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25 Fun Things to do in Boston in October and November

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Boston, Massachusetts is an amazing city to visit any time of year, but fall is an especially great time to see it. There are so many fun things to do in Boston in October and November. You’ll definitely want to add it to your fall bucket list.

Fun Things to Do in Boston during October.

Although the sun and warmth have waned a bit, fall is still one of the perfect times to visit Boston. This is one of the oldest towns in the US and has an undeniable rich history.

The history is one of the many attractions you will find in the town. There are a lot of other activities to engage in when you are here and festivities that you won’t want to miss.

Is October a Good Time to Visit Boston?

The month of October is a GREAT time to visit Boston! The weather is fresh and crisp but not too cool, making it perfect weather for walking around and exploring.

There are plenty of fun activities in the Boston area throughout October and November, including several free things and many special events.

And because Boston is filled with trees, you’ll enjoy beautiful fall colors everywhere you go. So, if you want to take in magnificent New England fall foliage and enjoy the best of Boston attractions and events, make plans to visit the city this October.

What to Pack for a Fall Visit to Boston

Layers are the secret to staying comfortable during a fall visit to Boston. Most days will be cool, but if you’re walking around in the sun you may get warm. Start with a shirt, with a sweater or sweatshirt over it, and perhaps a lightweight jacket.

As you near the end of October and head into November, the temperature drops further and you’ll want to make sure you’ve packed a warm jacket for your top layer.

Comfortable shoes are a must since Boston is best seen by foot. Also pack a hat, gloves, and scarf for chilly days along the water.

Top Things to do in Boston in Fall

Everywhere you turn, there are fall themed events and people seem to be having fun in one way or the other. The air is cool and light and the leaves have already started changing color, creating a beautiful spectacle that makes this town an amazing delight to be in during the fall season.

Here are some of the fun things to do in Boston in the fall.

Walk the freedom trail

As one of the oldest towns in the nation, Boston has a rich history and there are monuments all over the town to remind people of this heritage. The freedom trail is one of these.

When you visit in the fall, you have to take this trail. As you enjoy the fresh autumn air, you get the chance to see different important sites and buildings that hold a place in the history of the town.

a plaque on a brick wall that has the words The Freedom Trail Boston

These include the Old North Church where the Boston Massacre occurred, the Boston Common, the bunker Hill monument, the USS Constitution, the Paul Revere house, and much more.

It’s a 2.5-mile trek that will also be quite eye-opening. It could be a learning opportunity for you and your kids as well.

Enjoy a Walk to the Sea

If you want to learn more about the city’s history and how it has grown and developed over the last 400 years, head to the Norman B. Leventhal Walk to the Sea. This one-mile walking tour leads you from Beacon Hill to Long Wharf with freestanding glass information panels located at several stops along the way to highlight Boston’s history.

a man and a girl looking at signs on columns with the cityscape in the background

Tour the Boston Tea Party Museum to learn about the American revolution

The Boston Tea Party Ships & Museum document the town’s history and its role in the creation of the wider US. As one of the oldest cities in the US, founded in 1630 and under British colonial rule for so long, there is much to see and learn about American history.

the Boston Tea Party Museum on the water with a boat in the background

The city was at the forefront of the American revolution and various key events in history can trace their origin here. For instance, the Boston Tea Party, The battle of Bunker Hill, the Boston Massacre, and much more. Visiting the museum in the fall will guarantee fewer crowds in the popular museum.

Walk among the dead at King’s Chapel burying ground

Take your kids through a haunted walk among the dead in the King’s Chapel. As the season prepares for Halloween, you can take a walk in the oldest cemetery in the city, where many of the city’s prominent residents now lie.

a plaque on a wrought iron fence about the King's Chapel Burial Ground

This cemetery attracts many visitors who come to pay their respect to the heroes of the American revolution. Many have talked of the place being haunted by ghosts of the people who were buried alive there. The dead here are not at peace yet, and they are keen to show that.

Celebrate Halloween in Boston

Boston is a perfect place to celebrate Halloween and trick or treat with your kids. The town’s history and documentation of grisly events make it the perfect place for the haunted.

There are numerous graves and cemeteries in the city and talks of ghosts are rife everywhere you go. The ghosts and gravestones tours that take you through the King’s Chapel burial ground are a good example.

Join the neighborhood locals as they celebrate this event and have some fun. There are plenty of Halloween events for young and old.

Go to a giant pumpkins show

The Boston Public market is a very popular place during this period. The farmers come from all corners of the state to showcase their produce.

The giant pumpkins always steal the show here. Take some time to admire these gigantic specimens and marvel at what nature can produce.


While you are at it, grab some hot coffee at the markets and savor the way this helps you beat the cool weather.

Take a hike at the Boston’s public garden

The Boston’s public garden is beautiful and breathtaking, inviting you to take long walks in the fall foliage and enjoy the beauty of cool weather and the pure, cool air.

The trees start changing color in the fall and the metamorphosis is spectacular. It is time to take some beautiful photos against some of the most beautiful backgrounds in the city.

a tree with orange and yellow leaves with a lake and more trees in the background and a bench in the foreground

Go apple picking

The local farms around Boston are inviting and you can spend a productive day picking out apples. There is no shortage of farms around and they grow different varieties of apples.

Some of these farms, such as the Boston Hill Farm, offer more than apple picking. They usually hold events and activities that your kids can enjoy throughout the season.

Get to enjoy some of these festivals in stunning scenery and make sure you carry some fresh apples back home. It’s the perfect day trip during October or November if you live in the area.

