Hillcrest, a vibrant neighborhood nestled between Mission Hills, Balboa Park, and North Park, has evolved over the years to become San Diego’s most spirited and welcoming community, particularly for the LGBTQ+ population.
Originally marketed as a quiet suburb in the late 1800s by George Hill, Hillcrest underwent significant changes as the decades passed.
The post-World War II boom brought developments more suited for the automobile era, exemplified by the Sears building in 1952.
However, as the 1960s rolled around, attention shifted toward Mission Valley, leaving Hillcrest to briefly fade into obscurity.
But this decline was only temporary.
With older bungalows needing maintenance and long-time residents moving away, the affordability and distinct charm of Hillcrest attracted new faces.
The 1960s saw the arrival of The Rail, San Diego’s first gay bar located at Fifth and Robinson avenues, marking the onset of a transformation.
The LGBTQ+ community flourished, injecting passion and energy into Hillcrest, turning it into a colorful, eclectic, and inclusive area.
Today, Hillcrest is alive with activity during events like Pride and CityFest, where the sidewalks come alive with crowds.
Rainbow flags flutter from windows, murals enliven alleyways, and the lively atmosphere spills over from rooftop bars, indie cafés, drag brunches, and taco stands.
The neighborhood’s architectural landscape boasts a mix of old bungalows, midcentury motels, modern mixed-use towers, and small storefronts, creating a rich tapestry of stories that reflects its ongoing evolution.
Keystones of the community include Urban Mo’s Bar & Grill, The Alibi, Bread & Cie, and Rich’s, signaling a neighborhood marked by both resilience and innovation.
As Hillcrest Kiwanis president Benny Cartwright remarks, “What makes it work is the people who care to see this neighborhood succeed.”
The area is also known for its generous “Hillcrest pour,” as noted by Rick Cervantes, who runs the Instagram account @hillcrestsandiego.
Even for non-drinkers, the friendships forged in Hillcrest are formidable.
Regarding historical tidbits, Hillcrest has its share of interesting facts.
In 1891, the notorious Wyatt Earp purchased property at the intersection of Fifth and University avenues, where it is rumored he ran a brothel.
The Hillcrest sign, donated by the Hillcrest Women’s Association, was originally installed at Fifth and University avenues in 1940 and was later illuminated in 1984 before receiving a rainbow LED renovation in 2023.
Zillow reports the average home value in Hillcrest is approximately $835,000, indicating a robust real estate market.
Moreover, Hillcrest has a notable history in healthcare as well, with St. Joseph’s Hospital opening on Eighth and University avenues in 1891 and San Diego County Hospital beginning operations at the north end of Front Street in 1904.
The neighborhood was also the birthplace of San Diego’s first city-permitted Gay Pride Day and parade back in 1975.
For visitors and locals alike, Hillcrest offers a plethora of enjoyable activities and culinary delights.
Cervantes, who moved to San Diego from Lodi, highlights Uptown Tavern as a neighborhood hub for social gatherings, with its famed chicken strips being a must-try.
Marinated in herbs and buttermilk for 48 hours and then hand-breaded and fried, these strips signal the delightful culinary offerings available.
For a lively weekend brunch, Urban Mo’s is a top spot, with its brunch bash featuring decadent offerings with the signature fat-ass chocolate-chip pancakes.
Adventurous diners are encouraged to indulge in both sweet and savory selections, including a breakfast burger topped with a fried egg.
Faster breakfast options can be found at Sunnyboy Biscuit Company, which serves comforting sandwiches reminiscent of homemade fare.
Lunchtime leads people to Crest Cafe, a family-owned establishment since 1983, where patrons can enjoy any item from the menu any time of the day.
Their butter burger has gained immense popularity, even catching the eye of Guy Fieri on “Diners, Drive-Ins and Dives.”
The café also serves a holiday prix-fixe menu, celebrating with traditional offerings like tamales during Christmas.
Food enthusiasts can partake in the holiday feast at Urban Mo‘s as well, where a Thanksgiving meal is served featuring turkey and all the accompaniments.
A stroll through Hillcrest offers opportunities to appreciate local businesses and the community vibe.
Cervantes recommends visiting Bread & Cie for delicious pastries and connecting with friendly shop owners who make the neighborhood thrive.
Three years ago, he and Cartwright established Hillcrest Honors to recognize the local business owners contributing to the area’s charm.
The inaugural award went to Humanity, a popular LGBTQ lifestyle boutique, embodying the neighborhood’s fun spirit.
While exploring, don’t miss Green Florals, where houseplants and fresh blooms can be found, perfect for last-minute gifting, along with treats from Babycakes next door.
Art enthusiasts can delight in Mural Alley, located just outside The Studio Door gallery on Fourth Avenue, showcasing the neighborhood’s creative expressions.
Looking ahead, Hillcrest is on the verge of new developments that promise to reshape the landscape.
Cervantes points out a notable absence of parks in the area, with Balboa Park not being a substitute, which spurred the $27.5 million Pride Promenade project to break ground in February 2025.
This initiative will transform Normal Street into an outdoor gathering space, with plans for a rainbow-striped pedestrian and bicycle zone set to complete by late 2026 or early 2027.
Residents have also campaigned for years for improvements to a vacant piece of land at the intersection of University Avenue and the 163 freeway, which may soon develop into a small green area.
As you navigate through Hillcrest today, the skyline reflects a narrative of progress, as new apartment buildings arise where century-old homes once stood, contributing to a denser urban landscape.
This transformation is not without challenges, as it leads to concerns about displacing some members of the LGBTQ community, as articulated by Cartwright.
Significantly, the recently adopted Plan Hillcrest (2024) opens the door for the construction of up to 20 new residential towers, ushering in a new chapter for this historically significant neighborhood.
However, this change embodies cultural shifts, too, with exciting new ventures like Madi set to occupy the vacant Panera location at The Hub on Cleveland Avenue, which will bring beloved brunch offerings to Hillcrest.
In addition, this year’s debut of Good News, San Diego’s first non-alcoholic bar, illustrates a fresh approach to nightlife by providing craft mocktails while also offering a bottle shop for take-home fun.
With a burgeoning culinary scene, community leaders envision Hillcrest embracing a more sophisticated dining profile, as newcomers like Cellar Hand, Origen, and Frenchy’s Hideout add an elevated touch to the area while retaining its boisterous charm.
Hillcrest is not just changing in buildings but is also redefining the vibrant spirit that has characterized it through the decades.
image source from：sandiegomagazine
