LGBTQ Travel Guide: Boston

"Boston Strong" is also very much "LGBTQ Strong," thanks to a thriving, diverse community, queer-inclusive events-rich calendar, sports leagues, and progressive spirit. The capital of Massachusetts—the state that first legalized same-sex marriage back in 2004—and its neighboring city of Cambridge also boast plenty of LGBTQ history, which is chronicled in collections and exhibitions by The History Project. There's also plus a lively young university population, and what could be the world's best chocolate chip cookie, Flour Bakery + Cafe's Chunky Lola, the name of which refers to a gay customer's bulldog.

Officially having celebrated its 50th year in 2020, June's Boston Pride Parade and Festival (the next is scheduled for June 12, 2021), caps off a weeklong series of events including the AIDS Walk, a Dyke March, and parties galore while sibling festivals include Latinx Pride and Black Pride.

Other calendar highlights include 36-year-old LGBTQ film festival, Wicked Queer, and there's typically a gay event or two that coincides with the annual Boston Marathon. For other what's ons and updated LGBTQ resources, also check out the Greater Boston Convention & Visitors Bureau website; EDGE Boston; Boston Spirit; Bay Windows;

The Best Things to Do

First, take a stroll around a couple of buzzing hoods: The Innovation District, a.k.a. Seaport District/South Boston Waterfront, and The Fenway. The latter is home to Fenway Park, and while once sketchy around that iconic home to the Red Sox has been developed over the past couple of years into a slick, fabulous eating, drinking, shopping, and residential neighborhood.

The former's anchor, Institute of Contemporary Art, was an architecturally edgy early arriver in 2006 and hosts rotating exhibitions, while admission is free Thursdays from 5 p.m. to 9 p.m. The nearby retail incubator storefront, For Now, features a curated selection of up and coming Boston small business brands including apparel and home goods. Fans of locally-crafted edibles, meanwhile, can find everything from Boston honey, chocolate, pastries, and coffee to New England's best micro-craft brews and spirits at the 35-vendor Boston Public Market, which also includes a prepared foods area.

Harvard teacher and art historian, Professor Andrew Lear, leads a two-hour "Gay Secrets of the Museum of Fine Arts" tour that can be booked through Oscar Wilde Tours. It includes admission to the Museum of Fine Arts and smashes through the Puritanism of Boston's olden days to get at a major gay 18th-century scandal, "Boston marriages," and the "sexiest Jesus of the Italian Renaissance." During June and also by private booking at other times throughout the year, walking tour company Boston By Foot offers a "Boston's LGBTQ Past" stroll, produced in partnership with The History Project, traverses landmarks and events from the 1840s to 1980s. You can also self-guide and read up about the Boston Equality Trail, which follows the route of Boston's first Pride march in 1971.

Some of Broadway's best touring productions play the historic Citizens Bank Opera House (first built in the 1920s it was restored in 2004). 2021's line-up currently includes Aaron Sorkin's take on "To Kill A Mockingbird," "Jesus Christ Superstar," and "Dear Evan Hansen." Also be on the lookout for performances by The Theater Offensive, which presents shows by and for LGBTQ people of color and youth.

Don't forget to cross the water to Cambridge for a look-see around Harvard, including its bookstores like Harvard Book Store and Porter Square Books, which carry plenty of LGBTQ-interest tomes and host readings, signings, and events.

The Best LGBTQ Bars and Clubs

"RuPaul's Drag Race" contestants Katya, Jujubee, and Charlie Hides have sprung from (or at least lived for a while) in Boston, and you can catch queens in action at Back Bay's long-standing restaurant and nightclub Club Cafe (established 1983). The Club also houses a dedicated cabaret space, the Napoleon Room, for both local and visiting performances.

Drag reigns at the residential Bay Village hood's colorful and cozy Jacque's Cabaret, which also hosts an open mic comedy showcase on Sundays (show begins 6:30 p.m.) and Wednesday karaoke buffets. Celebrating its sixth year in 2020, the South End's Trophy Room boasts a comfort food menu and signature cocktails to go along with drag brunches (on last Sundays) and Drag Race viewing parties.

