An exclusive bucolic community with stunning landmark estates
In a profile of soaring Redwood, Cedar and Oak trees, sits Woodside- a quaint and whimsical town that embodies rural living. The town of Woodside dates back to the early nineteenth century when settlers arrived to cultivate the logs of the redwoods.
In 1849, Matthias Alfred Parkhurst, age 20, purchased 127 acres of John Copinger's Rancho Canada de Raymundo near old Mexican saw pits to embark in what would soon become a bustling lumber industry. Dr. Robert Orville Tripp, a dentist, arrived in Woodside shortly after to join him with several business partners, all from Massachusetts. They opened a direct road from the redwood forests to the head of the tidewater in Redwood Creek and the lumbar was dragged by oxen teams down this road and then floated by raft to San Francisco. Eight sawmills and one shingle mill were established in the town to sustain the industry.
Parkhurst and Dr. Tripp opened what later became Woodside Store, a small general store on King’s Mountain Road that also served as a post office and dental office. Their partnership later dissolved and Dr. Tripp took over to operate the business. Dr. Tripp’s history in Woodside was eminent and he made his mark as a San Francisco county supervisor, U.S postmaster, San Mateo County deputy sheriff, public administrator, deputy assessor and custodian of the library.
By 1852, prosperous San Francisco families began to migrate to Woodside to build grandiose country estates. The hills of Woodside grew with farms, small cattle ranches and vineyards all to create an idyllic country setting. A regular stagecoach service to San Francisco was established, which only attracted more people to the beautiful town. Woodside’s first schoolhouse was built in 1859 to nurture the intellect of the children and the community continued to evolve with churches, libraries, a town hall and a number of saloons. Residents incorporated the town in 1956 to preserve its rural integrity.
Today, Woodside remains a rural haven that encompasses copious amounts of nature trails, equestrian properties, open space preserves and an artists’ colony. Although it has a bucolic setting, Woodside is one of the most affluent places to live in the country. This charming town in the woods attracts those who have an affinity for nature’s beauty, but still want to be able to easily access the surrounding Silicon Valley areas. Woodside is extremely safe and friendly, making for a perfect place to raise a family. The school system in Woodside is unparalleled to the rest of the Bay Area and ranks #1 in schools and teachers.
Idyllic Countryside Setting
Soaring Native Trees
Expansive Open Preserves
Equestrian Community
Premier Top Rated School System
As one of the most opulent towns in the nation, Woodside offers country living at its finest. Housing options are diverse and vary from horse ranches to modern, luxurious mansions- all nestled in the stunning setting of majestic trees and hidden from public view. Homes sell for upwards of $4,945,000. Neighboring Silicon Valley areas are all a short commute away.
From its history of sawmills to its sprawling estates, Woodside is known for its spaciousness. Residents value connection to nature, as well as a strong sense of community. Separated from the ocean by the Santa Cruz Mountains, Woodside is home to some of the largest and most stunning native trees. Offering elements of tranquil sophistication, the town serves as one of the most desirable places to live in California. Residents consist of Silicon Valley’s most renowned movers and shakers to include CEOs, venture capitalists, artists and musicians. Woodside embraces an equestrian community and is ideal for horse lovers. Surrounding vineyards highlight a culture of wine and are a destination for residents and visitors alike. Downtown Woodside displays a distinct Western inspired atmosphere with historical features. Woodside is a family-oriented town and boasts the top school system in the Bay Area.
Known for its knickknack-festooned decor and reputable comfort food, Bucks Restaurant of Woodside is an eatery that locals enjoy frequenting. Bucks offers an array of dishes, from French Toast to sandwiches and burgers to wood fired pizza, all served in a casual, family-friendly atmosphere.
Come relax in a large and tranquil outdoor courtyard garden at The Village Hub. This haven was created as a place to welcome all to “The Heart of Woodside”. Enjoy craft coffee from locally curated Cafe Con Lucha coffee beans and a daily fresh pastry or scone as you work from free WiFi or socialize with friends. Vegan and gluten-free options are available.
Experience nature’s bliss at Alice’s Restaurant, which is tucked away in the redwoods. Established in 1960 by Alice herself, this family-owned local spot is reminiscent of a rustic cabin and serves mouthwatering dishes made from locally sourced ingredients. Featuring upscale burgers, scrambles, homemade pie and more, Alice’s Restaurant serves a place to come together and enjoy a wonderful meal.
The Woodside Bakery & Cafe serves as both a sit-down restaurant and a quick stop for coffee and a decadent baked treat. The restaurant offers a full service breakfast, lunch and dinner with expansive menu options. Gluten free options are available.
The Village Pub is an upscale American eatery that features gourmet seasonal fare and fine wines. Perfect for an exquisite meal to celebrate or take a date, this establishment takes pride in its locally sourced and organic produce. The Village Pub is also known for the unprecedented wine and spirits program that they offer. Thomas Fogarty Winery delivers a limited wine selection, highlighting quality over quantity. Relish in beautiful views of the bay, while sipping grapes at this 360 acre estate that is mostly open space preserve. A destination for weddings and events, corporate and private, this vineyard aims to produce wines of the highest quality conscientious stewardship.
Originally dubbed as “Whiskey Hill”, The Pioneer Saloon is a classic Western saloon that has served the residents of Woodside for over 100 years. A watering hole that pours vivacious spirits and elixirs, The Pioneer Saloon features weekly karaoke and live music on the weekend, making for a fun locality to come socialize and engage with friends.
