This travel spot is featured in our seventh blog series, Sheps Stay. Photo by 2026 Time Out No trip to Chicago, Illinois with your dog is complete without a visit to Montrose Dog Beach, the city's only official off-leash beach. Here, your pup can splash in Lake Michigan, run through the sand, and make new furry friends while you take in stunning views of the Chicago skyline. This one-of-a-kind destination combines the excitement of a big city with the freedom of a lakeside ad

The Leelanau Peninsula of Michigan is a dream for dogs and their humans. There is fresh lake air, walkable villages, and plenty of places where pups are more than welcome. From charming harbors to forest trails, every town offers its own unique canine-friendly charm.

Planning a family getaway with your dog? Luie Boone wants you to know that Door County, Wisconsin, is the perfect destination. It’s a place where every member of the family—including the four-legged ones—is welcome to join in the fun. This scenic peninsula blends charming small towns, outdoor adventures, and plenty of pooch-friendly places to sniff out and enjoy together.