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The Grown-Up’s Guide to Music Festivals

How to enjoy 5 amazing events this summer and fall

Therese Carlson, 57, had never been to a music festival before last summer, when she attended Lollapalooza, a three-day festival in Chicago’s Grant Park that draws hundreds of thousands of music lovers each year. Carlson, who lives in Chicago’s western suburbs, wanted to attend the festival because her teenage children raved about it. But, she had some concerns: “I don’t like crowds, heat, using port-a-potties, getting soaked in the rain. Most of all, I don’t like seeing teens compromised by alcohol and drugs.”

So, Carlson joined a group of adults 45 and older attending Lollapalooza under the expert guidance of Val Haller, founder and CEO of the boutique music website Valslist.com, which specializes in introducing busy adults to new music.

Haller is also in her 50s and understands why big festivals such as Lollapalooza, which tends to attract teens, can seem intimidating to an older crowd. “I hate crowds and oppressive heat, too, and I don’t want to be in a mosh pit,” she says, “but I love music.”

She started the group Lollapalooza trips last year in hopes of showing adults all the festival has to offer. Festivals are an amazing way to discover lots of new music in a series of small bites, “like a box of chocolates,” she says. Adults attend less for the scene and more to listen. Finding a new band they love makes them feel young again and the experience is an adventure they’ll talk about for years to come.

Last year, Haller’s Lollapalooza group was captivated by the bands Trombone Shorty, Johnnyswim and Space Capone, which has a ’70s disco vibe. Overall, “the music was fresh, danceable and energetic,” says Carlson, who particularly loved listening to up-and-coming bands on the smaller stages.

Here are the top five music festivals from around the country Haller recommends (either she’s visited, or it’s on her bucket list) and her expert tips for having a successful music festival experience:

Newport Folk Festival
July 24-26
Newport, R.I.

This festival has long been on Haller’s bucket list because she’s heard from many friends that it’s “digestible, intelligent, beautiful and well-planned.” It’s on the water, in Newport — a famously posh and stunning place — and offers a stellar lineup of top folk musicians every year.

July 31-August 2
Chicago, Ill.

This massive festival boasts over 130 acts, in various genres. This year’s headliners are Metallica, Paul McCartney and Florence + the Machine. Haller loves it because there are so many bands to see, and it’s held in Grant Park, which offers cool breezes from Lake Michigan and great views of the Chicago skyline.

Outside Lands
August 7-9
San Francisco, Calif.

There’s so much to love about this fest: a top-notch lineup, excellent food and the backdrop of San Francisco’s Golden Gate Park, with many of the city’s most popular sights nearby. “I would get a three-day pass and just come and go as I pleased,” Haller says. San Francisco’s temperate weather also makes this fest a pleasure to visit.

Grand Point North
September 12-13
Burlington, Vt.

This two-day festival is headlined both nights by the eclectic rock band Grace Potter & the Nocturnals. Nine other bands play each day. “It’s small and very doable,” says Haller. Burlington is a low-key town with a hippie vibe; it borders Lake Champlain and is known for its outstanding local, organic food.

Austin City Limits
October 2-4, 9-11
Austin, Texas

This festival is held over six days, on two back-to-back weekends, each with somewhat different lineups. It’s similar to Lollapalooza in terms of attendance and artists. This year’s lineup includes Drake, The Strokes and the Foo Fighters. “Austin is such a great town for music,” Haller says, and the breakfast tacos don’t hurt, either.

Tips for a Successful Fest Experience

Here are some tips to have a great time at festivals:

Dress for comfort and the weather, and have fun with your wardrobe. Haller says, “Wear whatever you like. Go and be your alter-ego. If you want to wear hippie clothes, wear hippie clothes. People really aren’t looking at you. In this selfie-obsessed, look-at-me society, music festivals are surprisingly anonymous places, which is really relaxing, freeing and makes you feel young again.”

When it comes to footwear, keep in mind that some of these festivals — such as Lollapalooza — are very spread out, and you’ll be moving from stage to stage, so be prepared to do a significant amount of walking. If there’s lots of rain, wear rain boots, as outdoor fests tend to get muddy.

Make sure to eat, and always have a bottle of water with you. Food at these fests aren’t just burgers and hot dogs; these days, there are many gourmet options. Staying well fed keeps your energy up, Haller says. There are usually filling fountains where you can replenish your water bottle, too. It’s essential to stay hydrated, especially in places like Austin, where temperatures have been known to top 100 degrees.

Do a little homework and have a plan. It’s definitely fun to wander around these festivals and discover new music serendipitously, but Haller says you’ll likely get more out of the experience if you’ve done your research before you go. Look at the schedule and listen to a few of the bands that are unfamiliar by searching for them on YouTube. Often, you can sample artists’ work on the festivals’ websites, or through the festival’s app; there may even be a free, downloadable playlist.

Once you’ve done some listening, make a shortlist of the bands you want to see and put together a schedule for yourself, keeping in mind the time it takes to walk between different stages, with crowds. If one stage has a few acts you’re interested in, you may decide to stay there for hours and relax on a picnic blanket.

Don’t rely on cell phones. Cell phone service is spotty in big, crowded music festivals, so alternatives such as walkie-talkies are a good idea. Or, Haller says, simply have a Plan B so that if you don’t hear from someone or you get separated, you know to meet at a certain place at a specific time.

Pack wisely. Haller likes to keep her hands free for eating, drinking and taking pictures, so she recommends a lightweight backpack, fanny pack or a cross-body bag. Essentials to pack: a hat, sunglasses, a bandana, sunblock, earplugs, a picnic blanket if you want to sit, a poncho and a plastic bag for your phone, in case it rains. You might be at a festival from mid-morning to well after sunset, so bring an extra layer. Haller’s pro tip: Buy a Frogg Chilly Pad (a towel that stays cold all day when wet) to keep you cool if it’s going to be blazing hot outside. And one more tip: pack your own camping-style roll of toilet paper, just in case the port-a-potty runs out.

If you dislike crowds, stick to the smaller stages and go earlier in the day, before the throngs hit. At Lollapalooza, for instance, the gates open at 11 a.m., and the crowds of rowdy teens don’t arrive until much later. The smaller stages are where you’ll likely discover an emerging band you love, Haller says — and that band just might become the next big thing.

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