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What to Do in Boston in October

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Updated: October 3, 2023
 By Brian Burgess

This post lists the top things to do in Boston, Massachusetts, in October 2023, as well as things to do at night, free activities, and family-friendly events.

As local Boston tour guides, we know that October is one of the best times to visit the city. Fall colors peak mid-month and the pleasant autumn temperatures are perfect for outdoor events, at least during the early part of the month.

Many of the activities included in this post are things that we do regularly, particularly in October.

And we have taken our experiences as local experts leading thousands of visitors in October (and answering your questions) to help forge this guide.

We also included tips from the roughly 15k members of our popular Boston Travel Tips Facebook group.

October in Boston Tips

Our group consists of locals, like our tour guides, veteran visitors, and newbies to Boston.

There is no need to become a member to read the posts, comments, and recommendations.

So, once you are done reading this post, check the group out to help plan your trip to our wonderful city.

TOP 10 THINGS TO DO IN OCTOBER

In this section, we will cover the ten most interesting activities you can enjoy in Boston during the month of October.

Boston is full of lively neighborhoods.

If you’re looking for even more fun things to do in Boston, make sure to check out some of our other posts such as: 

It’s also worth noting that you can save money on some of the most entertaining attractions in and around the city with a Boston tourist pass.

1. 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 were laid to rest.

This is also where you will find Paul Revere and Mother Goose!

If you’re interested in digging a little deeper (no pun intended), head to Copp’s Hill Burial Ground to see graves dating back to the 1600s.

Other historic locations and top attractions you might like to visit include the Boston Massacre Site, Boston Common, and Faneuil Hall near Boston Harbor. These are included in either our pay-what-you-wish guided Freedom Trail tour or our self-guided outing.

We recommend this activity for anyone who is interested in the history of Boston and wants to see some of the creepier sites in the city.

2. Go to a Concert

The Boston area 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 musicians playing in and around the Boston area this October.

Concerts

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

NOTE: If you’re more interested in classical music, keep in mind that the Boston Symphony Orchestra will be performing at the Symphony Hall all month.

3. Attend a Sporting Event

Sports fans will have plenty of opportunities to see a live game in Boston throughout the month of October.

This month marks the beginning of the basketball season in the NBA, which means there will likely be more than a few Boston Celtics games to see.

Football

Note that you can take guided tours of both TD Garden and Gillette Stadium, which is sometimes free with a discount pass.

Hockey

Baseball

However, Red Sox fans might enjoy a tour of Fenway Park!

Soccer

Motorsport

Click here to see even more sporting events in October in Boston.

4. See a Hit Stage Performance

There will be a few great musicals and other shows to see in and around Boston during the month of October.

Musicals

Performance Art or Magic

Family-Friendly Shows

5. Take a Crime Tour

If graveyards aren’t enough, you might also want to consider celebrating Halloween with a tour of historic crime scenes in the Boston area.

We offer a pay-what-you-wish Beacon Hill Crime Tour which covers several notable sites tied to the Boston Strangler.

You’ll also learn about Professor John White Webster, who was convicted of murder in 1850.

Searching Availability...

There are some graphic details included in this outing, so it is only available for guests who are 16 or older. 

This is a great opportunity to discover the darker side of Boston’s history and find out about some of the more grisly crimes that have taken place in this city.

What better way to get in the mood for the spookiest day of the year?

6. Attend Boston Lights

The Franklin Park Zoo brings back the Boston Lights event with this year's title being "A Lantern Experience."

All 72 acres of the zoo are lit up with fantastical creatures made of light. This wonderland of brilliant color is truly magical

You might run into a 33-foot sphinx or experience the history of China through lantern scenes.

The event runs throughout October.

For tickets and additional information, visit the Boston Lights page on the Franklin Zoo website.

7. See a Famous Comedian Perform Stand-Up

If you're in need of a good laugh, there will be several notable comedians performing in Boston during the month of October.

Comedy Shows

Comedy Clubs

To find even more shows by some very funny stand-up comedians click here.

