10 Things to Do in Boston in October

The month of October is synonymous with two things in Boston, autumn and Halloween. During this month many of the activities are harvest and Halloween related.

Verónica Álvarez

Verónica Álvarez

10 min read

10 Things to Do in Boston in October

Boston | ©Jimmy Woo Man Tsing

During the month of October you can enjoy many of the best things Boston has to see and do and most of the activities are linked to pumpkin, apple and other seasonal harvests. Beer also has a place of importance in this month in Boston with the traditional Oktoberfest.

Halloween related parties and events are also present in the October calendar in Boston and tours specialized in occult or horror themes are the most sought after. I invite you to know the 10 best things to see or do if you are visiting Boston in October.

1. Drink some of the best beers in Boston during Oktoberfest

Oktoberfest in Harvard Square| ©Patrick Haney
Oktoberfest in Harvard Square| ©Patrick Haney

The traditional beer festival, known as Oktoberfest, is celebrated in several locations around Boston. During the first two weeks of October, several places organize activities with a common denominator: good music, lots of delicious food, dancing, entertainment and, of course, large quantities of beer.

In Boston there are several options to celebrate Oktoberfest, but two of the most popular places are:

  • Harvard Square: Harvard Square Oktoberfest includes food, arts and crafts, live music and their traditional HONK parade. Location: Brattle St, Cambridge, MA 02138
  • Harpoon: Harpoon Brewery 's Oktoberfest includes tastings of various types of beer, music from new bands and lots of dancing. It's a must-visit festival if you love beer. Location: 306 Northern Ave, Boston, MA 02210

Bostonians take Oktoberfest very seriously with a series of very interesting concerts and activities. You can check out the full Boston Oktoberfest calendar and plan which events you'll want to be a part of. And if you're left wanting more beer, taking a pub crawl around Boston is always a safe bet.

Details of interest

  • When: during the first two weeks of October.
  • Price: around 40 €.

Book a pub crawl in Boston

2. Participate in the main sporting events in Boston

Red Sox Stadium| ©Richard Eriksson
Red Sox Stadium| ©Richard Eriksson

During the month of October, Boston is a center of sports in all the major sports in the United States. You will be able to watch the games of the 5 main sports teams in Boston:

While it is true that the games can be seen throughout the season, during the month of October, due to the calendar of the different championships, the games are usually followed by fans because the positions are not yet defined and each game is a display of adrenaline.

If you want to ensure a place in the stands, you must book your ticket in advance because they sell out quickly, especially those of the NBA and MLB.

Details of interest

  • When: dates change depending on the game.
  • Price: depends on the game, the location in the stadium and how far in advance you buy your tickets.

Buy your ticket for a Boston Celtics game

3. Attend the Head of the Charles Regatta

Head of the Charles Regatta| ©Christopher Schmid
Head of the Charles Regatta| ©Christopher Schmid

The Head of the Charles Regatta, also known as HOCR, is one of the main events held in the city of Boston in October as it is the largest two-day regatta in the world. It gathers annually around 11000 sailors, 1900 boats and around 60 events related to the regatta are held.

The fun of the event is not limited to being a simple spectator, but you will be able to enjoy other related events, such as the Weld exhibition, the rowing and fitness exhibition, etc., although you can also watch the race relaxing from the Eliot Bridge.

In addition, there is another point of interest in the city in the so-called Reunion Village. This is a fair located on the banks of the Charles River on the Cambridge side where the participants of the event come and where you will find stalls with food, drinks, exhibitions, etc. A must during the Head of the Charles Regatta.

Details of interest

  • When: last week of October (may change, it is advisable to consult the official website of the Regatta).
  • Price: watching the regatta is free of charge. Entrance to Reunion Village costs around 9 € per person.

4. Have fun with festive Halloween weather

Halloween in Boston, Decorations| ©Andrew Watson
Halloween in Boston, Decorations| ©Andrew Watson

The Halloween holiday season invites a plethora of events. Almost every theater offers a horror and fun show to revive the spirit of Halloween in Boston during the month of October. If you prefer movies, you can also attend film festivals dedicated to this holiday in the city. Tickets, in most cases, can be booked online.

