Los Gatos is a town in Santa Clara County, among the beautiful Sierra Azules of the Santa Cruz mountain range. Known for its rocky terrain, perfect for hiking and mountain biking, and its many beautiful wineries, many of which have tasting rooms right in town, Los Gatos is only 60 miles south of San Francisco, and it is a fun and relaxing place for a day trip or weekend getaway.

1. New Museum of Los Gatos

New Museum of Los Gatos
© New Museum of Los Gatos

The New Museum of Los Gatos, or NUMU as it is more often called, is a museum that highlights the history, culture, and modern society of Los Gatos. Visitors can explore exhibits like the Los Gatos History Gallery, where they will learn about the town’s past through a series of artifacts, photos, documents, and more, or the Artist’s Studio, where artists are featured on a rotating basis. The museum also hosts a plethora of programs for members and visitors, from arts and crafts events for the kids to artist led workshops and ‘wine and travel’ experiences for adults.

106 E. Main Street, Los Gatos, CA, 95030, Phone: 408-354-2646

2. Castle Rock State Park

Castle Rock State Park
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Castle Rock State Park encompasses one of the highest ridges in the entire Santa Cruz range, and it is a haven for natural recreation. With sculpted sandstone rocks for rock climbing, bouldering, and scrambling, 34 miles of hiking trails for hikers of all ability levels, and a rustic camping site accessible only for backpackers, visitors at Castle Rock State Park can enjoy the area on foot, on a bike, or on the back of a horse. With redwood trees in the lush forests and gorgeous mountain vistas above the treeline, Castle Rock State Park is an amazing natural playground that should not be missed.

15000 Skyline Blvd, Los Gatos, CA 95033, Phone: 408-867-2952

3. Oak Meadow Park

Oak Meadow Park
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Oak Meadow Park is conveniently located on the Los Gatos Creek Trail, meaning it’s easy to access the park from Vasona Lake Park or any of the other beautiful parks on the trail. With 12 acres of grassy fields, picnic facilities, and more, Oak Meadow Park is a great place to spend an afternoon with family and friends. The park features a bocce ball court, the acclaimed Billy Jones Wildcat Railroad, and a kids’ playground with a real USAF T-33 Jet that has been decommissioned. There are picnic areas available on a first come first served basis for groups of under 25, and reservable picnic sites available for groups up to 50 people.

233 Blossom Hill Rd, Los Gatos, CA 95032, Phone: 408-354-6834

4. Byington Vineyard and Winery

Byington Vineyard and Winery
© Byington Vineyard and Winery

A visit to Byington Vineyard and Winery will give guests access to the 95 acres of gorgeous vineyard where Byington grows their grapes in full view of the stunning Santa Cruz Mountains. Their tasting room is open Thursday through Sunday from 11am until 5pm, and for a small tasting fee, visitors can try five different ypes of Byington’s wine as they tour the facilities. Sunday visitors can also take advantage of a unique opportunity to tour the wine cave at Byington - a space 40 feet below the surface of the ground where the winery stores their wine and barrels - and taste some wine straight from the barrel. Byington also has picnic facilities, an aptly named “Wedding Hill”, and live music every Sunday from 2 to 4.

1850 Bear Creek Rd, Los Gatos, CA 95033, Phone: 408-354-1111

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5. Testarossa

© Testarossa

Testarossa’s Los Gatos tasting room is open seven days a week from 11am to 5pm, and visitors can check out the space, located in the caves and cellars of Novitiate Winery, a historic winemaking facility in Los Gatos that started making wine in the 19th century. There are several different tasting programs available: the Cuvee tasting, which features 4 wines, and the Appellation tasting, which features 5 single vineyard wines. On weekends, guests can opt to tour the historic cellars and learn about their significance in the winemaking process. Picnic tables, live music, and Wine Bar 107, a wine and cheese experience on the patio, are available as well.

300 College Avenue, Los Gatos, CA 95030, Phone: 408-354-6150

6. Loma Prieta Winery

Loma Prieta Winery
© Loma Prieta Winery

Loma Prieta Winery isn’t a big organization - with fewer than three thousand cases of wine each year, it’s downright small, but this little winery is actually the largest producer of Pinotage in the entire continent of North America. This primarily South African variety of grape is a hybrid between Pinot Noir and Cinsault grapes, and Loma Prieta has captured the market on the unique wine, which is made by very few wineries in California - or anywhere outside of South Africa, really.

26985 Loma Prieta Way, Los Gatos, CA 95033, Phone: 408-353-2950

7. Regale Winery & Vineyards

Regale Winery & Vineyards
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Practically everything about Regale Winery and Vineyards is inspired by Italy. With a large wrought-iron gate at the entrance, leading to the gorgeous, villa-style winery within, Regale is full of beautiful rose gardens, olive trees, intricate fountains, elegant decor, and lovely landscapes. Visitors to Regale can check out the tasting room, open on Saturdays from 11-4 and Sundays from 11-5, which has a beautiful outdoor tasting bar with amazing views of the vineyards and surrounding mountains, as well as an indoor tasting bar which is open during inclement weather and available only for members.

