This Memorial Day, the fourth edition of Pete LeBlanc’s Daydream Festival will take place at Main Line Brewery. The all-RVA lineup has become a nascent tradition, as solid as any single promoter event at the mercy of late spring weather can be.

This year, the headliners are DJ Harrison and Sam Reed, capping off a day stacked with a cross-genre selection of the area’s finest. Also on the bill, dreamy neo-rockers Rikki Rakki, rapper Nicolas F, Palm guitar wizard Charlie Glenn, reanimated Former Champions, a band led by ace drummer Dusty Ray Simmons, and the all-star R4d4nzzo Big Band. Richmond producer Ant the Symbol and DJ Duffy will spin mixes between the sets.

The eclectic lineup reflects LeBlanc’s cross-community ethos.

“I’ve always had the knack for bringing people together. In high school, I was co-captain of my football [team], and always in a  lot of different friend circles,” he says. “That has translated to what I am doing now.”

In a music community where relationships go back for decades, coming in from outside may be an advantage, too. LeBlanc was born and raised in Massachusetts, studied saxophone performance and broadcasting at the Hartt School in Connecticut, and moved here a decade ago when his father got a job with Bon Secours.

“I had been working on cruise ships for about three years,” LeBlanc says. “And I didn’t see much reason to pay rent in Hartford and never be there.”

As a baritone sax player — a specialty reflected in his company name, “Baripete Productions” — his first connection was with bassist Gabriel Santamaria’s bands. He started sitting in with popular local soul/rock band Dance Candy, whose leader trumpeter and entrepreneur Mark Ingraham opened connections to the wider community (including Sam Reed, powerhouse vocalist and Daydream Fest headliner.)

At the same time, he was working 40 to 60 hours a week painting apartments and working on the weekends as a line cook at the Hoffheimer Building. That led to booking shows in the building’s compact upstairs venue which held the former Richmond Camera space, and was named for its historic function, “The Dark Room.”  For several years at the end of last decade, it was one of the best places in Richmond to see music of every genre, from folk to hip hop to adventurous jazz. “I wanted to try putting on some shows,” LeBlanc says. “Mainly to feature the bands that I was working with and the musicians I was meeting.”  (The space has been redefined once again into “The Library.” It’s the new home of Calvin Brown’s long-running, Baripete-produced, biweekly Roots Jam.)

LeBlanc branched out other venues. For a while, he booked the Black Iris off Broad Street in the Arts District. The venue featured great local and out-of-town players but struggled because on weeknights, the area was a ghost town. Brambly Park, located in the increasingly booming Scott’s Addition, was more successful. The timing was fortunate for the most unfortunate of reasons: COVID was making indoor events impossible, and Brambly is an expansive outdoor space.

In retrospect, scaling up to a local festival when the COVID cloud lifted somewhat in 2022 was a natural next step. Initially, it was a joint production with Zavi Yueske Harmon, but since last year LeBlanc has been flying solo with sponsorship help from Former Champions-aligned hemp clothing firm Walton Select.

Crafting the lineup is a selfless challenge.

“What I like is not as relevant as what the bands are doing. How active are they? How is the community responding,” LeBlanc says. A lot of the bands have played Daydream Fest before, albeit in different lineups. Sam Reed has been there with NoBS! Brass, Charlie Glenn twice with Palm Palm. Local legend Devonne Harris has performed before as DJ Harrison and is a vital part of Butcher Brown (he is likely to play again in bandmate Andrew Jay Randazzo’s R4nd4zzo Big Band). Like the RVA music scene, the day promises to be a recombinant kaleidoscope, a local all-star remix. It’s also a leap of faith.

Even without city permits and superstar riders, it costs a lot to put on a music festival. At an outdoor venue, there is uncertainty about the weather. It can be brutally hot, or a late spring downpour. (Currently, the prediction is for a rainless, perfect 70 degrees.)  But there are no guarantees. “It’s been harder and harder each year to get people to commit to buying advanced tickets to shows,” LeBlanc admits. Without advanced sales, he has no certainty at all if costs will be covered. It makes it hard, even with a good forecast and a great lineup.

“In my heart I don’t think anyone’s ever had a bad experience at Daydream. The second year, when it rained, 500 people came out. I missed my target, and took some pretty heavy losses that year,  but my silver lining was that all those people came out in the pouring rain, and they are probably going to come every year from now on.”

Personally, I was there both years and don’t remember anything bad. The sun could have been less intense one year, but there was plenty of shade. There was a passing shower, followed by a lovely rainbow. I enjoyed some bands I hadn’t heard about before. The beer was good, and there was a devilishly flavorful alcoholic slushy booth to attempt to avoid in a far corner.

The event was one of the highlights of the year.

The Daydream Fest takes place at Main Line Brewery at 1603 Ownby Lane on Monday, May 26 from 1 p.m. to 10 p.m. Tickets are $35 in advance, $45 at the door. All ages.