The LGBTIQ+ travel guide to Boston: the best gay bars, drag events and more

Thanks to its cosmopolitan nature and outstanding learning institutions, such as Harvard and MIT, Boston has long been a hub for progressive thinkers and the LGBTIQ+ community. In fact, Massachusetts was the first US state to legalize gay marriage back in 2004.

To this day, Boston remains one of America’s most LGBTIQ+ friendly cities and has a large queer community actively shaping the city's future, ensuring it remains one of the world’s foremost gay destinations for generations to come.

The best LGBTIQ+ bars and clubs in Boston

Boston has a wide array of LGBTIQ+ bars and clubs, but the most notable is easily Jacques Cabaret. Located in a small neighborhood that’s smooshed between the Theater District and Chinatown, Jacques is Boston’s oldest operating gay bar and the city’s premier establishment for drag shows. In fact, drag superstar Katya Zamolodchikova got her start here before shooting to international fame on season 7 of RuPaul’s Drag Race.

With a giant red neon "Jacques" sign behind the bar and an intimate stage that’s surrounded by tables, Jacques hosts drag events seven nights a week, from variety shows to comedy nights, karaoke, Drag Race watch parties, and more.

For a more varied scene, head over to Club Café. Housed within a beautifully restored factory building in Boston’s busy Back Bay neighborhood, Club Café is actually composed of multiple spaces. The main area serves as a restaurant that dishes out New England fare like lobster mac 'n' cheese, crispy calamari, crab cakes, and more, while also doubling as the main space for nightly events like viewing parties and bar trivia. Also in Club Café is the Napoleon Room, which is Boston’s only true cabaret and sees nightly live piano performances and lounge singers.

As evening turns to night, Moonshine, Club Café’s thumping DJ-fueled club, opens up and Boston’s young LGBTIQ+ crowd comes out to dance the night away at weekly parties like Club Café Fridays and the Fourth Saturday events.

My personal favorite LGBTIQ+ hangout is dbar. The space is a restaurant during the early evening hours and is popular amongst the locals, both gay and straight. But as the sun goes down, the restaurant transforms into “dbar After Dark”. After the restaurant finishes serving dinner, bright neons infuse with the purple glow of black lights and DJs turn dbar into a hardcore club. On certain nights, dbar After Dark even hosts events, like show tunes night, karaoke, and special parties.

As a fan of dbar’s weekend brunch (you must try their huevos rancheros), I can attest that even during the day and evening hours, dbar's clientele is mostly LGBTIQ+. Also, it’s located just a few blocks away from the Savin Hill T station and the beach, making it a great way to spend an afternoon (and night if you feel like dancing!).

Excellent LGBTIQ+ spaces beyond the clubs

One of the city’s most inclusive spaces is Trident Booksellers & Cafe. Located on Newbury Street, Boston’s famous shopping street where all the stores are built into historic brownstone homes, Trident walks a tightrope somewhere between hippie-chic and classic New England.

Trident’s two floors are loaded with a huge collection of books, with selections for BIPOC, LGBTIQ+, and AAPI communities, and it is committed to being a safe space. Plus, with its cafe and weekly events that include Drag Race trivia nights, book readings, and even speed dating, Trident is more than just a bookstore, it’s an inviting community hub. But be warned, weekend afternoons can get very busy when tourists start meandering down Newbury Street. Visit during the week if possible.

For some delicious food, Tiffany Faison is one of the most celebrated chefs in Boston. She competed on Top Chef and later became a judge on Chopped. She’s also a lesbian and has been involved in the fight for equal rights for decades. She operates a few restaurants in Boston, but her most famous is Sweet Cheeks Q.

Sweet Cheeks was Faison’s passion project to bring her family's southern cooking up to Boston. Now, the restaurant is renowned for its house-made biscuits, buttermilk fried chicken, and succulent selection of BBQ-like smoked ribs, pulled chicken, and pork belly. During June, Sweet Cheeks even serves rainbow pride cake.

Inside, the restaurant looks like a glammed-up southern roadhouse that’s decked out with lots of metal and exposed wood, along with hanging camp lights and the smell of barbecue in the air. This is all juxtaposed by the fact that Sweet Cheeks is built in a new high-rise building in the now very trendy Fenway neighborhood and is surrounded by towering apartments, hotels, and even a Lucky Strike.

How to find the LGBTIQ+ community

Sadly, due to complaints of racism, Boston Pride was dissolved in early 2021, and the city hasn’t had a main Pride event or organization for the last two years. It’s been a major blow to the LGBTIQ+ community, but at the same time, will hopefully result in the creation of a new, more diverse Pride alliance.

