Top 10 Things You Must do in Boston This October (2019)

This post lists top things to do in Boston in October 2019 as well as things to do at night, free activities and family-friendly events.

 

 


TOP 10 EVENTS AND THINGS TO DO

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

If you’re looking for even more fun things to do in Boston, make sure to check our posts: 

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.

These historic locations and many others 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

This city usually attracts a lot of notable musical artists throughout the year, and October is no exception.

There will be several famous and popular bands performing in Boston this month.

 

 

If you’re interested in hearing some great live music, consider one of the following concerts:

Find all the concerts in Boston this month here.

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.

 

 

If you don’t mind leaving the city, the New England Patriots will be playing two home games this month versus the New York Giants (Oct 10th) and the Cleveland Browns (Oct 27th).

October is also the month that the Boston Bruins will begin their next season, and there will be a total of 6 home games to attend.

Baseball fans may also have an opportunity to see the Red Sox, as there’s a chance they will play a role in the postseason.

Finally, it’s worth noting that the New England Revolution will be playing their last home game of the season on October 6th.

Find all the games in Boston here.


(4) See a Hit Musical

There will be a few great musicals to see in Boston during the month of October, and Frozen will likely be the most popular option.

Based on the hit Disney film with the same name, this is sure to be a popular option for families visiting Beantown.

Purchase Frozen: The Musical tickets or learn more.

 

 

Alternatively, you can also see Tootsie at the Citizens Bank Opera House from October 20th – 31st.

Purchase tickets for Tootsie or learn more.

If you’re looking for a different kind of musical, consider seeing Blue Man Group instead. This theatrical troupe has become one of the most popular shows in the world!

See all the theatrical events happening in Boston here.


(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.

 

 

There are a lot of 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 the Titanic Masquerade

Over the past few years, Boston Nightlife has been hosting a special masquerade and costume party in honor of Halloween.

This event takes place on the Spirit of Boston Yacht, which will cruise around the city for three hours during the party.

 

 

There will be 3 DJs on hand performing a variety of music on 2 floors of the yacht over the course of 4 hours.

Although costumes are not required, this is a masquerade, so it is encouraged to dress up in some way for this activity.

TIP: If you’d rather just take a quiet cruise around the city, there are several Boston dinner cruises and sunset boat tours you may want to consider.


(7) Go on a Halloween Themed Cruise

What better way to see Boston from the water than on a spooky cruise? Spirit of Boston Cruises are decorating their yacht for Halloween. 

This family fun lunch cruise includes a buffet-style meal, Halloween themes activities, and creepy music to set the tone.

 

 

Guests are encouraged to wear their costumes and there will be Halloween candy for all the kids on board.

NOTE: Even if you miss out on this activity, you may want to consider going on a Boston Harbor cruise at some other time during the month of October.

It should also be noted that some Boston tourist passes include a cruise, allowing you to save 50% or more on ticket prices.


(8) Celebrate Columbus Day

This official Massachusetts state holiday is celebrated every 2nd weekend in October, which means that there will be a lot of fun things to see and do from Oct 12th – 14th in 2019.

One of the most popular activities is the Columbus Day Parade, which will kick off in Boston on October 13th and head through the North End on streets such as Atlantic Ave, Hanover St, and Cross St.

 

 

In addition to marching brass bands, there will also be military units, colonial militias, duck boat floats, and a variety of entertainers/politicians appearing in the parade. This event is entirely free to attend.

There will also be a variety of sales available at local businesses, but it should be noted that banks, state offices and schools will be closed.

If you’re looking for even more great things to do that won’t cost a thing, make sure to read our section covering free things to do in Boston this October.


(9) Attend the Great Pumpkin Festival

Every year, the Cambridge Brewing Company hosts a pumpkin festival in honor of Halloween with plenty of different drinks to try.

The focus of this event is Pumpkin-flavored beers from across the country, and there are usually 30+ different brands available to choose from. There will also be a lot of great foods to eat!

 

Cambridge Brewing Company
This photo of Cambridge Brewing Company is courtesy of TripAdvisor

 

This event takes place during the last weekend of October and tickets are offered in three different sessions:

  • Session 1: 12 pm – 3 pm
  • Session 2: 4 pm – 7 pm
  • Session 3: 8 pm – 12 am

Purchase tickets or learn more.

With hours running late into the night, this is one of the most interesting nighttime activities of the month. 

That said, if you’re looking for even more fun after dark, make sure to check our section which covers things to do at night in Boston this October.


(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:

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.

 


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FREE THINGS TO DO

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.

  • Day 1 Hours: October 19th from 11 am – 6 pm
  • Day 2 Hours: October 20th from 10 am – 4 pm
  • Location: 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.


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!

  • Day 1 Hours: October 19th from 10 am – 6 pm
  • Day 2 Hours: October 20th from 11 am – 5 pm
  • Location: University Hall at Lesley University
  • 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, so 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!


Watch a Rowing Competition

Over 9,000 athletes will be competing in the Head of the Charles Regatta on October 19th – 20th.

