New York Deli, 1929

While today’s New York Deli regulars may return time and again for a Reuben on the rooftop, karaoke and late-night revelry, the patrons of yore frequented the restaurant for the pastrami and knockwurst counters and shelves stocked with more than 2,000 pantry items.

Almost a century old, New York Deli is “always reinventing itself,” says current owner Demetrios Tsiptsis.

The deli lays claim to being both the oldest, continually operating restaurant in the city and the home of the famous Richmond Sailor Sandwich.

When Tsiptsis took over ownership in 2004, he told former owners Ken and Jack Boucher that, while he would honor this legacy, he would also update the space so that it wasn’t an outdated deli concept but a “deli-inspired restaurant.”

Tsiptsis added a full bar and entrees to the menu and later hours. They added the popular Rockaway Beach Rooftop Bar in 2022.

After 100 years, the anecdotes abound. There are one-offs, like the story about the woman who gave birth in the Vienna Room when she couldn’t make it to the hospital. Then there’s the history of the Vienna Room itself, which was added to the restaurant in the 1950s by the Brandeis family.

Arthur Brandeis and his wife, three sisters and two brothers-in-law escaped the Nazis in Austria with help from the Thalhimer family (of Thalhimers Department Store) and took over the deli in the late 1940s.

“Three, four hundred people come to eat for dinner every day, and as many on the weekends to buy for home,” Arthur Brandeis told The Richmond News Leader in 1957.

While devoted regulars are certainly a feather in the hospitality cap, perhaps the greatest testament to the staying power of the deli is one person, chef Jacqueline Lee.

Lee started in the kitchen in 1986, and only left for a few years before returning to 2920 W. Cary St. to continue her impressive tenure.

“It’s the atmosphere for me,” she says when asked what keeps her going. “I see familiar faces, kids growing up, getting married, getting pregnant. We’ve had lots of weddings and receptions here. It’s just a really cool place to come and visit.”

Helen’s, 1935

Helen’s is one of those restaurants with different connotations depending on when you’ve been a diner. The red neon sign may have you conjuring images of rail drinks in a busy bar, or you may drift into the memory of a slow, delicious Sunday brunch.

You may also get goosebumps. Purported to be very haunted, Helen’s is one of the oldest Richmond restaurants (though not continually operating) still standing. It was originally a pharmacy, Fletcher’s, before the Donati family took over in 1927.

Helen Donati was gifted the restaurant for her 21st birthday in 1935. Her brother, John, stepped in after her death in 1967 and ran the restaurant, which he renamed Helen’s Inn, until 1994 when current owners Leslie and John Tuite took over.

In 2015, Leslie told Style: “Particularly when we first got here, many things happened… I was working on the place and getting a pizza delivered. A woman with an apron just floated right by me into a booth.”

Helen’s was even named the “most haunted restaurant in Virginia” by the Food Network in 2019. It may not technically have the most years under its belt, but the “most visited by spirits” is still an admirable achievement.

O’Toole’s Restaurant and Pub, 1966

James Edward O’Toole (Jim) and wife Marie opened their Forest Hill Irish pub in 1966. “It’s a comfortable place to come,” says their son and current owner John O’Toole. “Neighbors feel like it’s part of their home.”

O’Toole says his parents moved to Richmond in 1959, his mother hailing from New York and his father from Pittsburgh. They had four boys (Jimmy, Bill, John and Tom) one born in New York and the rest in the River City. They’re all still close today—O’Toole’s brother Tom owns the Midlothian location of the restaurant, which opened in 2019.

The pub has long been a gathering place for Southside denizens, and they always kick things up a notch on St. Paddy’s Day with kilts, bagpipes and overflowing pints galore. Even when you aren’t chasing a pot of gold, the pub is a cozy spot to sup with an expansive menu ranging from typical fried bar fare like onion rings and mozzarella sticks to traditional Irish eats like bangers and mash and shepherd’s pie.

Bamboo Cafe, 1974

This circa-1916 building at 1 S. Mulberry St. was originally a confectionery before becoming The Briefcase, Mulberry Tavern and the current, much-loved neighborhood bar, Bamboo Café.

The timeline of ownership is not completely clear, but to the best of current owner Adrienne LaPrade’s knowledge: Diane and Jim Bandette opened the restaurant in 1974 before John Anderson and Gary Morgan quickly acquired the business within a couple years. Jay and Becky Barrows bought out Anderson in 1977. Martin White became owner in 1982. LaPrade took over in 2004 after her husband, White, passed away.

“We’ve had regulars who have been coming in for generations,” says LaPrade. “We have such an eclectic range of patrons and it’s so welcoming. You can come in alone and be guaranteed to know at least one or 10 faces amongst the crowd.”

The well-worn dining room and bar play host to everyone from grad students to restaurant industry folks to diners who “bring their children in, and we watch them grow and bring their own families in,” LaPrade adds. Familiar Richmond musicians have tended bar from bands such as Bio Ritmo and Piranha Rama.

The half-century-old restaurant has also had more than one brush with fame; it made an appearance in the 1985 HBO movie “Finnegan Begin Again” and in the 1989 ABC movie, “My Name is Bill W.”

They haven’t let the stardom go to their heads, though. The mainstay offers standard, solid bar fare—plus potstickers and egg rolls—seven days a week. You won’t find any “signature cocktails” on a fancy drink menu, but you can order a mighty fine, dirty martini.

The Locker Room Bar, 1981

Once you enter The Locker Room, your clothes will not let you forget about your visit for days. That’s part of its charm, really. Another part is that the Forest Hill dive bar has essentially remained unchanged for almost 44 years.

“It was originally supposed to be a sports bar [hence the name] long before sports bars were a thing,” says owner and operator Lisa Ann Peters.

Peters was in middle school when her mother and uncle first opened The Locker Room in 1981. She waitressed there in her 20s and officially took over ownership in 2015. Peters says she added a new point-of-sale system to replace her mother’s old Costco cash register, plus security cameras, more food and karaoke.

But the biggest change was the bar’s messaging. “We made a post about not allowing homophobia and racism and stuck it out front,” says Peters, who says the post made its rounds through the Reddit community. “We saw a burst in business from younger clientele, and a lot more diversity.”

The bar is old-school without being hampered by old ways. Yes, you can light your Marlboro Reds inside. But you’re also guaranteed to make a friend.

The Locker Room is a regular on the Richmond Reddit scene (as noted above). Peters says she can’t believe how many threads she’s been sent about the bar.

One particularly memorable thread started when a new-to-town man posted on Reddit that he wanted to make friends and said he’d be at the Locker Room at a certain time and day. “The post had about 1,000 likes on it,” says Peters. Apparently at least eight to 10 strangers showed up to greet this newbie and buy him drinks.

“People continued to come through the night,” says Peters. “He posted pictures and we reposted them. He ended up making a lot of new friends.”