For a five-year-old at Disney World or Disneyland in 2026, the answer is almost always "yes." While a five-year-old may be energetic at home, a typical day at a Disney park involves walking between 8 and 12 miles (13-19 km). The combination of high heat, massive crowds, and long hours on their feet leads to "meltdowns" and physical exhaustion by mid-afternoon. A stroller provides a "safe space" for the child to rest, nap, and take a break from the sensory overload, which ultimately allows the adults to stay in the park longer. It also serves as a mobile storage unit for snacks, water bottles, and souvenirs. In 2026, you can either bring your own (ensuring it meets the 52" x 31" dimension limit), rent a plastic "Mickey" stroller from the park (which are sturdy but don't recline), or use a third-party rental service like ScooterBug that delivers a comfortable, reclining stroller to your hotel. Even if your child hasn't used a stroller in years, the "Disney Mile" is a different beast entirely, and having one can be the difference between a magical day and a miserable one.