The best things to do in Boston in September 2026

Step through the gates of King Richard's Faire and leave modern-day Massachusetts behind for a full day of medieval revelry. Set across 200 wooded acres in Carver, New England's largest Renaissance festival brings together armored jousting tournaments, live music, comedy, fire performers, artisan markets and costumed characters who roam the grounds in character. With more than 70 daily shows across 11 stages, it's easy to spend hours wandering between taverns, demonstrations and interactive performances, stopping for a turkey leg or a mug of mead along the way. Each weekend features a different theme, from pirate takeovers and wizard gatherings to Viking celebrations, giving returning visitors a fresh experience throughout the season. Whether you arrive in full costume or everyday clothes, King Richard's Faire offers an immersive escape that feels worlds away from the city.

Karol G's return to Gillette Stadium on September 12 is one of the bigger Latin music nights on the fall calendar, but the interesting part is what she is bringing with her this time. Viajando Por El Mundo Tropitour marks her first Foxborough show since 2023, with Elena Rose joining the bill. The 7pm start gives the night a proper concert scale, while the stadium setting makes sense for an artist whose shows have become increasingly elaborate. For Boston fans who caught Karol G's last stadium appearance, this is a chance to see how the production has evolved rather than simply repeat the same night.

Wicked flips the Oz story you think you know, digging into the tangled friendship and rivalry between Elphaba and Glinda long before Dorothy ever dropped in. The show’s been packing houses for years, but there’s a reason locals keep coming back: the production’s sly humor and sharp political edge still feel fresh, even if you’ve seen it before. The set design is a spectacle in itself, with clever visual nods to the original film and enough detail to reward a second look. If you’re the type who usually skips big musicals, this one’s worth reconsidering. The script’s wit lands with a local crowd, and the score has a way of sticking with you for days. It’s a rare blockbuster that actually earns its hype, and seeing it live is a reminder of how much fun a night at the theater can be.

Boston Lights turns Franklin Park Zoo into an evening walk through illuminated displays, giving the zoo a very different purpose after dark. The appeal is seeing familiar paths and animal habitats transformed by large-scale light installations, with the route designed more for wandering than rushing from one exhibit to the next. It is an easy choice when you want an outdoor night out that feels distinct from the usual summer plans, particularly with kids or visiting friends who have already done the standard Boston sightseeing circuit. The zoo itself becomes part of the experience, even though the focus shifts away from the animals and toward the lights. Go after sunset so the displays can do the work, and give yourself enough time to take the route at an unhurried pace. It is less about checking off attractions and more about having a reason to linger in the park after dark.

Charli XCX’s live shows have always felt like a party you actually want to be at, and this tour is shaping up to be her most unapologetically fun yet. She’s rolling through with a setlist that leans hard into her new era—think maximalist pop, clubby beats and a sense of chaos that’s more calculated than it looks. If you’ve caught her before, you know she’s not interested in nostalgia trips or safe choices. Instead, she’s doubling down on the hyperpop edge that’s made her a cult favorite, with visuals and production that feel more like a warehouse rave than a standard arena gig. The crowd here isn’t just along for the ride—they’re part of the spectacle. If you want a night that feels like the future of pop, this is the one to circle on your calendar.

Festival Viva México is a good excuse to spend an afternoon celebrating Mexican culture through food, music, dance and community rather than treating Mexican Independence Day as a one night affair. The 2026 festival brings together Mexican vendors, performers and local organizations for a family friendly gathering, with traditional food and cultural programming at the center of the day. It also lands at a useful point in the calendar, just before Mexican Independence Day on September 16, making it a natural kickoff to the city's wider Hispanic Heritage Month programming. For Boston's Mexican and Mexican American communities, the appeal is as much about gathering as entertainment. For everyone else, it is a chance to discover local businesses, performers and community groups in one place. If your September plans lean toward neighborhood events with a strong sense of place, this is one worth making time for.

Craig Robinson’s comedy has always had a musical streak, and that is a big part of what makes his live shows worth catching. Best known for his work on The Office and a long list of film and TV roles, Robinson brings a mix of stand-up, crowd work and music to the stage rather than sticking to a conventional comedy set. The live format gives him plenty of room to play, especially when he gets behind the keyboard. His shows can move quickly between jokes and songs, with the audience becoming part of the rhythm. For anyone who knows Robinson mainly as an actor, seeing him in a room built around his own material is a different experience. It is loose, interactive and more unpredictable than a standard theater comedy show, making this a solid pick for a night when you want your stand-up with a little more variety.

