Events | Crest Cafe
BOGO Burger Night
Thursday, May 7, 2026 | 5:00 PM to 10:00 PM | Crest Cafe, Hillcrest
Buy one burger, get one free with the purchase of two beverages. The first Thursday of every month is the best burger deal in Hillcrest, and May is no exception. Whether it is date night, a catch-up with friends, or a well-deserved solo treat, BOGO Burger Night is how we kick off the month at Crest Cafe.
🌺 Perfect Pairing: Two Butter Burgers with Sweet Potato Fries and a Local IPA
Mother’s Day Brunch at Crest Cafe
Sunday, May 10, 2026 | All Day | Crest Cafe, Hillcrest
Treat Mom to a no-fuss, all-heart brunch at the neighborhood spot that has been feeding Hillcrest families for over 43 years. All-day breakfast favorites, $6 mimosas all day, fresh juice options including OJ, grapefruit, and our seasonal squeeze, plus the kind of warm, welcoming service that makes every mom feel like the most important person in the room. Walk-ins welcome but reservations are highly encouraged this day.
🌺 Perfect Pairing: Creme Brulee French Toast and a Mimosa
Rainbow Latinas Game Night
Tuesday, May 12, 2026 | 5:30 to 7:30 PM | Latin@x Services at The Center, 3909 Centre Street
A welcoming monthly game night for women who identify as part of the LBTQ+ community, hosted by Latinx Services at The San Diego LGBT Community Center. Grab your friends and enjoy an evening of fun, laughter, and connection in a safe and affirming space right in the heart of Hillcrest.
🌺 Perfect Pairing: Baja Chicken Wrap and a Mango Smoothie
AANHPI Heritage Month at The Center
All Month | The San Diego LGBT Community Center, 3909 Centre Street
May is Asian American, Native Hawaiian, and Pacific Islander Heritage Month, and The Center celebrates with programming all month long honoring API queer voices, history, and leadership. Check the calendar for panels, mixers, and community gatherings that lift up the beautifully layered identities that make up our neighborhood.
🌺 Perfect Pairing: Sesame Chicken Salad and a Lavender Lemonade
Dreamgirls Revue
Wednesdays in May (May 6, 13, 20, 27) | 6:00 to 8:30 PM | Urban MO’s, Hillcrest
San Diego’s most iconic and longest-running drag spectacular returns every Wednesday with show-stopping performances from a dazzling cast of queens, all hosted by the legendary Chad Michaels. This is Hillcrest nightlife at its finest. Arrive early, grab a seat, and prepare to be dazzled. $15 to $20.
🌺 Perfect Pairing: BBQ Pulled Pork Fries and a Craft Cocktail
Bubbles for Brunch
Saturdays in May (May 2, 9, 16, 23, 30) | 11:00 AM to 2:00 PM | Urban MO’s, Hillcrest
San Diego’s only Saturday morning drag show and interactive brunch experience. Featuring a rotating cast of drag queens from reality TV fame to local favorites, all hosted by Kickxy Vixen. Sip, eat, and be fabulous. $20.
🌺 Perfect Pairing: Apple Cinnamon French Toast and a Mimosa
Babette’s Bingo Mother’s Day Edition
Sunday, May 10, 2026 | 11:00 AM to 2:00 PM | Urban MO’s, Hillcrest
San Diego’s legendary Babette Schwartz brings the laughs, the looks, and the prizes for a second-Sunday bingo extravaganza that just happens to land on Mother’s Day this year. Bring the family, bring your chosen family, or bring the most fabulous matriarch in your life. Outrageous fun with a drag twist.
🌺 Perfect Pairing: Crab Benny and a Bloody Mary
Gayme Night
Mondays in May (May 4, 11, 18, 25) | 5:00 to 11:00 PM | Urban MO’s, Hillcrest
Board games, card games, and playful competition every Monday night at MO’s. Bring your crew or come solo and make new friends. It is low-key, welcoming, and the perfect start to the week.
🌺 Perfect Pairing: Loaded Nachos and a Honey Blonde Ale
Sassy Sunday Funday
Sundays in May (May 3, 17, 24, 31) | Afternoon | Urban MO’s, Hillcrest
Hillcrest’s signature Sunday party, complete with drag, DJs, and that unmatched MO’s patio energy. Sassy Sunday Funday is the best way to close out the weekend with the whole neighborhood in one place.
🌺 Perfect Pairing: Hangover Omelet and a Bloody Mary
Circuit Papi with Joe Pacheco and Geovanni Pacheco
Saturday, May 2, 2026 | 9:00 PM to 4:00 AM | Rich’s San Diego, Hillcrest
One of Hillcrest’s hottest Cinco de Mayo weekend parties takes over Rich’s with headliners Joe Pacheco and Geovanni Pacheco plus a special Gala Varo birthday bash. Expect lights, go-gos, and a dance floor that does not quit until sunrise.
🌺 Perfect Pairing: Spicy Pastrami Hash and a Cold Brew the morning after
Rich’s Weekend Parties
Fridays and Saturdays in May | 9:00 PM to 2:00 AM | Rich’s San Diego, Hillcrest
San Diego’s most popular gay nightclub keeps Hillcrest dancing every weekend with rotating DJs, themed nights, and go-go dancers that bring the heat. Check the Rich’s calendar for headliner announcements all month long.
🌺 Perfect Pairing: Butter Burger and an Espresso Martini
Kim’s Convenience at The Old Globe
May 15 to June 14, 2026 | The Old Globe, Balboa Park
The San Diego premiere of Ins Choi’s award-winning comedy that inspired the hit Netflix series finally lands at The Old Globe, directed by Weyni Mengesha. Warm, funny, and deeply human, it is a love letter to family-owned corner stores and the immigrant families who run them. Just a short drive from Hillcrest.
