Anchor ads are not supported on this page.

4S Ranch Allied Gardens Alpine Baja Balboa Park Bankers Hill Barrio Logan Bay Ho Bay Park Black Mountain Ranch Blossom Valley Bonita Bonsall Borrego Springs Boulevard Campo Cardiff-by-the-Sea Carlsbad Carmel Mountain Carmel Valley Chollas View Chula Vista City College City Heights Clairemont College Area Coronado CSU San Marcos Cuyamaca College Del Cerro Del Mar Descanso Downtown San Diego Eastlake East Village El Cajon Emerald Hills Encanto Encinitas Escondido Fallbrook Fletcher Hills Golden Hill Grant Hill Grantville Grossmont College Guatay Harbor Island Hillcrest Imperial Beach Imperial Valley Jacumba Jamacha-Lomita Jamul Julian Kearny Mesa Kensington La Jolla Lakeside La Mesa Lemon Grove Leucadia Liberty Station Lincoln Acres Lincoln Park Linda Vista Little Italy Logan Heights Mesa College Midway District MiraCosta College Miramar Miramar College Mira Mesa Mission Beach Mission Hills Mission Valley Mountain View Mount Hope Mount Laguna National City Nestor Normal Heights North Park Oak Park Ocean Beach Oceanside Old Town Otay Mesa Pacific Beach Pala Palomar College Palomar Mountain Paradise Hills Pauma Valley Pine Valley Point Loma Point Loma Nazarene Potrero Poway Rainbow Ramona Rancho Bernardo Rancho Penasquitos Rancho San Diego Rancho Santa Fe Rolando San Carlos San Marcos San Onofre Santa Ysabel Santee San Ysidro Scripps Ranch SDSU Serra Mesa Shelltown Shelter Island Sherman Heights Skyline Solana Beach Sorrento Valley Southcrest South Park Southwestern College Spring Valley Stockton Talmadge Temecula Tierrasanta Tijuana UCSD University City University Heights USD Valencia Park Valley Center Vista Warner Springs

12K-14K expected at Rolando Street Fair

Vintage trucks with beer taps & kegerators

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

Past Event

Rolando Street Fair

  • Sunday, March 20, 2022, 10 a.m. to 6 p.m.
  • Intersection of Rolando Boulevard and El Cajon Boulevard
  • Free

“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.”

Sponsored
Sponsored

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.”

Here's something you might be interested in.
Submit a free classified
or view all
Previous article

40th floor of Marina District’s Harbor Club for sale

Your chance to look down on Downtown San Diego
Next Article

Encinitas blufftop house barely hangs on

Owner of Neptune Ave. duplex wanted to demolish and re-build under old rules
Sutton James, happy to move from the driveway to the Street Fair.
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.)

Past Event

Rolando Street Fair

  • Sunday, March 20, 2022, 10 a.m. to 6 p.m.
  • Intersection of Rolando Boulevard and El Cajon Boulevard
  • Free

“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.”

Sponsored
Sponsored

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.”

Comments
Sponsored
Here's something you might be interested in.
Submit a free classified
or view all
Previous article

Encinitas blufftop house barely hangs on

Owner of Neptune Ave. duplex wanted to demolish and re-build under old rules
Next Article

Tamale Guy Comic Book Release Party, Chef Fest at Broadway Pier

Events February 24-February 28, 2024
Comments
Ask a Hipster — Advice you didn't know you needed Big Screen — Movie commentary Blurt — Music's inside track Booze News — San Diego spirits Classical Music — Immortal beauty Classifieds — Free and easy Cover Stories — Front-page features Drinks All Around — Bartenders' drink recipes Excerpts — Literary and spiritual excerpts Feast! — Food & drink reviews Feature Stories — Local news & stories Fishing Report — What’s getting hooked from ship and shore From the Archives — Spotlight on the past Golden Dreams — Talk of the town The Gonzo Report — Making the musical scene, or at least reporting from it Letters — Our inbox Movies@Home — Local movie buffs share favorites Movie Reviews — Our critics' picks and pans Musician Interviews — Up close with local artists Neighborhood News from Stringers — Hyperlocal news News Ticker — News & politics Obermeyer — San Diego politics illustrated Outdoors — Weekly changes in flora and fauna Overheard in San Diego — Eavesdropping illustrated Poetry — The old and the new Reader Travel — Travel section built by travelers Reading — The hunt for intellectuals Roam-O-Rama — SoCal's best hiking/biking trails San Diego Beer — Inside San Diego suds SD on the QT — Almost factual news Sheep and Goats — Places of worship Special Issues — The best of Street Style — San Diego streets have style Surf Diego — Real stories from those braving the waves Theater — On stage in San Diego this week Tin Fork — Silver spoon alternative Under the Radar — Matt Potter's undercover work Unforgettable — Long-ago San Diego Unreal Estate — San Diego's priciest pads Your Week — Daily event picks
4S Ranch Allied Gardens Alpine Baja Balboa Park Bankers Hill Barrio Logan Bay Ho Bay Park Black Mountain Ranch Blossom Valley Bonita Bonsall Borrego Springs Boulevard Campo Cardiff-by-the-Sea Carlsbad Carmel Mountain Carmel Valley Chollas View Chula Vista City College City Heights Clairemont College Area Coronado CSU San Marcos Cuyamaca College Del Cerro Del Mar Descanso Downtown San Diego Eastlake East Village El Cajon Emerald Hills Encanto Encinitas Escondido Fallbrook Fletcher Hills Golden Hill Grant Hill Grantville Grossmont College Guatay Harbor Island Hillcrest Imperial Beach Imperial Valley Jacumba Jamacha-Lomita Jamul Julian Kearny Mesa Kensington La Jolla Lakeside La Mesa Lemon Grove Leucadia Liberty Station Lincoln Acres Lincoln Park Linda Vista Little Italy Logan Heights Mesa College Midway District MiraCosta College Miramar Miramar College Mira Mesa Mission Beach Mission Hills Mission Valley Mountain View Mount Hope Mount Laguna National City Nestor Normal Heights North Park Oak Park Ocean Beach Oceanside Old Town Otay Mesa Pacific Beach Pala Palomar College Palomar Mountain Paradise Hills Pauma Valley Pine Valley Point Loma Point Loma Nazarene Potrero Poway Rainbow Ramona Rancho Bernardo Rancho Penasquitos Rancho San Diego Rancho Santa Fe Rolando San Carlos San Marcos San Onofre Santa Ysabel Santee San Ysidro Scripps Ranch SDSU Serra Mesa Shelltown Shelter Island Sherman Heights Skyline Solana Beach Sorrento Valley Southcrest South Park Southwestern College Spring Valley Stockton Talmadge Temecula Tierrasanta Tijuana UCSD University City University Heights USD Valencia Park Valley Center Vista Warner Springs
Close

Anchor ads are not supported on this page.