Friday, Sep 01, 2023 9:00a -
Sunday, Oct 01, 2023 10:00p

Surrounding areas
Boston, MA

EventScheduled OfflineEventAttendanceMode


Date Idea, Drinks, Farms, Festivals & Fairs, Food, Kid Friendly, Music, Outside, Party, Seasonal

Event website:

It’s time to start planning that September calendar! As the unofficial start of fall, September doesn’t just mean back to school and work, it means Fall Festivals, County Fairs, Oktoberfest celebrations (stay tuned for the roundup), and so much more.

by Celina Colby

Allston Christmas

When: Friday 9/1

Where: Allston (and around Boston)

Info: Allston Christmas is one of Boston’s most cherished annual traditions. Every year on September 1st hundreds of students, and other renters, move apartments. What’s left is a treasure trove (or nightmare depending on your perspective) of items left for free on the sidewalk. Scrounge the streets of Allston primarily, but other neighborhoods as well, for loot.

Moving Day Party at Sam Adams Brewery

When: Saturday 9/2

Where: Jamaica Plain

Info: If you’re one of the brave souls moving on September 1st, celebrate making it through with an ice cold brew at the Sam Adams Moving Day Party. They’ve even developed a new beer, Mover’s Currency, in your honor.

Sunflower blooms in Boston and beyond

When: Throughout September

Where: Greater Boston

Info: Greater Boston is home to some truly spectacular sunflower fields. Keep an eye on their social media to know exactly when the flowers are in peak bloom and then head to Colby Farm and other farms near Boston to see the show. City bound? No problem, check out these sunflower fields in the city.

King Richard’s Faire

When: Saturday 9/2 to Sunday 10/22

Where: Carver, MA

Info: Transport yourself to another time, one of duels, mutton legs, and craftsmanship. At King Richard’s Faire you can experience live entertainment, challenges and games, thematic food, and more.

Free Admission to the ICA on Labor Day

When: Monday 9/4

Where: Seaport

Info: Visit the ICA Boston for free on Labor Day. Take full advantage of this contemporary art experience by booking (free) timed tickets for the water shuttle that will take you across the harbor to the Watershed facility in East Boston. 

Labor Day White Party at Tall Ship

When: Monday 9/4

Where: East Boston

Info: Don your best all-white ensemble and head to Tall Ship for a Labor Day blowout. Enjoy live beats spun by DJ SNAX, drinks, a private party seating area, and unmatched views of the Boston city skyline.

Fenway Flea Labor Day Market & Day Party

When: Monday 9/4

Where: Fenway

Info: Shop more than 40 small businesses and vintage sellers, jam out to a live DJ, sip frozen cocktails on the Daiquiri Deck at 401 Park, and sample bites from an array of restaurants in Time Out Market. 

Welcome Little Amal to Boston

When: Thursday 9/7

Where: Downtown

Info: Little Amal (meaning “hope” in Arabic) is a 12-foot puppet representing a young Syrian refugee child. She travels around the world bringing a message of hope to displaced people. Little Amal will take her first steps in America in Dewey Square and will also walk in Harvard Yard and at the ICA Watershed. Keep an eye on all Little Amal events here.

Free First Thursdays at the Isabella Stewart Gardner Museum

When: Thursday 9/7

Where: Fenway

Info: Experience the site of Boston’s most famous art theft for free on the first Thursday of every month. In addition to viewing the beautiful collection, enjoy sketching in the galleries, live music, and other programming.

Somerville Greek Food Fest 

When: Friday 9/8 to Sunday 9/10

Where: Somerville

Info: Fuel up on authentic Greek food, wines, and pastry, then head to the dance party under the big tent featuring live, local music.

98th Annual Italian Feast of Saints Cosmas & Damian

When: Friday 9/8 to Sunday 9/10

Where: East Cambridge

Info: This festival features local and national artists on the entertainment lineup, food vendors, amusement rides, carnival games, a beer and wine garden, a healing service, and more. 

NOVA's 11th Annual Trung Thu Festival

When: Saturday 9/9

Where: Dorchester

Info: This festival and night market celebrate the Mid-Autumn Moon Festival with a spectrum of live entertainment, tons of local food vendors and engaging, family-friendly activities including food contests, lantern making, and much more.

