In the late 19th century, Cloverdale was just a little town of sawmills and citrus groves located on the northern tip of Sonoma County. Even though it was once called one of the coolest small towns in America, it’s still under the radar for a lot of folks exploring Wine County. It shouldn’t be: Cloverdale has its own assortment of wineries (including its own AVA), a solid foodie scene, and lots of historic charm that still resonates around its cobblestone-lined town plaza. Here are 8 ways to tap into this hidden gem.

1. Fuel up with local flavor

Start your day with an espresso at one of the town’s foodie magnets: Plank Coffee, which house-roasts its beans and offers locally made green juices and baked goods from the Healdsburg Bagel Company. Get more local farm-to-table flavor at dinnertime at Trading Post, which features plenty of local produce and wine. Come on Wednesday evenings April-November when the menu is fueled by the current selection at the Cloverdale Tuesday Farmers’ Market.

2. Step into a 19th-century time machine

Both architecture fans and looky-loos will love the Gould-Shaw House. The Victorian-era Gothic-Revival Cottage, which is on the National Register of Historic Places, was built in 1862 and is still furnished with period décor. Go next door to the Cloverdale Historical Society’s History Center and check out its 65,000-artifact collection that ranges from antique farming machinery to Native American art and early 20th century fashions.

3. Check out the public art

Cloverdale and nearby Geyserville boast more than 30 large outdoor sculptures and you can see them all on the Cloverdale Sculpture Trail. The pieces change over time, and the current assortment includes giant abstract geometric works, a Wine Buddha, and a whimsical “pigasus.” Download the trail map to start exploring; while you’re walking, stop by the Sciaini building on Cloverdale Boulevard to see the historic society murals depicting the town’s early days.

4. Paddle the Russian River

Note: As of presstime, the Russian River is experiencing flooding. Check the Sonoma County site for updates on safety and road closures.

The name may be associated most often with wine, but the actual Russian River offers all sorts of outdoor delights. See it up close from the Cloverdale River Park, which has a mile-long scenic trail, a riparian habitat, a launch for kayaks and canoes, and picnic tables that are suitable for, well, opening a bottle of Russian River Valley wine

5. Taste more local wines (and a little beer)

Cloverdale has nearly a dozen wineries, stretching into the Dry Creek, Anderson, Russian River, and Alexander valleys. Each has its own personality: Fritz Underground Winery offers cave tours and regular hikes up the vineyard’s hill, while BobDog Winery (located in the new AVA, Pine-Mountain-Cloverdale Peak) has its own hill to climb and hearty reds like a dark-chocolate-accented Choco Port and a Mountain Cloud that’s a blend of Cabernet Franc and Merlot. Call ahead to family-owned J Rickards Winery and you can have a picnic lunch from Healdsburg-based Big John’s Market waiting for you to pair with your new bottle, under a shady tree. For more exercise while wine tasting, choose one of the town’s bicycle-friendly loops with lots of wine country scenery.

Beer enthusiasts, meanwhile, can taste brews like the Pine Mountain Pale Ale, Cloverdale Ale, and Raisin Oatmeal Cookie Stout on tap at the Cloverdale Ale Company.

6. Do a comfort-food tasting tour

Cloverdale specializes in approachable cuisine, most notably burgers and barbecue. Hamburger Ranch & BBQ draws you in with its cheery red-barn-style facade but keeps you with its barbecued brisket, baby back ribs, pulled pork, and chicken. During summer months you can enjoy an outdoor grilled feast on the patio featuring steaks, salmon, and oysters. Also nearby, the red train-depot-style Railroad Station Bar and Grill is beloved for its burgers and pot roast.

The elder statesman of the local food scene is Pick’s Drive In, which first opened in 1923 and is one of the oldest burger joints in the U.S. It was recently bought by the owner of the nearby Healdsburger but the new owners have pledged to keep the classic menu items intact, which you can enjoy at the outdoor counter or on picnic tables. 

7. Catch a cool show

The 99-seat Cloverdale Performing Arts Center has a charmingly intimate setting for a reliable lineup of plays, including John Steinbeck's Of Mice and Men and The 39 Steps, based on the 1935 Hitchcock classic. It also offers an inviting calendar of other performances, from jazz vocalists to storytelling nights with wine and cheese.

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8. Sleep inside a yesteryear landmark

Befitting the small town charm, Cloverdale offers a number of B&B-style lodgings. For an Old West vibe, book a room at the ranch-style Old Crocker Inn, which started out as a hunting retreat in the 1880s. For a more traditional B&B stay, choose Kelley & Young Wine Garden Inn, housed in a 1901 Queen Anne Victorian that’s listed on the U.S. Register of Historic Places. Even the local camping scene has good Wine Country views: Cloverdale Wine Country KOA Campground sits on 60 acres overlooking the Alexander Valley and offers cabins along with tent and RV sites outfitted with hook-ups, fire pits, picnic tables, and even wifi.