There are people who will try to tell you with a straight face that the sweaty and grueling summer months, or more believably the Santa Claus -focused sprint from Black Friday to “Auld Lang Syne,” can lay claim to being the best time of any given year. Given the existence of Halloween , these people would be wrong .

Megan Thee Stallion , mercifully, kickstarted the 2026 Halloween season earlier this month with the latest entry in the Grammy winner’s long-running series of well-timed photos of herself in full pumpkin-headed regalia. For those somehow unfamiliar with this tradition, here’s the gist: When Megan drops the pumpkin pics, Halloween has formally begun .

Of course, a key aspect of the season is keeping tabs on people with virtually unlimited resources who opt to throw some bills in the general direction of thrills and chills every October.

Below, we take a look at this year’s highlights (so far).…