Festivals, Flowers, and a 5K: Your Chicago Weekend 

Forget the weekday grind, it’s time to unwind! From running with Rover to seeking out cool cars and beautiful blooms, sniff out these bark-worthy adventures in dog-friendly Chicago.

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1. PAWS Chicago 5K

Montrose Harbor-Grove 16, Chicago
Saturday, September 10, 7:30 a.m.; Registration Required

It’s been a long week, and your mutt wants to move! Get in motion together at the 22nd annual PAWS Chicago 5K, Chicago’s largest dog-friendly charity event that raises funds for shelter pets. This isn’t your typical race to the finish, the route is open from 7:30–10:30 a.m. for walkers and runners to complete at their leisure! Beyond raising funds for homeless animals, the PAWS Chicago 5K is a day of costumes, dog agility courses, live raffles, entertainment, treats, and so much fun.

2. Chicago’s Classic Car Show

3800 W. Ogden Ave., Chicago
Sunday, September 11, 12–5 p.m.

Your classic canine can’t wait to get her kicks on Route 66! Just point her paws towards Chicago’s Historic Route 66 Classic Car Show this Sunday. This free event was created to bring the community together in celebrating the history of America’s most cherished highway and the cars that have driven it. It’s family-friendly, dog-friendly, and did we mention there’s food?!

3. Renegade Craft Tour

Wicker Park, Chicago
Saturday, September 10 and Sunday, September 11, 11 a.m.–7 p.m.

The best of community and creativity will be on display this weekend as the Renegade Craft Tour takes on Chicago. Grab woofer’s wallet and shop a beautiful collection of products from some of the best local artists and craftspeople. The event is free, but a small donation is suggested to allow organizers to continue bringing artists together.

4. Mayfair Fest

Mayfair Park, Chicago
Saturday, September 10, 12–8 p.m.

Pack up the whole fam (pup too!) and spend the day at Mayfair Park. This year’s Mayfair Fest features a whole day of games, kids activities, live music, aerial dancers, food trucks, vendors, and more. Puppers will love taking in all the smells of the park, just make sure to keep your fair-hound leashed at all times.

5. Dog Day at Morton Arboretum

Morton Arboretum, Lisle
Sunday, September 11; tickets required

Pets are only allowed at the Arboretum on special days, and your floral floof is pulling on his leash to go! Grab your ticket for this Sunday’s Dog Admission Day and get ready to sniff out 16 miles of trails. They’re also hosting a Tails on the Trails event that day, where you and pupper can enjoy the sights (and smells) while getting in some re-tail therapy at the on-site Pet Expo.

6. Dog Daze

Fishel Park, Downers Grove
Saturday, September 10, 12–4 p.m.

The line-up for Dog Daze is the stuff pup’s dreams are made of! A peanut butter licking competition, agility course, doggy splash zone, free caricature portraits, a photo booth, food trucks, pet vendors, adoptable dogs, and live music—holy puppin’ fun!

Don’t have a dog already? Get a heckin’ dog!

Sniff out these local adoption events happening this weekend to meet your new slobbery soulpup.

Traveling Tails Dog Rescue

  • The Palos Heights Public Library is hosting a dog adoption event featuring the adorable pups from Traveling Tails Dog Rescue on Saturday, September 10 from 11 a.m.–1 p.m. Palos Animal Hospital will be there to answer questions and will donate a Palos Animal Hospital gift certificate to anyone who successfully adopts a dog to cover its first physical exam.

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!

Photo by Jamie Street

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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