8. Watch a Rowing Competition

Over 11,000 rowers will be competing in the Head of the Charles Regatta on October 20th & 22nd.

This rowing competition will be free to watch, and there are several different venues offering viewing locations along the 3-mile stretch where the event will be taking place.

If you’re interested in attending, consider watching it from one of the following sites alongside the Charles River:

  • Weld Exhibition | food, merchandise
  • Rowing and Fitness Expo | Rowing machine testing, merchandise
  • Reunion Village | lively and energetic
  • Eliot Bridge Enclosure | relaxed setting with great views

Learn more about this event.

Parking availability is limited, so it is recommended to use public transportation to reach the Regatta.

If you’d like to get out on the water yourself, consider Boston dinner cruises and sunset boat tours.

9. Take a Haunted Bus Tour

Join the “trolley of the doomed” and follow your guide on a two-hour tour learning about Boston’s darker side.

The Ghosts & Gravestones tour covers a variety of disturbing subjects such as the Boston Strangler and various reported hauntings throughout the city.

In addition to seeing sites related to these terrifying tales, you’ll also visit both Copp’s Hill Burying Ground and the Granary Burying Ground to see the final resting place of several historic figures.

For tickets and information, visit the Boston Ghost Tours With Ghosts and Gravestones website.

NOTE: If you’re looking for a more affordable outing, you can visit both the cemeteries included on this tour for free!

10. Save Money With a Tourist Pass

Several of the most popular attractions in this city are included with various Boston tourist discount passes.

There are a variety of different pass options to choose from, and depending on which service you pick, you could save 50% or more off general admission prices.

While all-inclusive passes give you access to dozens of different activities for a specific number of days, there are also companies that allow you to pay one flat price for a set number of attractions.

Here are some of the more notable activities you can enjoy with these services:

  • Hop-on-Hop-off Trolley
  • Boston Duck Tours
  • Fenway Park Tours
  • Skywalk Observatory
  • New England Aquarium
  • Salem Witch Museum
  • Franklin Park Zoo
  • Museum of Science

In addition to the potential savings, these passes also offer skip-the-line privileges at some locations.

For more details, make sure to read our post covering Boston attraction discount tourist passes.

FREE THINGS TO DO IN OCTOBER

This section will provide several fun activities that you can enjoy in Boston without worrying about your budget.

Don’t forget to check our other sections for additional ideas such as the Columbus Day Parade, looking at the Fall Foliage, taking a self-guided Salem Witch Trials tour, or visiting a historic graveyard.

If you’re looking for even more affordable attractions in the city, make sure to read our post about free things to do in Boston.

Visit a Free Museum

There are a lot of museums in Boston that offer free admission either all the time or on certain days each month.

If you’re looking for somewhere creepy to visit in honor of Halloween, consider one of the following locations, which include a lot of medical history that may disturb some guests:

  • The Ether Dome
  • The Russell Museum
  • Warren Anatomical Museum

Alternatively, you can also take a trip to one of the many history or art museums that offer free entry.

For more details about all of the options available, please read our post covering every free museum in Boston.

Attend the Boston Veg Food Fest

Whether you’re a vegetarian or you’re just interested in trying some plant-based meals, this food festival is definitely worth checking out.

Not only is admission free but there will also be free food to sample and several fun activities for kids to enjoy.

In addition to the food and family-friendly fun, there are also presentations from various speakers and opportunities to learn about different ways you can help animals or protect the environment.

  • October 14th & 15th
  • Saturday | 10:00 AM to 6:00 PM
  • Sunday | 11:00 AM to 4:00 PM
  • Reggie Lewis Athletic Center
  • Learn more about this event

TIP: If you’re interested in learning about the variety of food available in this city, consider taking one of our Boston food tours.

Attend Harvard Square's Oktoberfest

Join around 100,000 other folks for the free Oktoberfest celebrations in Harvard Square.

Of course, you'll find beer gardens, but also a parade, food, live music, crafts, family-friendly activities, and more.

This year's activities take place on Sunday, October 8th.

Visit the website for more information.

