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Atherton

Rating as one of the wealthiest cities in the country year after year, Atherton was ranked #1 on Forbes Magazine’s annual list of America’s most expensive zip codes in 2013. Not surprisingly, the town features some of the country’s most beautifully manicured mansions. The city’s multi-million dollar estates are home to a cosmopolitan population dominated by prominent figures, with Atherton’s long list of notable residents including celebrities, professional athletes, executives, and tech moguls.

While being located close to everything on the Peninsula, Atherton maintains a secluded atmosphere, due in large part to efforts taken by the town’s residents. The community is free of major businesses and large retail establishments, and a land-use plan prohibits commercial or industrial development in the city. Atherton’s thickly wooded landscape is host to a multitude of pine, redwood, and cedar trees, and many residents are afforded pristine views and bucolic settings. The town is centered around the Menlo Circus Club, with its private stables and dual rings. Started in 1920, the club has a unique and fascinating history, steeped in charity work, polo, and family events.

One of my favorite spots in Atherton is Holbrook-Palmer Park, a municipally owned 22-acre garden setting with a ball field, tennis courts, playground, gardens, and walking paths. The park’s historic structures are definitely worth checking out, with both the 135 year old Water Tower and the 126 year old “Gen Merrill” Carriage House still standing at the park today.

Burlingame

Known as the “City of Trees,” lovely Burlingame maintains a lush ambiance, due in large part to the town’s verdant parks and gorgeous open spaces. Most residential properties in Burlingame have trees owned and protected by the city, and the community also has many eucalyptus groves that add to the large number of trees the town boasts.

A city of friendly and unique areas, Burlingame neighborhoods range from the charming streets and historical homes of Easton Addition, to the exquisite views and numerous Eichlers of Mills Estates. Burlingame is also home to two distinct main street areas, each with its own personality. While lively Burlingame Avenue features outstanding dining and boutique shopping as well as anchor stores like Pottery Barn and Banana Republic, Broadway is more of the locals’ scene with a variety of small service stores, bistros, and cafes.

Besides being in close proximity to San Francisco and SFO, what attracts me to Burlingame are the small town quirks and historic Bay Area novelties that give the city its singular character. The community’s Pez Museum features an example of every Pez candy dispenser ever sold, and the town is also home to the It’s-It, the one-of-a-kind ice cream sandwich invented in San Francisco in 1928 by an amusement park owner. But its Burlingame’s sense of community that attracts me most. The town hosts top-notch local events year after year, including The Burlingame Art and Jazz Festival, Pet Parade, and Burlingame on the Avenue, and has also established Fresh Market – one of the few community-owned farmer’s markets in the Bay Area.

Cupertino

Originally a town of fruit orchards and agriculture, modern Cupertino sprang up rapidly from its roots as a farm village into the leading place for innovation and invention, not only in the Bay Area, but the entire world. Considered by many to be the hub of Silicon Valley, tech giant Apple was founded in the city in 1976, and today the community is home to the company’s headquarters and large campus, as well as numerous other high-tech companies. With such an environment of achievement and advancement, it is not surprising that Cupertino also boasts some of the best schools in the area, along with residents who went out of their way to ensure they lived in the district.

Nestled on the western edge of the Santa Clara Valley and extending into the foothills of the Santa Cruz Mountains, recreational options abound in the town, and include golf courses, parks, a community center, and city museum. Cupertino doesn’t have a traditional downtown, but instead boasts what is known as “The Crossroads” at the intersection of Stevens Creek and De Anza boulevards. Once the site of Cupertino’s first general store, post office, and blacksmith shop, “The Crossroads” now offers a number of shopping and dining options. Cupertino is also home to De Anza College, a focal point for culture and education, as well as a center of activity in the city. The college offers a planetarium, museum, art gallery, and also hosts a monthly flea market.

