Weekend Layover: Dogtown, Santa Monica

Media portrayals of Santa Monica show wide sandy beaches, a family-friendly pier and the perpetually packed Third Street Promenade. A different side of Santa Monica, however, exists just south of Pico Boulevard. About a decade after the Civil War, settlers first developed Santa Monica and Ocean Park as two separate neighborhoods divided by a gully, which eventually became the Santa Monica Freeway (I-10) in the 1960s. In the early 20th century, part of Ocean Park became its own city, eventually renaming itself Venice in 1911, while an amusement park made the rest of the neighborhood a major tourist destination.
Fast forward to modern times, and Santa Monica proper now claims the tourists with Pacific Park on the Santa Monica Pier, while Ocean Park more closely resembles Venice Beach with an artsy surf vibe and a vibrant Main Street filled with boutiques, bars and restaurants. Old-school surfers and skaters know this area as Dogtown, home to the infamous Zephyr Competition Team (or Z-Boys), who popularized aerial-style skate moves in the mid-1970s.
Day One
Morning
The beach is a must when visiting Santa Monica, but avoid an uncomfortable sunburn by hitting the waves in the morning. Anywhere on the sandy expanse is good, but for a bit of history, hit the water just south of the Sea Colony towers near Ocean Park Boulevard. This is the former location of the Pacific Ocean Park, a pier-based entertainment complex name-checked in the Beach Boys’ “Amusement Parks U.S.A.” (1965). The park fell into disrepair by the 1960s, but before the city demolished it in 1975, this dangerous surf spot was a favorite of the Z-Boys. Hit up Perry’s at the Beach (with six Santa Monica locations) for breakfast, drinks and beach-centric rentals. In the late morning, wash off the sand and get ready to explore.
Afternoon
Start with lunch at Cha Cha Chicken, a colorful Caribbean joint with dishes like coconut fried chicken and salmon negril during the weekdays and sweet spicy jerk eggs for weekend brunch. Fans of Mad Men-style lunches will appreciate the restaurant’s BYOB policies, and Star Liquor is only two blocks away on the corner of Main and Bay Streets.
After lunch, head one block east to Main Street, turn right and walk past Star Liquor to the southeast corner and grab a caffeine boost at Dogtown Coffee. This java spot with house-roasted beans is the original location of the Zephyr surfboard shop opened by Jeff Ho, Skip Engblom and Craig Stecyk in 1971. On display at Dogtown Coffee are some of the original Z-Boy skate decks. In the early days, Main Street-adjacent Bay Street was one of the many spots where the team liked to skate when they weren’t surfing.
Travelers seeking a more traditional cultural experience can check out the California Heritage Museum at Main Street and Ocean Park Avenue. This elegantly restored 1894 Victorian house contains a museum with rotating exhibits that highlight early California culture. On various days, the lot near the museum features a farmer’s market or a collection of food trucks. Those who could care less about museums can head south on Main Street to explore the many shops, galleries and salons. Notable boutiques include Fedora Primo retro hats, Trendy Sunglasses, Streetcraft LA creative studio and store, Love Adorned jewelry and many others. At 4 p.m. or soon after, dive into one of the many bars offerings happy hours specials (more info on happy hours below).
California Heritage Museum
Evening
Start the evening with a stop at the beach to watch the sunset. Check an online weather site for the sunset time, and arrive at least 40 minutes earlier. (Remember, “sunset time” is when the sun has already set.) After that, head to Main Street and watch the retail row transform into a dinner and drinking hot spot. The top culinary choice is an old-school classic, Wolfgang Puck’s Chinois on Main. In 1982, the Austrian chef opened the original Spago on Sunset Boulevard, and a year later, he fused classic Asian dishes with French technique and California farm goods inside this Barbara Lazaroff-designed beauty. Signature dishes include the Chinois chicken salad, the Shanghai lobster with curry sauce and the catfish with ginger and ponzu sauce.
After dinner, head to the speakeasy-style Basement Tavern inside The Victorian. With a setting seemingly ripped from a Turner Classic Movie, the old school subterranean bar has a cozy vibe with oversized chairs in various shapes, and the soundtrack includes artists like the Doors, Sublime, the Offspring and Led Zeppelin. Upon entering the Victorian, head straight back, and once you pass the stairway, turn left to find an unmarked door with stairs leading down. What the Basement Tavern lacks in draft beer it makes up for in whiskey flights.