Rolando Street Fair Postponed

Celebrating Craft & Community

Once a year, Rolando welcomes all to one of San Diego’s only neighborhood street fairs.  With live bands, local performances, over 100 vendors, Beer Garden and an interactive kids area, this all day event is free to enter and has fun for everyone.   Enjoy live music, grab a bite to eat and enjoy a beer with friends.  Check out up-and-coming talent on the community stage, browse local arts and crafts, or just let the kids run wild through the inflatables and activities of the kids zone.  It all happens on the beautiful tree lined streets, under the vintage acorn lamp posts of Rolando.

Live music all day on the Main Stage hosted by Tim Pyles of 91X FM and Chris Cantore of 100.7 FM.  Plus, more local performances on the community stage!  

Main Stage Headliner:

Buck O Nine Band Logo

National headliners and San Diego natives known for fan favorites like “My Town” and “Irish Drinking Song.”    The band has been combining elements of reggae, rocksteady, rock and punk into a unique amalgam of music since 1991. Amazingly, their lineup also features six out of seven founding members and their “newest” musician, bassist Andy Platfoot, has been in the band for 19 years.

Main Stage Performances:

The Routine

This four-piece Funk-Rock band packs funk, rock, soul, afro-beat, and psychedelia into an infectious groove that always brings the heat to the dance floor. Since inception, they have taken their memorable live performance across the western United States and established themselves as one of So-cal’s “must-see” acts.

The Sure Fire Soul Ensemble

The Sure Fire Soul Ensemble is a heavy, original, instrumental soul band drawing influence from the masters of the style from the past and modern day, including: Quincy Jones, Jimmy McGriff, Mulatu Astatke, Isaac Hayes, and The Poets of Rhythm.

Whitney Shay

Four-time San Diego Music Award winner, including 2019 Artist of the Year. Shay’s latest release, A Woman Rules the World, is receiving high praise from music critics who are calling the singer “a future blues icon” (Blues Matters!), “one of the next best things in soul music” (Blues and Rhythm Magazine), and “the epitome of a rising star” (Elmore Magazine).

Kahlil Nash

Up-and-coming Funk/Rock and R&B recording artist/producer and multi-instrumentalist who’s played shows at the House of Blues San Diego’s Voodoo Room and Main Stage, The Irenic, Soma, Backup sang for Grammy-nominated artist Andra Day at the RiseUp As One concert and has been on stage alongside Bootsy Collins.

Click here to see the schedule and find out who is playing when.

Enjoy street fair food classics, along with healthy options, coffee and tea.  Visit the Beer Garden to enjoy local brews while you check out what’s on the mainstage.  

This year’s kid zone is all about interactive and $5 gets you unlimited access all day.  Check out the bungee run, inflatable basketball court, obstacle course, multiple bounce houses and more!

Over 100 vendors including, local artisans selling their handmade arts & crafts, boutique bath & body products, fashion apparel, home & garden wares and more!


Over 20 Years of Community Fun

The Rolando Street Fair is the product of a dedicated team of volunteers.  For over 20 years the Rolando Community Council has put together this neighborhood event for all San Diegans to enjoy.  Starting as a small neighborhood block party, the Rolando Street Fair has grown into a legacy event attended by thousands.   Though the times have changed and the fair has expanded its footprint, the purpose remains the same – to celebrate the inclusive comradery of Rolando and enjoy the beautiful neighborhood streets with good food, good people and good fun.

Frequently Asked Questions

Where is the Rolando Street Fair?

The fair takes place along Rolando Blvd. between El Cajon Blvd and Solita Ave.

How much does the Rolando Street Fair Cost?

Admission to the Rolando Street Fair is free and you’re welcome to come and go throughout the day.   Admission includes viewing of bands, community stage performances and an unlimited use kid zone wristband is just $5. 

How do I get to the Rolando Street Fair – Is there parking?

On-street parking is available throughout the neighborhood but can be limited.  We suggest walking, biking or taking ride shares like Lyft and Uber or Public Transportation.  Please note the following streets will be closed to through-traffic and parking during the fair: Rolando Blvd. between Solita Ave. and El Cajon Blvd., Solita Ave between Filipo Dr. and Rolando Blvd., and Alamo Dr. between El Cajon Blvd. and Solita Dr., and Shannon Ave.

To reach the fair using public transportation, take bus route “1” between Hillcrest and Grossmont which runs down El Cajon Blvd. Get off at the El Cajon Blvd./Rolando Blvd. stop, and the fair will be in sight. The nearest Trolley stop is SDSU. From the SDSU Trolley stop, take the 856 or 936 bus to the College Ave./El Cajon Blvd. stop and transfer to the “1” bus per the instructions above. Bike racks will be provided at the fair on Shannon Ave.

What can I bring with me?

No outside alcoholic beverages or weapons are allowed at the Rolando Street Fair.  Any bags or persons attending the street fair are subject to search.  By entering the street fair you may be photographed.  Any photographs will be used for future Rolando Street Fair marketing and promotions.

How do I get involved in the Rolando Street Fair?

Interested in being a Vendor or Sponsor of our Fair? Learn more here.

Volunteers are needed on the day of the Street Fair and to distribute advance flyers and posters in the neighborhood. If you can volunteer for either activity, please contact us.