24040 Summit Road, Los Gatos, CA 95033, Phone: 408-353-2500

8. Limekiln Trail

Limekiln Trail
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The Limekiln Trail is a hiking trail that runs through Kennedy Limekiln, one of the four main areas of the massive, 18,000 acre Sierra Azul Open Space. The Kennedy Limekiln Area is easily accessible from Kennedy Road in Los Gatos, and the area opens each day from half an hour before sunrise until half an hour after the sun goes down. Dogs, horses, and bicyclists are allowed in certain areas throughout the park, but camping, fires, and smoking are prohibited. The Limekiln Trail is a popular part of the Kennedy Trail/Limekiln Trail Loop, which together makes for a beautiful 14 mile hike through the gorgeous Sierra Azul space.

Limekiln Trail, California 95033

9. Castle Rock Falls

Castle Rock Falls
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An easy drive down Highway 17 from Los Gatos, Castle Rock State Park is a natural playground of a park, with many natural wonders including rock formations, Pacific Ocean views, and Castle Rock Falls. There is a well-designated trail that leads slightly downhill for 0.8 miles to reach Castle Rock (which means the way back is uphill, unfortunately), and visitors will find a viewing platform where they can see the beautiful waterfall, which is approximately 70 feet high. From the falls, hikers can choose to continue on the Castle Rock Trail, which leads to Castle Rock itself, part of a group of imposing rock formations, or on the Saratoga Gap Trail, which leads to higher ground for bigger vistas.

15000 Skyline Blvd, Los Gatos, CA 95033, Phone: 408-867-2952

10. Burrell School Vineyards & Winery

Burrell School Vineyards & Winery
© Burrell School Vineyards & Winery

In 1854, a little red schoolhouse was built on the grounds where Burrell School Vineyards and Winery now sits. This little building is still a place of learning, though today it specializes in wine and winemaking. At Burrell School Vineyards and Winery, visitors can enjoy the historic schoolhouse, which still stands, and visit the tasting room. There, guests can learn about - and try, of course - some of the amazing wines that Burrell School Vineyards and Winery produces, including syrah, pinot noir, chardonnay, cab franc, merlot, and a unique blend called Valedictorian.

24060 Summit Rd, Los Gatos, CA 95033, Phone: 408-353-6290

11. Vasona Lake County Park

Vasona Lake County Park
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One of the most popular and frequently visited parks in Santa Clara County, Vasona Lake County Park features 152 acres of beautiful, peaceful recreational land. With wide sweeping lawns for picnicking and playing frisbee or kickball, a playground, 9.5 miles of trail for hikers, and even a summer music and concert series, Vasona Lake County Park has plenty of activities ready to explore. On the lake, visitors can rent paddle boats or row boats, and in Los Gatos Creek County Park, accessible via the Los Gatos Creek multiple use trail, visitors can fish for rainbow trout, bluegill, black bass, crappie, and more. The park is open daily throughout the year from 8am until sunset, and fees are collected for vehicle entrance and use of the lake.

Vasona Lake County Park, 333 Blossom Hill Rd, Los Gatos, CA 95032, Phone: 408-356-2729

12. David Bruce Winery, Los Gatos, CA

David Bruce Winery, Los Gatos, CA
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David Bruce Winery is one of the oldest wineries in the region, founded in the 1960s by David Bruce, a dermatologist who started making wine as a hobby. The winery grew and grew, and David Bruce became well known in the local industry as a pioneer who brought in French oak barrels, crushed grapes by foot, and advocated for techniques such as secondary fermentation for white wine, and whole berry fermentation for reds. David Bruce Winery was one of twelve wineries that took part in the Judgment of Paris, a famous 1976 blind tasting in which California wines outperformed French ones.

21439 Bear Creek Road, Los Gatos, CA 95033, Phone: 800-397-9972 or 408-354-4214

13. Silver Mountain Vineyards

Silver Mountain Vineyards
© Silver Mountain Vineyards

Silver Mountain Vineyards has been making wine since 1979, and their gorgeous winery facility, located in the mountains with breathtaking views, is open to the public weekly on Saturdays from 12pm to 5pm, or by appointment. Their tasting room, located in Santa Cruz, is open Fridays 3-7pm and weekends 12-5pm. At the winery itself, visitors will find amazing views of mountain peaks and valleys lined with stunning redwood forests, which they can enjoy to the fullest as they sip a glass of handcrafted and organically grown pinot noir or chardonnay, which are made in small batches to really increase the intensity of the flavors.

