The Spiced Pumpkin Painkiller is the holiday cocktail of our dreams, and you can get it at both the original Three Sixty in downtown St. Louis and the newer Three Sixty Westport in Maryland Heights. Created by Tim Wiggins of Bangers Only cocktail consulting company, this isn’t your typical overly sweet, over-spiced seasonal drink: It’s strong, balanced and surprisingly nuanced. Dark rum anchors the cocktail, while pumpkin spice, coconut cream, orange, ginger, lime and a little streusel come together in a mix that’s perfectly complex and delightfully delicious.
Both locations are running their Up on the Rooftop holiday pop-ups through the entire month, and you don’t need a reservation to get in on the fun. We tend to gravitate toward the Westport spot for the overall vibe, but the cocktail list is identical at both. And if you’re chasing views, the downtown rooftop is hard to beat with 360-degree panoramas that sweep over the Arch, Busch Stadium and Kiener Plaza. Both locations offer open seating, but reservations are available for groups of 10 or more.
This article appears in December 2025.