Nestled on the western edge of the Santa Clara Valley and extending into the foothills of the Santa Cruz Mountains, recreational options abound in the town, and include golf courses, parks, a community center, and city museum. Cupertino doesn’t have a traditional downtown, but instead boasts what is known as “The Crossroads” at the intersection of Stevens Creek and De Anza boulevards. Once the site of Cupertino’s first general store, post office, and blacksmith shop, “The Crossroads” now offers a number of shopping and dining options. Cupertino is also home to De Anza College, a focal point for culture and education, as well as a center of activity in the city. The college offers a planetarium, museum, art gallery, and also hosts a monthly flea market.

One of my favorite places in Cupertino is De Anza College’s Flint Center for the Performing Arts. The venue brings in international talent that ranges from the San Francisco Symphony to Beijing Acrobats, and each year, invites celebrities and dignitaries for public speaking engagements. After a show, you can walk over to Paul & Eddie’s Monta Vista Inn. Established in 1943, this Silicon Valley landmark is known for its pool tables, great drinks, and dollar bills stuck to the wall with personalized messages drawn on them by decades of past patrons.

Los Altos & Los Altos Hills

Originally a village of summer cottages and second homes for San Francisco’s wealthy, the Los Altos of today is a thriving community known for its beautiful parks and tree-lined streets. Country lanes run throughout the town, and create an upscale version of bucolic charm, while commercial zones within Los Altos are strictly limited to downtown and a few shopping centers and office parks, helping to maintain the community’s small town feel. Set in the foothills of the Santa Cruz Mountains, recreational opportunities are all near at hand. Most notable is Rancho San Antonio with its 23 miles of hiking trails, ranging from a short stroll out to Deer Hollow Farm, an educational center celebrating Santa Clara County’s agricultural history, to the challenging PG&E trail, which offers spectacular views of the valley and bay.

With its hilly terrain and commanding views, neighboring Los Altos Hills provides unspoiled preserves, rolling hills, and picturesque valleys. Many of Silicon Valley’s most prominent executives and successful entrepreneurs reside here, making elegant mansions and handsome custom homes the norm. And, with a minimum lot requirement of one acre, many estates offer superb amenities such as tennis courts, swimming pools, and equestrian facilities. As you might expect, the building and zoning codes are designed to preserve this exceptional area, and laws are in place to protect the town’s lovely redwoods and oaks as well.

Los Altos Hills shares amenities with Los Altos, including the outstanding schools, which consistently score high within the state. Residents of both cities enjoy the downtown district, which features exceptional dining, such as the new American fare at Los Altos Grill, bakeries, sidewalk cafes, boutiques, art galleries, and community activities including a summer farmer’s market. Make sure to check out the town’s Art & Wine Festival. Running annually for over 30 years, this popular local event showcases arts and crafts, local wineries, and day-long free concerts.

Menlo Park

Set in the heart of the Peninsula, charming Menlo Park exudes small town character everywhere, from its historic train station constructed in 1867, the oldest continually operating train station in California, to the town’s tree-lined avenues and bustling main street. It’s a city of beautiful neighborhoods with an eclectic range of architectural styles including the bungalows of Allied Arts, sprawling ranch homes in hilly Sharon Heights, and custom Craftsman-style homes on the winding lanes of Felton Gables.

Close to everything the Peninsula has to offer, Menlo Park is also adjacent to Stanford University, giving it an academic and innovative vibe. The town is home to the Stanford Linear Accelerator research facility, and tech giant Google was founded in Menlo Park in 1998. Facebook moved its headquarters to the city in 2011 and is now the town’s biggest employer, and the town is also home to the corporate offices and show gardens of Sunset Magazine. Downtown Santa Cruz Avenue boasts charming restaurants and unique boutiques, as well as playing host to local community events, such as the Connoisseurs Marketplace summer festival, while a weekly farmer’s market takes place on Sunday mornings right behind the main drag.

Be sure to stop by historic Kepler’s Books and Magazines, an independent bookstore founded in 1955. With deep ties to the community, Kepler’s hosts literary events and offers a broad selection of books of local interest, along with best sellers and classics. This local cultural hub has attracted loyal customers, including Stanford students and faculty, since opening its doors, and the shop was even a meeting point for Bay Area counter culture figures of the 1960’s. The local hangout, Café Borrone is right next door, has also been around for years. Their outdoor patio is a nice place to have coffee and check email, and a great spot for grabbing a fairly quick, healthy breakfast or lunch.

