The best things to do in Boston this weekend: July 24–26

Boston’s Puerto Rican Festival transforms Franklin Park into a kaleidoscope of color, music, and movement, anchored by a parade that pulses through the city with infectious energy. The air fills with the rhythms of salsa and bomba, while the scent of lechón and pastelillos drifts from food stalls run by local families. Artisan vendors line the walkways, their tables crowded with handwoven crafts and vibrant prints that nod to the island’s heritage. Community groups take the stage, weaving together dance, poetry, and storytelling that speak to both tradition and resilience. The festival’s scale is unmistakable, drawing tens of thousands who gather not just to watch, but to participate in a living tapestry of Puerto Rican identity. It’s a weekend where Boston’s cityscape feels unmistakably Caribbean, if only for a few days.

There are plenty of road races in Boston, but only one lets you charge through the gates of Fenway Park and finish at home plate. Run to Home Base turns one of the city's most iconic landmarks into the final stretch of a 9K run and 5K run and walk, giving participants the rare chance to experience the ballpark from a player's point of view. The annual event raises funds for Home Base, a program of the Red Sox Foundation and Massachusetts General Hospital that provides care and support for veterans, service members, military families, and families of the fallen. The atmosphere is unmistakably Boston, with Red Sox pride, cheering crowds, and a sense of purpose woven into every mile. Even if you've been to countless games at Fenway, crossing home plate on your own two feet is an experience few fans ever get to claim.

On the best Sundays of summer, Newbury Street belongs to people instead of cars. Open Newbury transforms the Back Bay's most famous shopping street into a mile-long pedestrian promenade, where strolling becomes the main event and every block feels a little more alive than usual. Boutiques roll open their doors, restaurants spill onto the sidewalks, and local businesses bring the street to life with pop-ups, performances, and outdoor activations that change from week to week. Whether you're shopping, grabbing brunch, or simply people-watching, the lack of traffic completely changes the rhythm of the neighborhood. Stretching from Berkeley Street to Massachusetts Avenue, it's a reminder of just how enjoyable Newbury can be when there's room to wander. If there were ever a day to ditch your plans and see where the afternoon takes you, this is it.

The Cambridge Jazz Festival has spent more than a decade proving that world-class jazz doesn't need a ticket price. Returning to Danehy Park for its 11th year, the free, two-day festival brings together Grammy-winning artists, rising talent, and local musicians for an afternoon of performances that span traditional jazz, Latin rhythms, global influences, and contemporary sounds. This year's lineup includes Paquito-inspired Brazilian music from TRIAD+, vocalist Kavita Shah, percussionist Eguie Castrillo, saxophonist Tia Fuller, and the Berklee Global Jazz Quartet, among many others. Families can make a day of it with food vendors, a beer garden, children's activities, and wellness programming woven into the festival grounds. The relaxed park setting makes it easy to drift between performances or settle in for an entire afternoon of music. Whether you're a longtime jazz fan or simply looking for a great free summer festival, this is one of the season's standout weekends.

Hundreds of glowing lanterns drifting across the water make for a scene that's hard to forget. Light the Night: Water Lantern Festival invites participants to decorate a floating lantern with messages, memories, or wishes before releasing it onto the water alongside hundreds of others at dusk. The evening unfolds at an easy pace, with food vendors, music, and time to gather with friends and family before the lantern launch becomes the focus of the night. As daylight fades, the individual lanterns come together to create a quiet, shared moment that feels surprisingly personal despite the size of the crowd. It is equal parts art installation, community gathering, and summer tradition, with the illuminated water providing a backdrop that photographs can never quite do justice.

Who says Christmas has to wait until December? Deck the Hulls flips the calendar on its head with a holiday-inspired boat parade that sends illuminated vessels gliding across Boston Harbor in the middle of summer. Created as part of Boston's 250th anniversary celebrations, the inaugural event invites boaters to dress up their vessels while spectators claim spots along the Harborwalk, waterfront parks, and piers to watch the procession unfold. As dusk settles over the harbor, the glowing flotilla provides an unusual backdrop against one of the city's most recognizable skylines. It's equal parts nautical spectacle and seasonal novelty, proving that festive lights feel just as magical in July as they do in winter. Boston has no shortage of events on the water, but this one stands out for embracing the unexpected.

An Idiot’s Guide to Wine pairs sharp stand-up with a guided tasting, all orchestrated by comedian and certified wine buff Merrick Watts. The show unfolds at Nick’s Comedy Stop, where Watts uses his WSET Level 3 expertise to lead the audience through six distinct wines, weaving tasting notes with punchlines. The format sidesteps the usual wine snobbery, instead inviting guests to laugh at the quirks of wine culture while actually learning something about what’s in their glass. Each pour comes with a story or a joke, making the experience as much about the comedy as the cabernet. The crowd is a mix of curious drinkers and comedy fans, all drawn in by the promise of a night that’s equal parts education and entertainment. It’s a rare chance to taste, laugh, and maybe leave a little wiser.

If you've ever wandered through the North End in July or August and heard a marching band before you saw it, chances are you stumbled onto one of the neighborhood's legendary feasts. St. Joseph's Feast has been carrying on that tradition for more than a century, filling the streets with live music, Italian street food, and one of Boston's most cherished religious processions. The statue of St. Joseph winds through the neighborhood as bands play, families gather, and generations of locals keep long-standing traditions alive. Between the music and the processions, the streets are lined with vendors serving everything from arancini and grilled sausage to cannoli, zeppole, and other Italian classics. It's loud, crowded, and wonderfully nostalgic, capturing the spirit of the North End at its very best. Come hungry, but don't be surprised if it's the atmosphere that sticks with you long after the last bite.

Movie nights have a way of bringing strangers together, especially when they're under the stars. Summer Flicks turns the Prudential Center's South Garden into one of Boston's most inviting outdoor cinemas, where free Saturday screenings begin at dusk after live music sets the mood from 6:30 p.m. The lineup spans everything from nostalgic favorites to crowd-pleasing blockbusters, giving people plenty of reasons to return throughout the summer. Bring a blanket, grab dinner from one of the Pru's many restaurants, and settle onto the lawn. It's one of those classic Boston summer traditions that never seems to lose its charm.

Boston looks a little different from 750 feet in the air, especially when it's dressed for summer. Summer Reimagined transforms View Boston's 52nd-floor observation deck with bold floral installations, colorful immersive design, and interactive spaces that put a fresh spin on one of the city's best views. The experience goes beyond the scenery, with seasonal cocktails, live entertainment, and the Golden Hour Series bringing extra energy to sunset from Thursday through Saturday evenings. On select nights, the open-air rooftop also hosts DJs from Big Night Entertainment Group, turning the skyline into the backdrop for a sky-high night out. The installation is included with general admission, making it easy to pair with the observation deck's sweeping 360-degree views. Even if you've been to View Boston before, this seasonal makeover gives you a new reason to head back to the top of the Prudential Tower.