San Diego is brimming with special, local businesses. Today, we’re shining the spotlight on five legacy businesses in America’s Finest City — operating since 1869, 1885, 1938, 1943, and 1949.

Built in 1827-1829 and restored and reopened in 2010, The Cosmopolitan features 10 rooms and a restaurant. | Photo via Monica Garske + SDtoday

The Cosmopolitan Hotel & Restaurant, Old Town

Built 1827-1829 as the home of settler Juan Bandini, this is one of San Diego’s oldest standing buildings. Stagecoach operator Albert Seeley bought it in 1869, added a second story, and turned it into a popular hotel. The Cosmopolitan underwent a major $6.5 million restoration and reopened in 2010.

Tivoli Bar and Grill was converted into a saloon in 1885. | Photo via Michael Beausoleil + SDtoday

Tivoli Bar and Grill, Gaslamp Quarter

Billed as “the Gaslamp’s oldest bar,” this spot was built in 1864 and converted into a saloon in 1885 — where Wyatt Earp was an early patron. With a brothel above it, Tivoli was part of the city’s red light district. Today, the bar and grill remains open daily until 2 a.m. — with its original cash register.

San Diego Chicken Pie Shop, North Park

This comfort food staple opened in 1938 and moved from Hillcrest to North Park in the early 1990s. Eight decades later, the same Chicken Pie recipe remains on the menu, keeping customers coming back for more.

The hobby store on Park Boulevard is the oldest train set shop in the US. | Photo via Monica Garske + SDtoday

Frank the Trainman, University Heights

This model railroad and hobby store has been running since 1943 — making it the oldest train set shop in the US. Its namesake, Frank Cox, kept the biz chugging along until 1982; today, it’s operated by three generations of the Cooley family — right next door to the J.A. Cooley Museum.

Tried and true: This place has always been there for us. | Photo via Monica Garske + SDtoday

Rudford’s Restaurant, North Park

Open 24/7, this local retro diner has been serving hearty, home-cooked meals since 1949. Fun Fact: On June 6, 1963, President John F. Kennedy cruised El Cajon Boulevard on his way to deliver a speech at San Diego State, and the famous photo — with Rudford’s prominently in the background — is featured on the top of the menu.

Have a favorite longtime local business? Tell us about it.