Mountain View

Named for its sweeping mountain vistas, Mountain View maintains its vibrant personality and unique character while still being a bustling center of employment for the entire Bay Area. Home to NASA Ames Research Center and countless tech companies, the town is probably most notable for housing the headquarters of Silicon Valley giants Google and LinkedIn, and is a popular residential choice for their employees as well.

Entertainment options also abound in the city, with Shoreline Amphitheatre, one of Northern California’s favorite concert spots, attracting musicians from around the world. The town has a lively, pedestrian-friendly downtown that is flanked with sidewalk cafes, galleries, and boutiques, and also boasts a thriving nightlife. With both light rail and Caltrain stops at the top of Castro Street, downtown is incredibly convenient to get to, bringing in visitors to enjoy a show at the renowned Mountain View Center for the Performing Arts, or dine at award winning restaurants, including Michelin rated Chez TJ. Downtown dining options are limitless and span the globe, from the Vietnamese cuisine at Xanh, to Spanish tapas at Cascal.

And while San Francisco is the birthplace of the Mission-style burrito, my favorite around comes from Taqueria La Bamba. With three different locations in Mountain View, everything on the menu is great, but their carnitas are my favorite, hands down.

Palo Alto

As the home of Stanford University, Palo Alto is known worldwide for being a center of exceptional education. While the renowned university infuses the entire community with an academic vibe, with an endless line of visiting professors, speakers, and political dignitaries, the community’s public schools also rank among the best in the nation. The town is thought of by many as the birthplace of Silicon Valley, with Hewlett-Packard having been founded in a one-car garage in Palo Alto in 1939. The company’s headquarters are still located in Palo Alto today, and the town is home to many prominent technology firms, as well as Tesla motors, makers of the first fully electric sports car.

Palo Alto features charming residential streets and leafy boulevards in its variety of neighborhoods. From the Victorian homes and towering oak trees of Professorville, named for the Stanford professors who originally congregated there in the 1890’s, to the pastoral setting of Barron Park, each area is unique in personality and character. Stanford Shopping Center offers an upscale open air shopping option, while University Avenue serves as the epicenter of Palo Alto’s thriving downtown.

Featuring upscale galleries, boutiques, and a variety of high-end shopping, University Avenue also features some of the best dining on the Peninsula. Tamarine’s contemporary Vietnamese cuisine is a personal favorite, but I must also mention Baumé, on California Avenue (the town’s second downtown), the only two-star Michelin rated restaurant on the Peninsula.

Portola Valley

Ranked among the nation’s wealthiest towns, Portola Valley is tucked away in a lush valley full of natural treasures including rolling hills and sprawling open space. Development in Portola Valley has been much slower than in many other Bay Area communities, due in large part to concerted efforts taken by residents to protect the charm and splendor of their home. Measures were taken to maintain a low housing density, sustain the valley’s natural beauty, and balance development while retaining a pastoral atmosphere. All of this has combined to allow the town to preserve the same rustic ambiance that made it appealing to large landowners from San Francisco decades ago.

The town center hosts a cozy library, a community hall offering classes for both adults and children, and a variety of recreational areas including soccer and softball fields, as well as tennis courts. The Windy Hill Open Space Preserve features miles of trails for hiking and mountain biking, and the town boasts a magnificent trail system suitable for hikers, bikers, and horseback riders. In fact, the area is known as horse country, and the town is home to both Spring Down and Glenoaks equestrian centers.

When it comes to biking, I personally love the Portola Valley Loop with its roughly 17 miles of breathtaking views and serene surroundings. It is one of the most popular places on the Peninsula for a ride, and you can find it teeming with cyclists any time of day. The loop takes you right past the Alpine Inn, a historic watering hole dating back to the 1850’s. Previously named Rossotti’s, and still referred to as Zott’s by many locals, the old roadhouse might have changed names, but still feels like walking into an old saloon.