But undoubtedly one of the best Halloween activities is to hire a ghost tour in Boston, such as Ghosts and Gravestones, a 90-minute tour you will know the horror stories of the city and visit two cemeteries knowing in detail their stories.

This tour sells out very quickly, book your tickets in advance and keep in mind that this is not a tour suitable for children and not for sensitive or easily impressed people.

Details of interest

  • When: every day at different times.
  • Price: from 44 €.

Book a Boston ghost tour

5. Participate in the Fort Point Open Studios event

Boston| ©Tiago Henriques
Boston| ©Tiago Henriques

Fort Point Open Studios takes place during a weekend in October. Visitors can see and meet fine artists at the various live performances and even purchase some great fine art pieces.

The program is not limited to just fine art, but is also accompanied by music, live painting demonstrations, performances and art activities for children. If you are traveling with them, include this activity on your list of things to do with kids in Boston. They won't be bored.

Details of interest

  • When: one weekend in October.
  • Price: admission is free, but donations are welcome.

6. Take beautiful tours in Boston during the month of October

Boston| ©Brandon Olafsson
Boston| ©Brandon Olafsson

The best way to experience the true culture of the city is to take a walking or biking tour of Boston. October is the ideal time to do it because the weather is perfect for walking and enjoying the spectacular scenery that autumn brings to the city.

Tours with specialized guides are much more complete, since they will tell you everything about the city of Boston and you can also choose from multiple options: from booking a bike tour through the most interesting points of the capital of Massachusetts, to visiting the Harvard campus with an expert guide or hiring a subway donut tour. There is something for everyone!

Choose one of the best guided tours of Boston and enjoy one of the walking tours that the city has to offer.

Interesting details

  • When: every day at different times.
  • Price: depends on the type of tour you choose.

Book a guided tour of Boston

7. Boston Book Festival

Boston Book Festival| ©Hudson Valley Slim
Boston Book Festival| ©Hudson Valley Slim

The Boston Book Festival is one of the largest book fairs in the United States. It lasts two days and is packed with events, books and entertainment for the whole family. Throughout this literary festival, more than 150 renowned and Pulitzer Prize-winning writers are on parade.

Guest writers give presentations and discussions on a variety of topics. There are hundreds of books to choose from. You can also enjoy live music, food and various activities for children.

Details of interest

  • Where: 32R Essex St, Suite 5, Cambridge, MA 02139.
  • Price: Admission is free, don't miss it.

8. Pick up pumpkins for Halloween in Boston

Halloween in Boston| ©Massachusetts Office
Halloween in Boston| ©Massachusetts Office

Picking pumpkins is a great Halloween tradition in Boston. The pumpkin picking locations are farms that are located in the suburbs of Boston, so this activity is great to do during a day trip to the outskirts of the city.

You can choose the location you like best to organize this activity from your itinerary from an extensive list of pumpkin picking farms in Boston that usually hold special events in the month of October.

Each farm offers different services and activities. Depending on your interests, you may want to explore the different options. I'll leave you with the contacts below for two of the top farms that offer the pumpkin picking experience.

Hanson:

Connors:

  • Phone: (978) 777 1245
  • Address: 30 Valley Road (Rt. 35) Danvers, Massachusetts 01923

9. Tour the Boston Tea Party Museum to learn about the American Revolution

Boston Tea Party Museum| ©Robert Linsdell
Boston Tea Party Museum| ©Robert Linsdell

The Boston Tea Party Museum documents the history of the city and its leading role in the independence and creation of the United States.

The city of Boston, being one of the oldest cities in the United States, founded in 1630 and having been under British colonial rule for so long, has a lot of history to tell.

While this museum can be visited throughout the year, it is best to visit in the month of October for two reasons: the first is that you are assured of fewer crowds, so you can tour at your leisure, and the second is that the weather is not hot and not cold, which makes the experience more rewarding.

