At Richmond’s oldest restaurants, fresh food + old school eats go hand in hand.

We looked into some of the spots that have been operating in the city for decades. With culinary legacies like these, Richmond’s food scene is dine-amite.

Millie’s Diner, 2603 E. Main St.

Millie’s has been spicing up Richmond since 1989, when they opened near Church Hill. A brunch hot spot known for its signature messes, Millie’s experiments with different flavors to deliver a brunch that you won’t soon forget.

Fun fact: The Devil’s Mess — a frittata with spicy sausage, onions, green peppers, garlic, tomatoes, and mild curry — has been a favorite on the menu since opening day.

New York Deli, 2920 W. Cary St.

This Carytown restaurant claims seniority in Richmond. It first opened in 1929 and moved to its current location in 1934. Although the deli counter has been replaced with a bar, New York Deli still serves the classic sailor sandwich — that’s pastrami, swiss, grilled knockwurst and spicy mustard on toasted rye.

Helen’s, 2527 W. Main St.

Swing by this restaurant in the Fan and enjoy a helping of history with your dinner. The 1912 building was converted into a restaurant called D’s in 1927. The couple who owned the spot passed it to their daughter, Helen, in 1935. Since then, it’s been Helen’s — a home for music, swing, and comforting southern fare.

Chiocca’s, 425 N. Belmont Ave.

This Museum District deli has been slinging sandwiches since 1952. It runs on the gas-powered energy of Peggy, the 1930s Star broiler named after manager Mario Chiocca’s late wife. In 2010, restaurateur Scott Ripley bought the joint from Mario’s son, Timmy. They’re open from 11:30 a.m. until 12 a.m. every day with beers on tap and plenty of eats.

Joe’s Inn, 205 N. Shields Ave.

The Fan favorite opened in 1952 when Joe Mencarini set up shop serving a variety of dishes. Nick Kafantaris bought the place in 1977 and the Kafantaris still own it today. Try this: The Greek meatballs and enough Spaghetti a la Joe to feed a family of four.

This is what the menu looked like at Joe's Inn circa 1975. | Image via The Valentine

O’Toole’s Restaurant and Pub, 4800 Forest Hill Ave.

This Irish mainstay has been open in Southside since 1966. The O’Toole family emigrated from Ireland in 1920. When Jim O’Toole opened the pub, he received the commonwealth’s first by-the-drink liquor license. The family opened a second location in Midlothian in 2019.

The Village Cafe, 1001 W. Grace St.

The Village has been nestled in VCU since 1956. The cafe originally opened across the street, but moved to its current location in the late 80s. Whether you’re in the mood for a quesadilla, a sub, pasta, or omelettes, this college hangout has served a little bit of everything for a long time.

Hungry for more history? There's plenty more with that came from, like our roundup of the oldest family-owned businesses in Richmond.