Boulder Creek Brewery
Highway 9, Boulder Creek, CA
A warm and comforting roadhouse stop for anyone traversing windy, mountainous Highway 9, the Boulder Creek Brewery also happens to be a top-notch brewery with a dozen distinctive beers on tap, from the signature Redwood Ale to the award-winning Mudslide Stout. The capable kitchen turns out pub grub and comfort food ranging from enchiladas to burgers, making for an all-purpose, all-around destination bar.
11570 Highway 9, Brookdale, CA
A creek runs through the middle of the dining room. One of “America's Sexiest Bartenders” (according to Playboy magazine) works here. A ghost haunts the halls. And even without all that, this old hotel in the redwoods would still have character to spare. To top it off, the Lodge is a regular stop for touring tribute bands like Pink Freud and Riders on the Storm. Totally awesome.
6275 Highway 9, Felton, CA
Don Quixote's is a Mexican restaurant, a music venue, and a bar, so it's no wonder the place is a favorite hangout for Felton's over-21 crowd. Drawing musical acts from across the nation, as well as hosting the area's best local bands, DQ's offers great entertainment in an up-close-and-personal environment. Sound good? Now add chips and salsa.
9450 Highway 9, Ben Lomond, CA
Though it's earned a reputation over the years for being a rough ‘n tumble biker bar, Henfling's Tavern is actually a pretty mellow place to grab a drink should you find yourself in Ben Lomond. The roadhouse vibe is complemented by a wraparound porch complete with heaters. Local rock bands roll into the bar a few times a week, so check the listings for upcoming gigs.
13118 Central Ave., Boulder Creek, CA
It seems to be happy hour all the time at Joe's Bar up in the Santa Cruz Mountains. Locals often head to Joe's for the great jukebox with rock classics, the dart room, quarter pool tables, and to watch the game on the TVs. Drinks are always cheap and so are the activities. For even more excitement, head into Santa Cruz for Joe's Thursday night pool tournaments.
Malone's Grande Grille
4402 Scotts Valley Dr., Scotts Valley, CA
When they say "Grand" in Malone's Grand Grill, they mean it. The restaurant's food is unbeatable and the people are friendly. Just outside of Santa Cruz, Malone's has an event you won't be able to find anywhere else: Wine-Down Wednesdays from 5-7pm where local vintners from the Santa Cruz Mountains and other locations bring their wines for unlimited tasting for the low price of $10. Malone's doesn't stop there; they have live music on the patio on Fridays and karaoke on Saturdays. Come for the 4-6pm Monday to Thursday happy hour, or any time and you're sure to enjoy yourself.
Max's Lounge at the Hilton
6001 La Madrona Dr., Scotts Valley, CA
Santa Cruz hotels are easy to come by, but Max's Lounge at the Hilton makes this hotel stand out. The cocktail lounge offers a happy hour with half-off appetizers seven days a week from 5-7pm. The best part about it is that you don't have to drive anywhere after enjoying a few drinks because if you're staying at the Hilton, you're already home.
Trout Farm Inn
7701 E. Zayante Rd., Felton, CA
Regulars from Santa Cruz County are sure to be found at the Trout Farm Inn, an institution in Felton since after WWII. The cocktail lounge has a happy hour on weekdays from 4-6pm with appetizer and drink specials. The bar remains a great place to enjoy Monday Night Football with regulars and beer.
13300 Big Basin Highway, Boulder Creek, CA
A sumptuous menu, with phenomenal selection including a long list of desserts, make Scopazzi's quite the restaurant to head to. The wine list features selections from the Santa Cruz Mountains to Napa Valley and back again. The restaurant, just outside of Santa Cruz, also has a full bar to sit at and enjoy a drink.