Best Music Festivals for the 50 and Over Crowd


If you’re looking to take a road trip to see your favorite artists, here are the best music festivals for baby boomers. These festivals offer an array of live performances and a chance to experience the best in local cuisine, beverages and arts in a cool setting.

If a great road trip includes hearing your favorite bands, eating and drinking like a local, and visiting a “bucket list” place, consider attending a music festival. Music festivals not only give you a chance to hear performers you know and love but can also expose you to cool new artists. The festivals below provide the best experience for baby boomers whether you love bluegrass…or the blues or just drinking wine and hearing great tunes.


Northwest Folklife Festival May 22-25, 2020 (tentative) Seattle, Washington – 

Why Attend – Experience a music festival without paying high ticket prices

Northwest Folklife, held Memorial Day weekend on the Seattle Center grounds, is the “largest-access-for-all festivals in the country”. Admission is free although a $20 donation is strongly suggested. While NW Folklife lacks the headliners of other festivals, attendees can experience over 500 performers on twenty stages (with an emphasis on folk, blues and ethnic music) and over 200 art vendors.


Telluride Bluegrass Festival June 18-21, 2020 Telluride, Colorado –

Why Attend – The chance to see top notch bluegrass and Americana artists in an awe inspiring setting – 8700 feet high in the Rocky Mountains!

Artists -The headliner for this year is Allison Krauss and past performers include Emmylou Harris and the Nitty Gritty Dirt Band.

What Else – Bring your hiking boots and your camping gear (tent camping only at $70/person)

Tickets – Single day tickets for Friday and Saturday are sold out; Thursday and Sunday single day tickets still available starting at $95.


Lockin’ Festival   June 19-21, 2020 Arlington, Virginia –  

Why Attend – Eclectic line-up of acts, surprise collaborations and VIP packages  

Artists – Past performers include Robert Plant and Sheryl Crow while 2020’s lineup boasts the Brandi Carlile, Bruce Hornsby and David Crosby. 

What Else – One of the highlights of Lockin’ are the surprise collaborations such as Steve Winwood sitting in with Widespread Panic  

Tickets Three-day general admission/camping pass is $259. A “VIP 3-Day Festival Pass” is $899 and includes access to an air conditioned lounge with water, soft drinks, snacks, a “Welcome BBQ” and a fully catered Sunday brunch.


Lollapalooza July 30-August 2, 2020 Chicago, Illinois – 

Why AttendIf you’re a big rock fan or want to see millennial favorites   

One of the biggest music festivals in the country, Lollapalooza features 130 performers on eight stages at Grant Park on Lake Michigan  

ArtistsChildish Gambino and the Chainsmokers along with classic rockers such as Paul McCartney, the Red Hot Chili Peppers and Metallica. 

What ElseChow Town, a food festival where you can munch on authentic Chicago deep dish pizza and hot chicken sandwiches.

Tickets 2020 prices haven’t been announced, four-day general admission (GA) passes for 2019 started at $340.


Newport Folk Festival July 31-August 2, 2020 Newport, Rhode Island – 

Why AttendHear folk/country legends and legends-to-be in a beautiful, historic setting  

Artists – Past performers have included Kacey Musgraves, James Taylor and Dolly Parton along with folk pioneers such as Joan Baez and Bob Dylan   

What Else – One of the oldest music festivals in the country, held at Ft. Adams State Park, “situated at the mouth of Newport Harbor with (stunning) views of the Newport Bridge and the East Passage” and featuring four stages, food and craft vendors and beer and wine gardens.  

Tickets – Single day passes starting at $90. As of this writing, tickets are sold out for 2020 with a waitlist available.  


Outside Lands Festival August 7-9, 2020 San Francisco, California – 

Why Attend – The experience! Mild summer weather, fantastic food, art, chef demonstrations and the music.  

Artists – 2020 line-up is TBD; past headliners have included Paul Simon, Janet Jackson, The Who and Duran Duran.

What Else – World class cuisine, wine, beer, cocktails, cheese and some of the best seafood around; “GastroMagic” which pair famous chefs with musicians, comics and artists; a chance to see Bay area artists at work and “Grasslands,” a cannabis  

What’s Cool – Private cabanas that include a 450 square ft. private viewing area, curated wine selections plus food and drink.  

Tickets – Three-day general admission passes start at $349.50  


Wheatland Music Festival September 11-13, 2020  Remus, Michigan – 

Why Attend -If you want to experience a music festival on a tight budget, big crowds aren’t your thing or you want to “get your inner hippie on”

Artists – A focus on local and regional bluegrass performers in addition to more well-known acts such as Asleep at the Wheel and Rodney Crowell. 

What Else – Wheatland features traditional arts & crafts vendors, drum circles, acoustic performances and music classes. 

Tickets – 2020 Tickets on sale June 1. 2019 tickets were $110 with a “senior” ticket available for $90; Sunday one-day passes only $30.   