Silver Mountain Dr., Los Gatos, CA95033, Phone: 408-353-2278

14. Priest Rock Trail

Priest Rock Trail
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Priest Rock Trail is a mountain biking trail near Los Gatos, which is accessible via Alma Bridge Road. The trail is a doubletrack and is about 4.1 miles long. Rated as a Black Diamond for difficulty, Priest Rock has what is probably the most challenging climb for mountain biking in the Los Gatos area, with steep, rocky hills and a grade that reaches up to 25% in an upper area often referred to as Dogmeat, where few riders can make the intense climb without putting down a foot. Many bikers choose to come up the Limekiln Trail instead and use Priest Rock for their descent.

15. Villa del Monte Winery

Villa del Monte Winery
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This award-winning little winery makes great wines from small batches. Villa del Monte Winery uses local growers to create their single-vineyard, single-varietal wines, the quality of which is perfectly calculated and controlled through the small lots in which is it made. Villa del Monte is a small winery, and so the tasting room is only open on select weekends throughout the year, which are listed on their website. On those weekends, the tasting room is open from noon until 5pm, but groups can also call to make an appointment for a tasting as well.

23076 Summit Road, Los Gatos, CA 95033, Phone: 408-353-0995

16. Whitney Modern Contemporary Fine Art Gallery

Whitney Modern Contemporary Fine Art Gallery
© Whitney Modern Contemporary Fine Art Gallery

At the Whitney Modern Contemporary Fine Art Gallery, located in the historic 1921 Templeman building in the very center of Los Gatos’ downtown area, visitors will find carefully curated exhibitions and collections of some fantastic contemporary art. The upper floor space feels elegant and creative, with an open mezzanine area that makes for an open and inviting atmosphere. Visitors can enjoy the works of many artists, both emerging and well-established, in the museum.

24 N Santa Cruz Ave. 2nd Floor, Los Gatos, CA 95030, Phone: 408-402-5922

17. Tommy John’s

Tommy John’s
© Tommy John’s

Tommy and John, founders and owners of Tommy John’s, know that a good pint of beer or a delicious glass of wine are some of the simplest and most lovely pleasures in life, and their private tours of the local breweries and facilities in the Santa Cruz region work hard to spread that pleasure to their guests. Using their expert insider knowledge of local businesses, Tommy John’s offers a number of great tours, including the “Grape Escape” tour, the South Bay Brew Tour, and public weekend tours. Tommy John’s knows that Napa gets all the credit when it comes to wine in California, so they use their influence to show visitors that there are plenty of other wineries and breweries in California that know how to craft their product just as well.

San Jose, CA, Phone: 408-316-5337

18. Billy Jones Wildcat Railroad

Billy Jones Wildcat Railroad
© Billy Jones Wildcat Railroad

Located in Oak Meadows Park, the Billy Jones Wildcat Railroad has been delighting children and guests since 1968. The train is a real, historic steam engine, which takes guests around Oak Meadow and Vasona Parks, and the carousel is also historic, at over one hundred years old. Besides the railroad, there is also food, retail, and special events offered throughout the year like the Holiday Train and the Pumpkin Train. The train and carousel are open year round, though hours differ depending on the season and sometimes the rides close for inclement weather.

233 Blossom Hill Rd, Los Gatos, CA 95032, Phone: 408-395-7433

19. Dio Deka

Dio Deka
© Dio Deka

Greek food is more than just gyros and baklava, and Dio Deka knows it. This upscale Greek eatery focuses on floxenia, a word that means ‘hospitality’ in Greek, and they do it with a comfy atmosphere and amazing food. The menu utilizes elements like fresh fish, seasonal veggies, and of course, plenty of olive oil in their offerings, which meld Greek food with other Mediterranean traditions. Guests will also love the bar, where they can take a traditional shot of ouzo or enjoy a cocktail made with the Greek liquor, or have a glass of wine from Dio Deka’s truly extensive wine list, which features over 1200 wines.

210 E Main St, Los Gatos, CA 95030, Phone: 408-354-7700

20. Steamer’s Grillhouse

Steamer’s Grillhouse
© Steamer’s Grillhouse

At Steamer’s Grillhouse, customers can enjoy fresh, wild, and line caught fish and seafood, or a perfectly cut and grilled steak. This Los Gatos classic has been satisfying its guests since it first opened in 1979, and since then it has upheld its tradition of serving some of the best food in the region. With a beautiful atmosphere featuring a Hawaiian koa wood bar as well as wood and glass details, and a patio lined with tables under red umbrellas, Steamer’s delights guests with the selection at the oyster bar, the extensive wine list, and the fresh made desserts handcrafted by their pastry chef.

31 University Ave, Los Gatos, CA 95030, Phone: 408-395-2722

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