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A Guide to Boston in the Fall

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This guide is all about things to do in Boston in autumn, updated for 2019. We include a Top 10 list, loads of free things to do, concerts, festivals, special events, and family-friendly activities.

 

 


TOP 10 THINGS TO DO

This is our Top 10 list of things to do in Boston in autumn. Make sure to read the entire post for the fun events, concerts, free activities, family-friendly things to do, and more. 

Our other popular Boston posts include: 


(1) Sightseeing Tour

One of the easiest ways to see Boston is with one of our pay-what-you-wish walking tours. And with the pleasant weather and beautiful changing leaves, autumn is the perfect season to explore on foot.

 

 

Our Freedom Trail tour is the most popular Boston walking tour. If you’re interested in the darker history of the city, try the 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!


(2) See a Concert

Boston in the fall has great energy, which makes concerts especially exciting.

If you’re looking for a great musical experience, you’ll find it at one of Boston’s great venues: 

 

 

We have just a few of the biggest performers listed right here, but check out all the big-name artists playing in our posts of things to do by month.

Click here to see who is playing when you’re in Boston.


(3) Attend a Sporting Event

Fall sports season is always exciting, and that is no less true in Boston. Football, basketball, soccer, and hockey begin their regular-season games as baseball is headed toward the end of its season. 

 

 

Football

Baseball

Soccer

Hockey

Basketball

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

Click here to see all games and matches in Boston.


(3) Enjoy the Boston Harbor

Boston is right on the water - and what better way to enjoy the crisp air than by getting out on a boat? There are plenty of great boat tours in the harbor to choose from. 

 

 

Kids and families will love going on the amphibious Duck Tours that take you from the streets of Boston to the water. If you’re in the Halloween spirit, you can take a Halloween-themed family lunch cruise

If you’re looking for a romantic evening, why not go on a sunset cruise? The evenings are still warm enough if you’ve got a jacket with you! 


(4) Explore Faneuil Hall Marketplace

Faneuil Hall is right on the Freedom Trail and is called the “home of free speech” due to its pivotal role in political protests, debates, and town hall meetings. The full marketplace has four different buildings, the historic Faneuil Hall being one of them, and the famous Quincy Market full of food vendors is another. 

 

 

After walking the Freedom Trail with us, we suggest spending 30 minutes to a few hours at Faneuil Hall Marketplace. You can find delicious food and follow it up by window shopping.

If you're there at the right time of day you could enjoy one of the many street performances that happen every day. They'll often book talented school groups, church choirs, and other professional street performers.  


(5) Admire the Autumn Colors or Go Apple Picking

Autumn is when the leaves of Boston’s trees change colors and display vibrant reds, yellows, and golds. This is a perfect (free!) activity for all travelers, whether you’re going solo or with friends or family. 

 

 

If you want to take admiring the trees one step further, you can find apple-picking orchards and farms within 30 miles of Boston. The apples will be a delicious reward for an afternoon of fall fun. We have a full post on apple picking here. 


(6) Go to the Theatre

Theatergoers will enjoy their time in Boston because there’s always some play, musical, or performance happening. This fall you can find multiple popular shows, including: 

 

 

If you’re looking for something a little different, you can also take a look at the performances happening at these top Boston Venues: 

See all the theatrical events happening in Boston here.


(7) Get into the Spooky Spirit

Autumn is the time for harvest festivals, pumpkin carving, and spooky Halloween activities. Boston is the perfect place to spend this season if you’re looking for events to get you in the spirit.

Family-friendly Halloween-themed activities include pumpkin caroling for the musically-gifted, haunted bus tours that entertain and inform about Boston history, and fun pumpkin patches to visit with the youngest children. Take a look at our family-friendly section for more pumpkin-picking fun. 

 

 

Adults can enjoy a Halloween yacht masquerade on October 26 - 27 as well as the Cambridge Brewing Company’s Great Pumpkin Festival on the last weekend of October. The Great Pumpkin Festival features pumpkin-flavored beer from regional and national breweries, as well as other great local brews.

Classic horror film fans will also be excited to hear about the Halloween Horror Movie Marathon at the Coolidge Corner Theatre. The movies cost between $15 - $20 each. 


