Jack Rose Libation House
Jack Rose Libation House features delicious, creative drinks with an emphasis on crafted cocktails. Try out one of the house classics, such as the Jack Rose (a mix of Laird’s 100 Proof Apple Brandy, fresh lemon, and house-made grenadine) or opt for an expertly made Moscow Mule to be enjoyed on the large outdoor patio. Along with a woodsy ambiance, Jack Rose offers cool events such as Sunday Rumday, brunch in the beer garden, a summer music series, and a full, delicious menu of American eats.
Enoteca La Storia
Whether you’re looking for a new local wine or you have an international taste and a desire to broaden your knowledge about the wines of the world, Enoteca La Storia has something for you. It is the perfect refined wine bar at which to enjoy good conversation, dedicated staff, and classic Italian cuisine. Check the restaurant calendar for special events, such as Chocolate & Wine tasting and Wine School.
Enoteca La Storia, 416 N Santa Cruz Ave, Los Gatos, CA, USA +1 408 625 7272
Los Gatos Bar And Grill
Check out the Los Gatos club scene at Los Gatos Bar and Grill, and don’t forget to e-mail ahead for guest list and bottle service reservations, because this place gets packed. LGBG has a full dinner and late night menu, a spacious brick interior, and music that ranges from House to Hip Hop to Top 40. Come for DJ sets every Friday and Saturday and NFL games on Sundays. Get ready to party late, but be aware of the dress code, no ripped clothes, hats, sandals, or sports attire.
Rock ‘n’ roll plays from the inside of Los Gatos’s signature dive bar, and swords and shields are hung over the long, rich, wood bar. You can’t leave Black Watch without playing a round of darts and ordering the special, a pint of Kamikazes which comes with shot glasses on the side.
Black Watch, 141 N Santa Cruz Ave, Los Gatos, CA, USA +1 408 354 2200
Double D’s Sports Grille
Double D’s Sports Grille is actually named after Dean and Darin Devincenzi, who have been in the restaurant business for 35 years. This is the best place to fulfill all your sports bar needs in Los Gatos, with 20 flat screen TVs, touch screen jukeboxes, a pool room, a full bar, and traditional American grub.
Cin-Cin Wine Bar & Restaurant
Cin-Cin Wine Bar & Restaurant is a cozy, Michelin Guide–recommended Italian restaurant with an impressive selection of wine, high quality Italian spirits, and beer. Cin-Cin prides itself on offering sustainable, organic, bio-dynamic food, an attitude mirrored in its interior design, which is made with recyclable materials.
Oak & Rye
At Oak & Rye, try out fun, inventive cocktails like ‘Zombie Punch’ and the ‘Velveteen Rabbit’ while enjoying the adorable décor, complete with books, exposed light bulbs, and a gold pig’s head. This sophisticated pizza place also features a great selection of beers, including Firestone barrel-aged beers and boilermakers and a variety of classy wines offered by the glass or by the bottle. Be warned, even if you plan to go in just for a drink, you won’t be able to resist Oak and Rye’s mouthwatering, wood-fired pizzas.
Oak & Rye, 303 N Santa Cruz Ave, Los Gatos, CA, USA +1 408 395 4441
Escape the club scene at this local bar and enjoy some strong, fairly priced drinks. Carry Nations is a good place to catch a game during the day or escape the fist-pump crowds during late nights on the weekends.
Carry Nations, 8 N Santa Cruz Ave, Los Gatos, CA, USA +1 408 354 1771
Rootstock Wine Bar
At Rootstock Wine Bar, it’s all about the wine. The bar celebrates wines from local growers in the Santa Cruz Mountains and pairs them with a selection of organic small plates and antipasti. Guests can enjoy wine at the bar, where there is prime access to the knowledgeable staff, or out on the patio in the beautiful California weather.
Rootstock Wine Bar, 217 N Santa Cruz Ave, Los Gatos, CA, USA +1 408 354 7668
C.B. Hannegan’s is a homey, classic Irish bar, and the place to be on St. Patrick’s Day, but even on a regular night, you’ll be greeted by rocking music and good beer. The outdoor patio is pleasant, with a large fire pit and vine-covered walls.
C.B. Hannegan’s, 208 Bachman Ave, Los Gatos, CA, USA +1 408 395 1233