🎉 What’s Happening in Boston
September 7–27, 2026
Labor Day has arrived, but Boston is in no particular hurry to pack up summer.
The Red Sox are home, Newbury Street is still kicking the cars out on Sundays, outdoor festivals are filling the parks and waterfront, and before the month is over the Bruins will have ice at the Garden and Wicked will be back in Boston.
September may be one of the best months to be here. Here’s what I’d put on the calendar.
🎉 HAPPENING NOW
🖼️ Free Admission to the ICA — Monday, September 7
If you’re looking for something to do on Labor Day, the Institute of Contemporary Art is opening its doors for free.
Admission is free all day, although timed tickets are required. Then walk the Harborwalk afterward and remind yourself that September on the Boston waterfront is pretty hard to beat.
📍 Institute of Contemporary Art, Seaport
💰 Free
🔗 Institute of Contemporary Art
⚾ Red Sox vs. Angels — September 7–9
The Red Sox come home to Fenway after sweeping four games in Baltimore, and suddenly September baseball in Boston feels particularly interesting.
The Angels are here for three games beginning Labor Day afternoon. Monday’s first pitch is at 1:35 p.m., followed by night games Tuesday and Wednesday.
📍 Fenway Park
🐘 The Great Elephant Migration — Through September 13
If you haven’t gone looking for the elephants yet, this is your last week.
One hundred life-sized elephant sculptures are spread along Commonwealth Avenue Mall in Back Bay. They were created by Indigenous artisans in southern India from Lantana camara, an invasive plant, and each is modeled after a real wild elephant.
But you don’t need the backstory before you go. Just walk down Commonwealth Avenue and enjoy the wonderfully strange experience of finding a herd of elephants in Back Bay.
They leave Boston September 13.
📍 Commonwealth Avenue Mall, Back Bay
💰 Free
🔗 The Great Elephant Migration
🏝️ Boston Harbor Islands
Don’t give up on the Harbor Islands because Labor Day has passed.
September can be one of the best times to get out onto Boston Harbor. The biggest summer crowds begin thinning, the weather can still be beautiful, and you can take a ferry, bring lunch, walk around an island and look back at Boston from the water.
You don’t have to leave Boston to feel like you left Boston.
📍 Boston Harbor
🐋 Boston Harbor Whale Watches
The whales haven’t checked the school calendar either.
Whale-watch boats are still heading from Boston toward Stellwagen Bank looking for humpbacks, fin whales, dolphins and seabirds.
Bring another layer. Boston can be warm and sunny while the Atlantic is busy reminding you that it is the Atlantic.
📍 Central Wharf
🔗 New England Aquarium Whale Watch
🎸 Iron Maiden — Wednesday, September 9
If Labor Day was a little too peaceful, Boston has thoughtfully scheduled Iron Maiden for Wednesday night.
The legendary British metal band brings its Run For Your Lives World Tour to TD Garden.
📍 TD Garden
🕢 7:30 p.m.
🩰 Boston Ballet: Fall Experience — September 10–20
Boston Ballet opens its season at Citizens Opera House with Fall Experience, featuring two contemporary works: Akram Khan’s Vertical Road (Reimagined) and Alexander Ekman’s Cacti.
Performances run September 10–13 and return September 17–20.
If your idea of September culture involves something more graceful than Iron Maiden, Boston has you covered there too.
📍 Citizens Opera House, 539 Washington Street
🎨 THIS WEEKEND
⚾ Red Sox vs. Royals — September 11–13
Another weekend, another three games at Fenway.
Kansas City comes to town Friday through Sunday. Sunday also includes Boston Common Golf Day, a Nigerian Celebration and Kids Run the Bases after the game, weather permitting.
📍 Fenway Park
🎨 Boston Arts Festival — September 12–13
This is one I’d put on the calendar.
The Boston Arts Festival fills Christopher Columbus Waterfront Park with Boston-area visual artists and musicians for two days.
Local art, live music, Boston Harbor and no admission charge. That’s a pretty good September weekend.
📍 Christopher Columbus Waterfront Park
💰 Free
🚶 Open Streets Mattapan — Saturday, September 12
Blue Hill Avenue from River Street to Babson Street closes to cars and becomes a neighborhood gathering place with live music, food trucks, kids’ activities, local businesses and community groups.
This is what streets look like when the people get them back for a few hours.
📍 Blue Hill Avenue, Mattapan
🕥 10:30 a.m.–3 p.m.
💰 Free
🕺 Summer Dance Party — Saturday, September 12
City Hall Plaza isn’t quite finished with summer either.
The city’s Summer Dance Party Series wraps up with .Tribe Vibes, a multicultural evening of DJs, food and dancing right on City Hall Plaza.
📍 City Hall Plaza
🕔 5–9 p.m.
💰 Free
🎸 Rush — September 12 & 14
Rush comes to TD Garden for two nights as part of the Fifty Something tour, celebrating the band’s music, legacy and the life of Neil Peart.
Note the dates: Saturday and Monday. There is no Sunday show.
📍 TD Garden
🕢 7:30 p.m.
🚶 Open Newbury Street — Sunday, September 13
One of my favorite simple Boston ideas: get rid of the cars.
Newbury Street becomes pedestrian-only from Berkeley Street to Massachusetts Avenue, giving everybody the whole street for walking, shopping, eating and people-watching.
Walk down the middle of Newbury Street simply because, for once, you can.
📍 Newbury Street, Back Bay
🕙 10 a.m.–6 p.m.
