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.
10 Things to Do in Boston in October

More about: 10 Things to Do in Boston in October

During the month of October, you can enjoy many of the best things Boston has to see and do, and most activities are linked to the harvests of pumpkins, apples, and other seasonal products. Beer also plays an important role in Boston this month with the traditional Oktoberfest.

Halloween-related parties and events are also on the October calendar in Boston, and tours specializing in the occult or horror are the most sought after. I invite you to discover the 10 best things to see or do if you are visiting Boston in October.

1. Drink some of Boston's best beers at Oktoberfest

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

The traditional beer festival, known as Oktoberfest, is celebrated in various locations throughout Boston. During the first two weeks of October, several venues organize activities with a common theme: great music, lots of delicious food, dancing, entertainment, and, of course, plenty of beer.

There are several options for celebrating Oktoberfest in Boston, but two of the most popular venues are:

  • Harvard Square: Harvard Square's Oktoberfest includes food, arts and crafts, live music, and its 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 like beer. Location: 306 Northern Ave, Boston, MA 02210

Bostonians take Oktoberfest very seriously, organizing a series of concerts and interesting activities. You can check out the full Boston Oktoberfest calendar and plan which events you want to attend. And if you're still thirsty for more beer, 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. Attend major sporting events in Boston

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

During the month of October, Boston is a hub for the major sports in the United States. You can watch the games of Boston's five major sports teams:

Although games can be watched throughout the season, during October, due to the schedules of the different championships, the games tend to be closely followed by fans because the positions are not yet defined and each game is an adrenaline rush.

If you want to secure a place in the stands, you should book your ticket in advance as they sell out quickly, especially for the NBA and MLB.

Details of interest

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

Purchase 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 Boston in October, as it is the largest two-day regatta in the world. It brings together around 11,000 rowers and 1,900 boats every year, with around 60 events related to the regatta taking place.

The fun of the event is not limited to being a mere spectator, as you can also enjoy other related events, such as the Weld exhibition, the rowing and fitness exhibition, etc., although you can also watch the race in a relaxed manner from the Eliot Bridge.

In addition, there is another point of interest in the city called Reunion Village. This is a fair located on the Cambridge side of the Charles River, which is attended by event participants and where you will find food and drink stalls, exhibitions, etc. It is a must-visit meeting place during the Head of the Charles Regatta.

Details of interest

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

4. Enjoy the festive Halloween atmosphere

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

The Halloween holiday season invites a host of events. Almost all theaters offer a horror show and fun to revive the spirit of Halloween in Boston during the month of October. If you prefer cinema, you can also attend film festivals dedicated to this holiday in the city. In most cases, tickets can be booked online.

But without a doubt, one of the best Halloween activities is to book a ghost tour of Boston, such as Ghosts and Tombstones, a 90-minute tour where you will learn about the city's horror stories and visit two cemeteries to learn about their history in detail.

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

Details of interest

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

Book a ghost tour of Boston

5. Participate in the Fort Point Open Studios event

Boston| ©Tiago Henriques
Boston| ©Tiago Henriques

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

The program is not limited to the visual arts, but also includes music, live painting demonstrations, performances, and artistic activities for children. If you are traveling with them, include this activity in your list of things to do with children in Boston. They will not 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 get to know the true culture of the city is by taking a walking or bike tour of Boston. October is the ideal time to do this because the weather is perfect for strolling and enjoying the spectacular scenery that autumn brings to the city.

Tours with specialized guides are much more comprehensive, as they will tell you everything about the city of Boston and you can also choose from multiple options: from booking a bike tour of the most interesting spots in the capital of Massachusetts, to visiting the Harvard campus with an expert guide, or hiring an underground donut tour. There are options for all tastes!

Choose one of the best guided tours of Boston and enjoy one of the walking tours 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. More than 150 renowned writers and Pulitzer Prize winners take part in this literary festival.

Guest writers give presentations and hold 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, so don't miss out.

