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With its historic buildings, charming mom-and-pop shops, and rolling foothills, this Southern California city seems straight out of a storybook

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Old Towne Orange features a charming downtown square that wraps visitors and locals alike in a nostalgic hug. It remains loyal to its colorful past while warmly welcoming new restaurant concepts, craft breweries, and coffeehouses into the vintage structures nestled along tree-lined streets.

Founded in 1871 and built around a quaint pedestrian plaza, Orange is the largest nationally registered historic district in California. At the center of the iconic traffic circle, a mosaic tile fountain dating back to 1937 remains a local landmark and a testament to the city’s preservation efforts.

While much of the regional landscape has rapidly evolved over the years, Orange has maintained its diverse architectural styles, which number more than 50 and range from Classical Revival and Victorian to Craftsman and California bungalow. Many of the local businesses evoke an old-time feel, including Tiddlywinks toy store, Torpedo Comics, and even a vinyl shop, Mr. C’s, which specializes in rare records. More than a dozen antique shops and emporiums such as Orange Circle Antique Mall add to the district’s vintage vibe, drawing treasure-seekers in search of estate jewelry, china, and furniture.

Many of Old Towne Orange’s original buildings from the 1870s to the 1940s also remain in use, including Watson’s Soda Fountain & Cafe, a drugstore founded in 1899. Though the shop stopped filling prescriptions in 2011, Watson’s soda jerks still serve up chocolate malts, ice cream, and all-American diner food in a refreshed space that features an original druggist cabinet filled with medicinal bottles and vials.

Another place to see and be seen, The Filling Station caters to early birds with a down-home classic breakfast spread inside an old gas station established in 1913. Even newer restaurant purveyors pay tribute to the past, with Bosscat Kitchen & Libations restoring World War II pilot Rod Fraser’s old 1949 liquor store into the city’s hottest brunch and whiskey destination.

Upon the arrival of Chapman University in the 1950s, Orange became a college town. The Hilbert Museum of California Art, located on campus, is a real gem, showcasing an enviable collection of California Scene paintings, which are distinguished from earlier works of California Impressionism by the portrayal of people going about their everyday lives in settings as diverse as cities, harbors, and ranches, or in cars and trains; the style can also include dramatic landscapes.

What would a college town be without a few local watering holes and cafes? Chapman Crafted Beer is a family-owned favorite. Down the road, the owners of Smoqued California BBQ opened 1886 Brewing Company, serving up award-winning beers and brewpub fare in a refurbished antique shop space. Coffee connoisseurs can head over to Contra Coffee & Tea to build their own tasting flights in a bookstore filled with literary journals and works from independent presses.

Nearby Irvine Regional Park, the oldest in Orange County, is an outdoor escape with short hiking trails, picnic grounds, and a lake for paddle boating. Families can climb aboard the Irvine Park Railroad for a 12-minute scenic ride led by an overall-clad conductor or check out the OC Zoo’s exhibits featuring animals and plants native to the southwestern states. For a deeper trek into nature, adventurers can also take a guided horseback tour of the three-mile equestrian trail offered by Country Trails & Riding School.

Visitors planning a trip over Labor Day weekend can partake in a time-honored tradition: the Orange International Street Fair. The city hosted its first street fair in 1910 and revived the event in 1973 for its centennial celebration, complete with live entertainment and dozens of food booths.

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