Mutts-Do Dog-Friendly Chicago Fall Activities

Fall has…fallen! We’ve only so much time in this precious window between I-can’t-go-out-without-melting and I-can’t-go-out-without-my-face-hurting, so you and your pup gotta make the most of it. And whether it’s pugkin spice or bark to school that gets your bud’s tail wagging, there’s definitely a dog-friendly Chicago fall activity for you.

COVID restrictions in the city may change, especially as the weather gets colder and we do more indoors. Even if places are usually dog-friendly, you may want to call ahead to make sure pup’s welcome! 

1. Go Pumpkin Picking

Kick off fall the right way. Take your pal to a dog-friendly patch and sniff out the perfect pumpkin. Pro tip: Have pup wear her booties; those vines are prickly! 

2. Plan a Fall Getaway

In this Chicago writer’s humble opinion, autumn here is unmatched. Take pup on a staycation at one of our favorite dog-friendly hotels to ‘splore a different neighborhood in the city. But that’s not to say that the Midwest doesn’t have some other cute spots! Leash up pup and go on a fall getaway together.

I’m 21 in dog years. | @norpup

3. Visit Dog-Friendly Breweries

Chilly day? Share some cold ones at one of the dog-friendly breweries that welcome dogs inside. Want to go a bit more seasonal with a cider instead? Warm up with a cider at ERIS, a brewery and cidery with a heated, dog-friendly patio, or The Northman, Chicago’s first cider bar.

4. Enjoy Specialty Dog Days

There are plenty of spots to enjoy nature in Chicago, but not all are dog-friendly year round. 

Hit the trails at Morton Arboretum for their Dog Admission Days and Tails on the Trails. Get there early–this event gets packed!

For just 2 hours per year, your dog can go to the Botanic Garden; While the Spooky Pooch Parade was cancelled for 2021, that just means you have more time to plan for next year’s costume! 

5. Savor the Last of Patio Season

While true Midwesterners like to think that patio season never ends (you just need another layer!), let’s admit that patio season is starting to wrap up. Celebrate the last few weeks of al fresco dining with your bestie with a little hair of the dog and share some delicious brunchos

Feeling like celebrating Taco Tuesday instead? Get toasty together over margs and tacos at our favorite dog-friendly taco joints.

6. Celebrate Pup-kin Spice Latte Season!

Warm up with a tasty coffee at one of our most-loved dog-friendly coffee shops. If you’re feeling more of the DIY route, check out these pumpkin spice dog products.

7. Shop Local

Pup knows that we need to support the local economy and shop local; when Chicago decides to throw some rain into the fall forecast, enjoy the great indoors and stay dry in a store.

Reading to dogs is as great way to help them destress, and Fluffy could use it after the week she had at work. Pick up a new book at these dog-friendly bookstores. Trying to find a new ‘fit? Ask Spot for his honest opinion on if you can pull off culottes at one of these dog-friendly boutiques.

What other Chicago fall activities are on your list? Give us a howl in the comments, and be sure to tag #SidewalkDog in all your autumnal adventures.

Featured photo by Tim Golder

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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