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Top September Events in Boston and Beyond

What to do in Boston in SeptemberBoston September Events 2021

Things to Do in Boston in September 2021

Summer might be winding down, but Boston shows no sign of easing up in the month of September.  

The school year begins and Boston shines brighter than ever while bustling with festivals and celebrations to satisfy every taste.  There is also Fall foliage to admire, fitness events, hobby events and a plethora of fun and oftentimes free things to do.  September is full of events guaranteed to offer a memorable start to the Fall season!


SoWa Open Market

Stroll along through the Boston's SoWa Open Market as it continues its season gathering local artists, farmers, chefs, brewers and musicians every weekend all the way through the month of October.


Pick Your Own Apples

It's apple picking time! Head to local farm for pick-your-own variety of fun and deliciousness. Apples raspberries and pears and more.  Visit their on site farm markets for specialty items and baked goods to satisfy your farm fresh cravings.  


Introducing your family to gardening through pick-you-own farm locations is a great way to get everyone in touch with nature and to value our locally grown foods. Check out some of these great local farms  which also feature playgrounds and this list of must-visit corn mazes for continued family fun.


Davis Mega Farm Festival & Corn Maze

Fall in New England means corn mazes and hayrides and outdoor fun.  Flaunt your navigation skills as you maneuver your way through an intricate corn maze.  Other activities include knocker soccer and quad carts to corn cannons and archery tag; OR you can simply sit back, relax and listen to some live music, Davis Mega Farm Festival is a fun, seasonal outing for the entire family!

Photo courtesy of Davis Farm Mega Maze

Revels RiverSing

Raise your voice in song as Revels waves goodbye to summer and welcomes in the fall at this free family-friendly Equinox celebration at the Herter Park Amphitheater in Allston!  Enjoy pre-show family festivities, a beer garden for adults, & lots of communal singing every year at the annual Revels RiverSing.

The Big E

Experience all that the The Big E has to offer!  Be a part of the New England autumn tradition and the ninth largest fair in North America.

There is absolutely no better place to enjoy the sights, sounds and taste tempting aromas of the fall season than at The Big E.  While not exactly in Boston, the fair takes place about 1 1/2 hours west in the city of Springfield, MA, and makes for a wonderful day trip.  


Annual Allston Village Street Fair

Boston's Hippest Multicultural Festival Event is always the Allston Village Street Fair.  Family fun for all ages, featuring 3 Stages, Live Bands, a Multitude of Multicultural Street Performances, International Food Court, Amusement/Arcade Area, Artists & Vendors Gallery, Giveaways, & more - it's definitely the September event to remember.  

Hub on Wheels Bike Ride

Grab your helmet and cycle and ride through historic neighborhoods and see views of the Charles River during the Hub on Wheels Bike Ride, where riders can choose from a course of 12 or 40 miles.


Cheer on the Red Sox at Fenway Park

Take in a game at one of America's most beloved ballparks, Fenway Park and cheer the Red Sox on to victory!  From the quintessential Green Monster, pesky's pole, belting out Sweet Caroline in the 7th inning stretch, to the right field manual scoreboard, it is always a great day at Fenway. 

Smithsonian Museum Day Free Admission

Join Smithsonian Magazine and celebrate "boundless curiousity" on Smithsonian Museum Day!  Smithsonian Magazine offers free, ticketed admission  for two to museums across the country in this annual event. Participating museums around Boston include the Museum of Fine Arts, the Harvard Art Museums, the Harvard Museum of Natural History, the Museum of African American History, just to name a few.


Plan to spend Labor Day at The Institute of Contemporary Art and the Isabella Stewart Gardner Museum, as both offer free admission to all patrons as part of Frank Hatch Free Day!

Free Summer Movies at Frog Pond

Grab a blanket and some snacks and enjoy free film screenings at the  Frog Pond on the Common which begin at dusk sponsored by the city’s parks department, Mayor Walsh’s office, and Northeastern University.  

Spectacle Island 5K

Get your fitness on with a 5K or 5-mile run on the trails of Spectacle Island, followed by a lunch and awards as you take a relaxing cruise back through breezy Boston Harbor.


