This establishment, situated a stone’s throw from the cliffs at 38th Avenue, has a long and exciting story. Constructed in 1902 by an Irishman named Henchy, midway through the effort it was decided to install a saloon on the bottom floor. By the ‘20s, the Roadhouse was somewhere farmers and hunters would go to wet their whistle and is rumored to have also offered brothel services, with rooms upstairs for rent.
Continue exploring the people, places and the lore that make Pleasure Point such a unique place.
During Prohibition, booze was snuck in by boat from suppliers from San Francisco. Under the cover of the night, bootleggers would transfer the hooch onto the sand; in the morning, buyers would dig their prize out. After the Depression cooled down the partying, the building was used as a residential unit for years, its quirks attracting young surfers and artists.
With such a storied history, this iconic building was dear to many longtime locals, a few of them even championing efforts to establish it as a historical site. Their pleas went unheard, however, and in 2008, the building was razed and more luxury condos sprang up like magic, or mold, depending on your viewpoint.
Origin of “Pleasure Point”
The “traditional designation” of Pleasure Point was adopted formally in large part due to Dr. Norman Sullivan, an in-demand physician who for many years served as Santa Cruz city health officer. Upon retirement in the 1950s, Sullivan moved to the Point and was a notable champion for the colorful community and for officially naming the area “Pleasure Point.”
Prior to acquiring its nickname, Pleasure Point had long been known as Point Soquel. It was originally a part of the old Rodeo Rancho of Mexican land-grant days, before being bought by Irish immigrants. From the turn of the century until the mid-1920s, the vast majority of visitors were groups of men who fished, dug clams or hunted the waterfowl that inhabited the area’s many lakes and lagoons.
These tourists pitched tents along the road or stayed at the Roadhouse, which was the busiest speakeasy in Santa Cruz during Prohibition. With such a reputation as a hotspot for revelry, the area soon became referred to as “Pleasure Point” and the name started to appear on maps as early as 1934.
It’s quite difficult to scale a slippery cliffside with a surfboard in one’s hands. Prior to the installation of cement stairs, the breaks at Pleasure Point were once one of the most dangerous parts of a surf session.
Down at The Hook, where 41st Avenue meets the cliff, surfers had to make do with a series of ropes, creating an extremely risky factor that discouraged beginners. The billy-goat trail at First Peak, now with its nice cement staircase with railings, consisted of a zig-zagging cut in the cliff, with only a couple handles bolted in and a little rope at the end. For those unfamiliar with the pathway, it acted as a huge deterrent for beach access. I can still close my eyes and perform the rock dance in my mind like it was yesterday.
Pleasure Point Night Fighters
This group was first established in the 1940s as a community effort to fight fires and regulate out-of-control revelry. It was during the ’80s when Harry and Ray Conti revived the group, installing garbage cans along the Point and holding an annual “Pack Your Trash Day,” a communal cleanup aiming to publicly educate locals and tourists alike.
The Pleasure Point Night Fighters Park lies above the staircase leading to the surf and was a place where surfers would gather and party. There was even a horseshoe pit. Legendary artist Jim Phillips created a spiffy logo for the group, as well as a now-iconic “Pack Your Trash” logo, featuring a littering kook about to get blindsided by a lurching wave. Now the group is less official yet the spirit lives on in the locals still left.
At the apex of the Point, just beyond 30th Avenue, a pump house used to face the sea, sending sewage out directly into the water. Surfers named the break next to the pipe “Sewers” because of the awful smell. A wave for experts only, Sewers breaks onto a shallow slab of a reef, and can be accessed using a walkway and staircase lovingly — and appropriately — known as “Piss Alley.” The sewer is no longer active, but the giant pipe is still hiding below the surfers, gathering rust as it slowly becomes part of the natural reef.
When the tide gets really low along the Point, the reef begins to show itself, creating spectacular tide pools as the water drains out. It’s the perfect place to take off your shoes and wade into a world of wonder. Sea anemones, urchins, crabs and starfish, to name a few. It’s an awesome place to take the family, where parents can give their little ones a glimpse into the diverse and thriving underwater ecosystem.
Just don’t slip on the kelp-covered reef — you might want to leave your phone at home just in case. In the winter, with the extreme lows of the annual king tides, a giant expanse of the reef is exposed and it’s not unusual to see hundreds of curious ocean lovers spread out across it, staring downward. If you look hard enough, you might even spot the old sewer pipe.
Over the Hill Gang Saloon
A little bit of the Wild West, plunked down in the middle of the Point, complete with the swinging doors of a frontier watering hole. There’s great, yet eccentric, live music and covered seating outside, as well dice and electronic darts.
There’s usually got a taco truck parked outside this locally beloved dive bar at 3530 Portola Dr., providing a bit of a Tex-Mex experience. With all of the spiffy and formal bars and restaurants along the Point, this dive bar is a breath of fresh air.
This public swimming pool was in the basement of one of the earliest buildings on the Point, the Owl House. A place for people to swim and frolic in the shallows, the Plunge was a popular hangout for families up until 1962, when a crack in the pool caused its closure.
Just prior, in 1959, a 13-year-old boy died in the pool, during a “Santa Cruz Frogmen’s Club” tryout, while attempting to complete the 40-yard underwater swim. It depends on whom you ask but some say the boy’s vengeful spirit is what caused the damage and closure.
Pleasure Point was typified by small lots of beach cottages, but now you’ll find multimillion-dollar luxury homes in abundance. The area east of Portola Drive was home to larger lots, and years ago was known for its chicken ranches and flower gardens. If you look hard enough, you might see a weathered, wooden water cistern sticking up from someone’s property.
The Live Oak and Pleasure Point area is known for its many mobile home parks, which have, sadly, become one of the few outlets for retirees and first-time buyers in this overheated housing market.