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Jim Winsor’s Out & About: Cinco de Mayo in Hillcrest

Cinco de Mayo at Uptown Tavern
Photo credit:
Jim Winsor/SDPIX

Tomorrow is Cinco de Mayo. This Mexican holiday, popular both south and north of the border, falls on a Friday this year, hence promising to be quite lively indeed. 

That being the case, here’s a quick run-down of some of the festive fiestas happening here in Hillcrest: 

Remember you can get to some of these holiday festivities or get closer to them by taking the free shuttle offered by the Top of the Bay Cinco de Mayo event going on at the Porto Vista Hotel:

From 6 pm to 10 pm: Cinco de Mayo Top of the Bay with DJ Tristan Jaxx

“Go high atop one of the most beautiful hotels in San Diego, The Porto Vista with DJ Tristan Jaxx! Featuring spectacular views and top-notch entertainment this is the best way to get your weekend started early. There will be a $5 nacho and $2 taco bar and $2 house infused Tequila Jalapeno shots in honor of Cinco de Mayo!”

Plus attendees get free entry into Rich's until midnight with wristband from Top of Bay.  

The shuttle schedule is as follows (times are approximate, please allow a 5-10 minute variance in case of traffic):

Leave Porto Vista Hotel at 5 pm to Caliph – Arrive 5:10

Leave from Caliph at 5:10 pm to The Loft – Arrive 5:15

Leave from The Loft at 5:15 pm to Rich’s – Arrive 5:20

Leave from Rich’s at 5:20 pm to Mo’s – Arrive 5:25

Leave from Mo’s at 5:25 to Porto Vista Hotel – Arrive 5:35

This schedule will be repeated until 10 pm.

Here's the rundown of other exciting things happening in Hillcrest for the Mexican holiday: 

Friday, May 5 

2 pm: Fiesta del Cinco de Mayo at Urban Mo's

“¡Ándale reina, venga a la fiesta del cinco de mayo a Urban MO’s! ¡Venga a beber y a diviértete! It’s Cinco De Mayo! Let’s get ready to party this Friday at Urban MO’s! We’re going South of the border for the afternoon starting at 2PM until closing time …”

3 pm to 10 pm: Cinco de Mayo at Hillcrest Brewing Company

“Hillcrest Brewing Company is Celebrating Cinco De Mayo! Come to the fiesta on Friday, May 5th, and let’s do it south of the border style with our new pizza of the month–Coochie Coochie Carnitas Pizza and Carnitas Street Tacos.  Come have one of our local craft beers and some good eats and let’s celebrate the night away!  See you on Cinco De Mayo.”

3 pm to 2 am: Cinco de Drinko at Uptown Tavern

“Uptown's turning Cinco de Mayo into Cinco de Drinko - some get ya tequila on with us! We'll have El Jimador Specials ALL DAY + a Mariachi Band and DJ Joey JImenez & DJ Rick Betta will be joining us to liven up the festivities.”

9 pm: Cinco de Mayo at Gossip Grill

“Head to Gossip Grill to celebrate Cinco de Mayo! Featuring DJ Kinky Loops & The Family Jewels!”

9:30 pm to 1:30 am: Uptown After Dark: 5 de Mayo Edition at Uptown Tavern

“Let loose this Friday at Uptown Tavern with Uptown After Dark - 5 de Mayo Edition. Drinks and dancing. Courtesy of our rotating DJs. This Friday 05/05 featuring DJ Rick Betta.”

10 pm to 2 am: Electro Pop Cinco de Mayo Fiesta at Rich's

“Head to Rich's Electro Pop Friday event for a Cinco de Mayo Fiesta! DJ K-Swift in the main room; Moody Rudy in the front room. $5 Casamigos Shot Specials all night long; $7 Casamigos Margaritas all night long.”

10:30 pm: Cinco de Mayo at #1 Fifth Avenue

“Cinco de Mayo falls on a Friday this year! Come celebrate the international day of getting drunk with your favorite queens! RuPaul’s Drag Race will be playing at 8 on the Patio and showtime is at 10:30 pm! We will be performing to your favorite Mexicana Stars and playing the best Latin music all night!!! Never a cover! Always a blast!!”

Other fun stuff this week


7 pm to 9 pm: Out at The Archives: 45 Years of Noble Deeds, The Imperial Court at Rich's

6 pm to 9:30 pm: Dana Goldberg in You've Got to Be Kidding at Martinis Above Fourth

9 pm to 2 am: Flicker at Flicks


All day: White Party Palm Springs

4 pm to 7 pm: Happy Birthday Benny Cartwright at Babycakes

6 pm to 10 pm: SDPIX presents Top of the Bay at the Porto Vista Hotel

6:30 pm to 10 pm: RuPaul's Drag Race Viewing Party: Season 9 at Urban Mo's

7 pm to 10 pm: Divas Welcomes the Other Tyra: Tyra Sanchez at Rich's

7 pm: Finger Me Fridays at Gossip Grill


All day: White Party Palm Springs

10 am to 2 pm: Mexican Brunch at Baja Betty's

1:30 pm to 4 pm: Paint & Sip Fundraiser benefiting the LGBT Community Center at Brick Ba

3 pm The San Diego Women's Chorus Presents Reflections: Looking Back on Our First 30 Years at the University Christian Church

6:30 pm: Free Community Showing of "Moonlight" at the Jacobs Center

10 pm to 2 am: The Pink Party with T.S. Madison at Rich's


All day: White Party Palm Springs

11 am to 3 pm: Gospel Brunch at Lips

12 noon to 5 pm: Heat Sunday Pool Party at the Lafayette Hotel

1 pm to 6 pm: F-Monday It's Sunday Funday at Uptown Tavern

3 pm: The San Diego Women's Chorus Presents Reflections: Looking Back on Our First 30 Years at the University Christian Church

3 pm to 8 pm: Church at Babycakes


6 pm to 11 pm: 50₵ Wing Night at Hillcrest Brewing Company


4 pm: Happy Hour at the San Diego Eagle


7:30 pm to 10 pm: Pictionary Night at #1 Fifth Ave.

Last week’s events

Check out SDPIX.com for all the new albums from last week, including photos from Urban Mo’s, #1 Fifth Avenue, and the San Diego Gay Men’s Chorus. Happy viewing!