Run, Party, and Cruise Through Your Chicago Weekend

We’re just a week away from the first day of fall, so grab puppers and spend one more unforgettable summer weekend together! Read on for suggestions on where to go in dog-friendly Chicago.

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1. Run for Beer

Whiner Beer Company, Chicago
Saturday, September 17, 11 a.m.–2 p.m.; Registration Required

Everyone has their own reasons for running—the folks at the Illinois Brewery Running Series run for beer! Leash up your jogging buddy and head to Whiner Beer Company 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 local craft brew at the finish line.

2. Cruise with Roo

Mercury Cruiseline on the Riverwalk, Chicago
Sunday, September 18, 10 a.m.; Tickets Required

Cruising Chicago’s waterways is always a treat, but this outing also does a whole ‘lotta good! Grab your lil skipper and Cruise with Roo. This annual boat cruise with your dog raises funds for Live Like Roo, an organization that assists pets through a cancer diagnosis by providing financial and emotional support for their humans. 

3. 569 Bark Park’s 8th Birthday Party

Skinner Bark Park, Chicago
Sunday, September 18, 10 a.m.–1 p.m.; Tickets Required

Who doesn’t love a birthday pawdy?! Come celebrate 569 Bark Park’s 8th year with an event focused on the love of our furry frens. You and pup will enjoy mini dog photoshoots, caricature drawings, raffles to win gift cards, local vendors with free swag and samples, and more. Proceeds support the maintenance of this beloved dog park.

4. Fall Nature Fest

Labagh Woods – Foster Ave. & Cicero Ave., Chicago
Saturday, September 17, 12–3 p.m.

Grab the whole fam (pup too!) and head to Labagh Woods this weekend for the Fall Nature Fest. Meet animal ambassadors from the Brookfield Zoo, hear live music, watch a performance by the Jesse White Tumblers, drool over food trucks, enjoy family-friendly activities, and connect with eco-friendly organizations and businesses from across Chicago.

5. Plant Chicago Harvest Fair

Plant Chicago, Chicago
Sunday, September 18, 3–6 p.m.; Tickets Required

Floof knows Plant Chicago’s fall fundraiser is tail-waggin’ fun. Sniff out the Harvest Fair for tasty treats, cocktails, yard games, and live performances. Get crafty with DIY activities like taffy apple making, soap scrub making, mending, and tie dyeing. Try your hand at ring toss for a chance to take home a top-shelf bottle of Paw Paw liqueur from Apologue Liqueurs. Leashed and well-behaved pups are welcome, organizers just ask that you be mindful of other attendees and onsite chickens.

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.

Naperville Area Humane Society

  • Eat The Frog Fitness is hosting an adoption event for Naperville Area Humane Society on Saturday, September 17 from 11 a.m.–1 p.m. Come shake paws with these adorable adoptables and see if you can make a ruv connection!

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: Jan Dix

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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