8. Pick up pumpkins for Halloween in Boston

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

Pumpkin picking is a great Halloween tradition in Boston. The pumpkin picking locations are farms located in the suburbs of Boston, making this activity perfect for a day trip outside the city.

You can choose the place you like best for this activity from an extensive list of pumpkin picking farms in Boston that usually hold special events in October.

Each farm offers different services and activities. Depending on your interests, it's a good idea to explore the different options. Below are the contact details for two of the main farms that offer pumpkin picking experiences.

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 prominent role in the independence and creation of the United States.

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

Although this museum can be visited throughout the year, it is best to visit in October for two reasons: first, you are sure to find fewer crowds, so you can explore at your leisure, and second, the weather is neither hot nor cold, making for a more enjoyable experience.

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. When you visit this museum, you will learn all about the Salem witch trials and why they are so important in the history of this city located about 15 miles from Boston.

The Salem witch trials took place in 1692 and ended with the burning at the stake of many women considered to be 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 seeing it online, you'll definitely want to visit it in person.

Interesting details

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

What are the climate and temperatures like in Boston in October?

Boston| ©Chris Rycroft
Boston| ©Chris Rycroft

During October, temperatures drop significantly in Boston, but they still remain at levels that make outdoor activities possible. The average temperature in Boston in October is around 15ºC during the day and 13ºC at night. Minimum temperatures of 8ºC can be recorded, so a coat is necessary.

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

When planning your trip, remember to check the weather forecast in Boston so you can be prepared.

How busy is Boston with tourists during the month of October?

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

During October, not only do temperatures drop in Boston, but so does the number of visitors to the city.

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

This is great news in some ways, because you'll have many of the city's main attractions all to yourself. Waiting times in lines also decrease, although it is still better to buy tickets online to skip the lines because it is not pleasant to have to wait in line in the rain or cold.

Are prices in Boston high during October?

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

I have more good news for you: prices also tend to drop during October. As we enter the low season for tourism, prices tend to decrease. The drop is noticeable in some sectors, such as clothing sales.

During October, you can get 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 buy a tourist pass.

You'll save a lot of money on tickets, as well as on transportation, restaurants, and stores in general.

Purchase your Boston tourist pass

What should I pack in my suitcase to visit Boston in October?

Packing| ©Marissa Grootes
Packing| ©Marissa Grootes

Temperatures drop significantly in October with the arrival of fall, so it's very important to bring warm clothing. You may encounter minimum temperatures of 8ºC, so bring jackets, sweaters, warm hats, gloves, and a scarf.

As for footwear, it is advisable to bring warm and waterproof shoes, as there is a high chance of rain. If you plan to go out at night, you should bring even warmer clothes, as it can get very cold in Boston in October.

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 that public transportation is excellent. Renting a car is only necessary if you plan to leave the city or go to the countryside.

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

  • The city of Boston offers many free entertainment options, from concerts to exhibitions. I recommend keeping an eye out for them.

  • If you plan to stay for more than a week, you can buy a seven-day pass to get around the city's subway and bus stations.

  • 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, shops, transportation, etc.

  • Buy your tickets in advance and online to secure your spot. By doing so, you can also get better prices and tickets that allow you to skip the line.

  • Have fun, enjoy yourself, and experience all that Boston has to offer in October.

Reviews from other travellers

4.7
· 4404 Reviews
  • F
    F. J.
    5
    (0 Reviews)
    Great tour. Lots of fun. Sam was a great guide!
  • P
    P. S.
    5
    (0 Reviews)
    The tour was well conducted
  • C
    C.
    5
    (0 Reviews)
    I went with my family during the school vacations and it was a good mix of learning about the history of Boston and eating doughnuts.
  • D
    D.
    5
    (0 Reviews)
    This experience was very fun, delicious and informative. Our tour guide was very nice and knowledgeable about the history of donuts.
  • F
    F.
    5
    (0 Reviews)
    Our tour guide was amazing. His energy made it a great experience. We also enjoyed trying donut flavors that we wouldn't normally pick out.