No Rest for the Wicked (or the Well-Traveled): Boston Calling on Practically Zero Sleep

Avril Lavigne performs at Boston Calling in Allston, Massachusetts, on Saturday, May 24, 2025

*One year ago today, on May 24, 2025, my traveling companion and I journeyed to the magical, faraway land of Boston, Massachusetts, in the heart of New England to experience a musical event known as Boston Calling. Held at Harvard Athletic Complex in Allston, the festival brought together some of our favorites: Fall Out Boy, All Time Low, The Maine, and a few others.

Naturally, we were jazzed. But then we decided to take things one step further by being just a little crazy, forgoing a hotel room, Airbnb, or accommodations of any kind, and instead booking an extremely early return flight for the morning after with no place to sleep on the itinerary. The question, of course, is: how did we, two “old” people, handle something better left to Monster- and Adderall-fueled college co-eds? Read on to experience for yourself what it was like spending roughly 19 hours in Boston without a place to stay.

Attending a music festival in another state was nothing new, but there was going to be an added element to this rodeo. We were going to tackle Boston Calling — a three-day musical extravaganza with a lineup comprised of the likes of Fall Out Boy, All Time Low, Cage the Elephant, and Avril Lavigne — in a fashion that would likely make even the most reckless gambler cringe: two old heads flying out to the East Coast and pulling an all-nighter as if we were teenagers again.

The festival was a Friday-Saturday-Sunday affair, but we had our sights set on the day sandwiched in the middle. This was mostly because of my traveling companion’s affinity for Fall Out Boy, who was the main headliner on Saturday. It certainly didn’t hurt, however, that they were packaged alongside All Time Low, which ranks as one of my top five favorite bands of all time. Throw in The Maine, Cage the Elephant, and Avril? Uh, yeah, that’s a party I want to go to.

SEE ALSO: 11 Things You Should NOT Do at a Summer Music Festival

We landed at Logan International right around 11 a.m. on Saturday and promptly Uber-ed ourselves over to Cambridge. For the next few hours, the section of John F. Kennedy Street just north of the Charles River became our little hub of operations. Armed with nothing but the clothes on our backs and a pair of fanny packs (#poetry), we set out to conduct the first order of business: finding some bloody marys.

In that vein, we popped into Russell House Tavern just up the way to see if we could nab a couple. Russell, as it turned out, served up a fine bloody, featuring perhaps the longest piece of celery known to mankind (or bloody mary-kind, for that matter). We both ordered the standard tavern breakfast — eggs, bacon, sausage, home fries, and an English muffin — to help wash those down, as one does.

And then came the rain. Not a lot of it, but certainly enough for both of us to cast a concerned glance in the other’s direction. We cautiously ventured back out to the street, not exactly sure what we’d do next, mildly worried that a downpour might ensue at any moment. Perhaps to help shove the thought out of our minds, we ended up heading for Grafton Street Pub & Grill, where there was one item on the menu that would surely calm our nerves. That’s right: say hello to the second round of bloody marys. Now, I’ve got to admit that Grafton didn’t have the same kind of bloody game as Russell and the crew, but even if the drink was mid, as the kids say, the atmosphere was on point. It didn’t hurt that we got a pair of prime seats at the bar either.

By the time we’d finished playing “Drink the Bloody Mary” for the second time, we were feeling peachy keen and ready to make a scene. And by that, I mean it was time to make way for the entrance to the festival. As we moseyed over, the sun kindly reappeared overhead, turning Saturday afternoon’s frown upside down. (Oh god, what is with all this rhyming?) Neither peachy, nor keen, nor frown-upside-down was the fact that security made me toss a ziplocked bag of Oreo-infused granola that I had in my fanny pack before I was allowed inside.

The first band we were eager to see — The Maine — was slated to hit the stage at 3:45 p.m. That still gave us plenty of time to venture over to the nearest merch tent and pick up our pre-ordered items, a T-shirt for me and a hoodie for the lady. We did not realize then just how much those extra layers of warmth would come in handy once the sun went down. It might have been late May, right on the cusp of summer, but a cold front was a-brewin’.