🌺 Perfect Pairing: Tuscan Benedict and a Cappuccino
Alien Girls at The Old Globe
Through May 10, 2026 | The Old Globe, Balboa Park
Catch the final weeks of Amy Berryman’s world premiere, directed by Jaki Bradley. A smart, surprising new play that has been the talk of the spring season. Closing weekend is Mother’s Day, so make it a double feature with brunch at Crest Cafe.
🌺 Perfect Pairing: Avocado Omelette and a Cappuccino
RENT at Diversionary Theatre
May 2026 | Diversionary Theatre, 4545 Park Blvd, Hillcrest
Diversionary’s 40th anniversary season closes with a daring, immersive production of Jonathan Larson’s iconic musical. Five hundred twenty-five thousand six hundred minutes of love, loss, and community, staged just steps from Crest Cafe. Check the Diversionary site for exact performance dates.
🌺 Perfect Pairing: Mediterranean Platter and an Espresso Martini
Finest City Improv Live Comedy
Thursday to Sunday throughout May | Finest City Improv, 3746 6th Ave, Hillcrest
Hillcrest’s home for improv and sketch comedy keeps the laughs coming every weekend with multiple shows nightly. Audience-driven games, competitive showcases, and house teams like One Tree Hillcrest keep it live, unscripted, and always surprising. Tickets start at just $5.
🌺 Perfect Pairing: Baja Chicken Wrap and a Honey Blonde Ale
Spring Oasis Experience at InsideOUT
Through May 31, 2026 | InsideOUT, Hillcrest
Final month to step beneath the canopy of life-size cherry blossom trees at InsideOUT’s immersive Spring Oasis dining experience. A seasonally inspired menu, themed cocktails, and a space that has been completely transformed into San Diego’s most beautiful spring setting. Date Night specials run every Wednesday.
🌺 Perfect Pairing: Spicy Pastrami Hash and a Craft Cocktail
Happy Hour Bingo at Cork & Stem
Select Wednesdays in May | 6:30 to 8:30 PM | Cork & Stem, 1035 University Ave, Hillcrest
Do you like free wine? Cork & Stem’s happy hour bingo is back with lucky winners taking home glasses of wine. All-day happy hour prices, great music, and the thrill of B-I-N-G-O at Hillcrest’s coziest wine bar and flower shop. Check their calendar for exact May dates.
🌺 Perfect Pairing: Avocado Omelette and a Lavender Lemonade
Cinco de Mayo in Hillcrest
Tuesday, May 5, 2026 | All Day | Hillcrest neighborhood
Cinco de Mayo lands on a Tuesday this year, which means the whole neighborhood leans into Taco Tuesday mode. Hillcrest is packed with spots to sip a margarita, crush a plate of tacos, and celebrate in true San Diego style. Start the day right with brunch at Crest Cafe, then wander Fifth and University to find your favorite happy hour.
🌺 Perfect Pairing: Loaded Nachos and a Spiked Lemonade
Asian Pacific Cultural Festival
Saturday, May 16, 2026 | Balboa Park
The 13th Annual Asian Pacific Cultural Festival returns to Balboa Park with performances, traditional food, dance, and cultural exhibits from across the API diaspora. Free, family friendly, and one of the best AAPI Heritage Month events in the city. Walk it, bike it, or park in Hillcrest and stroll over.
🌺 Perfect Pairing: Sesame Chicken Salad and a Mango Smoothie
Hillcrest Farmers Market
Every Sunday in May (May 3, 10, 17, 24, 31) | 9:00 AM to 2:00 PM | University Ave between Herbert St and Park Blvd
One of San Diego’s best farmers markets, right in the heart of Hillcrest. Over 175 vendors with fresh produce, artisan goods, prepared foods, flowers, live music, and that unmistakable Sunday morning neighborhood energy. Grab your market haul, then stroll to Crest Cafe for brunch. It is a Sunday tradition we never get tired of.
🌺 Perfect Pairing: Avocado Omelette and a Mango Smoothie
Spreckels Organ Society Free Sunday Concerts
Every Sunday in May | 2:00 PM | Spreckels Organ Pavilion, Balboa Park
Free outdoor organ concerts every Sunday at the world’s largest outdoor pipe organ. Civic Organist Raul Prieto Ramirez and guest artists fill the Balboa Park pavilion with everything from Bach to Broadway. Bring a picnic or swing by Crest Cafe first to grab breakfast to go.
🌺 Perfect Pairing: Crest Breakfast Burrito and a Cold Brew
San Diego Zoo Food, Wine & Brew Celebration
Select Friday in May | San Diego Zoo, Balboa Park
Unlimited bites from local chefs, regional craft beers and wines, animal observations, and live music, all in support of the San Diego Wildlife Alliance. It is one of the tastiest fundraisers in the city and a gorgeous way to enjoy the zoo after hours.
🌺 Perfect Pairing: Power Pancakes and a Cold Brew to fuel up beforehand
San Diego International Fringe Festival
Late May into early June | Various venues across San Diego
One of the wildest, most eclectic performance festivals in the country returns with a plethora of innovative performances from Pacific Beach to Baja. Dance, theater, music, cabaret, spoken word, and everything in between. Unpredictable, affordable, and always surprising.
🌺 Perfect Pairing: Mediterranean Platter and an Espresso Martini
Memorial Day Weekend in Hillcrest
Saturday, May 23 to Monday, May 25, 2026 | Hillcrest neighborhood
The unofficial kickoff to San Diego summer. Long brunches on the Crest Cafe patio, rooftop drinks, beach days in the morning, and neighborhood cocktails at night. Hillcrest is one of the best places in San Diego to spend the long weekend, and we will be open all three days.
🌺 Perfect Pairing: Power Pancakes and a Mimosa