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
  • Attager Row: Rowing & Fitness Expo
  • Reunion Village: Presented by Delta Air Lines
  • Eliot Bridge Enclosure: Presented by Aston Martin

Learn more about this event.

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


Go Pumpkin Caroling on Halloween

Who says singing carols is only for Christmas?

The Somerville Community Growing Center will be holding a special event this Halloween including what they call Pumpkin Carols and dancing.

This activity will run from 5 pm – 7 pm on October 31st and it is free to attend. All you have to do is show up and join in on the fun!

If you’re planning to take the kids trick or treating, this could be a great way to start the night.

Learn more about this event.


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 are included on both our Freedom Trail tour and our self-guided outing.

Learn more about visiting these historic locations.

 


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THINGS TO DO AT NIGHT

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 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.

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


See the View from the Skywalk Observatory

The Skywalk Observatory at Boston’s Prudential Center brings you up 50 stories for an incredible view. You also have the option to listen to an audio tour to learn about the history and facts about everything you can see. 

This attraction also includes the Dreams of Freedom Museum and a multimedia movie theatre providing even more entertainment. 

 

 

The observatory is open daily from 10 am-10 pm, which means you can enjoy views of the city well after dark.

TIP: Admission to this attraction is included with most Boston tourist passes which you can use to save 50% or more on tickets.


See a Comedy Special

The city of Boston tends to attract a lot of popular comedians throughout the year, and this month will be no exception as Gabriel Iglesias will be making an appearance at the Wilbur Theatre.

Alternatively, you can also see Demetri Martin at the Chevalier Theater in Medford. While this isn’t in Boston, it’s not too far outside of the city, and you can reach it from Beantown with ease. 

NOTE: Even if you can’t afford these shows, you may still want to consider enjoying some stand-up comedy in Boston, as there are several venues that offer free open mic nights throughout the week.


Grab a Drink at the Local Craft Spirit Festival

If you’re interested in trying out a variety of different cocktails, the 4th Annual Local Craft Spirit Festival is a perfect place to discover your new favorite drink.

Dozens of local vendors will be providing cocktail demos, artisan brews, and plenty of great food to enjoy.

Standard tickets to this event includes 20 beverage sampling tickets, giving you plenty of opportunities to try different drinks. VIP ticket holders will receive 23 sampling tickets, one meal voucher, and early entry.

TIP: Even if you miss this event, you can still take our Historic Tavern tour which 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 their 19th 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!

Tickets will be around $15-$25 per person. Learn more about this event.


Step On Board a Haunted Ghost Ship

When it comes to haunted houses, Boston has taken this classic idea to an entirely new level with Ghost Ship Harbor.

This isn’t just a place where people dressed up in spooky costumes will jump out at you – this location offers several interactive experiences including scenarios where you must escape a virus outbreak!

Visitors will also have the opportunity to go on a ghost ship that is reportedly haunted and perform a paranormal investigation.

Ticket prices start at $34.99 per person and the Ghost Ship Harbor is open every weekend in October.

Purchase tickets or learn more.


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. 

The program is free to attend, but it is also very popular. You can get tickets in advance online or try for unticketed admittance at the event. 

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.

 


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FAMILY-FRIENDLY ACTIVITIES

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 our family-friendly activities section.


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 which 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.

 

Connors Farm
This photo of Connors Farm is courtesy of TripAdvisor

 

If you’re looking for other nearby locations, check the following lists for more farms close to Boston which 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!


Attend a Spooky Zoo Event

The Franklin Park Zoo holds a special event in honor of Halloween every year, giving families even more of a reason to visit.

Younger visitors who dress up in their costumes will have an opportunity to walk down a trick-or-treat trail and get some candy while they’re here.

There is also usually a haunted maze to walk through, a costume contest, a howling contest and many other creepy activities.

All Halloween events are included with general admission, which means you won’t even have to pay any additional fees!

This also means that 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.

The “Boo at the Zoo” event typically takes place on the last weekend before Halloween (October 26th – 27th).


Find Out How Well Pumpkins Can Float

Boston Common usually holds special events for every major holiday, and Halloween is no exception. For the past few years, they have hosted a Pumpkin Float at the Frog Pond to celebrate.

Visitors are asked to bring an 8-inch or smaller hollowed out and carved pumpkin which will be lit and floated across the pond. Guests are encouraged to arrive in their best Halloween costumes.

In addition to this event, there will also be refreshments, music and other fun family activities to enjoy.

Best of all, the Frog Pond Pumpkin Float is entirely free to attend! All you have to do is bring a jack-o-lantern for the activity.


Go to the Columbus Park Fall Festival

In honor of Columbus Day, the Friends of Christopher Columbus Park host a fall festival every year in October. Usually this event takes place either the weekend of the holiday or the week before.

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.

There will also be several family activities such as a petting zoo, games, and other fun things to do – and it’s all free!

The Columbus Park Fall Festival is currently scheduled to take place on October 5th from 12 pm – 4 pm, but 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, 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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