This post covers the best things to do in Boston in September, updated for 2022 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

There's currently only one major musical scheduled for September 2022, and it's Tina - the Tina Turner Musical!

Boston Travel Tips and Hacks

This production of the Tina will be hosted by the Citizens Bank Opera House, and shows are schedules from September 20th - 29th.

If you're willing to travel over to Cambridge, The Spanish Villager will be at The Sinclair on September 18th.

See all theatrical performances 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 18th, 2022, 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 Daniel Tosh will have a chance to see him at the Orpheum Theatre on September 17th, while Craig Ferguson will be performing on September 17th at The Wilbur.

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 10th - 11th, 2022.

You can find live music, art, and vendors set up between 11:00 am and 6:00 pm at Christopher Columbus Waterfront 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 la 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 and are included thanks to Boston-area directors and producers. 

The 38th annual festival is running September 22nd - 26th, 2022 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.

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 runs from September 11th - September 18th, from 11:00 am - 6:00 pm.

Find more free activities in Boston below.


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:

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.

Sunset Cruise photo from Classic Sail Boston through Trip Advisor
This photo courtesy of TripAdvisor

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

View the Boston Skyline

There are several great places to get a good look at the Boston skyline.

One of the most historic locations is the Bunker Hill Monument, which is a 221 ft tall obelisk that you can climb to the top.

You'll need a pass to do this, but they are free! Just go to the Bunker Hill Museum and ask for a pass.

If you're willing to go a bit out of the way, consider a trip to Mount Auburn Cemetery in West Cambridge for almost unbeatable views of the city skyline.

Another option is at Piers Park in East Boston. While you won't get a view from above, it is one of the best places to see the skyline from below.

Go on a Sighseeing Tour

Just because the sun has gone down doesn’t mean you can’t take a tour of the city.

There are still quite a few places you can visit and learn about after dark.

Here are a few of the best tours available at night in Boston:

Beacon Hill Crime Tour 

This pay-what-you-wish walking tour covers some of the most notorious criminal histories that have taken place in the Beacon Hill area.

Ghost Tours 

In a city this old, it shouldn’t come as a surprise that there are more than a few ghost tours in Boston. Haunted history outings are available as either walking tours or bus tours.

We offer a pay-what-you-wish ghost tour on Fridays and Saturdays at 7pm during the summer season.

Evening Cruise 

If you’re interested in seeing the skyline of Boston from the water, consider taking either a dinner cruise or a sunset cruise.

Don’t forget that you can always take a self-guided tour of the Freedom Trail for free whenever you want. This is a great opportunity that is available both day and night.


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 17th, 2022, 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!

Boston TechJam

Head to the Lawn on D to join the block party and see what tech exhibitors have to show the over 3,000 attendees.

This all takes place on September 14th between 4:00 PM and 8:00 PM

You'll have access to all of the activities at Lawn on D such as lawn games and swings, and get to interact with new and innovative technologies.

TechJam is free to attend but you do have to register.

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.

Photo of Bunker Hill courtesy of TripAdvisor
This photo 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.

Watch Labor Day Fireworks

There are loads of places around the city to get a good view of the fireworks over Boston Harbor.

Before dusk on September 5th head to any of these locations to enjoy the show: the Fan Pier, Piers Park, Downtown Waterfront, Christopher Coumbus Waterfront Park.

It will truly be an evening to remember!


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:

Faneuil Hall Marketplace Street Performers

Kids will be excited to see the world-class performers who have been appearing here since 1976, making it part of the fabric of Faneuil Martketplace.

Acts include a man who can twist his body into a knot, a juggler, an amazing acrobat, and escape artist, and much more.

Note: nearby is a Dino Safari Tour that runs through September 2022.

Swan Boats Final Weekend

Head to the Boston Public Garden before September 5th, 2022, 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, senior $4.00, 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
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 24th, 2022, from 9:00 am - 5:00 pm.


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: julio 22nd, 2022
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