Festivals and the outdoors go together like granola and raisins, and it’s no different here in the Midwest. Except that it is.

From boot-stomping gatherings starring bluegrass legends, to electronic dance parties in a million-year-old cave, to rock-fueled bike rides on the country’s longest rail-trail, our region is brimming with authentic experiences in beautiful locations that can only be found here.

This year, we’ve put together a guide to five of the top outdoor music and culture festivals in our coverage area that are filled with the things we know you’ll love: homegrown music, local craft beer and spirits, stunning scenery, and outdoor adventure.

Let’s take a look at what each one has to offer.

Pedaler’s Jamboree

May 25-26 — Columbia to Boonville, Mo.


Music fans seeking an active experience this Memorial Day weekend can join the Pedaler’s Jamboree, a relaxed bicycle ride on the Katy Trail from Columbia to Boonville and back — 30 miles each way — with live bands, food trucks, and beer tents galore on both days.

Mike Denehy, an Iowa native, grew up riding in RAGBRAI, the famous eight-day festival that spans the Hawkeye State. When he moved to Missouri about 20 years ago, he brought the concept with him.

“You can just have everybody together and share moments. It doesn’t matter if you’re fast or slow,” said Denehy, a former endurance gravel racer who started “PedJam” in 2009.

Pedaler’s Jamboree. (Notley Hawkins)

This year’s event revs up with a Hoedown Kick-Off Party on Friday night in Columbia. It features The Spooklights, who perform a style of music described as “stompgrass,” and ends with a massive bonfire.

The ride officially starts the next day and includes stops in McBaine, Rocheport, and Franklin. Bands play throughout the day at each location, with trail-side buskers popping up from time to time to promote a carnival-like atmosphere. Plus, riders will have natural highlights to enjoy along the way.

“It’s really a perfect combination of the Katy Trail and the Missouri River and some of these small towns that we stop in that really give it that Missouri feel,” Denehy said.

McBaine, for example, has a population of 17, according to the 2020 Census.

“It’s a spot that might have had a lot of heyday a decade or two ago, but at this point, this is pretty much the only party that happens there,” said Denehy.

The overnight destination, Boonville’s Kemper Park, will host the main-stage entertainment, which includes Spirit of 76, Aaron Kamm and the One Drops, and Ha Ha Tonka this year, along with food and beverage vendors. Camping, as well as gear transport, is available and free for all registered riders.

“PedJam is a music festival scene, but unlike a normal music festival where people walk from stage to stage, you ride from stage to stage,” Denehy said. “Sometimes it’s eight miles between stages, and then you pedal into a party that’s already happening.

“Riding your bike is one of those activities that bridges all ages. It’s a great way for people to connect. You ramble out on Saturday, stumble back on Sunday.”

Pedlar’s Jamboree. (Notley Hawkins)

ReJuvenation Restival

May 30-June 2 — French Village, Mo.


While the ReJuvenation Restival at Astral Valley Art Park focuses on turntables and laptops rather than stringed instruments, the organizers are no less interested in building a connection between music and nature.

ReJuvenation founder Laura Lockton previously owned a river resort and venue in the Ozarks, where she invested money to make the property more energy efficient and produced biodiesel. After selling it in 2014, she still wanted to create events centered around conservation but realized people might not want to attend just to learn more about that cause.

“But if you bring them in for something that’s enjoyable and entertaining and use the music to get people there, then they can experience all these other things,” said Lockton, who held the first Restival (a cross between a retreat and a festival) in 2018.

In addition to electronic dance music (EDM) producers like Inzo and Maddy O’Neal, experimental rock group WookieFoot, and world music artist Poranguí, the four-day festival will feature about 100 workshops concerning mental and physical health. These include yoga and movement, meditation and breathwork, sound healing, and arts and crafts. Other highlights: live visionary art, aerial and fire dance shows, and a “healer’s village.”

ReJuvenation Restival. (AK47 Media)

“We can bring together so many people that are doing so many different things, and then people might just happen upon something that changes their life,” said Lockton.

The 700-acres at Astral Valley Art Park are covered with woods and meadows and feature a crystal clear creek, three caves, hiking and mountain biking trails, granite cliffs for climbing and bouldering, and up to 200 species of wild animals.

In other words, don’t leave your swimsuit, boots, bike, and climbing ropes at home.

Shawnee Cave Revival

June 7-9 — Murphysboro, Ill.


In 1976, before country music star Tanya Tucker was scheduled to perform at Shawnee Saltpetre Cave in Southern Illinois, the owner of the property tried to assuage concerns about hosting a festival at the site because of previous parking issues.

“We want to make it very clear that we are not in any way engaging in a festival activity,” Dennis Immel told the Southern Illinoisan.

Whatever Immel’s actual intentions were, put a band on a stage in an idyllic setting featuring a cave that extends 100 feet in the air before thousands of music lovers and you risk stirring attendees’ imaginations about the possibilities of a festival.

And what do you know, almost a half-century later, owners of what is now called the Shawnee Cave Amphitheater are preparing to, for the third time in recent years, hold festivals showcasing a mix of local and well-known national touring artists.

“The cave structure, which is millions of years old, is very special,” said property owner and festival promoter Shane Wade. “We’ve had a lot of our fans compare it to Red Rocks,” the iconic outdoor concert venue in Colorado.

Gilbert Todd constructed the cave amphitheater in 1969, and artists like Muddy Waters, T. G. Sheppard, and Dr. Hook & the Medicine Show performed there over the next decade.

Shawnee Cave Revival. (Shawnee Cave)

The venue can hold 3,000 people, and the grounds also offer tent camping, car camping, and a limited number of RV spaces. (All on-site camping is primitive.)

