Crisp mornings. Colorful leaves. Pumpkin everything.
There's no better time of year to grab the leash and head out on an adventure with your dog.
Whether your pup loves exploring new trails, meeting other dogs, or simply joining you for a fun afternoon, Chicagoland offers plenty of pet-friendly destinations to enjoy together.
Here are five outings we think both you and your dog will love this fall.
If your dog could plan the perfect day out, this would probably be it.
Join us for the Two Bostons Pet Wellness Fair on Saturday, September 12th at our St. Charles location for one of the biggest pet events of the year.
With more than 40 pet brands, you'll have the opportunity to:
Whether you're raising a new puppy or caring for a senior dog, you'll leave with new ideas to help your pet live their happiest, healthiest life.
Sometimes the best adventures are the simplest ones.
Chicagoland is home to dozens of beautiful forest preserves where leashed dogs are welcome to explore alongside you.
Cooler temperatures make fall one of the best seasons to enjoy longer walks while your dog experiences new sights, smells, and sounds.
Don't forget to pack:
Few places feel more like fall than Abbey Farms.
Leashed dogs are welcome throughout much of the property, making it a fun place to stroll the grounds, browse the farm market, snap a few seasonal photos, and soak up everything autumn has to offer.
Before your visit, be sure to review Abbey Farms' current pet guidelines, as access may vary for certain attractions like the corn maze or hayrides.
Looking for a relaxed afternoon?
Take your pup for a walk through Downtown Wheaton, browse the locally owned shops, and enjoy lunch or dinner at one of the restaurants along the seasonal Hale Street Tents.
The covered outdoor dining area creates a fun, walkable atmosphere where many restaurant patios welcome well-behaved dogs.
It's an easy way to enjoy great food, support local businesses, and spend quality time with your four-legged best friend.
If your dog isn't quite ready to say goodbye to summer, plan one more water adventure before cooler temperatures settle in.
Dog-friendly beaches and designated dog swim areas around Chicagoland give water-loving pups one last chance to splash, swim, and burn off energy before winter arrives.
Always check local rules, seasonal hours, and permit requirements before visiting.
No matter where you're headed, bringing a few essentials can help your outing go smoothly.
We recommend packing:
Need to stock up before you go? Two Bostons has everything from trail-ready treats and travel gear to leashes, harnesses, toys, chews, and other adventure essentials to help you and your pup make the most of every outing.
A little preparation goes a long way toward making every adventure enjoyable for both you and your dog.

The best memories don't always require a big trip.
Sometimes it's discovering a new trail, strolling through town, spending a day at the farm, or meeting fellow pet lovers at a community event.
However you choose to celebrate the season, fall is the perfect time to unplug, head outside, and make a few more memories with your favorite adventure buddy.
Wherever your next adventure takes you, we'd love to see it. Be sure to tag @TwoBostonsBoutique in your favorite fall photos!
What are some dog-friendly things to do in Chicagoland this fall?
Some great options include visiting the Two Bostons Pet Wellness Fair, exploring local forest preserves, strolling through Downtown Wheaton, visiting Abbey Farms, or spending time at a dog-friendly beach before the season ends.
Can I bring my dog to Abbey Farms?
Leashed dogs are welcome in many outdoor areas at Abbey Farms. Some attractions, such as hayrides or corn mazes, may have restrictions, so it's always a good idea to check their current pet policy before visiting.
Are dogs allowed at the Two Bostons Pet Wellness Fair?
Yes! The Pet Wellness Fair is designed for pets and their people. Leashed, well-behaved dogs are welcome to attend and enjoy the event alongside their families.
Are dogs allowed at forest preserves in Chicagoland?
Many Chicagoland forest preserves welcome leashed dogs on designated trails and paths. Be sure to follow posted rules, clean up after your pet, and keep them on a leash unless otherwise permitted.
What should I bring on a dog-friendly outing?
Pack water, a travel bowl, waste bags, treats, a leash, and any essentials your dog may need for the day. If you're heading to a beach or muddy trail, a towel is also helpful.
What's a fun fall activity to do with my dog?
Fall is a great time to explore scenic trails, visit pumpkin farms that welcome dogs, enjoy outdoor dining, attend pet-friendly events, or simply take a longer walk while enjoying the cooler weather.