Details of interest

  • When: open all year round.
  • Price: from 32 € for adults and 24 € for children.

10. Visit the Salem Witch Museum

Salem Witch Museum| ©Rebecca Siegel
Salem Witch Museum| ©Rebecca Siegel

October, the month of Halloween and witches, is the ideal time to visit the Salem Witch Museum. By visiting this museum you will learn all about the Salem Witch Trials and why it is so important in the history of this city located about 15 miles away from Boston.

The Salem Witch Trials took place in the year 1692 and ended with the burning at the stake of many women considered witches. The Salem Witch Museum is one of the best museums in Boston.

You can take a virtual tour of the Salem Witch Museum. After viewing it online, you will definitely want to visit it in person.

Details of interest

  • Where: 19 1/2 Washington Square North Salem, MA 01970.
  • Price: starting at approximately €15 per person.

What are the characteristics of the weather and temperatures in Boston in October?

Boston| ©Chris Rycroft
Boston| ©Chris Rycroft

During the month of October, temperatures drop noticeably in Boston, but still remain at levels that make outdoor activities possible. The average October temperature in Boston is around 15°C during the day and 13°C at night. Lows of 8 ºC can be recorded, so a coat is a must.

Rains can be present around 12 days of the month, but the sun still shines for at least 7 hours a day.

When you are organizing your trip remember to check the Boston weather forecast to be prepared.

What is the tourist flow in Boston during the month of October?

Tourists in Boston| ©Bart E
Tourists in Boston| ©Bart E

During the month of October, not only do the temperatures in Boston drop, but the number of visitors to the city also drops.

This is because many people have used up their vacation days over the summer months and also because most schools have resumed classes.

This is great news in some respects, because you will have many of the city's main attractions all to yourself. Waiting times in the queues are also decreasing, although it is still better to opt to buy tickets online to skip the lines because it is not nice to have to wait in line in the rain or in the cold.

Are prices in Boston during October high?

Go Boston Pass| ©Klook
Go Boston Pass| ©Klook

I have another piece of good news for you, prices also go down during the month of October, as a general rule. As we enter the low tourist season, prices tend to decrease. The drop is noticeable in some sectors such as clothing sales.

During the month of October you will be able to access great discounts in stores, but if you really want to save as much as possible during your visit to Boston in October, the best thing to do is to buy a tourist pass.

You will save a lot of money on entrance fees and also on transportation, restaurants and stores in general.

Buy your Boston Sightseeing Pass

What should I pack to visit Boston in October?

Preparing your luggage| ©Marissa Grootes
Preparing your luggage| ©Marissa Grootes

Temperatures drop significantly in October with the arrival of autumn, so it is very important that you pack warm clothes. You can expect temperatures as low as 8 ºC so bring warm jackets, sweaters, hats, gloves and scarves.

Regarding footwear, it is advisable to wear warm shoes and also waterproof, because there is a good chance that you will encounter a rainy day. If you plan to go out at night, you should wear even warmer clothes because you can get very cold during October in Boston.

Some useful tips for visiting Boston in October

Boston| ©kateryna.poliarus
Boston| ©kateryna.poliarus
  • Keep in mind that Boston is best explored on foot and public transportation is excellent. The option of renting a car is only justified if you plan to leave the city or go to the countryside.

  • Bring comfortable, warm, rainproof clothing and footwear for walking while enjoying the city.

  • The city of Boston offers many free entertainment opportunities, from concerts to exhibitions. If you plan to stay for more than a week, you can buy a seven-day pass to get around the city's subway stations and buses - It is also advisable to invest in the Boston CityPass or the Go Boston Card, which will allow you to visit many attractions for free and save money on restaurants, shopping, transportation, etc. - Buy your tickets in advance and online to secure your spot. By doing so you can also get better prices and skip the line tickets - Have fun, enjoy and see all that Boston has to offer in October.