The Seven Best Fall Festivals In Massachusetts For 2023 Will Put You In The Autumnal Spirit

Fall is finally here and I couldn’t be more excited! There is so much to do in Massachusetts during this beautiful time of year. My calendar is already filling up with plans to explore fun corn mazes, colorful fall foliage, and amazing autumn hikes. But the fall fair season is what I am most looking forward to!  Each weekend (and many weekdays) you can find fantastic fall festivals near Boston and beyond. Every event offers something a little different, but equally as fun and entertaining. So put on your fair shirt, grab your pumpkin spice latte, and join me in exploring these seasonal festivities.

King Richard's Faire, 235 Main St, Carver, MA 02330, USA

King Richard's Faire/Facebook

The fall fair season kicks off with the magical King Richard’s Faire which begins on Sept. 2 and runs weekends and holidays through through October 22. I can tell you from experience that this unique festival, which takes place in Carver, near the city of Plymouth, is so much fun! Enjoy rides, food, and entertainment as you are transported back to medieval times. Each weekend of the fair has a special theme. Don’t be afraid to come dressed in your favorite Renaissance costume. Find out more details at the King Richard's Faire official website.

1305 Memorial Ave, West Springfield, MA 01089, USA

The Big E/Facebook

The Big E in Springfield is one of the biggest and most popular agricultural fall fairs in Massachusetts. This year’s fair starts on Sept. 15 and runs through Oct. 1. Fairgoers can enjoy a circus, rides, a farmer’s market, a parade, yummy food, and agricultural exhibits and competitions. There will also be several musical performances taking place throughout the span of the festival. Highlights include performances by Third Eye Blind, John Fogerty, and Jimmy Eat World. Please refer to The Big E's website for a lineup of events and activities.

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Union Square, Somerville, MA 02143, USA

What the Fluff? A Tribute to Union Square Innovation/Facebook

This one-of-a-kind fall festival is by far the stickiest of all of the autumn fairs. If you are a lover of melted marshmallow, this fair is a must-see! 2023 marks the 18th anniversary of Somerville’s annual What the Fluff Festival. There will be games, music, and more Marshmallow Fluff than you could ever imagine. The fun takes place on Sept. 23 in the city of Somerville, right outside Boston, where fluff was invented in 1917. You can find out more about the 2023 What the Fluff Festival on their Facebook page.

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Harpoon Brewery, 306 Northern Ave, Boston, MA 02210, USA

Harpoon Brewery/Facebook

What better way to celebrate the fall season than with a cold beer or two? This year, you can enjoy a pint and have some fun at the 2023 Harpoon Octoberfest which takes place on Sept. 29-30 in Boston. The festival is packed with activities such as a pretzel-eating contest, Oompa music, and a group chicken dance. View the full Harpoon Octoberfest schedule on the Harpoon website.

Topsfield Fairgrounds, 207 Boston St, Topsfield, MA 01983, USA

Topsfield Fair/Facebook

If you are looking for a quintessential New England Fair, the Topsfield Fair is a top choice! This historic agricultural fair dates back to 1818. Enjoy parades, performances, fair food, live music, animal shows, exhibits, rides, and games. The highlight of the fair is the annual pumpkin weigh-in, where farmers compete to see who has grown the biggest pumpkin. The fair takes place in Topsfield from September 29 to October 9. Find out more about the schedule of events at the Topsfield Fair website.

Main Street, Main St, Wellfleet, MA 02667, USA

Wellfleet SPAT/Facebook

If you enjoy oysters, this is the autumn fair for you! The 2023 Wellfleet Oysterfest is one of the biggest fall events on the Cape. This year’s festivities will feature live music, a shucking contest, and lots of fresh seafood. This delicious event takes place in Wellfleet on Oct. 14 & 15. Please visit the Wellfleet SPAT Facebook page for more details.

Wachusett Mountain, 41 Mile Hill Rd, Westminster, MA 01473, USA

Wachusett Mountain

You can celebrate Applefest at Wachusett Mountain during the weekends of Oct. 14-15 and 21-22. The festival will feature live music, food trucks, and craft vendors. There will also be many family-friendly activities such as stilt walkers, inflatable slides, and pie-eating contests. End your day by taking a skyride trip up the mountain to view the beautiful autumn foliage. Find out more about this fun event at the Wachusett Mountain website.

Fall is such a fantastically fun season here in Massachusetts. Which events are you most excited to check out?

For more fall fun, check out our coverage of the best pumpkin patches in Massachusetts!