Pride in Boston lives in contrast—in the rush of a parade and the quiet of a neighborhood café, in the city’s layered past and the voices reshaping its future. June doesn’t just arrive; it gathers—across rooftops, sidewalks, bookstores, galleries—and asks you to take part in your own way.

At The Whitney Hotel, tucked into the quiet charm of Beacon Hill, you’re perfectly placed to take it all in—from the energy of the city to the stillness between. Each night offers a return to something quieter: thoughtful design, intuitive comfort, and a slower kind of luxury. And when you’re ready to step back into it, the city opens wide, with something new waiting around every corner.

A Month of Moments, Citywide

Boston Pride unfolds over days and across neighborhoods, offering a rich calendar of events to discover at your own pace. Plan a weekend or stretch it across the month—the city’s Pride programming is as varied and vibrant as the community it honors. 

Expect themed drag brunches that blend performance and play, rooftop parties where DJs and disco lights set the tone, and walking tours that trace the legacy of LGBTQ+ voices through historic streets. Join in on cookie decorating workshops, open-air music festivals, and the beloved Big Queer Picnic—a midday gathering as joyful as it is grounding. The season culminates in Beach Pride, a sun-soaked sendoff where celebration meets seaside serenity. 

June 9: Pride Night at Fenway

An essential chapter in Boston’s Pride Month, Pride Night at Fenway brings together culture, camaraderie, and the timeless thrill of a ballgame—all under one banner. Arrive early for the Pride Party on the Sam Deck, featuring entertainment and exclusive merch—including a Red Sox cap in Pride colors, with limited-edition jerseys for VIP guests.

Before the game, stop by Cathedral Station, a laid-back gay sports bar and neighborhood pub with a welcoming patio and classic game-day fare. It’s the perfect prelude to an evening that honors both Boston’s traditions and the people shaping them today. 

June 14 Weekend: The Heart of Pride

Amid a month of festivity, June 14 stands apart—a day when the city moves in unison and Pride takes to the streets.

Start the day at Boston Common with the Road of Rainbows 5K. Racing in glitter or cheering in sneakers, you’ll find yourself right at home in this treasured city tradition—open to all, built for everyone.

As the afternoon unfolds, the heart of the celebration moves to the Boston Pride for the People Festival & Parade. Organized by a volunteer-led collective, the event champions equity, culture, and the rich spectrum of LGBTQ+ identities. The parade winds through the city with unmistakable energy, culminating in a lively festival filled with local performers, food, neighborhood organizations, and more.

This is Boston in full voice—bold, layered, and proudly itself. 

All Month: Discover Queer-Owned Boston 

At The Whitney, we believe the most memorable experiences are personal, shaped by the people and places that give a city its character. Throughout Pride Month—and beyond—we invite you to explore Boston’s dynamic landscape of queer-owned businesses, each adding depth, flavor, and story to the fabric of the city.

A few to have on your radar: 

• FoMU: A queer co-founded scoop shop serving plant-based ice creams in bold, seasonal flavors. Perfect after the parade—or anytime the day calls for something sweet.
• Electric Lavender Art: Statement jewelry with a feminist, queer-forward lens. Think wearable art made for radical self-expression.
• Montgomery Green: A vintage reselling team offering affordable finds, inclusive sizing, and a welcoming, no-fuss vibe.
• Ethereal Hive Crafts: Small-batch soaps and bath goods from a queer-owned maker blending handmade craft with personality.

And of course, there are mainstay restaurants like Dbar, Jacque’s Cabaret, Blend, and Dorchester Brewing Company—each a gathering place with deep roots and open doors.

Our concierge is always happy to help you curate your own route through Boston. Wherever your day takes you—into a boutique, onto a barstool, or out beneath city lights—there’s something memorable waiting, and our team is here to help you find it. 

You’re Always Welcome Here

Amid the color and cadence of Pride, The Whitney offers a place to return and reset—a refined townhouse stay where detail matters, design is intentional, and comfort reigns without complication. Borrow a bicycle and pedal along the Esplanade, sip rosé beneath Beacon Hill skies, or linger over Mediterranean flavors at Peregrine—because slowing down is part of the stay. 

Come for a weekend—or linger longer—and let Pride unfold from a space that feels unmistakably yours. With generous hospitality and sophisticated simplicity, we welcome you to feel not just accommodated, but truly at home. 

This is your moment. Your Boston. Your place to stay.