Fall is finally here, and I couldn’t be more excited! There is so much to do during the beautiful season of fall in Massachusetts. 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 grab your pumpkin spice latte and join me in exploring the best fall festivals in Massachusetts.
1. King Richard’s Faire
The fall fair season kicks off with the magical King Richard’s Faire, which begins on August 30 and runs weekends and holidays through October 19, 2025. 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. Bring your finest medieval garb or buy some at the festival.
2. The Big E
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. 12 and runs through Sept. 28, 2025. 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 festival. Highlights include performances by Ludacris, America, and Public Enemy. It’s going to be a truly fun event for all! Get your tickets on The Big E website.
3. What the Fluff Festival
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 marshmallows, this fair is a must-see! 2025 marks the 20th 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 September 20th (with a rain date of September 21st) at Union Square in the city of Somerville, right outside Boston, where fluff was invented in 1917. Don’t forget to eat a fluffernutter sandwich while you’re here. This is certainly the most delicious fall festival in Massachusetts!
4. Harpoon Octoberfest
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 2025 Harpoon Octoberfest, which takes place on October 3-4 in Boston. The festival is packed with activities such as a pretzel-eating contest, Oompa music, and a group chicken dance. Bratwurst, beer, and Bavarian pretzels await you. If you love taking your pup everywhere, you can take them to the Harpoon Dogtober Fest on October 5th!
5. Topsfield Fair
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 Oct. 3-13, 2025. This event is so charming and fun for the whole family that you’ll probably want to go next year, too!
6. Wellfleet Oysterfest
If you enjoy oysters, this is the autumn fair for you! The 2025 Wellfleet Oysterfest is one of the biggest fall events on the Cape in a town that’s famous for its oysters. This year’s festivities will feature live music, a shucking contest, and lots of fresh seafood. This delicious event takes place in Wellfleet on October 18-19, 2025, celebrating its 25th year.
7. Applefest at Wachusett Mountain
You can celebrate the 2025 Applefest at Wachusett Mountain during the weekends of October 18-19 and October 25-26. 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. It’s one of the more silly and whimsical festivals, and so fun. You won’t want to miss it!
Fall is such a fantastically fun season here in Massachusetts, from festivals to corn mazes, leaf-peeping, pumpkin patches, apple picking, and more. Which events are you most excited to check out? You can also get up close to all the lovely fall colors by hiking at any of these beautiful destinations in Massachusetts.
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