Photo courtesy of Boston Magazine

Summer in the City Entertainment at the Boston Harbor Hotel

Flock to Cambridge Common as Cambridge’s Summer in the City series wraps up with its annual free performance from Vermont’s Bread and Puppet Theater on Cambridge Common. 

Get the creative juices flowing at the Stamp and Scrabook Expo at Best Western Royal Plaza Trade Center in Marlborough. Scrapbookers can enjoy classes, an array of vendors, and get ahead at crop parties.


There is no shortage to the amount of festivals in the Boston area.  Check out this selection of a few that you might consider attending this September!

Boston Arts Festival

Make a day of it at the annual Boston Arts Festival.  The celebration kicks off Boston’s Arts Open Studios season, and features more than 70 juried local visual artists and craftspeople, plus local musicians performing on the Waterfront Stage.  The free and inviting event brings over 50,000 visitors to Christopher Columbus Waterfront Park. 

Cambridge Arts Festival

Stop by the Cambridge Carnival for a day loaded with fun!  Cambridge’s largest street festival features a grand costume parade as masqueraders dazzle the streets in striking handmade costumes. The festival runs along Mass Ave between Central and Kendall Squares.


Join independent game developers, hobbyists, and fans at a Gaming Festival!  Play digital games, tabletop games, and role-playing games at Boston FIGfest.  The celebration is moving to the Harvard Athletic Complex to accommodate for an even more expansive Festival.

Attend the South Boston Street Festival and enjoy two stages of live entertainment and more than 100 vendors take over East Broadway between I and L streets.


Get your Irish on at the  South Shore Shamrock Fest  featuring Irish and Irish-American performers onstage, plus family entertainment and vendors in Marshfield.


Get serenaded walking through the streets of Roslindale’s porchfest . Enjoy this low key family-friendly, alcohol-free version of this decentralized music festival  that welcomes over 100 acts to 70 locations in the neighborhood.


Photo courtesy of WBUR

Join the the biggest back-to-school bash in the region with a visit to College Fest at Fenway Park!    College students are welcome to spend the day at Fenway Park free of charge, grab some free swag from local vendors and enjoy a vaiety of live local music.

Somerville Fluff Festival

Celebrate the 101st anniversary of Fluff at the Somerville summer Fluff Festival Union Square. The event celebrates the  anniversary of the invention of marshmallow Fluff by Archibald Query right in Somerville in 1917. This year’s 13th annual festival will feature musical performances, a cooking contest, Fluff-themed games, and Fluff treats of every sort.


Celebrate everything " Made in Boston" at the Boston Local Food Festival. The free outdoor festival on the Greenway showcases farmers, local restaurants, food trucks, specialty food chefs and fisherman. Enjoy an array of chef demonstrations, a seafood contests, live music, and much more.

Celebrate everyone's best friend at the Greenway’s North End Park at the Greenway Carnival of Dogs  with a variety of dog-friendly vendors and activities, including adoption services, treats and toys.

Open Newbury Street

Open Newbury Street continues this year over a series of three Sundays this summer.   From 10:00 a.m. to 6:00p.m. on three summer Sundays, Newbury Street becomes a pedestrian-only walkway, closing to vehicles to allow pedestrians the opportunity use the full width of the street from Arlington Street to Massachusetts Avenue.


Photo Credit: @mikediskin

Put on your dancing shoes and let everyone see your moves at Let's Dance Boston.  Guaranteed to be fun, this free, five-day dance and live music extravaganza takes place at Dewey Square Park on The Greenway.  

Each event features a different style of dance along with a live bands. Enjoy a 45-minute free dance lesson taught by professional teachers in the dance style of the evening with a dance party with live entertainment to close out the evening.

Get into the spirit of fall and discover some fun pumpkin festivals and jack-o-lantern displays near you in our helpful guide to fall family fun. And you can visit our popular things to do in Boston guide to find fun things to do all year long.

Looking ahead, you can start perusing some fun things to do next month in our October events in Boston guide.   And for a daily view of what's going on in Boston - visit our Boston Events Calendar any time of the year. 

Stacey SaoStacey Sao has been the Managing Director of the family-friendly events and activities website, BostonCentral for over 20 years.  She continues to enjoy discovering and exploring new places to visit in the Greater Boston area.