Outside Lands is not for the faint of heart. Its goal is to encourage festival-goers from all walks of life. However, the tough terrain is no joke. Much of Golden Gate Park is just as hilly as the rest of San Francisco, except that, unlike the urban streets, the park is a hiking trail. Expect a workout if you even attend the festival as a single-day spectator. It’s incredibly strenuous as the city’s classic cold weather kicks in, making chilly nights the norm. Though a summer festival, most are bundled in puffer jackets layered over other shirts, cardigans, and hoodies. Festival fashion showed up and out, but in a unique way. Still, some were brave enough to bear it all, showing their natural-born assets despite, or perhaps despite, the bitter wind chill and drizzle that made the hikes a bit more dangerous. Most of the General Admission entrances are only accessible via grassy hills, which get very slip n’ slidey as the raindrops become denser.

My day began a bit later as legend Grace Jones took the stage. Her overwhelmingly bright aura was on full display to a packed mainstage crowd. Her crowd was arguably among the most diverse of the weekend, with unsuspecting diehard fans flocking to the front rows and backing out immediately after her last song ended. Though I spectated the later half of the evening from the media tent, Jones’ presence was unlike anything I had experienced before. There is nothing like watching legacy performers who command the stage with…grace. Sorry. I had to. I’d heavily anticipated Jones’ set after being raised on her music. Truthfully, I expected an eclectic crowd—not only because this is San Francisco, but because my trad goth, metalhead mother is among her most significant fans of all time. She demanded videos from her and her other favorites, reminding everyone that most music can resonate with anybody.

Finally, pint-sized pop star Sabrina Carpenter hit the stage for her first festival headlining set. Originally slated to be Tyler, The Creator, Carpenter had large shoes to fill. Some had underestimated her, leaving after Jones’ final song. However, one must recall that an Eras Tour opener has to know how to show up and show out. Her history as a Disney starlet is not nearly indicative of her adulthood career, which has matured in a much sillier yet practical way compared to those of her contemporaries. Carpenter has taken plenty of notes, learning how to march to the beat of her drum, using her quirks to her advantage. Thanks to her apparent physical beauty, she is mesmerizing and because she is having so much fun up there.

The Outside Lands set was significantly different from her Coachella performance. This time, her Hairspray-esque variety show charmed the audience from the start, with a narration introducing the show and immersing us into this world fully and immediately. There were a few songs in the set that I did not know, but I enjoyed them, a sign of a performer packed full of potential. Festival setlists are challenging for any artist to curate, regardless of their experience level, due to the uncertainty of the crowd. Carpenter catered to diehard fans and casual concert-goers, understanding that she may have had some grumpy audience members disappointed by the original headliner dropping out.

If anything, Carpenter went above and beyond to prove that she deserved the headlining slot. Her simple choreography is polished enough for pop but doesn’t feel forced. It’s almost tongue-in-cheek; she’s self-aware in her Barbie doll persona, so she moves to laugh with everyone so no one can laugh at her. It’s a genius tactic on her part, perhaps proving her celebrity mentors to be better teachers than anyone could have anticipated.

I’d already been a fan of Carpenter, but I'm not allowing my opinion to be swayed by Hollywood popstar beef. Her performance of “Because I Liked A Boy” made me wonder why the two did not join forces instead of letting a guy get between the two so severely. However, I will admit that the song itself is perfect, as was the performance of it.

Her best trick of the evening included a guest appearance by country starlet Kacey Musgraves. Their rendition of “These Boots Are Made For Walkin’” was met with thunderous applause.

Carpenter’s set was marked by big hits like “Nonsense” and “Espresso,” but deeper cuts were interwoven. Our “Nonsense” outro was expectedly silly, shouting out Carpenter’s upcoming album, which I believe will give her that final push into household-name territory once it is released. Many who begrudgingly sat through bubblegum pop will later be glad they did. There were many times this weekend when I felt like I was witnessing history in real time, and this was one of them. Outside Lands was designed to fill a Bill Graham’s Day On The Green-sized hole in the hearts of San Franciscans, and these moments are proving that it certainly can do just that.