Dog Days of Summer Cruise

When: Saturday 9/9

Where: Boston Harbor

Info: Take a scenic cruise around the Boston Harbor with man’s best friend. Enjoy drinks and snacks from a cash bar and meet other pups and dog owners while sailing around Boston.

The Boston Arts Festival

When: Saturday 9/9 to Sunday 9/10

Where: North End

Info: Watch live performances, take in visual art displays, and experience the work of more than 70 artists and craftspeople during this weekend long celebration of the arts.

JP Music Festival

When: Saturday 9/9

Where: Jamaica Plain

Info: Celebrate the musical talent of Boston, and more specifically JP, at this all-day music festival featuring local and neighborhood artists. In addition to grooving to the music, grab a bite from local food trucks and engage kids in family-friendly activities.

Gilman Square Arts & Music Festival

When: Saturday 9/9

Where: Somerville

Info: Listen to live music in a variety of genres (including kids’ tunes!) and peruse work by local artists at this vibrant local festival. Snag refreshments from delicious local vendors, including Winter Hill Brewing, Daddy Jones Restaurant and others.

Boston Taiwan Music Festival

When: Saturday 9/9

Where: Newton 

Info: Jam out to the music of local Taiwanese bands as well as sets by Berklee College of Music students honoring Taiwanese music. Festivalgoers are encouraged to bring blankets, chairs, and picnics to make a day of it.

Boston Seafood Festival 

When: Sunday 9/10

Where: Seaport

Info: Take full advantage of Boston’s position on the water and enjoy an endless array of fresh, local seafood at this crowd favorite festival. While you’re snacking, savor a lineup of local, family-friendly entertainment as well.

29th Cambridge Carnival

When: Sunday 9/10

Where: Cambridge

Info: The Cambridge Carnival is a city-wide celebration of the African diaspora featuring a grand costume parade, musical performances, traditional foods, dancing in the streets, and much more.

The Big E 

When: Friday 9/15 – Sunday 10/1

Where: Springfield, MA

Info: The Big E is one of the biggest and most exciting fairs in New England featuring musical acts like Lynyrd Skynyrd and G-Eazy. Shop the farmer’s market, go on rides, sip a brew at the Sam Adams Beer Garden, and watch the big parade that kicks off the fair.

Fiesta En La Plaza

When: Saturday 9/16 to Saturday 10/14

Where: Downtown

Info: Fiesta En La Plaza is Boston’s celebration of Latinx Heritage Month at City Hall Plaza. Learn to salsa dance, experience Latinx performances, watch Latinx film, and celebrate the culture within Boston.

Assembly Row Riverfest

When: Saturday 9/16

Where: Somerville

Info: Watch an extensive lineup of live local music, engage in free children’s activities for the whole family, shop at a vendor marketplace run by the Boston Women’s Market, and enjoy a spectacular fireworks show.

Revere Beach Arts Festival

When: Saturday 9/16

Where: Revere

Info: Watch an action-packed live art making competition as local creatives work to create a piece that captures the beauty of Revere Beach in a limited amount of time. During the festivities enjoy a series of arts activities and fare from food trucks.

Caribbean Rum & Food Festival

When: Saturday 9/16

Where: Roxbury

Info: Get a taste of the Caribbean without the airfare at this festival showcasing Caribbean foods, products, rum, and cocktails. You can even plan your next trip by learning about Caribbean destinations. 

KickBack Boston Presents: One Day Only Fest 2023

When: Saturday 9/16

Where: Downtown

Info: Six sets by live, local DJs will be the base line for this joyful festival celebrating emerging artists and BIPOC joy. Food and drinks (alcoholic and nonalcoholic) will also be available for purchase.

South Boston Street Fest

When: Saturday 9/16

Where: South Boston

Info: More than 5,000 guests come to revel at the South Boston Street Fest every year, a mammoth festival featuring two entertainment stages, food, drinks, children’s activities, and a huge market of local vendors.

Open Streets Dorchester

When: Sunday 9/17

Where: Dorchester

Info: For a whole day Dorchester Avenue will be shut down between Ashmont Street and Freeport Street. Instead of cars the community can gather for live performances, food and goods vendors, and more.

Boston Local Food Festival

When: Sunday 9/17

Where: Downtown 

Info: This massive local food festival celebrates cuisine and the people who cultivate it. Watch cooking competitions and demonstrations, tour the New England Village, participate in family-friendly activities and, of course, enjoy some great food.

