Hillcrest is one of San Diego’s hidden gems. It’s a town known for its delicious food, cheery and walkable neighborhoods, and unique nightlife. If you’re visiting San Diego—or if you’re a local—and you’re looking for that perfectly crisp glass of white wine, smoky scotch, craft beer, or somewhere that’ll host fun people to enjoy a night with, look no further. We’ll give you a San Diego tour of the best bars this neighborhood offers.

Keep reading for the best bars in Hillcrest San Diego, what makes them great, and the thing to do once you’re there. 

Martinis Above Fourth 

Photo Courtesy: Yelp.com

Looking for something opulent, ostentatious, and classy? Want to wear your favorite blazer or cocktail dress and feel like you’re at a Gatsby party? This is your spot. Martinis Above Fourth offers luxurious cuisine, incredible entertainment, and their “Late Night Happy Hour” which starts at 10 pm and lasts until they close. 

Throw on those heels, cuff those sleeves, and join this eclectic environment for a night you won’t forget (depending on how many martinis you drink).

• The Thing to Do: Martinis Above Fourth, in a shocking twist of events, is famous for their handcrafted martinis. Have one. Have two. Have seven. Become the Jazz… responsibly, of course. 

The Loft

Photo Courtesy: Kane (pictured), Bartender at The Loft

If you’re looking for underground films, up and coming musicians, comedy, and late-night DJs, this is your rumble. The Loft is one of Hillcrest’s pride and joys, known for its wonderful live performances and heavy-handed bartenders. Simply put: this is one of the best Hillcrest bars blessing the city. 

This dive bar, like many on the list, is a gay bar. That shouldn’t come as a surprise being that the history of Hillcrest is known for its lovely and vibrant LGBT community. 

• The Thing to Do: Jello shots. Seriously, this is not your sit down and enjoy lavish cocktails by the hearth type of place. This is a place where you start and end with jello shots. 

Flicks

Photo Courtesy: GayCities.com

Flicks, located on University Avenue, is one of the “OG” video bars not only in San Diego but in the United States as a whole. Head over to this gay bar and join their diverse crowd, where you can watch sports, shoot pool, make friends, or scream karaoke (Sunday, Monday, and Tuesday). This long-standing bar, opened in 1983, is celebrated by San Diegans for yielding a new experience every night.

• The Thing to Do: Welfare Wednesdays. On Wednesdays, Flicks serves incredibly inexpensive drinks and brings in a crowd that is as welcoming as it is lively. 

The Merrow

Photo Courtesy: San Diego Reader

Are you Irish? Do you love Celtic culture or Gaelic-themed anything? Then you should probably grab an Uber to The Merrow. This lovely Hillcrest bar is located just down the street from Hillcrest’s monument and landmark, the 65-foot pride flag, and features an array of different musicians that change the scene nightly. 

Give them a ring and see if you’re keen on their agenda. Then pop on over, have a whiskey, and stepdance like you’re Irish. 

• The Thing to Do: Karaoke. If you’re going to be heading in on a Sunday, then you should absolutely sign up your friends (and yourself) for a song. 

Urban MO’s Bar & Grill

Photo Courtesy: Urban Mo’s

If you’re looking for a place that perfectly represents the city of Hillcrest—then come visit Urban MO’s Bar & Grill. One of the many gay bars in San Diego, MO’s believes that every afternoon and evening should be colorful and FUN! They also believe that cocktails should be served with plastic farm animals and that people have more fun when they’re seated on a patio.

Come to Mo’s for live events, bottomless mimosas, long happy hours, “Kween Out Karaoke,” and spaghetti. To the latter, seriously, come for the spaghetti. 

• The Thing to Do: If you’re nearby on a Tuesday, then you should waltz over for their “Showtunes Spaghetti Tuesdays.” Not only is it an all you can eat dinner, but they play a ton of singalongs the entire restaurant belts throughout the meal. Sing, eat, drink, and let this merry place fill you with joy. 

Uptown Tavern

Photo Courtesy: San Diego Entertainer Magazine

If you’re looking for a spot that can yield multiple experiences in one, then it’s likely the Uptown Tavern is ringing a siren for your presence. From the lounge and private bar to a gorgeous outdoor patio to the main bar that is center stage for events, the Uptown Tavern has it all. 

Do you want to relax after a long day of travel? Have a drink in peace with some lovely conversation? Then maybe dance after that third glass of wine? Better yet, are you hungry? If you’re there during the week then know that:

• Monday = endless pasta
• Tuesday = incredible burgers
• Wednesday = charcuterie boards 
• Thursday = mac n’ cheese

Aside from dinner, what’s the thing to do here?

• The Thing to Do: From silent discos to themed DJ sets, if you’re looking to get weird, then look no further. Enjoy delicious food, great drinks, then head over to the dance floor to start your night. 

Gossip Grill

It’s entirely likely that you read that as Gossip Girl, when in fact it’s Grill. This LGBT-friendly, women-empowered bar makes a statement you won’t forget. From their events to their “Gossip ‘Bout It” club to the eclectic and amazing guests that pour into the residence, this is a place that welcomes anyone and everyone. 

The elegant and female-energized décor, tasty bacon-wrapped jalapenos, and burlesque themed events all blend into one unforgettable Yas Queen experience. 

• The Thing to Do: Enjoy the community and ambiance. Don’t set expectations, don’t even look at the menu; just trust in the experience. 

Have Fun and Uber

In terms of nightlife in San Diego, bars in Hillcrest have it all. If you want swanky and upscale, dirty and dive-y, cheap or opulent, any and all your desires will be fulfilled by one of Hillcrest’s many amazing establishments. And, being that this town is driven by its art and exquisite tastes, you might find that the drinks beckon you for more.

In that case, always remember to be safe and use a rideshare service. Both Uber and Lyft cater to the area—and local taxis are present, too. 

From fun bars to great restaurants in Hillcrest, you are sure to find new things that this town offers. Cheers to you! 

Sources:

SDGLN. Rainbow flag will fly high in Hillcrest. https://sdgln.com/news/2012/05/15/breaking-news-rainbow-flag-will-fly-hillcrest