The way to persevere is to focus on community
Gays About Town with Isaac MacDougal: cocktology, dance parties, Cocktail Mary's next chapter
Who: Isaac MacDougal, owner and operator of Cocktail Mary
Why: Cocktail Mary was my favorite neighborhood bar in Portland’s East End for years. Up against some challenges in their building, they closed last January. Now, Isaac has relocated the space to the “penthouse” above Oun Lido’s in the Old Port, where he’s imagining a new chapter for the space organized arocund dance parties and queer programming.
When and Where: Saturday afternoon at the new Cocktail Mary
You spent almost 15 years in Brooklyn. What was your road to Portland?
I grew up in Portland. I was born and raised in the West End, as were both my parents. I always knew I’d come back to Portland. My parents ran a sandwich shop called Vaughan Street Market from 1995 to 2015, when I moved home after my dad had open heart surgery. My parents had one employee and the two of them, so the sandwich shop did really well until the ’08 market crash. It never really recovered from that because “people stopped buying lunch”—that was what all the news was telling everyone to do.
I was ready to leave New York, but I didn’t have a compelling reason. I wasn’t thriving there anymore. I was just having fun and working in food and beverage. That was the impetus to move back. I thought, “I’m gonna give it a year. I’m gonna see if I can have a new chapter in the sandwich shop.”
How did Cocktail Mary come into the mix?
I have a background in theater, and pretty soon after moving to New York, I realized that it was going to be 10 years of me promoting myself to get new work, and it didn’t feel right. With food and beverage and with service, I got a similar sense of joy and purpose where I was engaging with people on a daily basis and feeding people, which is what my parents do. I switched careers with the intent of opening a hospitality business. I worked mostly in fine dining in New York City for 13 years. I made an effort to not stay anywhere too long, to get a sense of different types of operations.
I moved home because I needed to care for my family, and if it wasn’t the right decision, I could easily reverse it and move back to the city. But it clearly was the right decision. I found community here. I fell in love with my husband.
New York wasn’t necessarily a healthy place for me to be, and the financial burden of trying to open a business in New York City was not attainable, whereas here it felt more attainable. Also, the growth that happened in hospitality in Portland aligned with my professional growth. I had this beautiful experience of being in New York City when the cocktail renaissance was happening. Being a bartender throughout that, I was able to bring that knowledge and experience back.
What was important to you as you began making the space a reality?
There was this myth in the late 2000s and 2010s that queer spaces didn’t need to exist anymore because queer people were welcome everywhere. By the time I was able to open a place, it became clear to me that we’re losing culture as well. Having queer spaces is essential to not only our community but to the culture and broader community—understanding who we are and what we represent.
One of the things that Portland was lacking was a queer space. I grew up on Pine Street. Blackstones opened when I was 10. That was a beacon, just knowing that there was a gay bar on my street, but it isn’t necessarily a space where everyone feels comfortable. I was looking to create a space for all of the weirdos or queerdos to feel seen and wanted.
The moment I realized something like this needed to exist was the day that Trump got elected. I had very few resources, and it was a big risk to open a space for the queer community. There’s a huge queer community in Portland, but Portland’s a tiny place. There’s 60,000 people here. It wasn’t a smart thing to do with the tiny amount of resources I had, but it felt essential.
Portland is such a queer city with so few designated queer spaces. Why do these spaces matter, and what do they offer us?
They offer community. It’s important for us to have a designated space that not only is safe but also represents who we are as a community. It needs to be said over and over again that one of the things that is so wonderful about queer people is that we all have to fight, we have to shed so much to become who we are that there’s an inherent authenticity and joy in that. There’s a weightlessness to that existence that is an example, I hope, to the non-queer community.
That was also a problem with the old Cocktail Mary. The physical space was so small that I think the ally community literally didn’t want to take up space. We have a different opportunity here. I’m working hard to have our Friday dance parties be queer DJs and more queer-oriented, and then the Saturday parties bring in a broader community of DJs who bring their people in. Cocktail Mary is a queer space, but the next step that this opportunity allows us is to share what it is we’ve worked so hard to accomplish with the broader community.
The way to get through MAGA and Trump, the way to persevere, is to focus back in on community, which allows us to meet each other, get to know each other, and just come out and dance, feel joy, and remember what it is that we’re fighting for.
You’ve built such a devoted community. What do they have to look forward to?