Note that there are other Oktoberfest celebrations, but most take place in mid to late September.

Go to a Comics Expo

Fans of graphic novels and comic books may want to think about attending the Massachusetts Independent Comics Expo in Cambridge.

This event is entirely free to attend, and there will be several fun activities to enjoy including panels with artists/creators, workshops on how to create comics, and exhibitions about this art form.

In addition to all the things you can see and do, there will also be industry icons on hand to sign autographs and meet with the fans!

  • September 30th-October 1st
  • Saturday | 11:00 AM to 6:00 PM
  • Sunday | 11:00 AM to 5:00 PM
  • Boston University Fuller Building
  • Learn more about this event

Although admission won’t cost a dime, chances are you’ll see something you want to buy while you’re at this comics expo.

We recommend bringing at least a few bucks for those trinkets you can’t live without!

Find Something to Read at a Book Festival

The Boston Book Festival will be returning to the city this October with a variety of great activities to enjoy.

Visitors can expect dozens of author talks, writing workshops, seminars, and other informative presentations at this event.

Aside from that, there will also be plenty of books to discover, live music to enjoy, and plenty of entertainment for kids.

TIP: Even if you miss out on this activity, you may want to make a trip to the historic Boston Public Library for free tours and plenty of books to read!

Boston Book Fair

Over 3 days in November is the annual Boston International Antiquarian Book Fair, now in its 45th year.

Book lovers, book dealers, and book collectors come together at Haynes Convention Center to share their love of all things books.

Events take place October 27th - 29th. For more information, visit the fair website

Tour the U.S.S. Constitution & Bunker Hill Monument

These historic landmarks are always worth visiting, and they always offer free admission throughout the year. 

The U.S.S. Constitution (otherwise known as Old Ironsides) is one of the most legendary vessels in United States history, and you can still see the ship to this very day.

If you want a great view of the city, the Bunker Hill monument is 221 ft tall, and you can get free admission simply by visiting the nearby museum.

Each of these sites is included on both our Freedom Trail tour and our self-guided outing.

Learn more about visiting these historic locations.

THINGS TO DO AT NIGHT IN OCTOBER

The following section will include a variety of fun activities that you can enjoy after dark in Boston during the month of October.

Be sure to check our other sections for even more great ideas such as taking a crime tour, going to a concert, attending a sporting event, seeing a musical, going to a pumpkin festival, and more.

For even more fun after the sun goes down, make sure to read our post covering things to do at night in Boston.

Take Part in a Spooky Bar Crawl

If you’re interested in getting to try out a number of different bars in the Boston area and show off your costume, one of the following might be for you:

You're sure to experience some of Boston's haunted happenings while experiencing some of Boston's most fun bars.

TIP: Our Historic Tavern tour covers a variety of notable bars in Boston including Emmet’s, the Parker Bar, and Cheers!

Go to a Halloween Horror Movie Marathon

The historic Coolidge Corner Theatre will be hosting its 21st Annual Halloween Horror Marathon on the last weekend of the month.

In years past, this event has included popular titles such as War of the Worlds, Alien, Night of the Living Dead, and Zombie.

In addition to the spooky movies, there is also a costume contest, music, and other fun activities to enjoy.

This is an excellent opportunity to see classic horror films on the big screen right before Halloween!

Check here for updates on the 2023 events.

Go Stargazing at the Boston University Observatory

Most Wednesdays, the Boston University Observatory opens to the public for a night of astronomy and looking at the stars with the professionals. 

In the winter, the event begins at 7:30 pm. You can’t see stars through clouds, so they do cancel in the event of poor visibility.

If it’s a nice clear night and you want to see the stars, this is an excellent activity to enjoy either with the family or a significant other.

Location: Coit Observatory at Boston University. The program is free to attend, but it is also very popular. You can get tickets in advance online.

FAMILY-FRIENDLY ACTIVITIES IN OCTOBER

This section will include a variety of fun attractions and events that families can enjoy in Boston throughout the month of October.

You may also want to check our other sections for additional ideas like seeing a musical, attending a sporting event, visiting a historic graveyard, looking at fall foliage, going to the Columbus Day parade and more.

