Toward the end of the ascent from sea level to 1,400 feet, a landscape of boulder-strewn hills carves the path to Ramona’s straight-across-town thoroughfare aptly named Main Street. As the city’s low-key center of action, you’ll know you’ve arrived when San Diego County’s vibe has transformed from flip-flop fun to cowboy cool.

No longer known for its happenstance location along the road to Julian, this unincorporated, under-the-radar town has come into its own and is known for authenticity. So, follow me through Ramona—the place locals have long loved and the place visitors are beginning to fall in love with.

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Classic Rotors Museum Activewear sponsored by #prAna

Western Legacy

As the land of wide open spaces and skyscraper-free horizon, Ramona’s heritage aligns with its cowboy roots. Beginning along Main Street, a stop at the Guy B. Woodward Museum, located in an adobe of French Provincial design—the original 1886 Amos Verlaque House—showcases the area’s early Western culture. Fully furnished in period antiques, it gives a peek into the beginnings of Ramona, alongside such original structures as an 1800s jailhouse (in use until 1915), an 1874 cowboy bunkhouse, tack room, and blacksmith shop.

Less than a block away is the Ramona Town Hall, listed on the National Register of Historic Places—a former movie theater, library, bank, and even a basketball court. And among Ramona’s noted locals is the late rodeo legend, Casey Tibbs, whose long-ago Ramona wedding was reportedly attended by one of the most popular Western stars of his era—Roy Rogers.

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Tasting room/patio Vineyard Grant James. Activewear sponsored by #prAna
Oak tree and relaxing outdoor area at Vineyard Grant James.
Tasting room/patio Vineyard Grant James. Activewear sponsored by #prAna
Oak tree and relaxing outdoor area at Vineyard Grant James.

Maze of Murals

To best understand the town’s vivid and varied history, a visit to some of the H.E.A.R.T. Mural Project’s collection of fifteen oversized wall paintings is key. Using the sides of buildings and walls as canvases, the murals commemorate everything Ramona from the July 4, 1914 image of Main Street, to Casey Tibbs, to the town’s long ago Turkey Queen.  

Air Apparent

Classic Rotors Museum, one of only three in the world, is located at the Ramona Airport. Specializing in helicopters and other rotorcrafts, this hangar full of aircraft includes such specimens as a Russian Mi-2 and a Piasecki HRP-1 (nicknamed the “Flying Banana”), each complemented by videos of these flying machines in action.  


Marinade on Main’s signature burger.

Grapes of Craft

A combination of hot days, cool nights, high elevation, and rich soil contribute to an abundance of wineries in Ramona. While known for its Sangiovese, varietals such as Cabernet Sauvignon, Merlot, Muscat, and more are also grown in Ramona. The wineries are all different, and each one is special.  

Located on a Ramona back road is Vineyard Grant James, the creation of winemaker Susanne Sapier.  The vineyard is named for Sapier’s son, Grant, and her father, James—both key players on the winery’s team. Conceived approximately a decade ago, it has since been recognized by Travel + Leisure as the nation’s number two winery.

Situated along Main Street, winemaker Jennifer Lane is at the helm of Pamo Valley Winery. Known for Bordeaux varietals, it is Ramona’s only winery open daily. Named for a granite edifice that in profile replicates a turtle’s face, Turtle Rock Ridge Vineyard Winery’s sweeping panoramic views accompany each glass of wine. Salerno Winery is both a wine stop and art destination. A reflection of proprietor and art collector, Jaime Chaljon, the vineyard showcases a sculpture garden, bocce ball court, garden chess (played with three foot high pieces), and premier wines.

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Scone with strawberry jam and clotted cream paired with imported black tea the The London Bakery.

Food Fun

From Mexico to London to local, Ramona serves foods that run the gamut and won’t break the bank. La Cocina, a Ramona tradition since 1981, is the place to go for homemade Mexican. New to the scene is The London Bakery for afternoon tea, scones (made from British owner Joanne Bennett’s 100-year-old family recipe), and the opportunity to take a photo with a Prince William and Kate cardboard cutout. Featured on the Food Network’s Diners, Drive-Ins and Dives, and recognized for its one-half pound cinnamon bun, is the iconic Ramona Cafe.

Upmarket options include Marinade on Main, the town’s first farm-to-table eatery, which promises fresh ingredients and local produce accompanied by local beers and wines. Featuring an impressive menu, a popular entrée is its signature burger. Another top dining choice is D’Carlos, a restaurant known for beef—from prime rib sliders, to steak bites, to a 12 ounce ribeye.


Tea service with imported black tea the The London Bakery. Activewear sponsored by #prAna
Tea service with imported black tea the The London Bakery. Activewear sponsored by #prAna

Around the Calendar Action

January and February: Hawk Watch

April: Ramona Open Studios Tour

May: Ramona Rodeo/Old West Days

August: Ramona Country Fair

September: Grape Stomp

October: Taste of Ramona/Ramona Air Fair & Fly-In

December: Christmas Tree Lighting Ceremony    


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