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It’s also a hub for San Diego’s LGBTQ+ community, which has led to Hillcrest’s gay bar scene being the liveliest in the city.
When Greg and I first met, we lived in Hillcrest and loved it. For over forty years, Hillcrest has been the heart of San Diego’s Pride celebration. Either way, it’s hard to have anything but a good time here.
insideOUT
Just a few steps further east is insideOUT, a swanky spot serving up premium seafood, juicy steaks, and $7 happy hour beverages.
I don’t think insideOUT has many competitors when the decor comes into question, as the water features, hanging flowers, and slick countertops speak for themselves.
They don’t offer the same range of events as many of its neighboring bars, as insideOUT focuses on craft cocktails, impeccable food, and a relaxed vibe, with the occasional shindig thrown in.
Number One Fifth Avenue
The best way to describe Number One Fifth Avenue is as a unique blend of a gay club and a dive bar.
As the name suggests, this long-standing institution is located on Fifth Avenue.
There are so many things to do during Pride Season in Hillcrest. shot specials and awesome videos. You instantly feel warm and welcomed whenever you walk into a bar in Hillcrest, and if you go more than twice, they will treat you like a longtime regular.
Step three: Watch the San Diego Pride Parade.
Also cool.
karaoke @10:00pm with host rebekah.
Step one: Hillcrest CityFest is a month after Pride on the second Sunday in August on Fifth Ave. This celebration of community spirit features live bands, electric dance music DJ's, arts, crafts, and food that attracts over 150,000+ visitors
Step two: Get your costume for the Hillcrest Nightmare.
Sunday - Football & Karaoke
The event celebrates the culture, history, diversity and LGBTQ+ community through the Stonewall Rally, a drag happy hour, and two nights of massive dance parties. try our new wii bowling league. enjoy a $3 shot with every drink purchase, 9pm-close, best song selection in town!
Step two: Get your tickets to the Pride Block Party.
Widely regarded as one of the best gay bars in Hillcrest San Diego, Gossip Grill has a bit of everything, depending on what time of day you stop by, of course.
Mostly catering to women, Gossip Grill runs events all the time, from boozy brunches to drag shows, though you can also enjoy quieter nights around the firepit out back.
Not only have they nailed the perfect ambiance, but they’ve also created a fantastic menu with vegan and veggie options, plus quirky cocktails that go for as little as $12.
Alibi
If you’re after something a bit more laidback without being too quiet, Alibi on the corner of Richmond Street will fit the bill.
Matching the description of an old-school dive bar with ease, Alibi is a cash-only spot that’s kitted out with a pool table, jukebox, and healthy helpings of beer.
Don’t come hungry, as there’s no food served here, but what you will be treated to is famously heavy pours, reasonable prices, and hits from every decade.
Urban Mo’s
Urban Mo’s is an LGBTQ-inclusive bar that might just give Gossip Grill a run for its money.
Bingo, brunch, and diva nights will give you a flavor of what you’ll experience during a typical night at Urban Mo’s.
Grab a perch at a local Hillcrest patio on University Ave. and watch one of the largest Pride Parades in the county.