June 5, 2025

Summer Kickoff: Seasonal Events and Festivals in Boston This June

There’s no better time to experience Boston’s energy than June, when the city shakes off spring and comes alive with festivals, live music, and open-air events. And there’s no better place to call home during the summer kickoff than The Liberty Hotel-a former jail turned luxury lifestyle hub in the heart of Beacon Hill.

Whether you’re planning a weekend getaway or a local staycation, here’s your curated guide to the best events happening in Boston this June-plus why The Liberty makes the perfect launchpad for every summer moment.

Boston Calling Echoes Into June

While Boston Calling wraps up in late May, its impact lingers into June with a citywide buzz of live music and creative energy. All month long, you’ll find pop-up performances, album release parties, and independent music festivals echoing through neighborhoods like Allston, Fenway, and the Seaport.

After a night out, return to The Liberty’s signature scene-from craft cocktails at Clink to late-night bites in Alibi, all within a building that once held history’s rule breakers.

Boston Pride Celebrations

Boston Pride Month continues into June with vibrant parades, cultural events, and community programming across the city. The Boston Pride Parade, typically held in early to mid-June, weaves through downtown with colorful floats, live music, and powerful messages of inclusion and celebration.

Staying at The Liberty puts you just minutes from all the action-and gives you a stylish, celebratory space to refresh and recharge before heading back out.

SoWa Open Market & Art Walks

Every weekend in June, the SoWa Open Market takes over the South End with local artisans, gourmet food trucks, craft brewers, and vintage finds. It’s a must-do for travelers who love discovering new creators and soaking up the creative pulse of the city.

Pair your daytime art browsing with a return to The Liberty for a pre-dinner cocktail at The Liberty Bar, a sleek gathering spot that brings together bold design and relaxed sophistication—perfect for unwinding in style.

Juneteenth in Boston

Boston marks Juneteenth with a growing lineup of commemorative events and celebrations honoring Black freedom, culture, and community. From musical performances and art installations to educational panels and public gatherings, it’s a meaningful moment to connect with the city’s deeper stories.

As a hotel steeped in historic transformation, The Liberty offers a powerful backdrop to reflect on freedom—while enjoying the modern comforts that define today’s Boston.

Film, Food & Outdoor Vibes

June also signals the return of outdoor movie nights, open-air concerts, and food truck festivals across Boston’s neighborhoods and green spaces. Grab a blanket, bring your appetite, and join locals in enjoying the longer evenings along the Charles River Esplanade or at events like Boston Harborfest, which begins late June and builds into Independence Day celebrations.

Staying at The Liberty puts you just steps from the Charles River, with complimentary bikes available for exploring at your own pace-or snapping skyline selfies on your way to your next summer moment.

Where Culture Meets Character: The Liberty Hotel

With its bold design, rich history, and unmatched location in Beacon Hill, The Liberty Hotel offers the perfect balance of Boston tradition and modern luxury. This summer, enjoy spacious rooms with floor-to-ceiling windows, vibrant on-site dining and nightlife, and quick access to the city’s best seasonal events-all while staying somewhere that’s anything but ordinary.