(8) Sample the Local Boston Food

The Boston Local Food Festival happens in September and puts a focus on local and sustainable food in the Massachusetts area. If you’re interested in plant-based foods, you can also head to the Boston Veg Food Fest in October.

 

 

But you don’t need to make it to the festival to enjoy local Boston food. You can take our Little Italy Food walking tour to sample some delicious Italian food or the Chinatown tour to find Boston’s best Chinese restaurants. 

We also suggest exploring the food vendors in Quincy Market at Faneuil Hall Marketplace.


(9) See Boston’s Top Attractions

After school has started back up is the perfect time to visit Boston’s popular spots. There will be fewer crowds, thanks to fewer vacationing families. 

History buffs will enjoy spending more time at a few of the stops on the Freedom Trail tour, including the historic USS Constitution, Bunker Hill Monument, Granary Buyring Ground, Park Street Church, and the Faneuil Hall Marketplace

 

 

If you’re looking for some more modern attractions, why not visit the Museum of Fine Arts - the 5th largest museum in the US - or the Museum of Science.

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


(10) Get a Tourist Attraction Discount Pass

Some of the best attractions and activities in this city are included with Boston tourist passes.

 

 

These services provide some of the biggest discounts on general admission prices, up to 55%, and can save you time by allowing you to skip the ticket lines at select attractions.

For more information on how to save money with these services, make sure to read our full post covering which Boston tourist pass offers the best deals.

 


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FREE THINGS TO DO IN AUTUMN

Boston hosts a number of free events and activities throughout the autumn months. There are a lot of free performances and festivals to attend in the fresh fall air of the city. So get out and enjoy the bright red and gold leaves at a free event! 

 

 

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


Free Performances, Movie Screenings, and Concert Series


Free Festivals and Art Events

  • South Boston Street Festival - A free festival with live music, kids games and activities, and local vendors. 
  • CollegeFest - A festival run for college students at Fenway Park with live music, swag handouts, and local discounts. Held September 21.
  • Parade Concert and Exhibit - This art exhibition and concert is a free celebration of Boston’s cultural diversity on September 5. 
  • Boston Arts Festival - Boston’s best artists will be showing off their photography, painting, music, and art from September 7 - 8. 
  • South End Open Studios - Art galleries and studios are having their open houses from September 21 - 22. 
  • Boston Local Food Festival - Find local and sustainable food and produce vendors at Rose Kennedy Greenway on September 15.
  • Columbus Day Parade - Go to the North End from October 12 - 14 for Columbus Day festivities. The parade is October 13. 
  • Boston Veg Food Fest - Find plant-based meal ideas, free food samples, and fun kids activities from October 19 - 20. 
  • Boston Book Festival - This two-day book festival will be packed with author talks, seminars, writing workshops, and plenty of books for sale from October 19 - 20. 
  • Columbus Park Fall Festival - Head to Christopher Columbus Park for the fall festival on October 5, weather permitting. 

Take a Free Yoga Class

All through the summer and through the end of September, you can catch a free yoga class every Thursday afternoon from 6:00 pm - 7:15 pm at the Frog Pond in Boston Common. The instructors come from various studios in the area. 


Free Museum Day

On September 21, Smithsonian Magazine is promoting Free Museum Day. There will be various museums across the country participating, including Boston-area museums. Some of them include the Museum of Fine Arts, Gibson House Museum, and the Mary Baker Eddy Library. Find tickets and details on the Smithsonian Magazine website


Go Stargazing at the Boston University Observatory

Boston University Observatory opens to the public on Wednesdays - on cloud-free nights - for stargazing with the professionals. 

The event has no cost, but they do occasionally run out of space due to popularity. We recommend getting tickets in advance online

In the winter, the event begins at 7:30 pm. Keep in mind, they do cancel in the event of poor visibility.


Visit a Historic Graveyard

With Halloween just around the corner, this is the perfect time to make your way to one of the historic cemeteries and graveyards in Boston.

The most notable example is the Granary Burial Ground, which is the site where three signers of the Declaration of Independence and Paul Revere were all laid to rest. These historic locations are included on either our free Freedom Trail tour or our self-guided tour.