This does mean, however, that the city no longer has a centralized organization to host events and share info, potentially making it more difficult for visitors who are arriving in the city and looking for resources. But with a bustling and hardworking local population, the queer community is sure to only grow stronger by addressing the issue.

Two locals working to make Boston’s LGBTIQ+ community even better are Eric Tingdahl and his husband Joe Haley, who own and operate a fabulous B&B called the Oasis Guest House. The Oasis is a great place for anyone looking to get the feel of actually living in Boston. Built into an old brownstone, the Oasis isn’t the fanciest, newest, or the sleekest stay in the city, but it does give you a feel of what it’s like to live in a traditional Boston home. Both Eric and Joe are active members of the community and strive to better the city through activism and their involvement on neighborhood committees.

Best of all, the Oasis is located in the Fenway neighborhood, just a short walk away from Fenway Park and all the restaurants and shopping opportunities in Back Bay. Staying at the Oasis not only helps support a local LGBTIQ+ business, but Eric and Joe are also incredibly friendly and will give you an in-depth knowledge of the city that big-brand hotels never could.

If you're visiting during the summer months, you'll want to take a 90-minute boat ride from Boston to Provincetown (often called P-town), a small town at the very tip of Cape Cod. This is where you’ll find New England’s largest LGBTIQ+ community. It’s filled with an endless array of gay bars and clubs, and tons of LGBTIQ+-owned restaurants, inns, B&Bs, and more. In fact, P-town is known as one of the “gayest places on Earth''.

It’s a magnet for LGBTIQ+ East Coasters, including celebrities like John Waters, who spend their entire summers there. Others stay for a week, and some just a weekend. If you’re visiting Boston during the summer and notice a surprising lack of LGBTIQ+ folk, you’re probably going to find them in P-town.

Save the date: Boston’s best LGBTIQ+ events

Boston may not have the large-scale annual Pride celebrations any longer, but there are still a few events worth checking out. BAGLY, an LGBTIQ+ organization that helps queer youth puts on an annual Heels for Hope drag show every June, with all proceeds going towards the group.

The Boston LesbiGay Urban Foundation is another group that has continued to put on queer events and offer support to locals after the dissolution of Boston Pride. The group seeks to help inspire and nurture LGBTIQ+ people, especially those from BIPOC communities, and those who come from undeserved backgrounds. It hosts a variety of events each year, and every June puts on a massive Urban Pride celebration that spans a whole week and is filled with parties, concerts, conferences, and more.

What LGBTIQ+ travelers need to know before going to Boston

It’s important for queer travelers to remember that, even without Boston Pride, Boston is still one of America’s most progressive cities, and some of its surrounding communities, like Cambridge, are even more progressive. Seeing Pride flags and BLM signs hanging in apartment windows is common, and world-class universities like Harvard, MIT, and Boston University continually bring in a new generation of young residents.

Something all visitors should also note is that Boston is known for its history, arts, and sports, and no trip to the city would be complete without exploring the best things to do. In fact, it's home to so much history that many visitors make entire weeklong vacations to the city simply to experience it all. The Isabella Stewart Gardner Museum is one of the best art museums in the world, and also one of the most famous thanks to the infamous 1990 heist where 13 pieces were stolen, including works by Rembrandt and Degas.

The Boston Red Sox (and Fenway Park) are also an important and beloved part of Boston history, and The Freedom Trail tells the story of America’s independence. For those who are looking to explore both history and the LGBTIQ+ community, Boston By Foot hosts a Boston’s LGBT Past tour, which guides visitors through the city’s hidden queer history, going back to the 1840s. The tours are held in June and on certain weekends throughout the year, and can be booked individually year-round.

Resources and info for LGBTIQ+ visitors

Fenway Health is one of Boston’s major healthcare providers and is the main source of healthcare and testing for the LGBTIQ+ community. In fact, Fenway Health is actually one of the global leaders for LGBTIQ+ healthcare and research, and has hosted numerous studies that have changed the world forever – it even ran many of the early PrEP studies, which helped doctors verify that the drug was safe to use, offering the first real hope of ending the HIV/AIDS epidemic for good.

Now, LGBTIQ+ people can get free STD and HIV testing at the clinic, even if they have no insurance, and can receive free PrEP medication if needed. Throughout the year, Fenway Health also hosts fundraising events, social gatherings, and special symposiums, so keep an eye on its events page.

For the trans community, the MTPC (Massachusetts Transgender Political Coalition) is a great resource and puts on tons of events every month. It’s a great way to meet others within the trans community and learn more about Boston’s trans and nonbinary scene.