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Things to do in Boston in September

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This post covers the best things to do in Boston in September, updated for 2021 and including free, nighttime, as well as family-friendly activities.

Let's dive in!



This section will feature our top 10 September activities to enjoy in Boston. Check out events and activities that we've also marked as kid-friendly, free, or great to enjoy after the sun sets.

For tips on some of the most popular tourist activities in Boston be sure to check out our other popular Boston posts: 

Be sure to read our master things to do in Boston post for more ideas for any time of the year.

1) Attend a Major Concert

Boston is home to many different music venues, which means there's plenty of space for big-name artists and musicians to perform.

Below, we have listed several top concerts in town during this month, but you can also access a larger list here.

Click here to see the rest of Boston's September concerts.

2) See a Major Sporting Event

September marks the beginning of football season, which is great news for New England Patriots fans in Boston! And baseball fans are excited to see what happens with the approaching playoffs.

This means you'll have some great opportunities to see a major sporting event.



TIP: Red Sox fans might enjoy a tour of Fenway Park!

Click here to see all games and matches in Boston.

3) Enjoy the Theatre

Theatrical performances are returning to Boston this month after an unplanned hiatus due to the pandemic.

There's currently only one major musical scheduled for September 2021, and it's Tootsie!

Boston Travel Tips and Hacks

This production of Tootsie will be hosted by the Citizens Bank Opera House, and shows are schedules from September 1st - 12th.

If you're willing to travel a bit outside of the city, Little Shop of Horrors will be at the North Shore Music Theatre in Beverly, MA from September 21st - 30th.

See all theatre options in Boston here. 

4) Take a Sightseeing Tour

We offer a number of pay-what-you-wish walking tours that will lead you throughout the city of Boston.

Try our ever-popular Freedom Trail tour or dive into something a little more dramatic like our Beacon Hill Crime tour (not suitable for children under 16).

If you can't make one of our scheduled tours, try one of our GPS-enabled audio tours, available anytime! 

Another very popular option is to take a bus tour of Boston. The hop-on-hop-off trolley gives you a convenient means of transportation along with entertaining, live commentary.

Since the city is right on the coast, there are also several fun boat tours available for getting a different perspective of Boston from the water.

5) Boston Local Food Festival 

Taking place on the centrally located Rose Kennedy Greenway on September 19th, 2021, The Boston Local Food Festival celebrates local and sustainable food.

Join in on the fun and browse the offerings of local farmers, restaurants, food trucks, and more.

The festival also features a family fun zone and live music, performances, and demonstrations. This event is free to attend.

For more free things to do or family-friendly activities in Boston, check out the sections below. 

6) See a Stand-Up Comedian

There will be a few notable comedians performing stand-up in and around Boston this month.

Fans of Doug Stanhope will have a chance to see him at the Wilbur Theatre on September 2nd, while Tom Green will be performing on September 30th at Laugh Boston.

Here are a few other comedy shows you might want to catch:

Check this list of live comedy performances in Boston for additional options.

7) Boston Arts Festival

You can find Boston’s best artists showcasing their photography, painting, jewelry, music, and sculptures at the Boston Arts Festival on September 11th - 12th, 2021.

You can find live music, art, and vendors set up between 11:00 am and 6:00 pm at Christopher Columbus Park.

8) See Boston’s Top Attractions

There’s more to Boston than The Freedom Trail (though we recommend taking our free tour!). There are plenty of other attractions to see while you’re in town. 

Fans of the TV show can visit the Cheers Bar that inspired the series. Check out our full list of the many great attractions in Boston.

History buffs will enjoy seeing the historic USS Constitution, Bunker Hill Monument, Old State House, and the Faneuil Hall Marketplace

Check out our full list of the many great attractions in Boston.

9) Boston Film Festival

Providing a showcase for both emerging and recognized filmmakers, the Boston Film Festival seeks to entertain, educate and enlighten audiences. See films from a number of genre categories over this multi-day event.

Some of the movies have international releases, like Green Book, and are included thanks to Boston-area directors and producers. 

The 37th annual festival is running September 23rd - 27th, 2021 with showtimes between 12:30 pm and 9:00 pm. Check back on the website as more information becomes available! 

If you’re looking for more things to do in the evenings, check out the nighttime activities section below.

10) Save Up to 55% Off with a Tourist Attraction Discount Pass

The easiest way to see all the popular attractions while saving time and money is by utilizing a city discount pass. These passes work by bundling discounts to multiple attractions and tours.

Select activities also come on the pass with skip-the-line access, which means less time at the box office. 

A few great attractions and activities included in the passes are:

  • Hop-On-Hop-Off Bus Tour
  • Skywalk Observatory
  • Old State House
  • New England Aquarium Whale Watch
  • Boston Children’s Museum

For an in-depth comparison and look at reviews of all the discount passes available, take a look at our tourist pass post.

UNCONFIRMED: South End Open Studios 

Head to Boston’s South End for the 32nd annual open studios event where over 200 artists will be on hand to display and discuss their work.