💰 Free
🐘 Last Day for the Elephants — Sunday, September 13
This is it.
The Great Elephant Migration ends its Boston stay Sunday. If you’ve been saying, I have to go see those elephants, this would be the moment to stop saying it and go see the elephants.
📍 Commonwealth Avenue Mall
💰 Free
🔗 The Great Elephant Migration
🔭 NEXT UP
⛳ Upper Deck Golf at Fenway — September 17–20
Fenway turns into a golf course.
Sort of.
Upper Deck Golf lets players play a nine-hole round from stations around the ballpark’s upper deck, hitting toward custom greens on the field below.
It sounds slightly nuts until you remember where you are. Fenway has seen stranger things.
📍 Fenway Park
⛸️ Break ’N the Ice — Friday, September 18
This may be my pick for the wonderfully Boston event of the week.
Before the Bruins get the TD Garden ice back, you can get on it first.
Break ’N the Ice lets ticket holders skate on the freshly laid ice for the 2026–27 season and tour the Sports Museum. Skater tickets are $40, spectator tickets are $15, and skaters have to bring their own skates.
The Bruins don’t play their first preseason game there until Sunday.
So technically, for one evening, the ice is yours.
📍 TD Garden
🕔 5–6:45 p.m.
🎶 Berklee Homecoming Block Party — Saturday, September 19
Berklee is throwing its first Homecoming Block Party, bringing alumni, students, faculty and music fans together for an outdoor festival beside Fenway Park.
Susan Tedeschi, Tiwa Savage, Fabiola Méndez, Dogs in a Pile and Dreion are among the performers.
📍 73 Brookline Avenue, beside Fenway Park
🕐 1–6 p.m.
🔗 Berklee Homecoming Block Party
🎨 MassArt Night Market — Saturday, September 19
Downtown Crossing turns into an outdoor art market Saturday evening with more than 100 MassArt students and alumni selling original work.
Expect art, fashion, jewelry, ceramics, prints, handmade goods, music and hands-on creative activities.
And unlike quite a few things in Boston these days, admission is free.
📍 Summer Street Plaza and Washington Street, Downtown Crossing
🕔 5–9 p.m.
💰 Free
🔗 MassArt
🎤 Mt. Joy — Saturday, September 19
Mt. Joy celebrates 10 years with a show at TD Garden Saturday night.
📍 TD Garden
🕗 8 p.m.
🚶 Open Newbury Street — Sunday, September 20
Another September Sunday without cars on Newbury Street.
At this point I’m beginning to think Boston should just leave it this way.
📍 Newbury Street, Back Bay
🕙 10 a.m.–6 p.m.
💰 Free
🍴 Boston Local Food Festival — Sunday, September 20
Come hungry.
The Boston Local Food Festival takes over the Rose Kennedy Greenway with local food vendors, chef demonstrations, food activities and the annual Seafood Throwdown.
It’s a chance to wander around eating your way through New England without having to drive all over New England to do it.
📍 Rose Kennedy Greenway
🏒 Bruins vs. Capitals — Sunday, September 20
And there it is.
Hockey.
The Bruins play their first preseason game at TD Garden against the Washington Capitals Sunday afternoon.
Summer doesn’t officially end until September 22.
Boston puts the ice down early.
📍 TD Garden
🕔 5 p.m.
🍂 LATER IN SEPTEMBER
🧙 Wicked — Beginning September 23
Wicked flies back into Boston for a fall run at Citizens Opera House beginning September 23.
If you’ve never seen it, here’s your chance. If you have seen it, you probably already know whether you need to see it again.
📍 Citizens Opera House, 539 Washington Street
🌌 Cabin in the Sky — September 25–27
Here’s something genuinely different.
Boston’s Un-Monument initiative brings artist Ife Franklin’s Cabin in the Sky to Franklin Park for three nights. The free Afrofuturist experience combines a life-size ancestral cabin with augmented reality, live performance, projections and community participation.
📍 Overlook Ruins, Franklin Park
🕖 7–9 p.m.
💰 Free
⚾ Red Sox vs. Cubs — September 25–27
And Fenway gets one more September weekend.
The Chicago Cubs come to Boston for the final three games of the regular season, wrapping up Sunday afternoon at Fenway.
Depending on what happens between now and then, these could be three very interesting baseball games.
📍 Fenway Park
🎨 Stone Maps Opening — Saturday, September 26
A new Boston public-art installation arrives on Copp’s Hill Terrace in the North End.
Artist Kiyan Williams’ Stone Maps (Ruttier for the Dispossessed) opens with a free public reception overlooking Boston Harbor, part of the city’s ongoing Boston 250 public-art programming.
📍 Copp’s Hill Terrace, 520 Commercial Street
🕓 4–8:30 p.m.
💰 Free
🍂 September May Be Boston’s Best-Kept Secret
Everybody talks about Boston in October.
I wouldn’t rush September out the door.
The Harbor Islands are still there. Whale watches are still running. Fenway still has baseball. Newbury Street is going car-free. Outdoor festivals are filling the parks. The elephants are here for one more week. The ballet is back. The Bruins are putting the ice down.
And we still get those glorious September days when it’s warm in the sun and cool enough to walk all afternoon without melting.
Summer isn’t quite over.
Boston just gets more interesting.
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Know Something I Missed?
Boston has a lot going on. If there’s a festival, concert, neighborhood event, sports event, wonderfully weird Boston happening or something else you think belongs here, send it my way.
What’s Happening Boston is updated regularly. Last updated September 7, 2026.