A band called Valley was performing by the time we made way for the main stage. I’d never heard of them before, but after listening to a few bangers, including the title track of their 2024 album “Water the Flowers, Pray for a Garden”, I was fairly certain they’d earned themselves a new fan. And isn’t that what music festivals are all about? You go to see bands you already know and love, but also have the opportunity to discover something or someone new, too. It’s beautiful. Life is beautiful. You’re beautiful. Shut up.

What the hell were we talking about again? Oh right, so The Maine came on next! Up until seeing them for the first time at the now-defunct Sad Summer Fest in Chicago in the summer of 2024, The Maine was more of a peripheral band in my life. Having seen them play live a grand total of four times now, I can say with certainty that they’ve jumped into my personal top ten as far as rock/alternative/punk bands go. They didn’t fail to put on a bangin’ show at Boston Calling either, complete with some of my favorite tracks and an impromptu guest vocalist from the crowd who helped lead a chorus of “Girls Do What They Want”.

Following The Maine, in order, were All Time Low (No. 3 on my top ten); Cage the Elephant (who I am still mad at for beating out blink-182 at the 2017 Grammy Awards for Best Rock Album (although they do put on a good show)); and Avril Lavigne (or possibly her evil doppelgänger). Don’t worry, we’re not going to go song by song through all of these performances; ain’t nobody got time for that. All you need to know is that All Time Low rocked out as per usual, Cage the Elephant was solid, and Avril (or her body double) still has that spunk. And, in case you were wondering, the answer is yes, hearing “Sk8ter Boi” live was incredible.

The main-main event of the night was, of course, Fall Out Boy, my traveling companion’s absolute favorite. It was our second time seeing them in just a matter of months, as they’d also headlined at Riot Fest in Chicago the previous September. They rolled out much the same show in Boston, changing the look of the stage with lighting and video boards as they worked their way through essentially their entire discography, doing a couple songs from each (or almost all) of their albums. They were, in the words of Ryan Gosling’s Ken, “sublime!”, but what I will probably remember most about their set that night is that we were righteously freezing our nuggets off. By the end of the show, I believe the temperature was somewhere in the high 40s or low 50s — and our paltry T-shirt and hoodie layers could only do so much.

Fall Out Boy graces the stage at Boston Calling on Saturday, May 24, 2025

The plan afterwards was originally to head to an all-night diner in a different part of the city via Uber/Lyft. Not knowing much about Boston or what we might encounter in various neighborhoods late at night/very early in the morning, we opted to play it safe instead, heading back across the Charles River and hunkering down with our old friends at the Grafton Street Pub. Amazingly, hours and hours after sucking down those initial bloody marys and staying “hydrated” throughout the day, we were still a little thirsty and ended up closing out the night with a High Noon or two. The fried chicken sandwich coupled with some fried ‘tatos did its job, too.

The most, uhh… shall we say interesting?… part of our all-nighter in the greater Boston area came next. With our appetites sated, our adult beverage meters at full capacity, and the clock approaching 1 a.m., the only thing left to do was head back to the airport and wait for our 6 a.m. flight to begin boarding. We arrived at Boston Logan at about 1:30 a.m., at which time the security lines weren’t even open. That meant we had to post up in a nearby seating area. Efforts to stay awake for the next few hours were futile, but we were awoken at some point by a homeless man in a wheelchair who needed some assistance getting his shoe back on. Thankfully, a fellow passenger seated next to us came to the rescue, allowing us to remain in our vegetative states.

SEE ALSO: 'Ten Thousand Lightning Bugs': Experiencing Firefly Music Festival in the Woodlands of Dover

I believe it was 3:30 or 4 a.m. when the TSA security machine roared to life. Our flight left on time and we were back in Chicagoland around 9 a.m. local time. We arrived home in a state of delirium, reminiscent of the time I drove all through the night from Delaware to Michigan fueled by caffeine pills after exiting stage right from a different defunct music festival (RIP Firefly). But hey, we had done it. We had flown to Boston, spent roughly 19 hours there — mostly awake! — and lived to tell the tale. Not bad for a couple of old heads, if I do say so myself.

-LTH