*This is a partial list of restaurants. If you are a local restaurant and would like to be listed, please reach out to collaborate.
OrangeTheory Fitness Woodside Plaza implements interval training in which top tier certified coaches guide their clients through the five different heart rate zones- resting, easy, challenging, uncomfortable and all out. Employing a dynamic variety of exercise methods, OrangeTheory utilizes rowing, cardio and strength training as integral parts of its program.
The Peninsula Community Center serves its community and surrounding areas with a goal to healthy and meaningful connections through sports and fitness. Featuring a comprehensive and professionally run tennis program, an aquatics program and a weight room, instructors are dedicated to creating fun and challenging workouts to people of all levels and strengths.
Woodside Pilates is a private studio that incorporates a mind-body approach to fitness and believes in working “in”, not working out. It is owner Harriet Garfinkle’s mission to guide her students to create mobility, grace and poise through movement, all while preventing injury. It is through moving of the functional core that students leave class feeling alive and joyful in their body.
To help achieve one’s goal of cultivating a fully functional and active lifestyle, it is important to be Physically Focused. Corrective exercise specialists will utilize and implement their knowledge of anatomy, human movement and training programs to help their clients optimize their fitness lifestyle. Personal development and wellness coaching are available through individualized and tailored programs that guide people to a healthier life via exercise, behavioral modification, exercise, injury prevention and nutrition.
Created by expert personal trainer, Rahsaan Carty, Team Rahsaan Fitness 3.0 extends innovative fitness workouts that are designed to maximize performance and optimize the recovery period. Group classes commence regularly, or for a more personalized training experience, private training sessions are available with Rahsaan himself.
*This is a partial list of health and fitness related businesses. If you are a local health and fitness related business and would like to be listed, please reach out to collaborate.
Established in 1963, the Kings Mountain Art Fair is an annual event that is held every labor day weekend. This art fair takes place amongst the redwoods and is known for its unique and dynamic artists. All proceeds from the fair are used to support the Kings Mountain Volunteer Fire Brigade, the Community Center building, special programs for area youngsters and students and the publication of the community’s newsletter. A variety of food and drink vendors will serve eats and treats.
Mountain Terrace has been awarded as one of the most beautiful wedding and event venues in the bay area. Emulating rustic charm, this expansive meadow extends spectacular scenic views of the San Francisco Bay framed by towering Redwood trees and Live Oaks. An in-house culinary team and an expansive bar menu are available to ensure that all details are covered to create the event of one’s dreams.
With a mission to support and enhance the creativity of artists by providing uninterrupted time for work, reflection and collegial interaction, Djerassi Residents Art Program is internationally recognized for its distinguished artist residency. Sitting in a setting of preserved magnificent natural beauty, Djerassi aims to provide the best possible experience for a diverse range of superb talent.
Sharon Heights Golf & Country Club is located in neighboring Menlo Park and has been an integral part of the community for almost 60 years. Implementing a mindset of sustainability and growth in collective contribution, the country club’s projects over the years have focused on giving back and minimizing carbon footprint.
A Historical Landmark since 1949, the Woodside Store, also called Tripp Store, is a fully restored wooden structure that was initially used by Dr. Tripp as a general store, post office and dental office in the heyday of the lumber industry in Woodside. Today, the Woodside Store serves as a house museum with artifacts from its foundation, offering a glimpse into the past of this once bustling logging area. Additionally the Woodside Store is a local stop for any goods that a lumberman or blacksmith could need.
*This is a partial list of events and arts. If you host a local event or art production and would like to be listed, please reach out to collaborate.
Wunderlich Park- A vast space encompassing a hillside area of redwood forest, open meadows and beautiful native trees. A system of beautiful trails are available for horseback riding and hiking. Containing what was once the Folger family ranch, the estate stable and surrounding buildings have been restored to provide a historic treasure to the community.
Huddart Park- A 900-acre forested park that offers hiking and horseback riding trails, picnic areas with barbeque pits and an archery range. This park is a wonderful place to enjoy company with family and friends while exploring and admiring all that nature has to offer.
Teague Hill- A 626- acre nature area with an intricate hiking route- the Bay Area Ridge Trail. Located just above the town of Woodside, in the Santa Cruz Mountains, expansive views of nature are available for enjoyment.
Methuselah Tree (Sequoia sempervirens)- This soaring tree has stood tall for almost 2,000 years. Overlooking the ocean and the bay, this ancient tree has been subjected to storms, fires and wildlife, however through all the tree remains in its majestic beauty.
Thornewood Open Space Preserve- A small regional park located in the Santa Cruz Mountains that is perfect for a quick getaway. Offering 1.5 miles of hiking and equestrian hills, this park is conveniently located in the hills above the town of Woodside and overlooks 167 acres of preserved land. This park is dog friendly.
Jasper Ridge Biological Preserve- A 483 nature preserve and biological field station that was established in 1973. The preserve now provides a natural laboratory for researchers from all over the world and a refuge to plants and animals. Tours for the public are available.
The school system in the town of Woodside is unparalleled to any of those in the Bay Area and to most in California. Woodside School is currently ranked #1 for “Best Public Elementary School in the San Francisco Bay Area”, #1 for “Best Public Elementary School Teachers in the San Francisco Bay Area” and #1 for “Best Public Middle School Teachers in the Bay Area”.
Woodside Elementary School District
Portola Valley School District
Sequoia Union High School District
Woodside Parents' Nursery School
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