Crew's Quarters Boarding House: Affordable Ptown Lodgings with a 'Bad Boy Sailor's' Vibe

But the charismatic, handsome Jackson makes for a fine substitute. The British expat (he is an American citizen) recalls being intrigued with the Commercial Street property when he was in Provincetown working remotely during the pandemic, and he became transfixed when he visited it for the first time upon hearing it was for sale. That was in the summer of 2020. Fast forward to this summer and his "pandemic project" (as he calls it) functions both as a top guest house and something close to an art installation intended to evoke queer male culture from a time when Provincetown was one of few havens where gay men could feel safe while on holiday.

Jackson's intent was to create the "bad boy sailor tavern at the end of the jetty" (as he calls it), and he has happily succeeded. The antique-filled rooms run from simple, single-bunk spaces to larger ones with queen size beds. The public spaces — the showers and bathrooms — are handsomely appointed. The rooms are filled with period antiques, some cheeky (such as the small, framed photos of sailors); some beautifully homoerotic (such as a painting of a shirtless blonde man in one of the larger rooms). With rooms on three floors (along with a private space in the basement), Crew's Quarters Boarding House offers a playfully decadent Provincetown experience. If you have that randy sailor vibe, CQBH is for you.

The structure, which sits just steps away from Spiritus Pizza, dates from 1882 and has been a doctor's office, an art gallery, and an antique store before Al Stillson bought it and opened it as The Ranch in 1959. Stillson's had a concept that today looks ahead of its time. In a town where guest houses ooze generic, Cape Cod charm, he opened a theme-based guest house that would capitalize on a popular cultural theme of its time: cowboys. "I really respect what Al Stillson did," says Jackson. "He positioned The Ranch to the town as a place for guests to live out their cowboy passions. He had tuned into that social phenomenon of the late '50s and early '60s — the popularity of the Western on TV and the movies, and the image of the Marlboro Man. He embraced the machismo, And he did a beautiful job. The place looked like the Wild West Saloon in here — all the rooms had names on them. He did a really great job. And so it started, I think, with a real bang." Jackson honors Stillson's memory by displaying many Ranch artifacts in his basement, including the names of the rooms, which he placed on each step of the basement stairs.

But over the years and changes of ownership, The Ranch lost its edge, becoming what Out Traveler called "an almost corny bunkhouse geared toward the leather/Levi crowd but welcoming all men who will appreciate its down-home, rustic flavor." Others saw it closer to a bathhouse. New owners changed its name to Crew's Quarters, but it was pretty much held in lower esteem in a town filled with judgment.

"Recently the place had a reputation for being a sauna," Jackson recalls. "True. But that did not concern me whatsoever. In fact, I saw the place as a part of queer history and a gift, really, that needs to be nurtured, looked after, protected, and evolve. There were no liabilities, no concerns. I just saw a beautiful building and a great potential."

Nurturing that gift brought him to curate the interiors as they may have been in pre-Stonewall days. To do so he scoured antique stores, junk shops, street fairs and attics and basements in his search for artifacts to fill the rooms. The painting mentioned earlier is a fine example. Jackson says he found it being sold on the street in the East Village. Recently painted, he gave it an antique sheen and placed it in an old frame to give it an authenticity that feels real. It is that spirit that fills the rooms of Crew's Quarters Boarding House.

"I have always been collecting antiques or imagery, especially old male portraiture, or art. It was a personal passion, and this became the opportunity to bring all of that together. I decided to bring them into this and to create a place that I would want to go and hang out when I was in Provincetown."

The result has been transformative, all but erasing the space's down low reputation while keeping its spirit. "Somebody in town said recently to me something I thought charming and flattering. They said, 'I had taken sleazy and made it sexy.'"

And Jackson remembered Stillson again. "I have done what Al Stillson did, but I've chosen a different era," he says. And while it evokes a time of some hardship for the gay community — the 1950s saw The Lavender Scare in which gays were drummed out of the federal government thanks to an executive order by President Dwight Eisenhower — Crew's Quarters Boarding House celebrates when Provincetown was a mecca for gay men who found a safe space amongst its beaches, dunes, bars and clubs.

Throughout the process Jackson was well aware of his business model, that of a budget hotel based on a limited number of rooms. Add to this a commitment to providing an affordable space for younger visitors in a town where they are increasingly being priced out by rising costs.

"I learned from being a queer activist from my youth that ensuring and maintaining inclusion and diversity is really important to me. So, when I created this place, I wanted to be like one of those born good entities. And maintaining the price points where they are really provides economic diversity and access to people. I have younger folk that come in who may not be having the biggest, fattest wallet, but they still want to stay in Ptown. The lower price point gives them the opportunity. I did not want to create a model or an inn that would be exclusive to people based on money. You can stay here on the shoulder season in our cheapest rooms for like $100 to $120. Or during our peak weeks (Bear Week and Carnival) when the same rooms are about $240 when other places around town are charging $500 to $700 a night. We are intentionally operating at that lower quartile so people can come in and stay here."

"But," he adds, "the contradiction that I'm giving our clientele is that we provide a lush, curated experience that represents my brand. I'm really trying to deliver cheap chic within the speakeasy queer vibe. So I wanted to offer access, but I also wanted to offer a really unique, quality experience at the same time. You are just not coming to a budget hotel, you are coming to one of the best in town."

Jackson is presently in the process of expanding that number with renovations that will begin in September. In addition to adding two rooms, he will be able to add central air, relocate the deck, make his space ADA compliable, and expand the footprint of his lobby and bar. "I love the sweaty moments that are created by having no AC. But we're getting hotter as a planet, and people are used to air conditioning as a norm."

One trend that Jackson has happily embraced is that of Crew's Quarters Boarding House becoming Ptown's latest social space. In a time when socializing is hooking up on Sniffies, he has seen his bar become a great place for some old school socializing, the bar and patio packed during the season with those looking for a spot between TDance and late night activities. To enhance the experience, and to the enjoyment of many, Jackson projects movies onto the white wall of an adjacent building, so don't be surprised to see Marlon Brando or Tab Hunter larger-than-life while enjoying a cocktail.

"The bar is a central spot for people to connect. And I think it's a bit different than going to even just a bar, because this is so much more intimate," he says. "The way people connect today is through hookup apps. It is the way young people, and most people, connect. And they're great if you want to pick someone up, but as a way of just connecting on a more personal level, they can be limiting. So when they come in here, they realize that it's sort of like an analog experience that has some history to it. They're stimulated, motivated, turned on by it. They, they love it."

If anything, what Jackson is doing is bringing a Club Cumming vibe to Provincetown (Club Cumming is the East Village club run by actor Alan Cumming, where he hangs out when he can). A welcoming social space with a masculine edge, that is. "I am creating what would have been around for us in the decades before Stonewall. My idea is to recreate the bad boy sailors' tavern at the end of the jetty, but also bring a bit of urban cool into the middle of picture perfect Cape Cod. I am very much focused on creating a story and protecting a legacy, and I wanted to provide to the guests an experience that I don't think they have been offered in a gay context before. I'm keeping a gay legacy alive here, and I'm providing something that is more than just a nylon flag from Amazon."

And as for painting his residence black, Jackson has received some validation in a town where cookie-cutter Cape Cod vistas prevail. "I recently spoke to my contractor, who said to me that they've gotten five requests for the Crew's Quarters Boarding House treatment. So you see little black houses popping up around town now."

Check out the Crew's Quarters Boarding House's website for more.

Also visit its Instagram for a curated visit to the queer past that the Rooming House evokes.