Life After 50: My Ultimate Guide to Enjoying Music Festivals in Style
If you told me 30 years ago that I’d still be going to music festivals in my 50s and loving every minute….I might’ve laughed. But here I am, just returning from an unforgettable weekend at Lollapalooza 2025 in Grant Park, Chicago, and let me tell you: age ain’t nothing but a number.
This past weekend, we caught the best set of the weekend from Doechii in my opinion and Bossman Dlow, both of whom completely owned the stage. Their energy was unmatched, and seeing them live reminded me why I’ve spent the last 51 years chasing festival vibes across the country.
Let’s be honest: when you’re in your 20s, you can brave the crowds, the heat, and those mile-long bathroom lines without blinking. But after 50? Comfort, access, and convenience matter more than ever and that’s where VIP shines. I started upgraded my experienced early probably my first festival when I realized I had to use the bathroom in a Porta Potty. I couldn’t do it and when I realize VIP had upgraded bathrooms I paid the extra money just for that alone. I didn’t realize all of the extra perks that came with it until I got my first band. I was hooked on the VIP music festival experience ever since and never looked back.
What made Lollapalooza VIP worth every penny? For one, there were lounge areas with shaded seating so we could relax, recharge, and enjoy the music without pressure from the crowd or sun. There were private bathrooms that had AC, stayed clean, stocked, and accessible all day long. We didn’t have to wait in long lines or wander halfway across the park just to find one.
The viewing platforms gave us the perfect view of every performance without pushing through a crowd of thousands. And when we got hungry or thirsty, the premium food and drink options were far better than your standard festival fare. It was easy to get around in the golf carts, the staff was helpful, and the layout made the whole weekend feel like a breeze.
One of the best parts of the experience was seeing the incredible diversity in the crowd. I saw babies in noise-canceling headphones and elders comfortably seated in wheel chairs, walkers and canes. Everyone soaking in the music with joy. It was a powerful reminder that music festivals aren’t just for the young, they’re for the young at heart. I fully plan to be attending festivals well into my 80s and there’s no reason not to.
Over the years, I’ve been to some of the most iconic music festivals in the country, and each one holds a special place in my heart. Here’s a look at the music festivals I’ve attended over the past 51 years:
• Governors Ball Music Festival – Flushing Meadows Corona Park, Queens
• Rolling Loud New York – Citi Field, Queens
• Afropunk Brooklyn – Commodore Barry Park, Brooklyn
• Made in America – Philadelphia, PA
• Panorama NYC – Randall’s Island
• Coachella – Coachella Valley, California
• Roots Picnic – Fairmount Park, West Philadelphia
• Lollapalooza – Grant Park, Chicago
• Hyde Park Summer Fest – Midway Plaisance, Chicago
If I had to rank Lollapalooza? It’s easily one of the best. It was exceptionally well-organized, the staff was professional and friendly, and there were plenty of amenities to make the experience seamless. The layout was easy to navigate, the signage was clear, and the lineup was outstanding. I’m still thinking about that Doechii performance which was top tier! I still don’t understand why she wasn’t a headliner!
From the moment we stepped through the gates, it felt like this festival was created with everyone in mind not just the 20-somethings looking for their next big weekend. It was an environment full of freedom, fun, and vibrant energy for all ages.
Whether you’re 25 or 75, music festivals can still be for you. And if you’re over 50 like me, don’t shy away just be smart about how you attend. Choose VIP when you can. Pack light. Stay hydrated. Rest when you need to. And most importantly, allow yourself to enjoy every minute of the experience.
Life after 50 isn’t about slowing down. It’s about choosing joy, dancing smarter, and making sure you still feel the bass in your chest when the beat drops.
Dance like no one is watching!
Yours Truly,
Day
