The phrase "to crack the sidewalk" means to cause the pavement on a sidewalk to break or split, usually through applying a lot of force or pressure. Full definition
One mom says she takes her son over sand, dirt and cracked sidewalks with ease and her 3 1/2 - year - old boy was just as comfy as could be. (stroller-envy.com)
You can easily push it over cracked sidewalks and packed dirt paths and one mom even said she took hers over gravel! (stroller-envy.com)
They are the things we all live with like cracked sidewalks, staircases without handrails, or windows that stick when you open them. (springshomes.com)