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10 Things to Do in Boston in Fall

Boston in autumn gains even more luster because many events related to harvest festivities, Halloween and sporting events take place.

Verónica Álvarez

Verónica Álvarez

8 min read

10 Things to Do in Boston in Fall

Boston | ©Holly

The city of Boston is one of the favorite cities for international tourists to visit in the United States throughout the year. In fact, for its history, culture and nightlife it is one of the most visited cities in the country.

During the fall, you'll have plenty of activities and things to see in Boston. From concerts and fairs to harvest festivals, Halloween celebrations and much more. If you're a sports lover, you'll also have the opportunity to attend games of the city's iconic baseball and soccer teams - there's everything to do in Boston in the fall!

1. Take in a Red Sox baseball game

At Fenway Park| ©Joe Passe
At Fenway Park| ©Joe Passe

Sports for Bostonians are part of everyday life. As for baseball, one of the national sports of the United States, Bostonians are big fans of their local team, the Red Sox.

During the fall in Boston you can book a National League baseball game with the Red Sox as the home team and with the great advantage that the weather will allow you to endure the game outdoors, something that during summer or winter is not very advisable because of the weather.

It is best to get to know the Red Sox and the rules of baseball before going to the game so you can enjoy it better. You will find that once you understand the rules, baseball is a very interesting sport.

Buy your Boston Red Sox Tickets

Enjoy a soccer game in Boston

At a New England Patriots game| ©Beckwith-Zink (Diane)
At a New England Patriots game| ©Beckwith-Zink (Diane)

Bostonians, like most Americans, also love soccer and especially their local team, which they idolize. The city's team, the New England Patriots, hosts a home game every fall.

These fall soccer games draw thousands of people to Gillette Stadium every year and are warm-up games for the season that fans look forward to.

Enjoy these sporting events like a local but remember to book your New England Patriots tickets well in advance because they sell out quickly.

Buy your tickets to see the New England Patriots in Boston

3. Take a Halloween and Ghost Tour of Boston

During the Ghost Tour| ©Andrew Quinney
During the Ghost Tour| ©Andrew Quinney

It's impossible to pass through Boston in the fall and not book a ghost tour if it's Halloween or close to it. This type of guided tour takes in the top locations in Boston that have scary stories to tell. Many of the stories are really spooky, but they are worth knowing.

You should keep in mind that these are tours not suitable for minors or easily impressionable people due to the contents of the tour. It is also customary to use adult language, so children are not allowed to participate in this type of activity.

In this tour, you will walk through the main points of the city that have some macabre history to offer. The tour is mostly outdoors so it is a good idea to bring a coat because it can get quite chilly at night in Boston during the fall.

Book your Boston ghost tour

4. Take a romantic walk in Boston

Autumn in Boston Common| ©Bill Ilott
Autumn in Boston Common| ©Bill Ilott

The city of Boston has one of the most landscaped areas in the United States and that makes it very attractive, especially in the fall.

As the long, hot, sweltering days of summer are replaced by the short, pleasant, cool nights of autumn, you begin to see the colorful changing leaves of the trees in the streets, squares, parks and gardens of Boston.

This is an ideal time to enjoy the flora of Boston Common and the ever-changing colors of the Boston Public Garden. You can also enjoy Boston's greenery when you book a cruise, as viewing the fall foliage from the water is a different experience.

Book your cruise in Boston

5. Take an excursion to the island of Martha's Vineyard

Visiting Martha's Vineyard| ©Allan Johanson
Visiting Martha's Vineyard| ©Allan Johanson

The city of Boston is beautiful year-round, but in the fall it takes on an off-the-beaten-path charm that is felt in and around every corner of the city. One activity that can be done year-round but is much more appealing in the fall is a trip to the island of Martha's Vineyard.

Spending the day on the island, walking around it quietly, with a cool breeze and contemplating the dazzling fall colors of the vegetation is an experience that I highly recommend. In addition, in this season the atmosphere on the island is relaxed, as there are not as many tourists as at other times of the year.

You will return with a renewed spirit and recharged batteries after enjoying so much tranquility and beauty. Booking a Martha's Vineyard Island tour will usually take about half a day.

Book your Martha's Vineyard Island Tour

6. Tour Boston's orchards and pick apples

Apple Trees| ©Bureau
Apple Trees| ©Bureau

Fall in Boston is the perfect time to visit local farms and go apple picking. The New England area is known for the quality and variety of its apple orchards and also for the culinary delights they make from these fruits.

There are countless orchards around the city and each one offers different varieties of delicious apples to try. Some companies also offer free fruit farm tours and activities.

You can end the day tasting delicious apple dishes such as Boston' s famous apple cider donuts, apple cobbler, irresistible apple crisp and one of the city's specialties, hot spiced cider.

Boston HIll Farm

  • Address: 1370 Turnpike Street, North Andover, MA, 01845.
  • Telephone: (978) 681-8556.
  • E-mail: [email protected].