Straight-friendly LGBTQ sports bar and pub Cathedral Station, opened in 2014, is where you'll spot area queer sports leagues sharing some grub, drinks, pool, and laughs both inside and, during warmer months, around the outdoor patio. And locals will note that parking is free in the rare, a major and all too rare bonus for Boston venues.

Renovated with a big tech upgrade, the two-level The Alley Bar is a favorite of bears, cubs, and their friends, with dancing action, underwear (ahem, "underbear") parties, trivia nights, and the super-popular and award-winning monthly FUZZ party (DJ Brent Covington posts his setlists on their Facebook page, for those wondering what tunes they were too slow to Shazam). Also big with the bears and bearded set, Boston Eagle is one of the city's oldest gay bars to boot.

Over in the Fenway district, the two-level Machine Boston mixes things up with themed music nights including hip-hop and 1980s, viewing parties, karaoke, and 18+ entry on Fridays and some Saturdays (check their online calendar). Although Cambridge's multi-level dance club Paradise closed to much lamentation in 2018, check out the weekly dance and drag events by promoters Gay Mafia Boston, which take place in various locations and include Hot Mess Sundays at Candibar, Latino Wednesdays at Legacy, and more.

The Best Places to Eat

Before the awards were canceled, the 2020 James Beard Foundation Awards semifinalist list included two queer Boston chefs. Tifani Faison, who made a national splash on "Top Chef's" maiden season in 2006, heads up Fenway district's "adult snack bar" Fool's Errand, Sweet Cheeks family-style barbecue, and Southeast Asian-inspired Tiger Mama (with more openings on the way). The second nod went to South Boston's enoteca and pasta haven, Fox & Knife, which opened in 2019 and whose owner and chef, Karen Akunowicz, also graced a season of "Top Chef" (in 2015) and won the James Beard Award for Best Chef: Northeast 2018.

The casual-style Eventide Fenway—a spinoff of Portland, Maine's Eventide Oyster Co.–presents a ridiculously tasty spin on seafood, including a brown butter lobster roll and fish and chips.

Downtown Crossing's far more formal Ruka, meanwhile, is downright cinematic with eye-popping decor and specializes in Nikkei (Japanese-Peruvian fusion) cuisine.

Fans of urban markets and local-centric food concepts should definitely check out the Time Out Market Boston, which opened in 2019. Its more than 15 offerings include creative twists on chicken and dumpling dishes at Ms. Clucks Deluxe, from James Beard Award-winner Tim Cushman, and scrumptious lobster rolls (cold with mayo or warm in butter sauce) and sinful clam-pork belly chowder at Saltie Girl.

And don't forget dessert! With locations in Boston and Cambridge, Flour Bakery + Cafe is a must for its delectable Chunky Lola chocolate chip cookie, a delectable modern take on the Boston cream pie, and many other sweets as well as savories and fantastic coffee.

Where to Stay

Perched on the Innovation District's waterfront, Autograph Collection’s 136-room The Envoy sports incredible floor to ceiling views from its comfortable, ultra-functional, and smartly designed rooms. Urban and slick with dashes of earthiness (leather, wood, metal), the property is also home to a fantastic rooftop bar (reservations strongly recommended during summertime!) and lobby-level restaurant and bar Outlook Kitchen.

Opened in 2020 and occupying a glassy 61-story skyscraper, the 215-room Four Seasons Hotel One Dalton Street stands high above Back Bay (and is just across the street from a Flour bakery/cafe!), and is rich with perks and details. Floor-to-ceiling window views, an indoor swimming pool, two restaurants on the second floor - a location of chic Japanese Izakaya Zuma, and One + One - and lobby bar.

Completely renovated in 2018, Beacon Hill's 190-room Kimpton Nine Zero is another excellent boutique property, just off the Boston Common park. Each room includes an Eames chair, while suites include perks like vinyl records and players and telescopes. Back Bay's gay-owned Oasis Gay House and Adams Bed & Breakfast spread their 31 rooms over four neighboring brownstone buildings.

If you're keen on catching a game at Fenway Park or are a big music fan, consider The Verb, a retro-chic rock 'n' roll-themed 93-room boutique property. Opened in 2014 (in a former 1950s motor inn), it boasts an outdoor pool and complimentary access to the nearby Boston Sports Club and is in easy walking distance to gay nightclub Boston Machine.