We’re still the same Cocktail Mary. I’m using the dance party model as a way to stabilize the business financially and make sure that we’re able to be here in the long term. There were a lot of infrastructure problems in the last space. We had constant flooding from the ceiling. We often had to close. We have an opportunity at 30 Market Street where I can focus on engaging with the DJs and promoters and telling the story more actively.
I hope to build out other programming, like readings, maybe a book club, all sorts of things that we can do in this space that serve the community. I’m hoping to operate this as an event space, and potentially as a private membership club, not to make it exclusive but so that we are able to do more provocative and traditionally queer events here.
Were there particular spaces from your career that you see as models for this next stage?
I think the vibe of this particular space is very Lower East Side or East Village in the early aughts. To me, it feels warm and familiar that way. I spent 10 years at Metropolitan. There are parties that I really want to emulate, like Pat, which is a party that happens at Union Pool in Williamsburg.
Portland is such a food and beverage city, and it sees this huge influx of tourists in the summer. What do you see as challenges and as opportunities here?
One thing I haven’t mentioned, which I think is the other really exciting thing about this particular space, is the restaurant downstairs: Oun Lido’s. Bones, the chef, is queer, grew up in Portland, and started cooking at 15. The Old Port, for me growing up, wasn’t for queer people. It wasn’t even really for locals. It’s exciting and satisfying to have a business in the Old Port for our community, but also to be two businesses coexisting in one space.
I think my plan is to use as much of the money that we can pull from tourists in the summer to build the programming out in the fall. The seasonality is always a challenge for everybody in Portland. I’ve been adamant about communicating with the people in the Portland and Maine tourism boards about the fact that we don’t need any more marketing for summer tourism. You need to make people understand that hotels are $100 a night in February, March, and April, and you can get a table anywhere. There are great models in Montreal and Quebec City. Here, most businesses do 70% of their revenue in June, July, and August. We all survive on hopes and dreams and our line of credit with the bank to get through the slower months.
You’re involved with Supper Club, which recently opened. Can you talk about how that came to be?
I was originally looking at that space to move Cocktail Mary into. It was too big and felt like too much of a risk. My bar manager and head bartender, Jake Bosma, said, “What if we open something else there?” He’s known since he was 18 that he wanted this to be a career.
I’m a partner in the business, and I put in two years of sweat equity. I worked on lease negotiations, hired the designers, worked on a lot of the permitting, got our general contractor, and then we all did the build out together. To me, that was exciting because it feels almost like a socialist business.
It’s cool to see this lineage from Cocktail Mary to that team’s new venture.
I’m very proud of that. I wish that more owner operators would do things that way. It’s what we want every fucking politician to do—get the fuck out of the way and let a new generation take control, have ownership, and operate. I can be here as a resource if they need me.
Lightning round
Favorite spot in Portland?
Oun Lido’s downstairs. I like Speckled Ax for coffee. Print is the bookstore that I like to go to. Jewel Box, obviously—they were doing queer spaces way before I was and really solid mixology or cocktology before anyone else was. Loquat Shop is a beautiful space. The Washington Baths—I worked there for a number of years, and for me sauna culture was the one thing that was missing from Portland. The Russian & Turkish Baths on 10th Street in New York City were part of the reason I stayed in New York for so long because I had that as a place to unwind. It’s another beautiful way to find and build community that’s not centered around alcohol.
Current obsessions?
I have a new best friend.
Do you swim too?
I do. I haven’t in a really long time. I need to get back into swimming. I had a locker at the Y, and they threw all my stuff out, and I was like, “I’m not a member anymore.” But I swam the Peaks to Portland, and it’s my favorite way to exercise.
Other favorite queer spaces in Portland?
The Equality Community Center is a wonderful resource for people. They’re also building a 54-unit retirement home for queer people. They’re doing wonderful things for the broader queer community in general. Maine TransNet is another important organization. People’s Inclusive Welding is a school that’s specifically for queer people and people of color to train them and get them certified as welders so that they can work in the trades.
Cocktail Mary Single Jenni recipe
Isaac also shared the recipe for his favorite cocktail from the original Cocktail Mary, the Single Jenni, which is a riff on a Cosmo featuring cappelletti and “changes the whole dynamic of the cocktail.”
2 oz citrus vodka
1 oz cappelletti
.5 oz lemon
.5 oz lime
.5 oz simple
Shake, strain.
Up or Rocks.
Lemon twist.
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Reference Section
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