Photograph by Kristy Walker

Sutton James, happy to move from the driveway to the Street Fair.

The 24th annual Rolando Street Fair is set to go down for the first time in two years on Sunday, March 20. On the music front, five bands are scheduled to play on the main stage. The B-Side Players jumped in to headline after Buck-O-Nine had to back out due to their lead singer, Jon Pebsworth, suffering a massive heart attack on December 30. (BO9 also had to pull out of their January 13 gig at Soda Bar that was part of the In Defense of Ska Tour. Those January dates have been rescheduled for September.)

“The agent for the band was real good about it to me,” explains Rolando Street Fair talent booker Steve Kader. “They said, ‘We just don’t want you to get in a position where you have Buck-O-Nine playing and, three days out, we have to cancel if Jon can totally not play.’ They said, ‘Why don’t we play it safe? Next time you do the event again, we’re on board. We’ll do it in 2023.’ Everybody can wait. It’s fine. We’ve all waited this long. Let’s stay healthy and wait another year.”

The B-Side Players will be sharing the bill with The Sure Fire Soul Ensemble, blues singer Whitney Shay, and reggae hybrid Boostive, a younger act that Kader seems especially excited about. “They’re quite interesting; it isn’t all reggae. They mix it together. They have horns. There’s a jazz influence in there. They’re local, and they’re doing a lot of world festivals and reggae festivals. They’re on Slightly Stoopid’s record label. So, Slightly Stoopid is kind of behind them. They almost remind me of a younger version of Thievery Corporation. They’re doing quite well. They sell out Winstons. They’re doing 400-500 [patrons] at the Belly Up. I think they’re gonna be a big band in the next few years.”

The bill includes Americana artist Sutton James, who moved with his wife into the Rolando Village neighborhood in 2019. He had just completed an 18-month North American tour. “We were so excited just to attend the Rolando Street fair in March of 2020, and then boom, Covid hit. We decided to put on a concert of our own in our driveway on the day that the 2020 Street fair was supposed to happen. It was such a hit in the neighborhood, we continued to do it every other Sunday for the entire summer of 2020. To now have the Street Fair back for the first time in two years, and to be playing the event, is really exciting. I’ve put together a band of some of San Diego’s finest musicians and can’t wait to be the first band to rock the crowd that day.” James plans to debut new songs at the Fair, and a new album is in the works for later this year.

The event takes place on the stretch of Rolando Boulevard bookended by Solita Avenue and El Cajon Boulevard. Alongside the usual array of vendors and a kid’s zone with inflatables and climbing walls, there will also be a beer garden for the grownups. Among its attractions is the Tap Truck, an innovative concept that outfits vintage trucks with beer taps and kegerators. Tap Truck was co-founded by Corbin O’Reilly, whose barbeque restaurant, Corbin’s Q, resides on the other side of El Cajon Boulevard, just to the north of the Fair location.

Michael Rennie, a local musician and volunteer for the Rolando Community Council’s Street Fair Committee, mentioned that the ATM at the 7-11 at the corner of Rolando and El Cajon “does record business that day.” He also noted that the attendance for the event is typically 12K-14K.

“I think in terms of the street fairs and the big community events with music, this will basically be the first one in a long time,” says Kader. “Once we go into the summer here, other events will be popping up. I think the crowds are gonna be great. People are excited. There’s something for everybody. They’re excited about the music. The weather will be amazing. Nothing but positives on our end.”