[This article appears in the September/October 2023 print issue of Boston Spirit magazine. Subscribe for free today.]
As early as 1858, when it served as the last stop on Cape Cod’s stagecoach line, the rambling property atop the hill on Carver Street in Provincetown functioned as an inn.
Over the years, it has entertained American presidents (Grant, Roosevelt and Howard, to be specific), hosted theater companies (a young Al Pacino performed here), and been a vibrant hub of gay life. Not a night goes by that you won’t find guests and locals alike gathered around the lobby piano, spilling out onto the big and buzzy front porch, or dancing (probably with most of their clothes doffed) in its Club Purgatory, a steamy subterranean hotspot that may now be the oldest leather bar in the country. With so many high-spirited memories attached to the place, it’s no wonder that, if the many whispered ghost stories are to be believed, a handful of revelers have never left the Gifford House at all.
Today, though, the party continues under a new host: Steven Azar, who purchased the Gifford House from longtime owner Jim Foss earlier this year. In a matter of about six weeks, Azar managed to renovate the 33 guest rooms, reactivate the Gifford’s entertainment space and breathe rejuvenated life into a P’town landmark. (There’s also now a psychic salon, for those wanting to connect with the unliving, as well.)
“Provincetown has a special place in my heart, and this was a rare opportunity to invest in something that I really believe in,” says Azar, who left behind a career in the rat race of corporate real estate to become a Provincetown innkeeper in 2019, when he purchased the Roux Inn and transformed it into the successful Stowaway. Last year, Azar sold the Stowaway Inn to comedian Kristen Becker’s nonprofit Summer of Sass to serve as an organizational headquarters and provide housing for marginalized LGBTQ+ youth.
As the latest proprietor of the Gifford’s century-and-a-half history, Azar now views himself as part of a small wave of corporate expats who have recently moved to Provincetown to find a better quality of life and build their own businesses. He says they’re also trying to protect a place they love from becoming overrun by soulless developers who see dollar signs in P’town tourism, but don’t recognize the place’s important legacy of artistic queer community.
“There’s this protective warrior part of me that wants to hold and maintain the importance of queer spaces in America right now,” says Azar, who grew up in New Bedford, Massachusetts, where his mother was a schoolteacher and his father a social worker. He first discovered Provincetown as a place to “sneak off to” as a young adult. “My first experience was pre-Internet and pre-cell phones. I just hopped in my car, drove down, and went for a walk along the beach.”
Before long he found the famous nude stretch of sand, and “within two minutes, a funny, witty and welcoming group of friends,” he says. “Somebody threw a football at me, I ended up on a boat, and then they took me to dinner. It was nothing lascivious; no one was hitting on me. It was just a beautiful experience that told me everything was going to be okay.”
Considering the anti-queer, anti-trans sentiment roiling the country, it’s especially important that places like Provincetown be preserved as safe spaces, Azar says. That starts with supporting business owners who are actually putting down roots in the community: Azar was particularly touched when the similarly landmark Crown & Anchor resort, which was recently purchased by its longtime entertainment producer Jonathan Hawkins and his husband, Moderna CSO Paolo Martini, gifted their grand piano to the Gifford for its new Love Lounge, where the ivories are tickled seven nights a week.
In addition to launching the Love Lounge, beautifully updating the Porch Bar and guest rooms and resurrecting Purgatory, which had been shuttered since COVID, Azar has also introduced the all-new Wilde, a 100-seat, black box-style “theatrical speakeasy” for hosting diverse performers of all kinds (and, with its catering-friendly commercial kitchen, private events as well). Guests can also request tarot readings from an on-site intuitive, and Azar hopes the Gifford’s programming could eventually grow to include winter workshops on any number of topics to keep P’town’s economy stimulated in the off-season.
And just for the record, as spooky season approaches: Azar vouches for those tales that the Gifford House is haunted by friendly ghosts, including a certain shirtless cowboy that everyone claims to spot lingering in the same corner of Purgatory. He’s free to stick around; everyone is welcome here. [x]
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