Worth the Flight: Beat the Florida Heat With These 6 Music Festivals

(Photo by Anthony Delanoix)

There’s a reason all the snowbirds have fled this place by now: It’s just too damn hot. The time is never better to leave Florida; why not book a festival vacation in northern or western climes? Some of the year’s biggest fests have already passed us by, but these six holdouts offer a tuneful cornucopia.

Pitchfork Music Festival


When: July 19-21

Where: Chicago

Best flight rates from PBI: $471-$501 per person

Love it or hate it—and there’s probably little middle ground—the hipster website Pitchfork has been the dominant source for news, reviews and analysis of independent music for most of this century. As such, its annual festival from its home base of Chicago, now in its 14th year, tends to feature cutting-edge acts from indie rock, pop and rap’s burgeoning cusp alongside legacy acts performing event concerts. Representing the latter, France’s Stereolab makes a rare U.S. appearance, Belle and Sebastian play their landmark LP If You’re Feeling Sinisterstraight through, and the Isley Brothers perform a 60th anniversary set. In the former category, HAIM, Charli XCX and Sky Ferreira will keep the youth’s heads a-boppin’. And for those who accuse Pitchfork of being too pretentious, remember this: Sunday’s headliner in Robyn.

John’s pick for artist most worth seeing: Belle and Sebastian

Learn more: pitchforkmusicfestival.com

Newport Folk Festival

Hozier (Photo by Rachel Wright)

When: July 26-28

Where: Newport, R.I.

Best flight rates from PBI: $211-$338

The Newport Folk is one of the country’s most enduring festivals, with this year’s annual three-day bash marking its 60th anniversary. Its influence was perhaps never more outsized than in the ‘60s, when folk music married itself to the activist counterculture, and when Bob Dylan (in?)famously went electric for the first time. These days, Newport’s tent is still folk-fueled, but it’s broader than in its foundational days, regularly welcoming full-throated rock acts, and soul and reggae talents. Some of this year’s spotlight acts include Sheryl Crow, alt-rocker Hozier, Wilco frontman Jeff Tweedy, Phish’s Trey Anastasio, and Phil Lesh of the Grateful Dead. But as always with Newport Folk, its greatest potential pleasures lay in the discovery of a new favorite act, one that connects directly with the audience’s heartstrings with nothing but a dynamic voice and an acoustic guitar.

John’s pick for artist most worth seeing: Todd Snider

Learn more: newportfolk.org


Tame Impala (Photo by Matt Sav)

When: Aug. 1-4

Where: Chicago

Best flight rates from PBI: $370-$393 per person

A predecessor to pioneering road festivals like the Warped Tour, Lollapalooza, founded by alt-rock god Perry Farrell, toured major American cities for its first six years before lagging ticket sales forced its premature demise in 2004. Farrell revived the brand a year later, and it’s had a longer lifespan as a single-weekend festival. Smaller than Coachella but programmed with a similar catch-all mindset, Lollapalooza is an annual snapshot of established and emerging artists on the pop, R&B, rap and alternative charts; its roster is big enough, in 2019, to encompass Kacey Musgraves and Lil Wayne, Tame Impala and Gary Clark Jr., the Strokes and Ariana Grande. Farrell himself performs on the final night. The fact that I haven’t heard of the majority of acts means I’m probably too old for this festival.

John’s pick for artist most worth seeing: Sharon Van Etten

Learn more: lollapalooza.com

Outside Lands

Childish Gambino (Photo by Ibra Ake)

When: Aug. 9-11

Where: San Francisco

Best flight rates from PBI: $330-$400

Situated in historic Golden Gate Park, Outside Lands is engineered to stimulate the five senses, offering not just a music lineup of A-listers, but world-class art and food as well. There’s also podcasters, comedians and TED-style lecturers as part of Outside Lands’ Discussions About Virtually Everything programming. The headliners, continuing their runs on the summer festival circuit, include Childish Gambino, Twenty One Pilots, Flume and Blink-182; overall, the lineup has little differentiation from the season’s other festivals, although I believe it’s alone in booking Paul Simon at the top of the ticket. Those with reefer madness might want to skip this one, though: Grass Lands, its event-within-an-event, bills itself as the United States’ first “curated cannabis experience at a major music festival.” Gotta love California…

John’s pick for artist most worth seeing: Paul Simon

Learn more: outsidelands.com

Woodstock 50

Robert Plant (Photo by Mads Perch)

When: Aug. 16-18

Where: New York

Best flight rates from PBI: $432-$545 per person

With the 50th anniversary of the groundbreaking music festival fast approaching, the media has been Woodstock-obsessed lately, and this 50th anniversary concert seems just the event to capitalize on all the attention. Unfortunately, it’s been star-crossed from the beginning; as with the original Woodstock, its original venue, a racetrack in Watkins Glen, pulled out, and allegations of financial and legal difficulties have put the entire festival into question; as of now, tickets are still not available. If it’s canceled, it would be a mighty shame, because the lineup is a lovingly assembled collection of acts from the original Woodstock, like Santana, Country Joe McDonald and David Crosby, on through today’s alt-rock, Americana and indie marquee names. Robert Plant, whose Led Zeppelin did not perform in ’69, is on the bill this time, along with names as diverse as Jay-Z, The Killers, Miley Cyrus and Sturgill Simpson. Let’s hope it actually happens.

John’s pick for artist most worth seeing: Courtney Barnett

Learn more: woodstock.com

Riot Fest

Violent Femmes (Photo by Ebru Yildiz)

When: Sept. 13-15

Where: Chicago

Best flight rates from PBI: $364-$368 per person

This is a festival that likes it loud: Punk rock takes center stage, but alternative, metal, indie and hip-hop are well-represented too, and it’s a festival that respects its elders as much as today’s upstarts. Case in point: The first three bands on the top row of its 2019 lineup includes Blink-182—performing the entire album Enema of the State, now in its 20th anniversary—metal linchpins Slayer, in its final world tour; and feminist punk pioneers Bikini Kill. Read on, and the lineup is an embarrassment of riches, including New York icon Patti Smith, teen-angst torch-carriers the Violent Femmes, nerd-punk trail-blazers the Descendents, ska-punk breakthrough Rancid, and Boca’s own Dashboard Confessional, playing his album The Places You Have Come to Fear the Most—not to mention Jawbreaker, Guided by Voices, Bob Mould, the Flaming Lips, Nick Lowe, etc. If I could only make one festival this summer, Riot Fest would be it.

John’s pick for artist most worth seeing: Jawbreaker

Learn more: riotfest.org