End of Summer Block Party

When: Thursday 9/21

Where: Back Bay

Info: Celebrate the end of summer like an Italian with food and beverage tastings, oysters, raffles, games and activities, live music and more. Truly, it’s pasta as far as the eye can see.

Sam Adams Octoberfest Celebration

When: Friday 9/22 to Sunday 9/24

Where: Jamaica Plain

Info: Get into the brewing spirit with the Sam Adams Octoberfest. Listen to live music, participate in a stein hoisting competition, and sample food specials and festive, seasonal beers.

Roslindale Porch Fest

When: Saturday 9/23

Where: Roslindale

Info: Enjoy a free, neighborhood wide concert where you can watch musicians in a huge variety of genres perform on porches, lawns, and parks across Roslindale. 

Colby Farm Sunflower Field Bloom 

When: Saturday 9/23 to Wednesday 10/4

Where: Newbury, MA

Info: Why only see sunflowers on your Instagram when you can visit those neverending yellow fields for yourself? The Colby Farm sunflower season is supposed to hit full bloom in late September and you don’t want to miss the spectacular sight.

What the Fluff? Festival 2023

When: Saturday 9/23

Where: Somerville 

Info: In celebration of the invention of fluff in Somerville, the What the Fluff? festival offers fluff games, fluff competitions, and more fluff recipes for sampling than you ever thought possible.

Punk Rock Picnic at Bone Up Brewing

When: Saturday 9/23

Where: Everrett

Info: Listen to live indie and punk bands like Baabes, Muzzins, and The Grommets in the Bone Up Brewing beer garden. Pile on a plate of BBQ from Code1 and peruse a $1 record sale while you’re at it.

Taiwan Film Festival of Boston

When: Saturday 9/23 to Sunday 9/24

Where: Downtown Boston

Info: The Taiwan Film Festival of Boston will showcase short and feature length films around this year’s theme of “Faces of Life.” Eight films related to this concept will be screened at the AMC Boston Common.

World Sake Day Celebration 

When: Sunday 9/24

Where: Allston

Info: Celebrate World Sake Day with Sake Day East. Sample more than 60 varieties of sake and learn about the process of making and selling the beloved beverage.

Cambridge Science Festival

When: Monday 9/25 to Sunday 10/1

Where: Cambridge

Info: This week-long festival celebrates Science, Technology, Engineering, Art, and Math (STEAM) with a series of fun and interactive activities, demonstrations, workshops, and performances. The festival also heralds the official opening to the public of the Broad Discovery Center, run by MIT and Harvard.

Community Day Open House at Boston Athenaeum

When: Saturday 9/30 

Where: Downtown

Info: Tour the stunning, historic, and newly renovated Boston Athenaeum during the Community Day Open House, one of the few days you can enter the institution without a membership. Get a guided tour, listen to live music, connect with local artists, and snap lots of pictures of this stunning private library.

Central Square Dumpling Festival

When: Saturday 9/30 

Where: MIT Area

Info: Celebrate this beloved food by sampling dumplings from more than 30 local restaurants and food trucks. Then try to pick a favorite, a tough choice between traditional classics and avant-garde innovations.

The Great Northeast Jug Band Festival

When: Saturday 9/30

Where: Arlington

Info: Celebrating “good time” music from the 1920s and ‘30s through the present day, The Great Northeast Jug Band Festival will have danceable live music outdoors all day long.

MassRobotics 6th Annual Robot Block Party

When: Saturday 9/30

Where: Seaport

Info: Join more than 40 companies as they come together to show off their latest robotic technology in the Seaport. Watch robotic demonstrations, play games, and interact with the robots in a hands-one environment.

11th Annual Ignite! Global Street Food and Fire Festival

When: Saturday 9/30

Where: Somerville

Info: Sample global street food from a wide array of local restaurants, watch unique cultural performances by area artists, and enjoy vivid light installations at this annual festival.

Share this event

Add to:

01/09/2023 09:00:00 01/10/2023 22:00:00 America/New_York Everything Fun to do Around Boston in September 2023 <p>It’s time to start planning that September calendar! As the unofficial start of fall, September doesn’t just mean back to school and work, it means <a href="https://www.thebostoncalendar.com/eve... Boston, Boston, MA false DD/MM/YYYY