Lookout Farm

  • Address: 89 Pleasant Street South Natick, MA 01760.
  • Phone: (508) 745-3697.
  • Email: They do not make reservations by email.

Veronica's Traveller Tip

You can view the approximate fall apple picking schedule at Boston farms and plan your visit.

7. Attend or participate in the Head of the Charles Regatta

Head of the Charles Regatta| ©KrisNM
Head of the Charles Regatta| ©KrisNM

Since 1965, the Head of the Charles Regatta has attracted thousands of rowers every year to the Charles River to compete in the world's largest regatta for 3 full days.

This is a highly anticipated event for Bostonians and rowing enthusiasts from around the world. You can enjoy the Head of the Charles Regatta in comfort, because the city of Boston prepares very well for this fall event.

The Head of the Charles Regatta is held annually in October and has drawn an estimated 225,000 spectators, but if you prefer to watch the event in a quiet location, head to the Eliot Bridge or Reunion Village, a fairground located on the Cambridge side of the Charles River.

8. Visit the local breweries and the Oktoberfest

Oktoberfest.| ©Eric Veal
Oktoberfest.| ©Eric Veal

During the fall in Boston, if you like beer, you'll have plenty of fun and special activities. Major local beer brands, such as Sam Adams and Harpoon, organize interesting tours of their breweries and hold fall events for their annual product launches.

Also on the occasion of the fall festivities, many breweries make special product packages for you to purchase and enjoy back home.


Harpoon organizes the Oktoberfest. You'll want to book your visit to Boston' s breweries in advance to secure your spot.

  • Address: 306 Northern Avenue Boston, MA 02210.
  • Phone: 617-456-2322

Sam Adams

Hosts its now-traditional "Bostoberfest" where you can enjoy live music and interactive games while drinking the brand's beers from the time you arrive until the time you leave.

  • Address: 30 Germania St, Boston, MA 02130.
  • Phone: 617-368-5080

9. Visit the Massachusetts and New England Fairs

In New England| ©Neil Holden
In New England| ©Neil Holden

When fall arrives, so does fair time in the small towns surrounding Boston. There are fun fairs with parades, circuses and games. Some of the main ones are organized in the towns of Hopkinton, Deerfield and Topsfield.

All of these fairs follow the strict tradition of New England fairs, featuring lots of farm animals, games, giant vegetables, pig races, magic shows, treats, shows, music, animal contests, cooking contests, tastings and dancing.

For event dates and locations check out Massachusetts Fairs and Festivals.

10. Enjoy the "Boston by Little feet" experience

On the Tour| ©Dtrain891
On the Tour| ©Dtrain891

The city of Boston also has activities for families to do. There is an excursion (especially designed for families with children ages 6-12) called Boston by Little Feet.

It is a walking tour, lasting about 3 hours, that takes you through the city's most important historical sites while recalling the city's most important landmarks through interactive role-playing games.

While this activity is available starting in May, I recommend doing it in the fall for weather reasons. The three-hour walk during the summer months can be overwhelming for the little ones, so it is much better to do the walk in the fall.

Boston weather in the fall

Fall in Boston| ©Werner Kunz
Fall in Boston| ©Werner Kunz

Boston's fall weather can be quite warm during the first few days of the season and also quite cold during the last few days of fall, just before winter. Keep this in mind when packing your bags.

There may also be rainy days. I know it may be uncomfortable to carry rain gear in your suitcase, but it may be necessary. If you don't want to bring it from home, it's the perfect excuse to browse the stores in Boston and do some shopping.

You will want to bring a jacket if you are going out at night because temperatures drop considerably and it is best to be prepared. It is also advisable to wear comfortable shoes because many of the activities are outdoors.

Wear a little more formal clothing for the evening

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

In most places for tourists in Boston during the fall there is no set dress code. The idea is to be comfortable so that you can do all the activities comfortably.

But you should keep in mind that there are some activities that tend to require a bit more formal attire than others. Therefore, if you plan to go out at night to the theater or to a cultural event such as the ballet or a concert, it is better to wear more formal clothes.

It is not necessary to wear formal attire if the dress code does not require it, but it is customary in Boston to go a little more formal to these types of events.

Save money on your trip to Boston in the fall

Money in Euros| ©Pixabay
Money in Euros| ©Pixabay

The city of Boston, like major cities around the world, has a card system for visiting the city's main attractions. These passes are very convenient to save money on visits, as they give free admission to many activities and important discounts.

You also have benefits in several means of public transportation in the city. And if you are thinking of attending cultural events, buying the Boston Tourist Pass is an excellent idea because you will also get discounts.

These cards can be purchased online, which makes things much easier. The card is priced from 47 euros and gives you free entry to over 40 different attractions, including the city's major museums.

Buy your Boston sightseeing passes