Hillcrest San Diego

Hillcrest has been dubbed the Greenwich Village of San Diego. This eclectic neighborhood is the colorful epicenter of culture and diversity. It’s an urban neighborhood that oozes character, with an inclusive multi-ethnic and gay-friendly vibe. You can think of Hillcrest in comparison to its surrounding urban neighborhoods as their slightly cooler cousin. A casual stroll down University Avenue in this captivating neighborhood reveals stylish boutiques, trendy vintage clothing stores, unique ethnic and themed restaurants, chic wine bars, and a vibrant nightlife.

Hillcrest History

In its earliest days, the land where Hillcrest now sits was home to Kumeyaay Indians, and later came under the control of the Missions during Spanish colonization. George Hill, a railroad tycoon, purchased the land for development in 1907 and by the 1920s and 30s the namesake neighborhood of Hillcrest was Downtown San Diego’s first bustling suburban shopping area. It was destined to be a progressive neighborhood from its very roots. By 1940 a group of female shopkeepers, who had formed the Hillcrest Women’s Association, erected the iconic “Hillcrest” lighted sign in the heart of the neighborhood at University Avenue and 5th Avenue that, though replaced with a newer version in 1984, remains today.

The 1970s brought a vibrant revival to the aging neighborhood when it was adopted by the gay community who quickly began buying up residences and businesses. The next thirty-plus years brought the first annual city-permitted gay pride parade in 1975, the LGBT Community Center in 1980, the Hillcrest Business Association in 1984, Mercy Gardens – an HIV-positive community in 2001, the first Hillcrest Town Council in 2007, the privately funded Hillcrest Pride flag at the corner of University Avenue and Normal Street, and the renaming of Blaine Avenue to Harvey Milk Street in 2012. This active civic-minded neighborhood shows no signs of slowing down.

Hillcrest Highlights

Urban MO’s Bar & Grill, the self-proclaimed best gay bar in the world, is a Hillcrest classic and the best place to get into the spirit of the Hillcrest neighborhood. The playful gay restaurant is decidedly hetero-friendly, so don’t be shy, everyone is welcome here. Urban MO’s also has the distinction of serving their world famous Philly sandwich; another good choice is their world famous Mini MO’s – 3 seasoned mini burgers with melted cheddar, grilled onions, thousand island dressing, lettuce, and tomato. For those cool evenings, try MO’s famous beef chili. They have patio seating, dancing, a high energy ambiance, different theme nights like show tunes night, and interesting people-watching. Check their website for the next Dreamgirls Revue; you won’t want to miss it.

Hillcrest’s Restaurant Row tops everyone’s culinary must-do lists in San Diego. They have a wide array of ethnic restaurants here; you won’t find just one Indian restaurant, try four – Tandoori Hut, Monsoon, India Palace, and the one most talked about – Bombay Exotic Cuisine of India. There are just as many quality Thai restaurants like Bai Yook or Celedon Royalty Thai, for example. Restaurant Row has Greek, Afghani, Mexican, Japanese, French, and American restaurants too. Try Hash House A Go Go for a giant pancake or Chocolat for sweet or savory crepes. Get great pizza at Bronx Pizza, or satisfy your sweet tooth at Extraordinary Desserts or Babycakes. One thing you will not be able to do is leave Hillcrest on an empty stomach.

Hillcrest Nightlife

Hillcrest is notorious for their electric nightlife scene. If you’re into nightclubs, your best bets are The Brass Rail on 5th Avenue – check out Manic Monday, and Rich’s on University Avenue. If you prefer a tamer scene, locals favor The Loft for a friendly and comfortable neighborhood bar. Tap and Press is for the beer connoisseur; one traveler called it the “adult candy store” of beer with its wide selection of flavored and nitro beers. Martinis above Fourth is a swanky place voted #1 Martini Bar in San Diego where there is often live music. If you prefer your martini’s shaken, not stirred, check them out! Hillcrest is also known for its many wine bars. There are a ton of choices, but a few favorites are Wine Steals, 57 Degrees, Splash Wine Lounge and Bistro, and Voyou.

Hillcrest Things to See and Do

If you just can’t get enough of the cool vibe of Hillcrest, book your stay at Ann Callahan’s Hillcrest House, voted San Diego’s top bed & breakfast. The 1910 property offers five high-end, beautiful rooms – Coronado, Balboa, Gaslamp, Old Town, and Zoo, plus a two-bedroom vacation bungalow with private outdoor patio. They offer a delicious Heart Healthy Southern California Lifestyle breakfast complete with the aromas of freshly baked muffins each morning. Don’t stay just anywhere when you can experience the unique ambiance of this B&B and take advantage of their inside knowledge on everything Hillcrest.

Hillcrest is an entertainment hub that draws San Diegans from across the county. Their weekend Hillcrest Farmers Market is one of the best in the city with over 175 vendors, including a dozen artisans. Hillcrest has some of the most unique shopping options you’ll find anywhere. There are a few of the usual chain stores, but independent and boutique shops dominate this shopping scene with stores like the trendsetting House Boi, Cathedral, Twirl, The Village Hat Shop, and Flashbacks. There is even a vinyl record store for you old school shoppers. Landmark’s Hillcrest Cinemas, the neighborhood’s only movie theater, shows indie films almost exclusively, and is located on 5th Avenue between Washington Street and University Avenue.

San Diego’s annual LGBT Pride Festival, a staple in the Hillcrest neighborhood since 1975, is a wildly popular event for the whole city that draws attendees from across the country. It is held each July, with organizers working year-round to make it the best experience of the summer. Crowds at the San Diego Pride Parade and street festival number well over 400,000 people. Expect to see crazy costumes, floats, local politicians, corporate supporters, and fun…lots of fun, at one of the largest Pride events in the United States. San Diego Pride weekend kicks off on Friday night at the corner of Normal Street and University Ave with the Spirit of Stonewall Rally and Flag Raising.