A few years ago, a pair of older friends warned me that I’d soon get swept up in the chaos of wedding season. My instinct was to scoff. Maybe they were tired of the long weekend commutes, the pseudo high school reunions, the endless investment in Hallmark cards offering some flowery reiteration of “Congratulations!” But a true friend like me? I couldn’t wait.

As I write this, my fiancée and I are wrapping up what we’ve since dubbed “the summer of weddings.” The onslaught of RSVPs hit us like a Mack truck from May to August (with a few ceremonies trickling into the fall). By July, my threshold for celebrating love had reached its peak. It turns out, I wasn’t quite as impervious to the fatigue of wedding season as I once thought. But I reckon it’s not so much the obligations themselves that prove taxing (to all our friends: your receptions were beautiful, the food was fantastic, and your parents’ speeches were the perfect length). Instead, more than anything, I think it’s experiencing firsthand such a clear passage of time — and the adjustment to a new chapter — that makes the season carry so much weight.

In many ways, adjusting to new chapters seems to be the defining theme over the past few months. At the end of July, I travelled to Detroit to drive Jeep’s new electric vehicle, the Wagoneer S. Designed by the youngest team in the brand’s storied history, it represents a brave new chapter not only for Jeep but for the Motor City at large. Many of the watches in our September issue are also celebrating their most momentous chapters, from the Omega Seamaster becoming the official watch of NASA’s Apollo program to Longines’s century of the GMT/Dual Time complication.

Then, of course, there is the Toronto International Film Festival’s upcoming 50th anniversary. In preparation for the occasion, we interviewed CEO Cameron Bailey and emerging director Lloyd Lee Choi. With Bailey’s TIFF tenure stretching past 25 years and Choi debuting his first feature film at this year’s festival, the anniversary marks two entirely different moments for the pair: Bailey, reflecting on a quarter-century of evolving Canadian filmmaking, and Choi, celebrating a newly realized creative milestone.

But when it comes to a season of ushering in new chapters, our cover star, Finn Wolfhard, is perhaps Hollywood’s most intriguing example. The world saw Wolfhard grow up, literally, on Stranger Things. He became one of television’s most beloved characters and a global sensation for his role as wavy-haired pre-teen, Mike Wheeler. But as the show reaches its final season after nearly a decade-long run, the prolific young actor, director, and musician is ready for whatever comes next. “I feel like every time there’s an end, it turns into something else,” Wolfhard reflects in our cover profile.

Bidding farewell to a previous chapter and celebrating something new is an understandably taxing exercise, no matter how bright the future is. Whether it’s an actor exploring fresh roles, a legacy brand changing the industry, or a member of Table 9 watching his friends walk down the aisle toward their next life stage (again, and again, and again), the transition isn’t meant to be easy. But what my summer of weddings — and much of this issue — has taught me is that if you surround those transitions with the right people, the right intentions, and the right occasion, you create a celebration well worth the trip.

— David Stol, Managing Editor

Feature photo by Luis Mora. Suit by BOSS.