The Weekender: Where To Eat, Drink, Stay And Play in Gilroy, CA


My dad was born in Iowa and grew up in Gilroy, and the Central Californian city has a special place in my heart ever since. As a kid, our family would pack up our Suburban and head up The 5 to visit my aunt, uncle, and cousins, and as soon as I smelled the aroma of garlic in the air coming over the rolling, oak-dotted hills of Pacheco Pass, I knew we’d arrived.  

Gilroy was a sleepy town at the time — a great place to raise kids and build community, but admittedly light on the creature comforts of city life. (My brother and I fondly remember the excitement of the first McDonald’s coming into town, and the fanfare surrounding the now-iconic Premium Outlets — home to a whopping 145 shops including LuluLemon, Kate Spade, and Saks Fifth Avenue.)

While Gilroy is still known as the Garlic Capital of the World, a lot has changed since then. With a continued influx of cash and transplants from nearby Silicon Valley, more wineries are cropping up as well as new restaurants. Many of the region’s winemakers are getting accolades from the likes of Wine Spectator, too. Those awards have been a long time in the making, considering the first grapes in California were planted here, not Napa, as many are led to believe. 

Thankfully, all the recent growth is not to say it’s lost its down-home roots. (It is in the heart of Californian farm country, after all.) There are still plenty of roadside produce stands to explore and country breakfasts to be had. And you still feel that sense of Americana, making it a great place to enjoy a slow-paced wine country weekend. 

Here are my favorite spots to eat, drink, and explore in Gilroy. 


Breakfast: Josephine’s Bakery & Café

Pad your belly for a day of wine tasting at this charming, family-owned country cafe, where you’ll find excellent biscuits and gravy as well as one of the best Bloody Marys on the market, made with super spicy mix from local artisan producer Big Daddy’s. If you want to make friends with your winemaker, bring a tray of Josephine’s darling cupcakes and homemade cannolis along for your tasting.

383 1st Street, Gilroy, CA,

Wine Tasting: The Stomping Ground

This super cool co-op is home to a communal crush pad and a collection of small, design-forward wine bars featuring local winemakers. Be sure to stop by on Sundays when they do live entertainment — and don’t miss out on trying Alara Cellars’ bang-up pinot noir. 

6500 Brem Lane, Gilroy, CA,


Lunch: Cielito Lindo or Tacos Ameca

You’d be remiss not to hit up one of Gilroy’s amazing Mexican restaurants while in town. If you’re after a sit-down meal with some seriously incredible handmade flour tortillas, visit Cielito Lindo. If you’re a carnitas hound like me, make sure to head over to Tacos Ameca, whose sizzling outdoor plancha draws in droves of local Latinos on a Saturday night. The wait is well worth it.

Cielito Lindo: 7460 Monterey Rd., Gilroy, CA 95020
Tacos Ameca: 7001 Monterey Rd., Gilroy, CA 95020

Shopping: Antique Shops in Downtown Gilroy

There are heaps of great opps for antiquing along Monterey Street, but my favorite is Gilroy Antiques, run by Gracie Garcia. Her collection is so well curated, and you’ll find everything from vintage glassware and old-world jewelry to unique prints and more. Gracie was kind enough to show us her apartment upstairs — just one of those only-in-Gilroy moments that you just wouldn’t get back in L.A.— and it’s almost a museum in its own right, filled with quirky taxidermy and a wild collection of Catholic icons.

7445 Monterey St., Gilroy, CA 95020

Dinner: The Milias

Chef Adam Sanchez serves up Castroville artichokes with garlic aioli and amazing Greek-style lamb at this old Western-style bar and restaurant, which used to be a watering hole for folks like Clark Gable and Will Rogers when passing through town. They have live music nightly and a lovely selection of local wines too, so be sure to ask them to pair them with your food.

7397 Monterey Rd., Gilroy, CA 95020,


Breakfast: Fifth Street Coffee Roasting

Start out your day with a freshly roasted cup of coffee and a pastry, or if you’re daring, a serving of garlic ice cream. Fifth Street serves this local treat year-round, so you don’t have to wait for the annual Gilroy Garlic Festival in July.

7501 Monterey St., Gilroy, CA  

Lunch: Solis Winery

Enjoy a wine tasting and cheese board while seated on the patio of the gorgeous property at Solis. The family has been making wines since the early 20th century, and their tasting room is a must-see on the Santa Clara Wine Trail circuit. 

3920 Hecker Pass Road, Gilroy, CA,

Wine Tasting: Sarah’s Vineyard

Come for the bocce ball, stay for the pinot. Tim Slater is making some seriously stellar wines at this charming winery on Hecker Pass. It’s a definite must see, especially during the golden hour right before sun sets over the sprawling vineyard. 

4005 Hecker Pass Hwy, Gilroy, CA,

Dinner: Café Thyme 

Chef Diane Sturla has the Midas touch when it comes to handling the gorgeous California produce on offer from the region, and it’s hard to pinpoint a singular dish to try since the seasonal menu changes so often. But if the lemon thyme chicken (made with plenty of fresh garlic, natch) is on offer, get it. And be sure to save room for her earth shatteringly good bread pudding with caramel sauce. 

433 1st St., Gilroy, CA,


Shopping: LJB Farms, Garlic Shoppe, or Garlic World

You don’t want to come back from a trip to Gilroy empty-handed, right? An absolute must souvenir is a garlic braid. Pick up some produce from LJB too and perhaps even some spicy pickled garlic from Garlic World. It’s seriously the best addition to my simple salads, and you’re getting it right at the source. 

585 Fitzgerald Ave, San Martin, CA

Stay: Rosewood CordeValle 

If you’re a big spender (or golfer), a stay at the gorgeous CordeValle property is an absolute must. They have a fabulous Sunday brunch with a spectacular smoked Bloody Mary shaken tableside, and an added bonus is that you are just a quick golf cart ride to Clos LaChance Vineyards, so you don’t even need to drive to do some wine tasting. 

1 CordeValle Club Dr., San Martin, CA,

Pit Stop: Casa De Fruta

On your way out of town, you have to make a stop at Casa De Fruta. Originally opened as a roadside stand in 1908, this multigenerational family business practically deserves its own zip code. It now includes a coffee house, a chocolate shop, a deli, a massive Venetian carousel for the kids (and kids at heart!), and of course a massive produce stand selling local fruits, veg, and artisan products. Don’t forget to bring home one of their fabulous award-winning berry pies. Your co-workers back at the office will thank you! 

10021 Pacheco Pass Hwy, Hollister, CA,

Content created in partnership with Visit Gilroy and Travel Mindset.