Doggo spent all week nappin’ in the sunny spot on the floor—lil’ dude needs to get out! Lucky for you, we found plenty of dog-friendly activities for you to enjoy together. Here’s your 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. Fall Lincoln Roscoe Art and Craft Fair
North Lincoln Avenue & West Roscoe Street, Chicago
Saturday, October 1, 10a.m.–5 p.m.
Floof knows good art when she sees it, so she’s gonna ruv this northside event featuring paintings, sculptures, ceramics, jewelry, fashion wearables, and more. Meet the artists and artisans, hear live music, buy some snackies or a cold brew, and bring the human kiddos along if you’ve got ‘em cuz there’s kids activities too.
2. DOGtoberfest at Pilot Project
Pilot Project Brewing, Chicago
Sunday, October 2, 11 a.m.–7 p.m.; Reservations
Raise a glass (or dog treat) with your pup on the Pilot Project patio for their dog-friendly version of Oktoberfest. Secure your spot with a free reservation and enjoy Parisian “ruff” lattes (whip cream+spent grain dog treats), doggie play pools, a photo booth, vendors, and more. Purchase a discounted package ahead of time for $12 and get 1 beer, booch, or hard cider ticket, 1 spent grain dog treat, and 1 ROVM Hard Kombucha bandana.
3. Dog-Friendly Market
Midwest Coast Brewing Company, Chicago
Sunday, October 2, 12–5 p.m.
Beer? Check. Dogs? Check. Shopping? Check. Yup—this one’s got all our favorite things! Visit our canine loving frens at Midwest Coast Brewing for a night of drinks, doggos, and deals. They’re bringing in vendors that know just what your pet needs (okay maybe this is more of a wants situation), but either way make sure fluffers brings her wallet!
4. Beer Run
Alarmist Brewing, Chicago
Saturday, October 1, 11 a.m.–2 p.m.; Registration Required
Another nice weekend, another chance to run for beer! Leash up your pint-sized jogging buddy and head to Alarmist Brewing 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.
5. Halloween Cruise
Mercury Cruiseline on the Riverwalk, Chicago
Saturday, October 1 and Sunday, October 2, 10:15 a.m.; tickets required
Kick off the spooky season with a Howl-O-Ween cruise on Chicago’s waterways. Dress doggo in costume and come aboard for a special boat ride with pumpkin dog treats and prizes for the best doggie costumes. Mercury’s dog cruise offers safe outdoor seating, water bowls for thirsty pups, bar and snack service for humans, and a newspaper-lined restroom for your pet.
6. Rock Out For Rescues
Active! Dog Daycare and Boarding, Chicago
Saturday, October 1, 2–7 p.m.; Tickets required
We know your lil’ rockstar is always ready to pawty, so bring him to Rock Out For Rescues where he can party for a great cause! Chi-Town Pitties is raising funds while raising the woof with live music, food, drinks, and raffle prizes. Rockin’ out with a taco in hand? Yes, pawlease!
Don’t have a dog already? Get a heckin’ dog!
Chicago English Bulldog Rescue
- Meet a few Chicago English Bulldog Rescue adoptables at the Roscoe Village Angels with Tails event. The event will take place along Roscoe Street between Damen and Oakley in Roscoe Village on Sunday, October 2 from 12-4 p.m. Shop, grab coffee, and shake paws with pups lookin’ for homes.
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: Gabe
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.