Notable Sights & Landmarks
From the neon Hillcrest Sign hanging at 5th and University Avenues to its Rainbow Crosswalks, Hillcrest blends its distinctive setting with scenic canyon bridges, paths, and parks. Some of our favorite spots to visit include:
1. Spruce Street Suspension Bridge
- Connects the west end of Spruce St. to W. Spruce St. over Kate Sessions Canyon in Bankers Hill.
- Built in 1912 by San Diego mayor Edwin Capps, this 375-foot bridge is San Diego's only pedestrian suspension bridge. Supported by steel cables anchored into concrete blocks, it sways with wind and foot traffic, earning the nickname "The Wiggly Bridge." You can also explore short dirt paths along the canyon floor underneath, or connect to larger urban routes like the Seven Bridges Hike or Maple Canyon Trail.
2. Vermont Street Pedestrian Bridge
- This uniquely artful bridge connects Vermont St. in Hillcrest to Connecticut St. in University Heights.
- Built in 1994 to replace a historic 1917 wooden footbridge, this 420-foot steel span lets you cross safely over the Washington Street canyon traffic. Custom railings hold 28 laser-cut metal panels featuring iconic quotes from Dr. Seuss, Martin Luther King Jr., and local architect Irving Gill. Even the concrete deck underfoot is sandblasted with seven different dictionary definitions of the word "bridge".
3. Marston House Gardens & Grounds
- Sits at 3525 7th Ave on the northwest edge of Balboa Park, right where Hillcrest meets the park boundary.
- Built in 1905 for department store owner George Marston, the five-acre grounds feature formal English rose gardens, brick walkways, and native landscaping designed by Kate Sessions. You don't need a museum ticket to walk the beautiful outdoor property. Visitors can freely stroll the manicured lawns, sit under century-old pine trees, or pick up the dirt trail along the canyon edge that links into Balboa Park's larger trail network.
4. Hillcrest Pride Flag & Pride Plaza
- Located at the median of Normal Street and University Avenue.
- Raised in July 2012, this 65-foot flagpole flies a Progress Pride flag year-round and serves as the kickoff site for the annual San Diego Pride Parade. The surrounding space is now transforming into the Pride Promenade, a multi-block pedestrian park featuring shade trees, a rainbow bike lane, and a restored vintage streetcar concession stand.
5. See Mural Alley
- Runs parallel to University and Robinson Avenues in the alleyway behind 4th and 5th Avenues.
- Developed in collaboration with The Studio Door, this active alley showcases striking, large-scale wall murals that are updated every few months by local street artists. Because delivery trucks use the lane during business hours, the best window for photos is before 9 AM on weekends.
Memorable Restaurants & Nightlife
Hillcrest holds over 200 (!) different places to eat and drink across a few walkable blocks, with unique spots that include:
1. Creme Brulee French Toast at Crest Cafe
- Located on 425 Washington St between 4th and 5th Avenues in Hillcrest.
- Open since 1982, this neighborhood diner is famous for its bright pink neon sign, retro booths, and comfort food served late into the night. It gained national attention after being featured on Diners, Drive-Ins and Dives, where Guy Fieri savored its Creme Brulee French Toast. One of the few spots in Hillcrest that has full-menu dining until midnight or later daily.
2. Drag Brunch at Urban Mo's or Gossip Grill
- Located within a few blocks of each other: Urban MO's (308 University Ave), Gossip Grill (1220 University Ave), and Baja Betty's (1421 University Ave)
- These spots anchor Hillcrest's weekend drag scene. Urban MO's hosts a loud, high-energy show with indoor stage seating, packed outdoor tables, and pitcher-sized cocktails. Gossip Grill—one of fewer than 30 remaining women's LGBTQ+ bars in the US—offers a more intimate, outdoor patio show with shade sails and fire pits. Down the street, Baja Betty's runs its own weekend drag brunch paired with giant margaritas and Mexican food. Book at least two weeks out online; walk-ins rarely get tables once shows start at 11am.
3. Tasty Mocktails at Good News
- Located at 3810 Park Blvd, sitting right on the line where Hillcrest meets University Heights.
- Named after the Mac Miller song, San Diego’s first alcohol-free bar uses zero-proof distilled spirits, adaptogens, and house-made shrubs that land complex flavors with the heft of a real cocktail. Dark green booths, low lighting, and weekend hours until 11 PM create an ambient, stylish spot for ethanol-free enjoyment.
4. Small Plates at insideOUT
- Located inside the Eitol Towers courtyard at 1642 University Ave.
- The striking main dining area sits on a concrete catwalk suspended over a shallow pool and a water wall. Every few months, the staff takes down and completely rebuilds the outdoor overhead installations for new seasonal themes. Specializes in Mediterranean small plates built for sharing.
5. Find your Groove at The Rail
- Located at 3796 5th Ave at the corner of 5th and Robinson Avenues.
- Opened downtown in 1934 as the Brass Rail before moving to Hillcrest in 1963, this venue holds the title of San Diego's oldest LGBTQ+ bar. The owners officially shortened the name to "The Rail" during a 2015 remodel. Offers a daily happy hour with cheap draft pitchers, then transitions into drag performances, country line-dancing, and energetic weekend DJ sets.
Unique Shops
1. Explore the Hillcrest Farmers Market
- Stretches along University Avenue between Herbert St and Park Blvd (plus parts of Center St and Harvey Milk St).
- Operating every Sunday from 9 AM to 2 PM, San Diego's oldest market packs over 175 stalls into a weekly thoroughfare. Local growers set up tables stacked with regional fruits and vegetables. Ready-to-eat food stands anchor the mid-block delicious offerings and baked goods, while local vendors offer curated / handmade apparel, artwork, jewelry, and ceramics.
2. Vintage / Original Vinyl at Taang! Records
- Located at 3830 5th Ave between University and Robinson Avenues.
- Founded in Boston in 1983 as an independent hardcore punk label, Taang! Records opened its Hillcrest storefront in the late 1990s. Functions as both an active retail record store and the working headquarters for the label. Floor-to-ceiling racks hold new and used vinyl, cassettes, CDs, tour posters, and band apparel. Leans heavily into early punk, ska, reggae, and alternative rock, with original pressings alongside the label's back catalog from bands like Gang Green and The Lemonheads.
3. Find Your Next Great Read at Bluestocking Books
- Located at 3817 5th Ave between University and Robinson Avenues.
- Operating in Hillcrest since 1999, this independent bookstore takes its name from the 18th-century Blue Stockings Society, an early network for women intellectuals. The shop specializes in progressive politics, LGBTQ+ literature, local San Diego authors, and environmental history alongside current fiction. Handwritten index cards from staff pin down specific reviews, and a discount cart sits on the sidewalk.
4. Peruse the Village Hat Shop
- Location: Located at 3821 4th Ave
- One of the largest specialized hat retailers on the West Coast, stocking thousands of headwear options ranging from genuine hand-woven Ecuadorian Panama hats and formal fedoras to newsboy caps, berets, and sun hats. Staff use traditional hat stretchers and steam irons on-site to custom-fit headwear for customers.
5. One-of-a-Kind Gifts and Decor at Oates General
- Location: Located at 1625 University Ave between Herbert St. and Park Blvd.
- Fun Facts: Founded by a former television set designer, this boutique blends hand-picked vintage home decor with new gifts. Shelves hold retro barware, mid-century glassware, indie candles, vintage apparel, and humor-focused greeting cards. Open Thursday through Sunday, it opens at 9:30 AM on Sundays to align with the neighboring Hillcrest Farmers Market.