This free event is an excellent way to discover and explore Boston’s creative community!



The event typically runs through late September, from 11:00 am - 6:00 pm. Find more free activities in Boston below.

NOTE: The dates for this event have yet to be determined as of June 2021.



September evenings in Boston can be cool but the city is lively and there are lots to see and do! 

We have great ideas for things to do at night year-round in our full post. 



Here are a few more:

See a Free Outdoor Movie

Head to the Frog Pond at Boston common before sundown to find a nice patch of grass for the free film!

NOTE: This event has not been confirmed for 2021.

Take a Sunset Cruise

September means cooler days and nights, which means this might be the last month before spring that offers comfortable temperatures for a sunset cruise in the harbor.


This photo of Classic Sail Boston is courtesy of TripAdvisor


That means it's the perfect time to catch a beautiful Boston sunset with one of these boat cruises.

Catch an All Elite Wrestling Event

Wrestling fans will be happy to hear that AEW (All Elite Wrestling) will be hosting a show at Agganis Arena on September 8th, 2021.

This is an excellent chance to see some of the best athletes in the sports entertainment industry.

Purchase tickets or learn more.



Beantown hosts a number of free events and activities throughout the month of September. We've listed more free activities in our full post.



Here are a few more budget-friendly activities to do in September:

Free Museum Day

Hosted by Smithsonian Magazine on September 18th, 2021, over 1200 museums throughout the country will open their doors for free.

Some of the Boston area museums included are the Boston Fine Arts Museum, the Harvard Art and Natural History Museums, and the Peabody Museum of Archeology and Ethnology.

Free tickets must be reserved in advance. Check the website for more information on this free-for-all day!


If you’re a college student, this is the event for you!

Head to Fenway Park to enjoy live music, gather up some free swag, get some amazing local discounts, and hang with hundreds of other college students who are new to the Boston area!

CollegeFest is free to attend and goes from 11:00 am - 5:00 pm.

NOTE: 2021 dates for this event have yet to be confirmed.

Climb up Bunker Hill

Visit the grounds of the first major battle to take place during the American Revolution! While you’re at Bunker Hill, climb up the 221-foot Obelisk.


This photo of Bunker Hill is courtesy of TripAdvisor


This challenging climb (there are lots of stairs!) is worth it when you are greeted with panoramic views of the city at the top.

Stretch with Summer Yoga

Every Thursday afternoon in September from 6:00 pm - 7:15 pm, you can join the other yogis in Boston for a vinyasa flow yoga class at the Frog Pond in Boston Common.

The instructors will rotate out weekly and run a class that is suitable for all levels to participate in. Since it is a large class open to the public, you should have your own mat.

We've listed more free activities in our full post.

NOTE: This event was canceled for the 2021 summer season to prevent the spread of Covid-19. However, you can always go to Boston Common and perform Yoga on your own if you wish!


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The historic city of Boston is very family-friendly and offers a lot of activities for people of all ages.

Some of the events we’ve mentioned like the Free Museum Day are great for everyone, and we have more kid-friendly activity suggestions for year-round fun!



Here are a few more things the whole family can enjoy in September:

Revels RiverSing 

Presented by the Revels Music Group, enjoy this free equinox celebration and sing your way into Autumn!

The event will include multiple performances, a beer garden for adults, a lot of family-friendly activities, and some surprises!

Family activities begin at 5:00 pm at the Herter Park Amphitheater.

NOTE: This event has yet to be scheduled for September 2021.

Swan Boats Final Weekend

Head to the Boston Public Garden before September 6th, 2021, for your last chance of the year to ride the Swan Boats at the Boston Common Garden.

They operate from 10:00 am - 5:00 pm, weather permitting. Each Swan Boat ride lasts approximately 12 - 15 minutes with about a 5 to 10-minute wait to ride.

Adult tickets are $4.50 and children 2 - 15 years of age are $3.00.

Find the Tortoise and the Hare

If you’re in the Copley Square area, make sure to spot the Tortoise and Hare bronze statues conveniently located near the finish line of the Boston Marathon, Trinity Church, and the Boston Public library.


This photo of Tortoise and Hare is courtesy of TripAdvisor


They make a fun photo opportunity for children!

South Boston Harvest Festival 

A fun afternoon for the whole family, the South Boston Harvest Festival will feature a number of events including live music on two stages, children’s games and activities, over 100 local vendors, food, and dance performances!

The event is free to attend and runs September 25th, 2021, from 9:00 am - 5:00 pm.


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About The Author

Brian Burgess

Brian was born in Cambridge and has been living in the Boston area all his life. He is a graduate of Boston's Emerson College with a degree in communications with a journalism/history focus. He has been leading tours for Free Tours By Foot Boston since it was started in the city of Boston in 2012, and enjoys sharing his knowledge of Boston's rich history with not only the guests on his tours, but with everyone he meets.
Updated: October 12th, 2021
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