Your Dog-Friendly Chicago Weekend: October 14-16, 2022

Think this season is all about flannel shirts and pumpkin spiced lattes? Don’t get us wrong, sipping a PSL while rocking matching flannels with your pup sounds great, but there are so many more fall festivities to enjoy. Here’s your dog-friendly Chicago weekend to-do list.

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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. Yappy Hour

The Northman, Chicago
Friday, October 14, 5–8 p.m.

Doggo’s had a hard week, so he needs to start the weekend promptly at 5 on Friday. Luckily he’s invited to Javi’s Yappy Hour at The Northman on The Riverwalk. Between the drinks from Yavi’s Ranch Water and the heated covered pergola, you’ll be toasty warm at this pup-friendly party. RSVP for a free Javi’s Ranch Water upon arrival. 

2. Connect South Shore Arts Festival

7045 S Jeffery Blvd, Chicago
Saturday, October 15 and Sunday, October 16, 11 a.m.–7 p.m.

If you had one of those viral roller skating dogs, this event would be really cool. But even the most average pup will enjoy this Southside Arts Festival. This community event is rich in culture and features live entertainment, food, art, vendors and the big attraction—an outdoor roller skating rink.

3. Fall Fest on The Riverwalk

Island Party Hut, Chicago    
Saturday, October 15, 1–4 p.m.; Tickets required 

This one’s like taking pupper to the beach… but like, in autumn… and on the Riverwalk. Get your tickets for Island Party Hut’s Fall Fest and sip on delicious fall drinks, indulge in all-you-can-eat chili, share an apple cider donut with doggo, snap that perfect Insta pic in the pumpkin patch, play games, or just relax.

4. Beer Run

Empirical Brewery, Chicago
Saturday, October 15, 11 a.m.–2 p.m.; Registration required

Our frens at dog-friendly Empirical Brewery are hosting this weekend’s chance to run for beer!  Leash up your pint-sized jogging buddy for a 5k-ish fun run that starts and ends at the taproom. Complete the course as fast or slow as you please, then celebrate with a free craft brew. You’ll also receive a collector’s pint glass, a chance to win prizes, and access to event festivities.

5. Pumpkin Picking

List of locations, Illinois 
Hours vary depending on location

If you haven’t snapped dozens of pics of your little pup-kin at the patch this year, you’re falling behind! (See what we did there?) We’ve sniffed out 5 Illinois pumpkin patches that allow floof to tag along. Pack some snackies, take a C-A-R R-I-D-E to your favorite patch, and bring home some gorgeous gourds to get in the Halloween spirit.  

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

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

PAWS Chicago

  • PAWS Chicago has so many adorable doggos lookin’ for homes right now. Like Epic, a senior pittie who loves ham, long walks, cuddles, warm blankets, car rides, and fluffy toys. Seriously, all our fave things! Meet adoptable pets from PAWS this Saturday, October 15 from 12–3 p.m. at Glen Ellyn’s Main Street Recreation Center.   

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: Jayson Lorenzo

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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