See animals at the Franklin Park zoo

The day might not be complete before you take your kids to see animals at the Franklin park zoo. There is a lot to see here.

two lions on the grass with rocks behind them
Photo Credit: Zoo New England

There are hundreds of exotic animals here including giraffes, lions, and red pandas. Afterwards, the kids get to play in the playground here and have all sorts of fun.

Make plans to visit the zoo at night! From early August through late October, the zoo hosts the Boston Lights event. From 6:00 to 10:30 pm every night, you can witness dozens of beautiful lantern displays throughout the park.

Watch the Columbus Day parade

The Columbus day parade is held to commemorate the triumphs and voyages made by Christopher Columbus and the contributions others made to liberation of America.

It’s a 2-hour parade full of military bands and regalia, clowns, performers and even a display of some antique cars. There is a lot of color and pomp at this event.

Visit the Salem Witch Museum

The Salem witch museum is another location which has a rich history in the city. Learn about the Salem trials and why this has significance in the city’s history. You will be able to get guided tours.

the Salem Witch Museum with cars parked in front of it

The Salem witch trials occurred in the year 1692, eventually leading to the prosecution and burning at stake of many of these witches. This will be an education and eye-opening tour to learn more about the heritage that makes this city quite unique.

Visit Museums During Free Admission Days

Several Boston museums offer free admission days. Traveling Tulls has put together an extensive list of free and reduced museum admission options to help you find the right outing for your family.

Some of the options include the Boston Children’s Museum, the Museum of Fine Arts and even the New England Aquarium!

Attend the Boston Book Festival

For my fellow book lovers, if you’re planning a visit to Boston in October, try to time it around the middle of the month so you can attend this wonderful event. The Boston Book Festival is one of the best in the country and it’s free to attend and open to all.

Held in both Copley Square and Roxbury, the festival celebrates the strength of words and is designed to inspire a love of reading.

If you really want to geek out on books, also make time for the Boston International Antiquarian Book Fair. This three-day event occurs in late October and features rare book finds from around the world 

Find a place to observe the Head of the Charles Regatta

Every year, thousands of rowers flood the Charles River to participate in the regatta. Competitors row three miles upstream while tens of thousands of spectators cheer from the bridges and banks of the river.

a bridge with lots of people standing on it looking down to watch the people rowing boats on the water
Photo Credit: Carlos Ridruejo

For a great view, head to Memorial Bridge in Cambridge or any of the seven bridges along the route. The start line is at BU’s DeWolfe Boathouse and the finish line is at Herter Park.

Visit the City of Quincy

Okay, it’s not technically IN Boston, but it’s close to Boston (just south of the city) and it’s well worth a visit! Known as the “City of Presidents,” this charming town contains several historical sites and also a wide variety of wonderful restaurants.

During the fall, Hancock Adams Common is a must-see. It’s always a beautiful venue, but the breathtaking fall foliage make it spectacular.

a building surrounded by trees
Photo credit: Gintautas Dumcius

Make sure to stop by Hancock Cemetery where you can see the memorials of noteworthy individuals. Then head to the United First Parish Church to see where Presidents John Adams and John Quincy Adams are both buried.

Attend a Sporting Event

Boston is one of the best cities in the U.S. for sports fans. You can attend top-notch sporting events year round, but some of the most popular games take place in the fall.

College Football

According to the Boston Globe, Boston is home to 29 colleges and universities and those students make up almost one-fifth of the city’s population. So, if you really want to explore all Boston has to offer in the fall, you really should attend a football game at one of the many city colleges. Good choices are Boston College and Harvard.

Pro Football

If you’re a football fan, you’ll definitely want to take the opportunity to go to a New England Patriots game. The Patriots are tied with the Pittsburgh Steelers for the record of the most Super Bowl wins – six wins prior to 2023.

You can view the full schedule here. Ready to go? Click here to purchase tickets.

Pro Basketball

October marks the beginning of the NBA basketball season so it’s a perfect time to catch the Boston Celtics.

See their full schedule here. And once you’ve chosen your game date, click here to purchase tickets.

Pro Hockey

Boston is home to the Boston Bruins. Like the Celtics, they play at TD Garden.

NHL season kicks off in October, yet another reason October and November are great months to visit Boston! See the Bruins schedule here. And when you’re ready to go to a game, purchase your tickets here.

Other Fun Things to Do in Boston

There are, of course, dozens of other fun things to do in Boston. In the list above, I’ve tried to highlight the activities that are particularly well-suited for a visit in October or November.

Boston CityPass

If you want to see some of the cities most popular attractions, consider getting the Boston CityPass to save significantly off the admission price of four of the city’s top attractions. Included are the New England Aquarium and the Museum of Science, plus your choice of any two of the following:

  • Boston Harbor City Cruises
  • Harvard Museum of Natural History
  • Franklin Park Zoo
  • View Boston Observation Deck

Fenway Park Tour

You can get an inside look at “America’s Most Beloved Ballpark” and home to the Boston Red Sox — the 2018 World Series champions. These one-hour guided tours of Fenway Park are available year-round including game days!

Samuel Adams Brewery Tour

Another tour worth checking out is the Samuel Adams Boston Brewery Tour. Learn all about the brewing process and taste some of the brewery’s delicious lagers.

More Fall Fun

Is Boston too far for an autumn getaway? Check out one (or more) of the 10 Best Places to Visit in the Fall in the US. There are recommendations for great spots all across the country from the West Coast to the East Coast.

If you prefer to stick close to home, print off this One Month Calendar of Fall Activities that are fun for the whole family! Or head outside on a family walk and try to spot all the items on this Fall Scavenger Hunt.

Last Updated 08/01/2022

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