The History: Town-square aficionados will say that Orange, about 30 miles south of Los Angeles and founded in 1871, planned things right by starting with a plaza and building out. This area is now a one-square-mile historic district known as Old Towne, and it’s hard to take a step without stumbling upon history, beginning with the plaza’s 1937 fountain. You’ll find more than 1,300 homes and buildings here; many of them are originals that date back to the town's early years, and all are covered under the district’s listing on the National Register of Historic Places. It all feels very connected to the early 20th century, thanks to places like Watson Drugs and Soda Fountain, which has been a part of the fabric here for more than a hundred years.
Where to Play: Watson Drugs and Soda Fountain serves up the dishes you might expect from an authentic old-fashioned soda fountain. For more formal dining—with a view, to boot—head to Orange Hill, which, true to its name, sits atop the hills of Orange and offers sweeping panoramas out to Catalina. When it’s time to shop, Old Towne Orange is known as “The Antique Capital of California,” and you’ll find more than 40 antiques shops, like the Antique Station & Depot and the Chapman Antique Mall. Then check out live music at The District Lounge, built inside Orange’s first post office.