Redwood City

Serving as the county seat of San Mateo County, Redwood City is a long-established community that highlights its charm in countless ways – from events such as the historic Fourth of July parade, to the “Climate Best By Government Test” arches capping downtown. This quirky city slogan refers to a pre-World War I climatological survey that found Redwood City to have one of the best climates in the entire world.

Houses in Redwood City range from vintage older homes in historic neighborhoods such as Mount Carmel, to luxurious new construction with gorgeous views in Emerald Hills. The city is home to medical centers and tech companies, while the waterfront provides a yacht harbor and a deep-water port. The well-developed parks system ensures recreational opportunities are available throughout the town, with Red Morton Park serving as a local favorite with its numerous picnic areas and sports fields.

Redwood City has experienced a huge boom in the past few years, and has an up and coming downtown that shouldn’t be missed. Centered around historic Courthouse Square, a new theater led the charge for development, and downtown is now home to numerous community events such as a summer outdoor movie series and the annual Salsa Festival, along with great dining including Martin’s West gastropub, which features a picture of Wyatt Earp drinking at that very bar over 100 years ago.

San Carlos

Known as “The City of Good Living,” San Carlos is set in the heart of the Peninsula, and is a charming town with a great sense of community. Downtown Laurel Street serves as a cultural center for the city, and is home to boutiques and a variety of dining options, including my local favorite, Town restaurant. Also contributing to the town’s inviting atmosphere are numerous art festivals and community events, such as the yearly Hometown Days celebration. Historic homes steeped with character are common in San Carlos, and add to the city’s charm and small town feel. From the homes in the western hills with panoramic views, to the bungalows on tree-lined avenues in the White Oaks neighborhood, San Carlos has an upbeat, yet easy-going community energy.

Recreational opportunities in the city abound, with acres of open space close by, great for hiking and biking, including the local Pulgas Ridge Open Space Preserve. The city is also home to The Hiller Aviation Museum, which celebrates the spirit of discovery and innovation of aviation pioneers, and features over 50 aircraft from more than a century of aviation history.

Downtown San Carlos is the hub of the community. Laurel Street hosts a Thursday night farmer’s market that attracts not just San Carlos residents, but locals from up and down the Peninsula, and Saturday and Sunday mornings find the street lined with sidewalk tables of people enjoying brunch. Be sure to try The Refuge, located at the far end of Laurel Street, which turns out some of the best pastrami in the Bay Area, and has a fantastic Belgian beer selection. If you happen to stop by, the restaurant might look familiar – it was recently featured on the Food Network’s “Diners, Drive-Ins and Dives.”

San Mateo

San Mateo is a traditional Peninsula city with a long history and wide spectrum of neighborhoods, offering a great deal of variety and style. There is the elegant and wooded San Mateo Park, the tree-lined streets and large pre-war homes of Aragon, and the Highlands with its collection of Eichlers, just to name a few. The town is home to many well-equipped parks, including Coyote Point Park, offering picnic areas, trails for walking and bicycling, and CuriOdyssey, a hands-on science museum and native animal zoo, while the nearby Sawyer Camp trail at Crystal Springs Reservoir offers great hiking.

The town is also a hub for retail on the Peninsula, with the large Hillsdale Shopping Center, as well as the new Bay Meadows. The classic horse racing track has been redeveloped to combine residential, office, and retail spaces in a large communal area. The College of San Mateo and the San Mateo County Expo Center, home of the county fair and other major events, serve the entire region, and downtown pulls in shoppers and diners from up and down the Peninsula. Downtown features everything from fine dining and cozy wine bars to a large movie theater, and also plays host to local art, wine walks, and community events including Summerfest with its seven blocks of booths, music, food, and activities.

San Mateo is also home to one of the best kept secrets in the Bay Area. On a foggy day on the Peninsula, it doesn’t get much better than a big bowl of ramen from Santa Ramen on El Camino Real. You’ve probably never heard of this hole in the wall, but a dedicated clientele keeps Santa Ramen hopping, and it often has a line out the door. Don’t worry though, the excellent food makes it well worth the wait.