If you think you know Revere Beach, the annual Art Festival will make you look twice. The usual boardwalk bustle gives way to a pop-up gallery of local talent, with artists setting up shop right on the sand. The Live Art Competition is worth lingering for: you’ll see painters and illustrators racing the clock, brushes flying, with the Atlantic as their backdrop. It’s not just about browsing—kids and adults can get their hands dirty with interactive projects, and the live music lineup is reliably eclectic, skipping between genres as easily as the gulls overhead. The festival feels less like a formal art fair and more like a neighborhood block party, only with better views and a salty breeze. If you’re looking for a reason to spend a Saturday by the water, this is the one that actually delivers something unexpected.

Dermot Kennedy’s shows have a way of sneaking up on you. One moment, you’re in a packed room, the next you’re caught off guard by the rawness in his voice and the way he can turn a lyric into a gut punch. He’s not here to coast on streaming numbers or radio hits—his live sets are built for people who want to feel something, not just sing along. If you’ve only heard him through headphones, you haven’t really heard him. The production is polished but never slick, and there’s a sense of urgency that doesn’t let up. Kennedy’s knack for balancing vulnerability with anthemic hooks means you’ll leave with at least one line stuck in your head, probably for days. If you’re after a night that feels both intimate and massive, this is the ticket.

The Jonas Brothers are rolling into town, and if you haven’t caught them live since their Disney Channel days, you might be surprised by how much their sound—and their audience—has grown up. Their shows have become a kind of communal nostalgia trip, but with enough new material and sly humor to keep things feeling fresh. You’ll spot longtime fans belting out the early hits, but don’t be shocked if you find yourself singing along to the newer tracks, too. The setlists tend to be generous, and the brothers have a knack for making even the biggest arena feel a little more intimate. If you’re looking for a night that’s equal parts throwback and present-day pop spectacle, this is one of those rare big-ticket concerts that actually delivers on the hype. Just don’t wait too long—these tickets won’t last.

Few settings beat Boston Harbor at sunset, especially when the soundtrack jumps from nostalgic singalongs to festival-ready EDM drops. Remix & Rewind transforms the Provincetown II into a floating dance party, with multiple decks of music, skyline views and plenty of room to keep the energy going as the boat cruises through the harbor. DJ Gilly spins crowd-pleasing throwback pop, hip-hop, folk and country remixed into club anthems, while Seifer keeps the house grooves flowing on another deck, giving partygoers a reason to explore the ship between sets. Whether you're there to dance from departure to docking or simply soak in the city views with a drink in hand, the combination of music and waterfront scenery makes for a memorable night out. Just be sure to arrive before boarding, because once the boat leaves the dock, the party sails without you.

Iron Maiden’s 50th anniversary tour isn’t just another nostalgia circuit stop—it’s a rare chance to hear the band dig deep into the first nine albums that shaped metal as we know it. If you’ve ever argued over the best Dickinson-era deep cut or still have a battered Seventh Son cassette, this setlist is basically a gift. The band’s last few tours leaned heavily on newer material, so this is a sharp left turn into the classics, with a few surprises rumored for longtime fans. The timing is fitting: it’s been 45 years since Maiden first stormed North America, and they’re marking the occasion with a show that feels more like a victory lap than a greatest hits package. If you want to see what five decades of relentless touring and stubborn creativity looks like, this is the night to do it.

The Boston Film Festival returns September 17 to 21 for its 42nd edition, with a program that goes well beyond the usual indie film showcase. This year's lineup includes independent features, documentaries, shorts, animation, fall studio releases and a new sports category, with four world premieres among the highlights. The festival's strongest appeal is the chance to see films before they become part of the broader conversation, then stick around for post screening Q&As with filmmakers and other industry guests. There are also panels, parties and red carpet events woven into the schedule, so it feels more like a week of cinema than a string of screenings. For local film obsessives, that makes it worth browsing the full program rather than picking a single movie and calling it a day. The festival has been part of Boston's film culture for more than four decades, and this year's expanded program gives it plenty to dig into.

