Hillcrest CityFest Street & Music Festival returns

Posted: August 4th, 2017 | Arts & Entertainment, Features, Music, Top Story | 2 Comments

By HBA Staff

With nearly 100 years of history, the Hillcrest Business Association continues to shape the story of our community. And since 1984 — that story along with the story of the Hillcrest sign — is celebrated with CityFest, an annual street fair and music festival that draws over 150,000 people to the heart of the community every August.

This year’s 2017 event, named “Hillcrest CityFest Street & Music Festival,” takes place Sunday, Aug. 13, from noon until 8 p.m., when CityFest After Dark takes over at the intersection of Fifth and University avenues, and runs until 11 p.m.

CityFest at Night is a three hour dance party under the Hillcrest sign. (Courtesy of Hillcrest Business Association)

It all began in 1886 when the region known as University Heights began to grow northward. Subdivisions soon popped up to border Balboa Park and in 1907, William Wesley Whitson opened the “Hillcrest Company” to sell parcels of land, giving birth to the community of Hillcrest.

The Pavilion welcomes kids of all ages. (Courtesy of Hillcrest Business Association)

Over time, the neighborhood grew. Florence Elementary School opened in 1908 and in 1913, the Hillcrest Theater opened as the first theater house outside of Downtown. As the area expanded, the Hillcrest Association was formed by a group of neighborhood business owners in 1921. Years later, the Hillcrest Women’s Association donated the Hillcrest sign to the Hillcrest Association in 1940.

The Hillcrest sign ultimately served to help the neighborhood become a destination, but over the course of the next 37 years, the sign fell into neglect. In 1977, it was repainted but still in disrepair.

In 1984, Hillcrest residents and business owners launched an effort to refurbish the Hillcrest sign and on Aug. 18, 1984, the sign, now completely restored, was reinstalled. Two weeks later, on Aug. 26, the new sign was officially unveiled and celebrated; marking the first festivity we now call CityFest.

DJ Taj performs at CityFest at Night, from 9:30–11 p.m. (Courtesy of Hillcrest Business Association)

Since 1984, the HBA has hosted CityFest during August, boasting the most spirited street festival in all of San Diego. Hillcrest locales join neighboring San Diego visitors and beyond to celebrate the sign and welcome the spirit of Hillcrest for a daylong celebration that this year will last from noon until 11 p.m. on Aug 13 — making it the largest single-day street and music festival in San Diego County.

There will be a grand music stage and a DJ stage with live music and headliner bands all day long. Stay past sundown and dance the night away with Hillcrest’s best DJs under the Hillcrest sign during CityFest at Night!

A massive spirits garden with cocktails, beer and fun games will keep you hydrated, and entertained!

Artist Village and Alleys

Over 250 vendors will give you plenty of shopping opportunities, and Hillcrest’s quaint shops and restaurants along Fifth, Robinson and University avenues will give you a place to dive into and explore.

(Courtesy of Hillcrest Business Association)

CityFest’s Artist Alley offers one of the largest arts and crafts areas of any comparable street fair. It is the place to find one-of-a-kind specialty items and gifts. Booths lining Fifth Avenue (from University down to Pennsylvania avenues) will offer plenty to peruse, buy and explore. The Artist Alley will be open from noon to 8 p.m.

Grand Stage

The Grand Stage will be located at the heart of Hillcrest at the corner of University and Fifth avenues and hosted by community legend, Laura Jane Willcock.

(Courtesy of Hillcrest Business Association)

CityFest’s Grand Stage will host multiple local and regional musical acts throughout the day, from noon until 8 p.m., followed by local and regional DJs for CityFest at Night from 8–11 p.m.

Gigantic food courts

(Courtesy of Hillcrest Business Association)

With more than 50 food vendors, CityFest’s food court will offer plenty of variety for hungry attendees. Food vendors can be found along Robinson and Pennsylvania avenues between Fourth and Sixth avenues, and on Fifth Avenue between Pennsylvania and Brookes avenues. 

The Pavilion

CityFest welcomes youngsters of all ages and the Pavilion has something for everyone.

(Courtesy of Hillcrest Business Association)

The Pavilion returns to CityFest with the Rad Hatter, Kids Garden, Petting Zoo, Carnival Rides, Games and the Buskers Stage! Balloon artist Ms. Twisty, Cheer San Diego, and other buskers and street performers will be staged along the pavilion area and throughout the entire festival.

Beer and Spirits Garden

One of the popular aspects of the day-long street festival is the Beer and Spirits Garden, located on University Avenue between Fourth and Fifth avenues and directly beneath the Hillcrest sign.

(Courtesy of Hillcrest Business Association)

Sponsored by Cutwater Spirits, that entire block of University Avenue will be dedicated to the over-21 beer garden that will feature drink stations, a dunk tank and a great view of the Grand Stage from under the Hillcrest sign.


You will have the opportunity to benefit the Hillcrest Town Council by dunking a drag queen, friend, frenemy, or other prominent members of the community. As a volunteer-driven, nonprofit organization, the Hillcrest Town Council provides a voice for the residents of Hillcrest. Show your support for the cause by visiting the Beer and Cocktail Garden and taking your best shot to Dunk-a-Queen!

For more information about CityFest, including complete lineups for every stage, visit To learn more about the Hillcrest Business Association, visit


  1. Ashley Abramson says:

    Where’s the date for this year’s Cityfest? Am I missing it right at the top?

  2. Morgan says:

    It was kind of buried in the article due to the history, but I added it to the top. Thank you for asking.

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