New Orleans Jazz Festival & Heritage Festival – TBD Fall 2020

(Originally April 23-May 3) – 

Why AttendA chance to see music legends while eating Creole food or if you want to immerse yourself in jazz in the birthplace of jazz 

Artists – Every music genre imaginable – bluesR&BgospelCajunzydecoAfro-CaribbeanfolkLatinrockrapcountrybluegrass, and of course lots of jazz plus  music superstars such as the Beach Boys, Lionel Ritchie, Earth, Wind & Fire; the Dave Matthews Band, the Doobie Brothers, Tom Jones, Santana and Diana Ross.

What Else – Vowing “no carnival food”, attendees can experience crawfish beignets, an alligator sausage Po’ Boy and fried green tomatoes plus two chef stages, crafts vendors displaying Louisiana folk art and parades 

Tickets – Single day tickets start at $75-$90 depending on day and whether purchased online or at the gate.   


Bottle Rock   October 2-4, 2020 Napa Valley, California

(Originally May 22-24) – 

Why Attend – The Wine!  Or if you want a VIP experience with great music, food, spa treatments and more

Artists – 2020 music line-up is a mix of old and new – The Red Hot Chili Peppers, Blondie, the Dave Matthews Band and the Village People with current favorites such as Maren Morris and Khalid   

What Else – Bottle Rock also features food by Michelin-starred chefs, Napa Valley premier wine, craft beer, a bourbon bar, culinary performances featuring top chefs paired with musicians and athletes such Alice Cooper and Jerry Rice and a variety of spa experiences such as “Shampoo and Chardonnay”.

Tickets – Single day start at $159; three-day passes start at $349 or there’s the “Ultimate Bottle Rock” experience for $18,500 per couple that includes four days in a treeline suite, platinum VIP passes, spa treatments, private concierge and more.  


Austin City Limits Festival October 2-4 and 9-11, 2020  Austin, Texas – 

Why Attend – Music, beer, BBQ and VIP experiences

Artists – ACL offers over 125 performances covering diverse music genres. Acts haven’t been announced for 2020 (Several sites have rumored that Fleetwood Mac may headline.) but past performers include Guns & Roses, Mumford & Sons and Paul McCartney.  

What Else – ACL Eats food court with veggie and gluten-free offerings in addition to traditional Texas BBQ, the Barton Beer Hall allowing you to meet the brewmaster or watch your favorite NFL team and the “VIP and Platinum Experiences” with access to private bars, daily catered meals, mini spa treatments, nail and hair professionals, personal concierges, golf cart transportation to the front of the stage and complimentary locker with mobile phone charging.

Tickets – Three-day general admission passes for 2019 started at $265; three-day VIP packages started at $1250.   

Music Festival Tips

  1. Do Your Homework & Have a Plan – With so many performers to see, it helps to have a plan. Download schedules and venue maps ahead of time and have a strategy. Also, don’t just see your favorites – music festivals provide an opportunity to check out new bands. YouTube is perfect for getting a feel for an artists’ music.  
  2. Dress Comfortably – Expect to walk a lot, often on gravel or dirt, and stand a lot so wear comfortable shoes that you don’t mind getting muddy or dirty. Wear that tie-dyed T-shirt or cute maxi dress but keep in mind that you may be outside all day in ninety degree heat or in the rain. In many locations, it gets cooler when the sun goes down so make sure to pack a light jacket or sweater.
  3. Pack Well but Light – In addition to doing a lot of walking, you are also going to be shoulder-to shoulder with humanity so opt for a small backpack versus a handbag and pack light but well – hat, sunglasses, sunscreen, jacket, water bottle, perhaps a blanket or cushion to sit on and a roll of toilet paper. Also, some venues may restrict what you can and can’t bring in so follow tip one and do your homework.   
  4. Stay Hydrated – You’re going to be outside all day, often in the heat with no shade, drinking wine and beer –drink plenty of water too!  Most festivals have places to fill water bottles. You want to spend your festival enjoying the music, not stuck in a medic tent!
  5. Don’t Rely On Your Cell – Cell phone service can be spotty so don’t rely on texting or calling to stay together, set a meeting time and place. Also, phone charging spots are limited with others doing the same thing. Bring your cell but don’t depend on it.
  6. Know Your Comfort Level – Each festival is different. If you hate crowds, avoid something like Lollapalooza and opt for smaller events. Or go to morning performances or on a Thursday or Sunday, rather than on Friday night or Saturday which often feature the big acts. If you are averse to sleeping in a tent or waiting in long lines for food or the port-a-potty, it may pay to spend more for the VIP experiences, which often include access to air conditioned restrooms, better seats and lounges with snacks and private bars. 

Have Fun!  Wander around, check out new bands, try a crawfish beignet, dance like no one is watching – make memories!  For more suggestions, check out the link below.