So Mutts to Doo in Chicago This Weekend!

Run. Drink. Eat. Repeat. Sounds pretty perfect, right? Your dog-friendly Chicago weekend is packed with pupportunities to move your paws, fill your belly, and cheers to the fall season! 

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P.P.S. Keep doggo close with our exclusive Patio Leash™—it’s the pawfect length for when you’re out and about!

1. Oktoberfest Chicago

St. Alphonsus Church, Chicago
Friday, September 23, 5–10 p.m.; Saturday, September 24, 12–10 p.m.; Sunday, September 25, 12–7 p.m.

You don’t have to be a German Shepherd to celebrate German heritage. Pull out your lederhosen and head to one of Chicago’s most popular fall celebrations. Oktoberfest Chicago at St. Alphonsus returns for its 19th year of seasonal revelry. We’re talkin’ 3 days of beer, brats, bands, and all things Bavarian. Dogs are welcome, but leave pup home if he doesn’t dig large crowds.

2. Paws and Walls Chicago Art Run and Walk

Grant Park – Buckinham Fountain, Chicago
Sunday, September 25, 9–10:30 a.m.; Tickets required

Art hounds, get ready to move your paws and take in Chicago’s best murals! You can run a 5K or walk 1 mile, all while enjoying the city’s street art scenery. This Art Run and Walk raises funds for Big East Akita Rescue. Friendly pups are welcome to participate at no additional cost, and must be up to date on all vaccinations.

3. Beer in the Woods

LaBagh Woods, Chicago
Saturday, September 24, 2–6 p.m.; Tickets required

You like to drink and pup likes nature—we got you both! Sip beer and enjoy a day in the forest preserves at this unique event that’s been called “the best beer festival of the season.” Try samples from dozens of the region’s best breweries and cideries, enjoy guided nature walks, create nature-inspired art, win awesome raffle prizes, and mutts more!

4. BarktoberFest

Sheraton Grand Chicago Riverwalk, Chicago
Saturday, September 24 and Sunday, September 25, 8 a.m.–2 p.m.

This Oktoberfest has gone completely to the dogs! Point your paws toward the Chicago Riverwalk for BarkoberFest, an interactive marketplace featuring dog activities like peanut butter painting, training sessions, local vendors, raffle prizes, and more. Come hungry because Chicago Burger Company will have both human and dog menus, plus cold beers.

5. McKinley Bark 5K and Health Fair

McKinley Dog Park, Chicago
Saturday, September 24, 9 a.m.–1 p.m.; Tickets required

If your philanthropup could choose a cause to support, our guess is a dog park would top the list! Here’s their chance to show ruv for the McKinley Dog Park at this weekend’s 5K and Health Fair. Trot your way to the finish line and then check out vendors and demonstrations dedicated to pet health. Purchase a ticket for the race, or just come later for the free health fair. 

6. Veganlandia

Easy Does It, Chicago
Sunday, September 25, 12–4 p.m.

Whether you live a plant-based life or simply want to sample vegan goodies, sniff out Easy Does It on Sunday when Chicago Vegan Test Kitchen brings together local vegan chefs and cruelty-free artisans. Veganlandia features 15 vendors and a welcoming atmosphere complete with a family and dog-friendly patio.

7. Tiny Dog 500

One Tail at a Time, Chicago
Sunday, September 25, 2–5 p.m.; Tickets required

Chihuahuas, start your engines! One Tail at a Time is hosting a Tiny Dog 500 where the smallest canine athletes will see how fast their lil legs can go, and who will take home some sweet prizes. In order to race, dogs must be friendly with humans and other dogs, spayed/neutered, and up to date on shots. Athletes will be divided into three divisions: Featherweight 1-10lbs, Middleweight 11-20lbs, and Seniors 1-20lbs/10+ years.

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.

Rover Rescue

  • The adoptable dogs of Rover Rescue will be doin’ their cutest puppy dog eyes to find loving homes this weekend. Head to PetSmart in Bolingbrook on Saturday, September 24 from 12–2 p.m. You might just meet your new bestie!

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 Samson Katt

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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