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28 Fun Things To Do With Your Dog This Fall


The dog days of summer may be done—and with them, the days of sitting on bar patios with your pooch—but don’t despair: there are still plenty of awesome, dog-friendly places in the Chicago area for you and your four-legged friend to explore!

*Note: All addresses are located in Chicago unless otherwise noted.

1-4: Get Cultured

Your dog probably doesn’t appreciate art or history, but we’re betting he’d still love to join you as you check some out.

Take him along to Ellen Lanyon’s Riverwalk Gateway (Lake Shore Drive and Wacker Drive), a walking history and art passageway featuring 28 narrative panels that tell the story of the city’s history. Chagall’s Four Seasons Mosaic (10 S. Dearborn St.) which is sometimes called the city’s happiest piece of art for its bright, colorful tiles depicting six iconic Chicago scenes. Check out the amazing sculptures in Grant Park (337 E. Randolph St.), like “Agora”* on the park’s southwest end. If you’re in the mood for some history, head over to Ernest Hemingway’s Birthplace (339 N. Oak Park Ave., Oak Park)— though Fido isn’t allowed inside the house, he is allowed to walk with you around the grounds of the home where one of the country’s greatest writers (and cat lovers–– Hemingway’s six-toed cats were famous in their own right) was born and raised.

5-7: Garden State

Dogs love to stop and smell the roses (and trees and bushes and grass). Take your pup to one of these beautiful gardens, where she can sniff around to her heart’s content. Visit the Ladd Arboretum (2024 N. McCormick Blvd., Evanston) and admire the gardens and trees in their full autumn glory. While you’re in the area, stop by the Shakespeare Garden (Northwestern University campus, 2121 Sheridan Road, Evanston) featuring more than fifty varieties of plants common to the Tudor period, many of which were mentioned in Shakespeare’s works. Enter another world at the Osaka Garden in Jackson Park (5800 S. Lake Shore Drive)—a Japanese Garden complete with waterfalls, historic Japanese sculptures, and plenty of Zen greenery.

8-9 : A Day at the Pier

Sometimes the best days are just spent sitting on a bench and watching the world go by. You and your pup can get in some excellent sightseeing along the boardwalk at Navy Pier (600 E. Grand Ave.), and if you get hungry you can stop at Harry Caray’s Tavern (located near Navy Pier main entrance), where you can chow down on a Holy Cow burger while your dog enjoys a treat and souvenir water bowl.

10-15: Shopping Buddy

Your dog wants to spend as much time with you as possible, so why not let him join you on your next shopping trip? Plenty of local shopping destinations allow dogs to come along, like Nordstrom (55 E. Grand Ave.), Crate and Barrel (850 W. North Ave.), and the 900 North Michigan Shops. If you’ve got a good eye for antiques, take Spot along to peruse the delightful finds at SG Grand (1822 W. Grand Ave.). Farmer’s market season is winding down, but many are still open through the end of October and are great places to explore with leash in hand. Check out the Green City Market (1790 N. Clark St.), open Wednesdays and Saturdays though October 25 or the Logan Square Farmer’s Market (Logan Boulevard from Milwaukee Avenue to Whipple Street), open every Sunday through October 26,and stock up on organic seasonal treats your dog can enjoy too, like yams, butternut squash, and green beans.

16: Fall-Inspired Fun

Gather up the entire family and spend a day at Richardson Farm (909 English Prairie Rd., Spring Grove), where dogs are welcome and you can enjoy the world’s largest corn maze, a pumpkin patch, wagon rides, and large slides. We promise all dogs (and kids) will come home exhausted.

17-20: Take a Staycation

When you live in or near such a glorious city as Chicago, there’s really no reason to go anywhere else. Your pet is a welcome guest in the following hotels, which have no weight restrictions or pet fees and offer amenities like hotel-organized pet sitting and dog walking services: the Hotel Allegro (171 W. Randolph St.), Hotel Burnham (1 W. Washington St.), Hotel Monaco (225 N. Wabash Ave.), and the Hotel Palomar (505 N. State St.), which even offers pet acupuncture.

21-22: Make a Difference

Those that care together, volunteer together. Read about SitStayRead (SitStayRead.org) on page 10 and consider signing up as a Dog Team so you and your dog can help teach literacy skills to underprivileged students. Have you ever thought about having your sweet doggie trained as a therapy dog? Bark Avenue Playcare (1959 W. Fulton St.) offers classes that meet the guidelines of Canine Therapy Corps, a Chicago-based animal assistance organization.

23-26: Trail Blaze

What better way to enjoy your time with your pooch than to just get our there and walk? We recommend the gorgeous Lakefront Trail (along Lake Michigan from Ardmore Street to 71st Street) for 18 miles of scenic strolling (just don’t try to do all 18 miles in one day!). If you want to go somewhere a little quieter, head over to the Burnham Prairie Path (47th Street and Lake Shore Drive) and admire a short stretch of wild prairie life right in the city. Outside of the city, visit the Waterfall Glen Forest Preserve (Cass Road and Northgate Road, Darien), home to lots of trails, a serene waterfall, and tons of interesting flora and fauna. Or head to the Des Plaines River Trail (stretches across all of Lake County, entrance points varied) and soak in the gorgeous colors of fall.

27-28: All Aboard

Depending on the weather, you may be able to enjoy a bit of fun on the water with these local boat companies. Just make sure to call first before heading over so you can be sure they’re offering rides that day.

At Kayak Chicago (Montrose Harbor) you can rent a kayak for $20 and paddle out with your doggie. Orientation and safety training is provided, but make sure to bring your own doggie life jacket. For a more leisurely boat ride, check out Seadog Cruises (Navy Pier, 600 E. Grand Ave.)–– dogs ride free on their lakefront speedboat cruises, and you even get 10% off your ticket for bringing a furry friend with you!

* We originally stated that you could visit the famous sculpture “The Bean” in Grant Park. Please note that “The Bean” is actually located in Millennium Park, where dogs are not allowed. We apologize for the confusion! – TAILS Team

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