For even more family-friendly activities, make sure to read our post covering things to do with kids in Boston.

Take a Look at the Fall Foliage

October is usually one of the best months to look at the fall foliage in Boston.

The brilliant reds, golds, and yellows can be found throughout the parks just outside the city. 

While you’re out looking at the leaves, look into picking (with permission) some of the apples from the orchards as well. 

There are a few different farms within 30 miles of the city, giving you plenty of opportunities to enjoy this activity.

Read our post all about the common tradition of leaf-peaking!

Needless to say, this is a great activity to enjoy with the whole family. If you’re looking for even more to do with the kids, check out our family-friendly activities section.

Go Apple Picking

If you have a car and are willing to get outside of Boston, there are a number of spots where you can go apple-picking.

You'll also want to load up on apple cider, apple cider donuts, and s'more supplies.

Some farms offer hay rides and a farm animal petting area.

Visit this list of other best farms for apple picking near Boston.

Note: if you haven't managed to secure a giant pumpkin to create jack-o-lanterns, these are the best places to go pumpkin-picking.

Learn All About the Salem Witch Trials

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 to make a short day trip to the area.

In addition to tours that cover the subject, you can also visit the Salem Witch Museum to learn more about this event and about witches in general.

If you’re up to it, this museum also offers a self-guided tour that you can access for free which includes several notable sites in the Salem area and beyond.

For more details or to plan a visit, check this list of Salem day trips.

Take the Kids to a Corn Maze or Pumpkin Patch

There are a lot of farms just outside of Boston, and most of them offer corn mazes and/or pumpkin patches. 

One of the most popular options is at Connors Farm in Danvers, MA. This location always offers a themed maze, and they also have additional activities.

In addition to a Haunted Farm attraction, there are also opportunities to explore the maze by flashlight after dark on the weekends.

If you’re looking for other nearby locations, check the following lists for more farms close to Boston that participate in spooky activities for Halloween:

TIP: This could be a great activity to enjoy either before or after fall foliage viewing. 

It’s also worth noting that Connors Farm is close to Salem, so you could combine your trip to this famous location with a stop at their corn maze/pumpkin patch!

Go to the Columbus Park Fall Festival

The Friends of Christopher Columbus Park hosts a fall festival every year in October.

This event features a children’s parade through the park which your kids can either watch or join, as well as a variety of music and live entertainment to enjoy.

The Columbus Park Fall Festival is currently scheduled to take place on October 14th, 2023, from 12:10 pm - to 3:30 pm, though this may change depending on weather and other factors.

If you’re looking for other things to do in honor of this holiday, make sure to read our top 10 section for more details about the Columbus Day Parade!

Visit the New England Aquarium

Enjoy a day under the sea! Well, kind of. 

Welcoming visitors for over 50 years, the New England Aquarium is one of the premier tourist attractions in Boston. 

See penguins, seals, and dozens of different fish and meet the aquarium's most famous resident, Myrtle the Green Sea Turtle!

If you’re budget-conscious, it’s worth noting that they actually offer one exhibit of harbor seals for free right outside the ticket booth. 

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

Eat at Faneuil Hall Marketplace

This is a great place to grab a quick lunch, whether it be a lobster roll, New England clam chowder, mac & cheese, or pizza – and you can fit in some souvenir shopping while you’re there! 

Faneuil Hall Marketplace is an excellent location that is appealing to all ages.

In addition to dining and shopping, look out for street performers and musicians, as there’s almost always something fun to watch. 

Visitors who come on Mondays and Saturdays can also take a free Quincy Market History tour which covers the architecture, politics, and geography of this marketplace.

In addition to these activities, you can usually rely on Faneuil Hall to host a special event celebrating either Columbus Day or Halloween during the month of October.

Although they haven’t announced anything yet, we recommend keeping an eye on the Faneuil Hall Marketplace calendar to make sure that you won’t miss out on anything fun and family-friendly.

The marketplace is open daily; hours vary.

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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 3rd, 2023
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