National Dog Day, or International Dog Day around the world, is celebrated on August 26 every year. You probably see posts on social media stating that every day is a dog day, which is correct. It’s not, in fact, a federal holiday with paid time off, which leaves most of us working for more than treats and pets.
When you and your dog take some much-needed time off together, here are some of the best iconic, wine-pairing walks around Chicago. According to my dog Kol, who I adopted from the PAWS Chicago Animal Shelter, a tiny taste can’t hurt, but that’s up to you and subject to puppy eyes.
Dog walks and food and wine pairings are listed from south to north, in town and in the suburbs.
Stroll through Pullman National Monument Historic Park on the south side and around the old company district. You can park for free in the Visitor Center parking lot, but note that pets are not allowed in the park buildings.
Head to the Lexington Betty Smokehouse and get the classic Chicago-style barbecue combo of hot ribs and sausage, or a vegan pulled jackfruit sandwich. This is the second location for pitmaster Dominique Leach. This is normally counter service, but there is free parking with a dog-friendly off-street patio, and they will bring your order to you and your dog if possible.
Pullman National Monument, 610 E. 111th Street, 773-468-9310, nps.gov/pull; Lexington Betty Smokehouse Pullman, 756 E. 111th St., 708-927-5614, lexingtonbettysmokehouse.com
Stroll through Chinatown’s sprawling Ping Tom Memorial Park along the Chicago River. You might find Chinese elders practicing tai chi under the open-air pagoda early in the morning. You can park for free on the grounds of the estate, but only if you stay on site. If you’re going to visit the Dog Statue in Chinatown Square’s Zodiac Square, there’s paid parking on the street, but it can be chaotic.
Head to the flagship location of Hello Jasmine, the Taiwanese street food restaurant that started out in the influential basement food court long known as the Richland Center. Get their stellar popcorn chicken and boba tea (with customizable sweetness), plus they have the rare Chinatown combination of free parking and an outdoor sidewalk patio. They normally offer counter service, but they will bring your order to you and your dog if possible.
Ping Tom Memorial Park, 1700 S. Wentworth Ave., 312-225-3121, chicagoparkdistrict.com/parks-facilities/Ping-Tom-Memorial-Park; Hello Jasmine Chinatown, 2026 S. Clark St., 312-988-0920, hellojasmineus.com
Stroll through the beautiful Frank Lloyd Wright Home and Studio neighborhood in Oak Park, just west of the city. Remember that these are private homes, although some seem as big as museums.
Head to Johnnie’s Beef for the hottest dish of the summer: Italian beef. Get your beef the way you like it, but I prefer juicy hot, which is their love language for dunking in beef jus with hot giardiniera. They offer counter service, but there are a few free parking spaces, as well as dog-friendly off-street picnic tables.
Frank Lloyd Wright Home and Studio; 951 Chicago Avenue, Oak Park; 312-994-4000; flwright.org. Johnnie’s beef; 7500 W. North Ave., Elmwood Park; 708-452-6000; facebook.com/Johnnies-Beef-169537026394157.
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Don’t forget your sunscreen and wade to Montrose Dog Beach in Uptown. It’s technically free, but officially you need a Chicago Park District Dog Friendly Area permit and tag, so plan ahead. Don’t forget to check for daily swimming bans due to weather, surf conditions or water quality.
Go to the Argyle Street neighborhood and grab a banh mi from Ba Le Sandwiches or Nhu Lan Bakery, or really plan ahead and order a Chicago-style caramelized crust pizza at Milly’s Pizza in the Pan, maybe an Updog, given the canine celebration, with sausage and pepperoni. They are selling out, and there is only street parking, but there is a sidewalk patio that allows dogs.
Montrose Beach Dog Friendly Zone, 601 W. Montrose Ave., 312-74-BEACH (312-742-3224), chicagoparkdistrict.com/parks-facilities/montrose-beach; Milly’s Pizza in the Pan, 1005 W. Argyle St., instagram.com/millys_pizza_in_the_pan
Hike the unpaved Des Plaines Trail along its namesake river through Potawatomi Woods, named after the indigenous peoples driven from this land north of the city. You can park for free near the picnic grove which you will find near Dundee Road, just east of Milwaukee Avenue.
Head to the Superdawg Drive-In in Wheeling, where perennial hot dog couple Maurie and Flaurie await. Pick up a classic Chicago-dressed Superdawg (except for their unique Pickled Green Tomatoes) while driving, driving, or parking in the free parking lot, then sit down at a picnic table outfitted with menus and loudspeakers. You can also walk through Caldwell Woods near Devon Avenue and then walk to the original Superdawg across the street in Chicago.
Potawatomi wood; East Dundee Road, east of North Milwaukee Avenue near Northbrook; 800-870-3666; fpdcc.com/places/locations/potawatomi-woods. Superdawg Drive-In; 333 S. Milwaukee Ave., Wheeling; 847-459-1900; superdawg.com.
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