The best week O’Reilly’s Pub has had in its 10 months of existence came when Dead & Company performed three farewell shows in early August in Golden Gate Park. “Thursday, Friday, Saturday, Sunday — those were our four top-selling days,” says Neil Holbrook, owner of the Haight Street Irish bar. “It was fantastic.”

He’s hoping for a similar boost from bar-hopping Deadheads during Saturday’s Jerry Crawl and from the Haight-Ashbury Street Fair on Sept. 7. But when it comes to the neighborhood’s long-term potential, Holbrook is relying on more than people looking to relive the Summer of Love. His bar is one of a handful of food and drink destinations bringing new life to the historic neighborhood.

Holbrook, who hails from Ireland and has lived in San Francisco for 23 years, opened O’Reilly’s in the space that was formerly Milk Bar, a longtime home for stand-up comedy that shuttered abruptly in 2024. With comics, live music, and trivia seven nights a week, O’Reilly’s is a vivacious place, part of a wave of businesses to have opened in the past six months, including mom-and-pop Indian restaurant Jalebi Street and a revived Magnolia Brewing, the city’s quintessential, independently owned brewpub. Those establishments precede a trio of forthcoming projects at storied Haight Street addresses: a soon-to-be revived Club Deluxe, The Green Heron (in the former Hobson’s Choice), and Mary’s on Haight (in what used to be Trax). 

With all this new energy, the Haight is alive with what Holbrook calls colorful magic.  “All new additions bring eyes to the area,” he says. “Then the eyes will bring the feet.”

Peterson Harter of muffuletta shop Sandy’s says the difference between when he started selling New Orleans-style sandwiches in early 2023 and the current situation on Haight is like night and day. “I tell anyone looking to open a spot: If you want to do a lunchtime thing, Haight Street is the place to be.”

The tie-dyed part of San Francisco known worldwide as “Haight-Ashbury” and locally as the “Upper Haight” can appear almost impervious to change. Many of the street’s charming bars and restaurants — like the 46-year-old diner Pork Store Cafe, the 84-year-old martini den Zam Zam, and the roughly 100-year-old Gold Cane Cocktail Lounge — have stood the test of time and then some. Then there are powerhouses like The Alembic, a pioneer of craft cocktails and whole-animal butchery when it opened in 2006 and still a destination today, and the ever-affordable Parada 22, one of the city’s few Puerto Rican restaurants. 

But the street is not trapped in amber, as veteran Haight clothing shoppers can attest. Where there once were scruffy thrift and vintage stores, now there are pricey boutiques selling $100 T-shirts.

The same is happening to nightlife, with three shuttered bars reemerging with different demographics in mind. Trax, a relaxed queer bar that closed in June, is set to become Mary’s on Haight. Details are slim, but co-owner Maria Haught confirms that the team hopes to open in time for the annual Haight Street Fair, which draws an estimated 75,000 people to the neighborhood.

A block away, Hobson’s Choice has sat vacant for months — but not for much longer. The team behind Inner Sunset beer-and-wine hangout The Red Tail is sprucing it up ahead of an estimated October reopening as The Green Heron. Like its predecessor, it’ll offer a full menu of beer, wine, and spirits. Co-owner Conner Frederick says he’s not looking to make drastic changes; for instance, he invested several laborious hours one morning bringing Hobson’s bar stools back to their original glory. “They have a cushion and a comfort you can’t get out of a new bar stool,” he says.

Lastly, there’s Club Deluxe, a venue that closed in 2023 after a run of nearly a quarter century. Christian Beaulieu, a musician who tended bar there, is part of the team that took it over. He has a long history with the Haight, having “followed a caravan of punk musicians out here to talk myself into the band” in 1999. Now, he’s partnering with Jay Bordeleau of Mid-Market jazz club Mr. Tipple’s Recording Studio to see the renovation through.

No opening date is set, but Beaulieu says the vibe of Club Deluxe 2.0 will still be “classic cocktails meets musicians playing in the round.” The general contractor, he adds, was a regular who knows to leave the bones untouched. Name-checking the Cosmo Alleycats, Mitch Polzak & the Royal Deuces, and Barrio Manouche as the best shows he remembers seeing at the bar before it closed, Beaulieu promises that “not only is there going to be live music seven nights a week, but you’re going to see some familiar faces, for sure.”

Perhaps the strongest evidence of the Haight’s unique economic potency comes from a pair of wind-up chattering teeth. Bite Me Sandwiches, which features a sneaker-clad dental novelty as its eye-catching logo, has run a shop at 701 Cole St. since 2019. Last year, it debuted a smaller outpost less than one block away, at 609 Cole. It has the same menu and keeps the same hours. But according to owner Nidal Musleh, the shops serve entirely different clienteles. 

It sounds improbable, but to him, it’s simple. Tourists stay on Haight, while residents of Cole Valley, the tony neighborhood immediately to the south, avoid it. Occasionally, a regular at one Bite Me will “discover” the other, unaware of its existence. Stupefied, they ask if the business is in the middle of relocating. “It’s crazy,” Musleh says. Sixty years after people first started flocking to the Haight, the appeal is as strong as ever, and they keep on coming.