Take a Crime Tour

If graveyards aren’t spooky enough on their own, take our real-crime tour of historic crime scenes in the Boston Area. 

Our Beacon Hill Crime Tour covers several notable sites tied to the Boston Strangler and John White Webster. Keep in mind, this tour is not suitable for children younger than 16 years of age.

 


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THINGS TO DO WITH KIDS

Boston is a great city to visit with the whole family. From kid-friendly theatre performances to fun Halloween day trips, this is a great time of year to have some bonding time.

 

 

And we have more kid-friendly activity suggestions that are great to do in the fall or year-round!


See The Wiggles or Spongebob Squarepants Live

If you’re looking for a theatre experience appropriate for a younger audience, Boston has two musicals running this fall that are aimed at kids. 

Kids will enjoy seeing The Wiggles Tour live on September 5, 2019. The cast of this popular children’s show will be singing and dancing on stage. 

Another modern and family-friendly musical theatre experience is Spongebob Squarepants: The Musical running from October 15 - 27, 2019. 


Take a Day Trip to Salem

Boston is located quite close to Salem, MA – the site of the historic Salem Witch Trials. 

With Halloween fast approaching, this would be the perfect time learn about the historical Salem Witch Trials on a day trip.

You can visit the Salem Witch Museum to learn more about this event and about witches in general.

The museum offers a self-guided tour that you can download for free - which includes several interesting spots in Salem and the surrounding areas.


Explore a Pumpkin Patch

From mid-September through the last weekend of October you can find several pumpkin patches, farms, and corn mazes in the Greater Boston Area. Some of the more popular ones include Smolak Farm and Boston Hill Farm - both in North Andover. 

You’ll find wagon rides, fresh baked goods, face painting, and petting zoos. 


Boo at the Zoo

The Franklin Park Zoo hosts a Halloween event every year, which is a hit for the younger visitors. The kids can dress in costume and walk through the trick-or-treat trail as well as a haunted maze.

Events include a costume contest, howling contest, and other fun activities. 

TIP: You can actually enjoy this activity for up to 50% off, as tickets to Franklin Park Zoo are included with at least three different Boston tourist passes.


Visit the New England Aquarium

Kids will love the exotic fish, penguins, and other sea life at the New England Aquarium. They’re open every day 

TIP: You can save 50% or more on tickets simply by using a Boston tourist pass.


Go to a Kid-Friendly Museum

Boston has multiple museums that younger visitors will find interesting. If the weather isn’t cooperating, heading to a museum could be a great way to stay warm and dry. The Boston Fire Museum and USS Constitution Museum are both free to visit any day. 

Here are a few paid museums kids love: 

  • Boston Children’s Museum
  • Museum of Science
  • Harvard Museum of Natural History

TIP: These three museums are included on the Go Boston Card. The Museums of Science and Natural History are also on the Boston CityPASS

 


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PACKING GUIDE FOR AUTUMN IN BOSTON

The weather begins to cool off toward the end of August, but you’ll likely want to pack for summer with a few light layers. Afternoon high temperatures tend to be in the lower 80s F (27-28 C) early in the month falling into the mid to upper 70s F (24-26 C) near the end of the month.

September is a mild month, and you can pack summer clothing with a few light layers. Late night and early morning low temperatures will be trending colder this month. Early in September, the lows tend to be in the lower 60s F (16C to 17C) but fall into the low to mid-50s F (11C to 12C) by the month’s end. A few of the colder mornings towards the end of the month will dip down into the mid-40s F (6C to 7C). 

In October, we recommend dressing in layers and bringing sweaters. Early in the month, the days can be nice with afternoon temperatures in the upper 60s f (19-20C) and with morning lows in the lower 50s F (about 11C). As the month progresses, afternoon temperatures fall to the upper 50s f (about 14C) while overnight lows drop into the lower 40s F (5-6C).

By the time November hits, you’ll need to bring layers and at least one coat. Early in November the afternoon high temperatures in Boston tend to be in the mid-50s f (13-14C) with overnight lows in the lower 40s f (5-6C). 

 


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THINGS TO DO IN AUTUMN MONTHS

Our monthly posts are updated to include the best things to do during the end of summer and crisp autumn months. 

 


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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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