An LGBTQIA+ Travel Guide to Boston

The city continues to serve as a thriving metropolis for queer people from New England and beyond.

Dorchester Brewing Company

From cutting-edge technological advances in the medical field to sowing the tea-soaked seeds of the American Revolution, Boston and the surrounding Bay State have always been at the forefront of change—and LGBTQIA+ rights are no exception. In 2004, the Commonwealth of Massachusetts made global headlines as the first US jurisdiction to legalize gay marriage, sparking a nationwide movement that would usher in a new era of much-needed legal recognition for LGBTQIA+ people.

Nearly two decades after this monumental decision, the city of Boston continues to celebrate Pride month and serves as a thriving metropolis for queer individuals from New England and beyond. Whether you’re searching for a new place to call home or just stopping by for a quick weekend in the city, Boston is certain to leave a lasting impression.

Explore Boston’s craft beer scene at Dorchester Brewing

There’s so much to love about Boston’s largest neighborhood, but for certified beer aficionados, the multistory, gay-owned Dorchester Brewing Company is sure to top the list. The spot comes equipped with its very own rooftop greenhouse along with an idyllic open-air patio that provides a stellar view of the Boston skyline. But a brewery is ultimately only as good as its beer—and fortunately for visiting hopheads, the brews around here are pretty stellar. For first-time imbibers, the ultra-crisp Dad’s Lite Lager serves as the perfect starter beer, while the heavy O.F.D DIPA (Originally From Dorchester) is the perfect pairing for a rack of ribs from its in-house diner, M&M BBQ.

Sweet Cheeks Q

Dine in style at Boston’s finest gay-owned restaurants

Nothing in life quite compares to fine food and drink enjoyed in the company of others, but for a little added satisfaction, be sure to spend some time at one of the city’s many queer-owned dining venues. Just a few steps from Fenway Park, the vibrant Sweet Cheeks Q is a top spot for tantalizing Texas-style barbecue—including heritage breed pulled pork, smoked beef short ribs, and smoked Delaware chicken—all crafted at the behest of founder, restaurateur, and Chef Tiffani Faison. In the mood to watch the big game with a fresh pint in hand? Cathedral Station has got your back. Located in the South End, this gay sports bar has become a neighborhood favorite thanks to its laidback atmosphere, plentiful bar games, and decadent pub fare.

Take a stroll along the Boston Equality Trail

While the famous Boston Freedom Trail pays homage to the many historic sites that played a role in the Revolutionary War, the Boston Equality Trail traces the route taken during the city’s very first Pride parade, a radical 1971 event that marked a major tipping point for LGBTQIA+ recognition within the commonwealth. The route includes a wealth of iconic attractions, like the gold-domed Massachusetts State House, where Congresswoman Elaine Noble served as the nation’s first LGBTQIA+ state legislator, but also highlights the bygone social clubs that served as safe spaces for LGBTQIA+ people during a hostile period, ranging from the 1940s-era gay bar Jacque’s to the Napoleon Club.

Educate yourself on Boston’s LGBTQIA+ past with The History Project

Boston may be a bastion of queer culture in the modern era, but the unalienable rights and widespread acceptance that the city enjoys today didn’t emerge out of thin air. Just a few decades ago, countless LGBTQIA+ people put their safety and personal relationships on the line in the battle for equality—a fact that The History Project has gone to great lengths to document since 1980. Back in 1996, the organization’s Public Faces/Private Lives exhibit drew over 50,000 visitors to the Boston Public Library, showcasing close to 400 years’ worth of queer documents, personal accounts, and other artifacts. Today, the organization runs regular events highlighting the commonwealth’s LGBTQIA+ history examined through a multitude of different lenses.

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Immerse yourself in the world of natural wine at Rebel Rebel

Natural wine is having a moment, and for those who are curious about this newly-booming industry, no spot in Boston quite compares to Rebel Rebel. Housed in Somerville’s Bow Market, this cozy wine bar offers an unparalleled opportunity for visitors to get schooled on the principles of natural winemaking—and it’s all thanks to owner Lauren Friel, whose extensive array of wines has been carefully selected to highlight some of the most badass women winemakers working across the US. Whether you swear by the restorative power of natural wine or don’t quite consider yourself a believer, Rebel Rebel is here to welcome you with open arms.

Dance the night away at the city’s hottest gay clubs

Whether you’re looking for love or just trying to jam out to some Tinashe and Rina Sawayama with your girls, Boston is certain to have an LGBTQIA-centric haunt with your name on it. One particular mainstay in the local gay scene has been gracing the Back Bay district since 1983: Club Café. A purveyor of tasty American fare by day, this colorful venue transforms into one of the city’s most animated queer hangout spots on Friday nights. To double your fun, local favorite Trophy Room is just a few minutes down the street, serving as a popular pregame spot before the lively night begins.

Josh Camarco/Helix Pinecomb Photos

Start your day off with a bang at drag brunch

Stunning outfits, flawless makeup, and abundant mimosas on a Sunday morning—what more could you want in life? While drag brunch has seen newfound popularity across the city over the past couple of years, it was Beacon Hill-based Carrie Nation Cocktail Club that first embraced the trend back in 2017, launching the electric Drag Me To Brunch series and its action-packed performances each Sunday. After a lengthy pandemic-induced hiatus, Carrie Nation’s weekly shows relaunched last summer, inviting Bostonians from far and wide to get their brunch on in the most extravagant setting you could possibly dream of.

A. Priori Photography

Enjoy a flawless performance by the Boston Gay Men’s Chorus

Two hundred individual voices become one in the Boston Gay Men’s Chorus, a highly-acclaimed choir that’s been laying down complex harmonies since 1982. While the group has found major success in their native Boston, drawing more than 10,000 live listeners each season (in a normal year, at least), their resounding success has reached global levels, becoming the first LGBTQIA+ choir to perform in the Middle East back in 2015. This month, the choir returns to the stage for the first time after a 30-month COVID hiatus to celebrate Pride through the iconic music of Disney—a first-of-its-kind collaboration with Disney Concerts.

Take a day trip to P-Town, the queer capital of New England

Once home to a booming whaling industry in the 1800s, the Cape Cod village of Provincetown was a thriving hub for LGBTQIA+ culture, even in the mid-1900s—ultimately becoming one of the nation’s foremost destinations for gay tourists. Today, the town is a veritable treasure trove of bars—including Harbor Lounge, The Squealing Pig, and Old Colony Tap, just to name a few—but it’s P-Town’s classic coastal Cape Cod beauty that makes it worth visiting. Downtown Provincetown may be prime bear and otter territory, but the outskirts of the village are a paradise for visiting wildlife enthusiasts, with ample opportunity to spot piping plovers, harbor seals, and a wealth of other native New England species lounging on the shore.

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