Explore icons and the Ice Age in sunny L.A., float a river, and head north for black gold history and wine-country fun.

Trip length: 4 days
Total distance: 276mi/444km

DAY 1
HOLLYWOOD. Clip-clop to the top of Mt. Hollywood for top-of-the-world views and an up-close look at the iconic Hollywood sign. Sunset Ranch offers a variety of guided horseback rides along sage-scented trails. INFO Hollywood Chamber of Commerce ; 323/469-8311

LOS ANGELES (7mi/11km; 23min). See mammoths, saber-tooth cats, and other Ice Age creatures trapped eons ago at La Brea Tar Pits ; the naturally seeping tar is icky and sticky and everything kids like. INFO Los Angeles Tourism & Convention Board ; 213/624-7300

DAY 2
SANTA MONICA (10mi/16km; 19min). Watch local fisherman nab a meal from the iconic Santa Monica Pier, then take a spin on the Pier Carousel. Grab an old-fashioned malt at Soda Jerks and check out the “End of the Trail” sign designating the symbolic end of iconic Route 66. INFO Santa Monica Chamber of Commerce ; 310/393-9825

PACIFIC PALISADES (3mi/5km; 9min). Let the kids run free at Will Rogers State Historic Park ; a gentle three-mile trail loops from the Visitor Center to Inspiration Point. Picnic by the gurgling fountains of Getty Villa , an opulent homage to the arts and cultures of ancient Greece, Rome, and Etruria. Grab some visitor guides at the Oxnard California Welcome Center. INFO Pacific Palisades Chamber of Commerce ; 310/459-7963

VENTURA (61mi/98km; 1hr 8min). Explore funky boutiques and antiques stores downtown, then float the Lazy River at Lake Casitas (water park open all summer long and the family camping is great year-round). INFO Ventura Visitors & Convention Bureau ; 805/648-2075

DAY 3
OJAI (15mi/24km; 21min). Let your kids blow off some steam at the new Ojai Skate Park . At Bart’s Books peruse a million titles—drop 35 a few coins in the coffee can on the counter and let the kids pick a new read for the road. INFO Ojai Visitors Bureau ; 888/652-4669

VENTUCOPA (51mi/82km; 59min). High atop Highway 33, stop to stretch your legs and sample award-winning wines and wood-fired barbecue at Sagebrush Annie’s , a backcountry fantasy of California. INFO Taft Chamber of Commerce ; 661/765-2165

TAFT (29mi/47km; 34min). Learn the history of black gold in the Golden State at West Kern Oil Museum . Wind through a rusty forest of antique derricks, some dating back to 1890. INFO Taft Chamber of Commerce ; 661/765-2165

DAY 4
PASO ROBLES (93mi/150km; 1hr 50min). Let your kids stomp “grapes” (actually stain-free purple balls) in this wine country town’s Children’s Museum , located in a volunteer firehouse. Little ones love to climb Old Mack, the station’s original 1944 fire engine, and play dress-up with real firefighter duds. INFO Paso Robles Chamber of Commerce ; 805/238-0506

TEMPLETON (7mi/11km; 14min). Fuel up at Farmstand 46 , where locally sourced sustainable ingredients lead to wood-fired pizzas with fresh, seasonal toppings. Or consider tri-tip at Hoover’s Beef Palace (401 N. Main St., Templeton; 805/434-2114). INFO San Luis Obispo County Visitors & Conference Bureau ; 805/541-8000