Hello Hilcrest, you fabulous forest of fun. Nestled between Mission Hills, Balboa Park, and North Park, Hillcrest holds it down as SD’s glitteriest ’hood and the anchor of our Pride festivals and proud LGBTQ history.
But it wasn’t always this way. Originally marketed in the late 1800s by George Hill as a quiet, streetcar-accessible suburb, Hillcrest evolved with the times. The postwar boom brought car-friendly retail and the Sears building in 1952, but by the ’60s, the buzz had shifted to Mission Valley, leaving Hillcrest to fade—temporarily.
As early bungalows weathered and longtime residents moved on, the neighborhood’s affordability and untapped charm made it a haven for those on the margins. When The Rail (then Brass Rail)—San Diego’s first gay bar—landed on Fifth and Robinson avenues in the ’60s, a new era took root. The area’s LGBTQ community blossomed, pouring its heart and energy into transforming Hillcrest into the vibrant, eclectic, and unapologetically welcoming place it is today.
Community leaders Benny Cartwright (left) and Rick Cervantes.
Pride and CityFest pack the sidewalks. Rainbow flags wave from windows; murals color the alleyways; and vivacious energy spills from rooftop bars, indie cafés, drag brunches, and taco stands. A patchwork of old bungalows, midcentury motels, mixed-use towers, and sidewalk storefronts shows the story of a place in constant, confident flux.
Anchored by Hillcrest icons like Urban Mo’s Bar & Grill, The Alibi, Bread & Cie, and Rich’s, the neighborhood’s spirit is all about both staying power and reinvention. “What makes it work is the people who care to see this neighborhood succeed,” says Hillcrest Kiwanis president Benny Cartwright.
And it’s home to the famously heavy-handed “Hillcrest pour,” says Rick Cervantes, who runs the Instagram account @hillcrestsandiego. The drinks are strong, and, even for those who don’t imbibe, the friendships you make here are stronger.
Facts About Hillcrest
- In 1891, Wyatt Earp bought property at Fifth and University avenues. Rumor has it he operated a brothel there.
- Donated by the Hillcrest Women’s Association, the Hillcrest sign at Fifth and University avenues was first erected in 1940. It was illuminated in 1984 and renovated with rainbow LEDs in 2023.
- Zillow reports the average home value in Hillcrest about $835,000.
- Hillcrest has a history of hosting hospitals: St. Joseph’s came to Eighth and University avenues in 1891, and San Diego County Hospital opened its doors at the north end of Front Street in 1904.
- The first city-permitted Gay Pride Day and parade were held in Hillcrest in 1975.
Things to Do in Hillcrest
Cervantes moved to San Diego from Lodi and found his rainbow family in Hillcrest, where his adventures often begin or end at Uptown Tavern, a primary neighborhood hub and meeting-up spot. “Maybe it sounds basic, but [it’s] famous here for the chicken strips,” he says.
“They’re marinated in herbs and buttermilk for 48 hours and hand-breaded and fried,” adds Cartwright, a fellow Uptown Tavern fan who was born in the neighborhood and now lives in “Unicrest,” where the quieter, neighboring University Heights meets hoppin’ Hillcrest. More fabulous finger food? Hand-packed sliders with parmesan-rosemary fries.
On weekend mornings, you’ll find them at Urban Mo’s, which hosts a hoppin’ brunch bash every week. “Get the fat-ass chocolate-chip pancakes,” Cervantes says. “Go for it all: the sweet and the savory”—the latter being a breakfast burger with fried egg. “And go ahead and get the foo-foo drink with the plastic monkey; that’s why you’re here.” For a quicker bite, Cervantes and Cartwright recommend Sunnyboy Biscuit Company, serving comforting, low-key, delicious breakfast sandos like someone’s Southern grandma used to make.
Come lunchtime, head to Crest Cafe, which has been family-owned in the neighborhood since 1983. You can get any menu item all day (and night) here. “Meatloaf for breakfast?” Cervantes laughs. Why not?
“I could definitely eat the butter burger any time,” Cartwright adds. (Guy Fieri agrees—the indulgent, herb butter–stuffed patty was featured on Food Network’s Diners, Drive-Ins and Dives.) The café does a homey holiday prix-fixe menu with tradition in mind; last year, it was tamales for Christmas. And that’s not the only place to spend the holidays in Hillcrest: Urban Mo’s has turkey and all the fixings on Thanksgiving.
If you hit Hillcrest during daylight hours, grab a pastry at Bread & Cie, take a stroll, and pop in to say hello to some friendly business owners, Cervantes advises. He and Cartwright know pretty much everyone, and, three years ago, they started Hillcrest Honors to award the hard-working folks who make the neighborhood sparkle. The inaugural award went to LGBTQ lifestyle boutique Humanity. “No judgment here,” Cervantes says—just kinky gifts, lube, toys, fun outfits, and thongs, of course.
While you’re here, don’t skip the eye candy at Green Florals: houseplants, fresh-cut blooms, and pick-your-own bouquets. It’s a great spot to grab a last-minute gift before picking up a treat at Babycakes next door. Continue the feast (for the eyes) by perusing the art in Mural Alley, just outside The Studio Door gallery on Fourth Avenue.
What’s Next for Hillcrest
“Hillcrest has no parks,” Cervantes points out.
“Balboa Park doesn’t count,” Cartwright chimes in. The $27.5 million Pride Promenade project, which broke ground in February 2025, aims to change that, with a reconfiguration of Normal Street to create an outdoor gathering space. Already a place where the community comes together when things happen, the corner of Normal and University Avenue (where the giant pride flag flies) will soon be a rainbow-striped pedestrian and bicycle zone, slated for late 2026 or early 2027.
And, after a decade of residents plying Caltrans and the city to do something with a bit of otherwise undeveloped land at the southwest corner of University and the 163, the area might soon become a small green space.
Cruise through Hillcrest today, and the skyline tells the story: shiny, new apartment buildings now tower where rows of century-old bungalows once stood. Like much of San Diego’s urban core, Hillcrest is growing dense fast—and not without tension. “It’s also pushing some of the LGBTQ folks out,” Cartwright says. The recently adopted Plan Hillcrest (2024) paves the way for as many as 20 new residential towers, signaling a new era for this storied ’hood.
But change isn’t just vertical—it’s cultural. The long-vacant Panera space at The Hub on Cleveland Avenue is getting a fresh start with Madi, the beloved brunch spot, opening a Hillcrest outpost later this year. Earlier this year, Good News made headlines as San Diego’s first non-alcoholic bar, serving up craft mocktails and stocking a bottle shop so you can take the “free-spirited” vibe home.
Community leaders like Cartwright and Cervantes see Hillcrest embracing a more elevated culinary identity, too, with buzzworthy newcomers like Cellar Hand, Origen, and Frenchy’s Hideout adding a refined edge to the neighborhood’s famously rowdy charm. The future is rising, and Hillcrest is rewriting what it means to grow while staying true to its roots.
Where to Eat in Hillcrest
Where to Shop in Hillcrest
More Things to Do in Hillcrest
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