Allston’s annual street fair is the kind of neighborhood gathering that actually feels like a neighborhood gathering. The main drag transforms into a patchwork of local bands, food stalls hawking everything from Korean fried chicken to Salvadoran pupusas, and vendors selling things you didn’t know you needed until you saw them. The muralists at work are worth lingering over, especially if you like watching art take shape in real time. This isn’t a festival that tries to be slick or curated within an inch of its life. It’s a little chaotic, a little loud, and all the better for it. You’ll run into old friends, discover a new favorite snack, and probably leave with a tote bag full of random swag. If you want a snapshot of what makes Allston tick, this is the day to get out and see it for yourself.

Boston Ballet opens its new season with a program that is far more playful and provocative than the usual fall curtain-raiser. The evening starts with selections from Stravinsky's The Firebird, performed live by the Boston Ballet Orchestra, before shifting gears with Alexander Ekman's Cacti, a slyly funny work that pokes at our tendency to overanalyze art. Sixteen dancers, a live orchestra and string quartet turn the stage into a rhythmic playground, with platforms becoming percussion instruments under the dancers' feet. Then comes Akram Khan's Vertical Road (Reimagined) 2023, a more elemental piece inspired by Sufi traditions and the writings of Rumi. The contrast is what makes this program worth seeing: one half mischievous and self-aware, the other immersive and searching. For anyone who thinks ballet means tutus and storybook plots, this is a useful reset. Runs September 10 to 20 at Citizens Opera House.

Labyrinth turns 40 this year, and if you’ve ever wanted to see Bowie’s Goblin King on the big screen with a live orchestra, this is your chance. The film’s blend of practical effects, surreal set pieces and that unmistakable Henson weirdness still feels fresh, especially when you’re surrounded by fellow fans who know every line. The live score isn’t just a novelty—it’s a reminder of how much the music shapes the film’s off-kilter mood, from the synth-heavy ballads to the playful, puppet-driven numbers. This isn’t a nostalgia trip for its own sake; it’s a rare opportunity to experience a cult favorite in a way that actually adds something new. If you’ve only watched Labyrinth at home, you’ll be surprised by how much more immersive and strange it feels with a full orchestra in the room.

RoboBoston isn’t your usual tech expo—it’s a rare chance to get up close with the future, right on the sidewalk. The annual robot parade is a spectacle that manages to be both charming and slightly surreal, with machines rolling, walking, and occasionally wobbling their way through the crowd. But the real draw is the hands-on access: you can tinker with student-built bots, chat with startup engineers who are actually shaping the next wave of AI, and see demos that rarely leave the lab. It’s the kind of event where you’ll overhear a ten-year-old explaining computer vision to their parent, and nobody bats an eye. Whether you’re a robotics obsessive or just robot-curious, this is the one day you’ll want to wander, poke, and play. Just don’t be surprised if you leave with a new favorite robot.

Weezer’s knack for turning awkwardness into anthems has always set them apart, and this show promises a setlist that’s as much about nostalgia as it is about catharsis. If you’ve ever found yourself humming “Buddy Holly” on the T or debating the best track on Pinkerton with friends over late-night pizza, you know these songs are woven into the fabric of growing up here. The band’s live shows have a way of making even the biggest venues feel like a basement gig, with Rivers Cuomo’s dry wit and the band’s tight musicianship keeping things grounded. This isn’t just a greatest hits parade—Weezer’s recent material still surprises, and their willingness to poke fun at themselves keeps the energy loose. If you want a night that’s equal parts singalong and sly self-awareness, this is the one to catch.

The Boston Arts Festival is a good reminder that you don't need to trek across town or buy a ticket to spend a worthwhile afternoon with local art. Now in its 24th year, the free two-day festival brings Boston-area visual artists and musicians to Christopher Columbus Park for a waterfront showcase that feels genuinely connected to the local creative community. The setting helps, too. With the harbor just beyond the park, you can browse paintings, photography and other work at an unhurried pace, then stick around for live music. It is family friendly, rain or shine, and runs from 11am to 6pm on September 12 and 13. Since the festival is specifically focused on artists from the Boston area, it is also a useful place to discover people whose work you may not encounter in the city's larger galleries or institutions. Best of all, admission is free.

