly event again! Pupscribe to our newsletter.
P.P.S. Our Patio Leash ™ is grrreat for outings and adventures of all shapes and smells.

1. SailGP Lake Walk

Navy Pier, Chicago
Saturday–Sunday, June 18–19; race time 2–3:30 p.m.  

Turn up the intensity on your weekend lake walk by coordinating a stroll during the SailGP catamaran racing events. While the viewing area is strictly hoomans only, a Navy Pier jaunt provides a sneak peek, as well as pawfect views of the Chicago skyline. Pack a picnic and camp out for some racing and thrills. 

2. Paint Your Own Pet

Color Cocktail Factory, Chicago
Saturday, June 18, 2:30 p.m.; $50 tickets required

You’ve always said your dog was a bork of art—now make it reality by attending an afternoon “Paint Your Own Pet” event at the Color Cocktail Factory. While this event is technically not pet-friendly, before the class you’ll submit a photo of your pup that an artist will sketch for you. Then it’s just a matter of painting inside the lines and trying to capture those puppy eyes. 

3. Chicago Pride Fest

Northalsted, Chicago
Saturday, June 18, 10 a.m.–Sunday, June 19, 11 p.m., suggested $15 donation

Leash up your Cor-gay and get ready for some fun! Northalsted’s Pride Fest is the mutts-attend event this weekend. Support local artisans, Queens, and nonprofits while showing your support for the LGBTQ+ community. Then on Sunday, dawn your best rainbow gear and enter the Pet Parade at 12 p.m. This event will be packed and is best for pups who don’t mind a crowd. 

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

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


  • Our pals over at PAWS are showin’ some love for the big woofs and floofs by waiving their adoption fees on June 18 for dogs over 40lbs at the Lincoln Park Adoption Center! You can check out all the adoptable pups on their website here—and who knows? You may even find the new ruv of your life.

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: Rosemary Ketchum

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.

More reads you’ll ruv:

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.