While Shawnee Cave Amphitheater currently does not have any hiking trails on property, it neighbors the Shawnee National Forest. Wade says he talks with concertgoers who canoe, hike, and visit local landmarks like Inspiration Point and Bald Knob Cross and say, “We had no idea there was anything like this in Illinois.”

The three-day Shawnee Cave Revival on June 7 to 9 will feature Americana, blues, bluegrass, and folk music from performers like Greensky Bluegrass, Grace Potter, Samantha Fish, Red Clay Strays, and The Main Squeeze.

“Our venue is kind of in the middle of nowhere,” Wade said, “and we have to put on events that are special enough that people will book a ticket or go to their camper in Vermont and drive down to southern Illinois.”

Pickin’ On Picknic

July 11-14 — St. Clair, Mo.


Head an hour west of St. Louis in July and you can find musicians strumming guitars, banjos, upright bass, and more at the annual Pickin’ On Picknic bluegrass festival in St. Clair. This year’s lineup includes mandolin legend Sam Bush and younger artists like The Mighty Pines, Sicard Hollow, The Cleverlys, and Allie Kral.

“I kind of tried to back off the big-time headliners this year” and “curate a feast of up-and-comers and national bluegrass talent,” said Ryan Kemp, founder of the event, which recently converted from for-profit to nonprofit status.

Hosted at the Lost Hill Lake campground, the hundreds of attendees have access to both a swimming lake and the Meramec River, soaring bluffs, hiking trails, and loads of open space for tents and RVs — all of which made it the ideal setting for an eventful weekend outside.

Pickin’ On Picknic. (Glow N)

Primarily set up under a massive walnut tree grove, the festival has two stages that stagger performers throughout the days and nights. (If one stage isn’t busy, you know the other is rocking.) The grove also hosts vendor booths, food trucks, a kids’ corner, and plenty of hangout space for hammocks and concertgoers on camp chairs and blankets.

“We’re in the middle of July, but in the walnut grove, it’s about 20 degrees cooler than the open sun,” said Kemp. “I don’t know of any other festivals locally that have two options for swimming holes, whether it’s the river or the lake. We strive to be really family friendly … Everybody is super chill. The kids that are there bring joyful exuberance to the campground.”

The rest of the year, Lost Hill Lake is an event space and glamping venue, hosting weddings, retreats, group parties, and the like. The glamping opportunities are truly unique and feature a houseboat, converted school buses, campers, and VW vans, supported by an outdoor community kitchen, showerhouse, public gazebo, and sauna.

Mississippi Earthtones Festival

September 16 — Alton, Ill.


The Missouri and the Meramec rivers are, of course, not the only important waterways located in the Greater St. Louis region.

In Alton, Sara McGibany promotes conservation of the Mississippi River by hosting the annual Mississippi Earthtones Festival, which features 70+ educational booths, live music, interactive art experiences and performances, and local food and beverages.

“We just really want to celebrate being a river town, so we bring people to the riverfront to be able to enjoy it firsthand and create a community around celebrating the river and protecting it,” said McGibany, the executive director of Alton Main Street, a nonprofit that partners with the Sierra Club Illinois Chapter and the Jacoby Arts Center to stage the event.

Jake’s Leg, a local Grateful Dead cover band, has performed almost every year and will do so again in 2024. The festival will also feature a second headliner for the first time — Aaron Kamm and the One Drops — known for its mix of roots, reggae, river blues, and soulful vocals.

Mississippi Earthtones Festival. (Downtown Alton)

“The whole crowd is just all about peace and love and trying to make the world a better place,” McGibany said.

A family friendly paddle supported by the Mississippi River Water Trail Association will take place the morning of the event. (A variety of distances and safety boats invite paddlers of all ability levels.) The Sierra Club provides grants to artists who would like to build a sculpture, perform an interpretive dance, or conduct other public art projects on the festival grounds.

The Mississippi Earthtones Festival organizers also hope to enlist volunteers for a river cleanup the following Saturday, September 21. In the past, this cleanup has resulted in the collection and removal of 50 tons of trash from the river and its banks, according to McGibany.

“[The Mississippi River] is our biggest natural resource, and we need to protect it,” she said. “It’s everything from the water we drink, to transportation, and the economy and recreation.”


Thunder Ridge Readies for Opening

Not a festival but a great place for festivals, Thunder Ridge Nature Arena in Ridgedale, Missouri, is scheduled to officially open in May.

The state-of-the art venue was 10 years in the making and sits just a few miles from Branson, making it a great draw for performers touring the area. Chris Stapleton and Luke Bryan have appearances booked, and Garth Brooks, who already performed here, said, “There may be sites on this Earth that are as pretty, but there’s nothing prettier… It’s gorgeous.”

Thunder Ridge Nature Arena. (Thunder Ridge)

Thunder Ridge fuses a 20,000-capacity arena into the surrounding 1,200-acre preserve. Architectural highlights include the Ozarks Nature Tower, which rises 12 stories high and offers unrestricted views of Table Rock Lake and the scenic Ozark Mountains, and the main North entrance, which incorporates a centuries-old barn. Fans will enjoy a variety of food and beverage concessions, luxury suites, meeting spaces, and more.

The new outdoor amphitheater is part of the nonprofit Johnny Morris Conservation Foundation, with all net proceeds from events going toward supporting conservation and further enhancing the venue.

“We all love our Ozarks and are proud to be able to preserve and share the beauty of the place we are blessed to call home with others for generations to come,” said Morris.

Learn more at thunderridgenaturearena.com.

Author: Eric Berger is a regular contributor to Terrain Magazine.

Additional reporting provided by Brad Kovach.

Top Image: The ReJuvenation Restival. (AK47 Media)