Fall Festivities in Massachusetts: 6 Group-Friendly Events to Embrace the Season


Spooky events, harvest celebrations and plenty of New England charm highlight the Bay State during the prettiest weeks of the year. From the blazing palette of fall foliage to the dazzling jewel-tone shades of fruit ready for harvest, Massachusetts is the ideal canvas for planning an autumn tour.

Here are six group-friendly fall festivals in Massachusetts that you won’t want to miss.

The Big E: Where Tradition Meets Fall Fun

The Eastern States Exposition, commonly known as “The Big E,” is one of New England’s most renowned fall festivals. Held in West Springfield, Massachusetts, this colossal fair attracts over a 1.5 million guests annually, combining agricultural exhibits, live entertainment, amusement rides, and an astonishing variety of food vendors. The fair celebrates all six New England states, making it a great opportunity for your group to immerse themselves in regional culture and cuisine while enjoying the vibrant autumn atmosphere. Special group rates for admission and dining are available.

Step Back in Time at King Richard’s Faire

Located in Carver, Massachusetts, King Richard’s Faire is a unique fall festival that transports visitors to the enchanting world of the Renaissance. Held each September and October, you’ll find costumed characters, jousting tournaments, live performances, and an array of artisan crafts and delicious food options. Children and adults can revel in the magic of this bygone era, providing an educational and entertaining experience. Your group can feast on turkey legs, frolic in our forest, and save on admission prices with group rates starting at $35.

Related: Five Fabulous New England Festivals

Franklin County CiderDays: Sip, Savor, and Celebrate the Season

If your group has a passion for apples and all things cider-related, Franklin County CiderDays in Western Massachusetts is the ultimate fall destination. This free fall festival is a haven for apple enthusiasts, offering cider tastings, workshops, and orchard tours. Have fun with apple pressing activities and enjoy a wide range of apple-based libations. A visit to CiderDays is a delightful way to learn about the apple harvest and the art of cider making.

Salem Witch Museum

Salem Haunted Happenings: Spooky Fun for the Whole Group

If your group enjoys a little spookiness with their fall festivities, Salem Haunted Happenings in Salem, Massachusetts, offers a bewitching experience. This month-long celebration is billed as the largest celebration of all things Halloween on the planet. It features family-friendly activities, haunted tours, and costume parades. Alongside the event, explore the city’s rich history on a walking tour of witch trials and maritime heritage. Because October is Salem’s peak travel season, remember to book your group tours as early as possible. Many local attractions take reservations as early as a year in advance.

Topsfield Fair – New England’s Oldest Agricultural Fair

Located in Topsfield, Massachusetts, is one of the oldest agricultural fairs in the United States and a  fantastic fall festival for school groups. The event welcomes over 15,000 students from Massachusetts and New Hampshire each fall, with free admission for 5th grade and under. The festival offers over 15 educational programs, many of which align with common core or and state standards. With a wide range of livestock exhibits, agricultural displays, carnival rides, and live entertainment, it’s an event that brings both the traditions of the past and the excitement of the present together.

Wachusett Mountain AppleFestApples Meet Adventure at Wachusett Mountain AppleFest

Nestled in the scenic Wachusett Mountain State Reservation, the Wachusett Mountain AppleFest is celebrating its 40th year. Held in mid-October, it’s become a must-visit fall destination for travelers looking to blend the beauty of nature with the deliciousness of apple-themed treats. This festival, held in Princeton, Massachusetts, offers a variety of outdoor activities like hiking, apple picking, and scenic chairlift rides which offer breathtaking views of the vibrant fall foliage as you ascend the mountain. The festival also features over 100 craft beer vendors and unique food truck fare and giant lawn games.

New England truly comes alive during the fall season and no state better embraces the pivot to autumn as Massachusetts. As the leaves change into vibrant shades of red, orange, and yellow, communities across the state celebrate with a wide array of fall festivals and events. These are perfect for groups looking to immerse themselves in the autumn spirit, enjoy outdoor activities, savor delicious seasonal treats, and appreciate the beauty of New England’s fall foliage.

With a diverse range of fall festivals for groups to explore and enjoy, from the apple orchards of Applecrest Farm to the historical intrigue of Salem Haunted Happenings, the state is brimming with opportunities to celebrate the arrivals of autumn.  Get ready to immerse your group in the vibrant colors and festive spirit of Massachusetts’ fall festivals.

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