Saratoga

With its excellent public and private schools, easy commute to Silicon Valley employers, and gorgeous location nestled in the foothills of the Santa Cruz Mountains, Saratoga is one of the most affluent communities in the Bay Area, and ranks high on lists of best places to live in the country year after year. The town has managed to preserve a serene atmosphere and small town vibe, even while boasting one of the highest median household incomes in all of the United States. Homes reflect the affluence of their owners, and the area surrounding Villa Montalvo and the hills off Big Basin Way especially are punctuated by magnificent mansions and estates.

When it comes to cultural attractions, Villa Montalvo itself offers an elegant performing arts venue as well as an arboretum, while concerts are regular features at the Mountain Winery off of Pierce Road. The charming downtown offers antique shops, boutiques, bakeries, and a variety of restaurants with fine dining including the Michelin rated Plumed Horse.

As my hometown, Saratoga holds a special place in my heart. From community events such as the annual Street Dance and the weekly farmer’s market, to downtown with its warm neighborhood bistros like The Basin, and intimate tasting rooms of the wineries that dot the city’s foothills, the town has maintained a true community feel and small town allure, even while being one of the most coveted cities to live in not just in the area, but in the entire country. And as an avid cyclist, the foothills and mountains behind the town provide some of my favorite rides in the Bay Area. All in all, I can’t think of a better place to call home.

Sunnyvale

Situated along historic El Camino Real, the Sunnyvale of today has shifted from its agricultural past of cherry orchards and fruit canneries into a significant force in the Silicon Valley. The town is host to a number of high-tech firms including Yahoo!, office parks housing workplaces for major industry players like LinkedIn and Apple, and is also home to Lockheed Martin, making it a huge hub of employment in the Bay Area. This influx of business has resulted in a surge in newer housing and mixed use townhouse complexes, all popular among tech employees.

Remnants of the area’s agricultural history still dot the city, with the Heritage Park Museum and adjacent orchard, along with CJ Olson’s fruit stand, adding to the town’s classic character. Recreation and entertainment options are also numerous, with Sunnyvale showcasing many community parks, shopping, dining, and the popular Rooster T. Feathers comedy club. Downtown Murphy Avenue offers a wide variety of dining and popular night spots, and hosts a year-round farmer’s market on Saturday mornings.

You might check out downtown’s annual Music + Market event in the summer, which showcases weekly outdoor musical acts and artisan booths. Held on Wednesday evenings throughout the summer, it is a great mid-week event to enjoy after work.

Woodside

The bucolic town of Woodside is nestled among the redwood-covered mountains along the coastal ridge of the Peninsula, and exudes a natural warmth and rural character. The rustic downtown retains its historic feel through original architecture and storefronts, and along the downtown strip of Woodside Road is some of the best dining in the area, including the Michelin rated Village Pub.

The town is perhaps best known as a haven for equestrians within the Bay Area. An integral part of the local culture, numerous residents keep their own horses, and the town hosts many horse clubs and events while maintaining a vast network of equestrian trails.

Running and hiking trails abound for the outdoor enthusiast, and some of my favorite treks are in Huddart and Wunderlich parks. Woodside is also a destination for cyclists, and is often alight with bikers on some of its most popular routes including Old La Honda Road, King’s Mountain Road, and Cañada Road. The eight day long Tour of California bicycle race even includes several roads along and adjacent to Skyline Boulevard and Highway 84.

Another local treasure is Filoli, one of the finest remaining historic country estates of the early 20th century. It features a 36,000 square foot home, and world-renowned 16 acre English Renaissance garden surrounded by a 654 acre estate. Docent-guided hikes through the Filoli Nature Preserve, and summer Jazz at Filoli, are visitor’s favorites.

Cycling the hills of Woodside is one my favorite activities. On weekends especially the streets are lined with cyclists, many who stop off at Buck’s restaurant after a rigorous ride through the mountains. While it is a great place for locals, this unassuming restaurant has also seen some of the most lucrative deals in Silicon Valley history discussed at its tables.

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