Boston Local Food Festival isn’t just a market—it’s a full-on celebration of what’s actually growing, brewing and bubbling up in our own backyard. You’ll find the city’s most dedicated food folks here, from farmers who know their soil to chefs who can turn a rutabaga into something you’ll crave. The Seafood Throwdown is always a highlight, with local pros squaring off to see who can make the most of what’s fresh off the boat. It’s not just about eating, either: the chef demos are genuinely useful, and you’ll leave with a few new tricks for your own kitchen. Kids get their own space to run wild, and the music lineup is reliably eclectic. If you care about where your food comes from—or just want to taste what’s possible when you keep it local—this is the one day you’ll want to skip brunch.

DroneArt Show: Space Chase is not your average night out. The spectacle unfolds above Ohiri Field, where 1,200 drones become a fleet of luminous storytellers, sketching a cosmic chase across the sky. The narrative is simple—friendship, adventure, a dash of interstellar whimsy—but the execution is anything but. The choreography is tight, the visuals are genuinely surprising, and the music is more than just a background track; it’s woven into the experience, syncing with the movement of each drone. This isn’t a fireworks show or a laser display—it’s a fleeting piece of digital theater, best enjoyed with friends sprawled on the grass, eyes up. If you’re looking for a reason to linger outside after dark and see the city’s skyline reframed by light and imagination, this is it. Arrive early for the best vantage point.

Ringo Starr’s All Starr Band shows are a rare kind of rock nostalgia: loose, playful and full of surprises. The lineup changes every tour, so you never quite know which legends will be trading solos or swapping stories between songs. This year’s roster leans into deep cuts and unexpected pairings, with each musician stepping up for their own hits before diving into Beatles classics that still sound fresh in a live setting. Ringo’s charm is as unforced as ever, and the setlist is a grab bag of radio staples and songs you forgot you loved. The crowd skews older, but the vibe is anything but stuffy—think singalongs, spontaneous jams and the kind of musical camaraderie that only happens when everyone on stage has nothing left to prove. If you want a night that feels like a living jukebox, this is it.

If you think you know pizza, the Boston Pizza Festival will challenge your assumptions in the best way. This isn’t just a parade of margheritas and pepperonis—each booth is a chance to taste how far the humble pie can be pushed. You’ll find wood-fired Neapolitans next to wild-card toppings you’d never expect, all served up by pizzaiolos who take their craft seriously. The lines can get long, but that’s half the fun: swapping recommendations with strangers, debating the merits of a chewy crust versus a crisp one, and maybe discovering a new favorite style you didn’t know existed. It’s a rare opportunity to sample slices from spots you’d otherwise have to road-trip for, all without leaving the city. If you’re the type who plans weekends around what you’re eating, this is the event you’ll be talking about until next year.

Taste of the Fenway isn’t your average food crawl. It’s a rare chance to graze your way through the neighborhood’s best kitchens in one afternoon, all while bumping into neighbors you actually want to see. The lineup is a who’s who of local favorites—Cisco’s pours, MIDA’s pasta, Saloniki’s pita, and Ben and Jerry’s scoops—served up in generous, unlimited portions. The crowd is a mix of longtime regulars and newcomers, with a DJ spinning just loud enough to keep things lively but not drown out conversation. Kids under 10 eat free, so families can actually relax. The best part: your ticket helps fund affordable housing and job training right here, so you’re not just eating well, you’re doing good. If you want a snapshot of what makes Fenway feel like home, this is it.

Jungle’s new album, Sunshine, is the kind of record that makes you want to move, and their Boston stop this September is shaping up to be a proper celebration. If you’ve caught their live set before, you know they don’t just play songs—they build a groove-heavy world that pulls you in and keeps you there. The new material leans into their signature blend of funk, soul and modern production, but with a brighter, more playful edge that feels tailor-made for a late-summer night. The band’s knack for turning a cavernous arena into a sweaty, communal dance floor is no small feat, and with Sunshine in the mix, expect a setlist that’s both familiar and full of surprises. If you’re after a show that feels like a party with a thousand friends, this is the one to catch.