Fall Festivals in Massachusetts: A Guide to Seasonal Fun

Massachusetts, September 21, 2025

News Summary

As the fall season unfolds in Massachusetts, numerous festivals offer a variety of activities for families and visitors. From the medieval-themed King Richard’s Faire to the agricultural highlights of The Big E, residents and tourists can indulge in local traditions, food, and entertainment. Festivals such as the What the Fluff Festival, Wellfleet Oysterfest, and Topsfield Fair are highlights, showcasing weekend festivities that celebrate the harvest and community spirit. Each event promises unique experiences, appealing to all ages and interests.

Boston — Fall season has arrived in Massachusetts, bringing lots of activities to enjoy. The state’s fall fair season features numerous fun festivals every weekend and many weekdays, with events running from late August through October and offering family activities, food and seasonal traditions.

Overview: Major festivals and dates

Several large and long-running events are scheduled this fall across Massachusetts. The King Richard’s Faire starts on August 30 and runs on weekends and holidays until October 19, 2025, in Carver, near Plymouth. A major agricultural fair, The Big E takes place in Springfield from September 12 to September 28, 2025. City and town celebrations include the long-standing Topsfield Fair, and smaller neighborhood events such as the What the Fluff Festival in Somerville. Seasonal and food-focused events include the Wellfleet Oysterfest and the Applefest at Wachusett Mountain.

Event highlights

King Richard’s Faire

The King Richard’s Faire starts on August 30 and runs on weekends and holidays until October 19, 2025, in Carver, near Plymouth. The festival has a medieval theme with rides, food, and entertainment. Each weekend features a special theme, and attendees are encouraged to wear Renaissance costumes.

The Big E

The Big E, a major agricultural fair, takes place in Springfield from September 12 to September 28, 2025. Fairgoers can enjoy a circus, rides, a farmer’s market, parades, and musical performances including Ludacris, America, and Public Enemy. The event showcases agricultural exhibits, competitive shows, and regional vendors.

What the Fluff Festival

The What the Fluff Festival in Somerville celebrates its 20th anniversary on September 20, 2025 (rain date September 21). The festival features games, music, and an abundance of Marshmallow Fluff. It takes place in Union Square, where Fluff was invented in 1917, and focuses on family activities and community vendors.

Harpoon Octoberfest and Harpoon Dogtober Fest

The Harpoon Octoberfest is scheduled for October 3-4, 2025, in Boston. Activities include a pretzel-eating contest, Oompa music, and a chicken dance, with bratwurst, beer, and Bavarian pretzels available. Harpoon Dogtober Fest takes place on October 5, 2025, allowing attendees to bring their dogs.

Topsfield Fair

The Topsfield Fair, one of the oldest agricultural fairs, runs from October 3-13, 2025. The event includes parades, performances, rides, games, and an annual pumpkin weigh-in, continuing an agricultural fair tradition in the region.

Wellfleet Oysterfest

The Wellfleet Oysterfest will be held on October 18-19, 2025, celebrating its 25th year. The event features live music, a shucking contest, and various seafood offerings, drawing attendees interested in coastal cuisine and maritime activities.

Applefest at Wachusett Mountain

The Applefest at Wachusett Mountain is recognized as one of the best fall festivals, ranking No. 6 nationwide in USA TODAY’s 10BEST Readers’ Choice Awards. The festival takes place over two weekends, October 18-19 and October 25-26, 2025. It includes live music, food trucks, craft vendors, family-friendly activities like pie-eating contests, and scenic views of fall foliage via a Skyride.

What to expect and practical information

The fall fair season features numerous fun festivals every weekend and many weekdays. Many fall festivals in Boston and nearby areas cater to families with food, fun activities, and entertainment. Most fall festivals occur from September through October, providing a range of events suitable for all ages. Popular seasonal foods highlighted at events include pumpkins, apples, cranberries, and oysters, showcasing the region’s agricultural bounty.

Some events recommend or require online ticket purchases, while others have free admission. Online ticket purchases are advisable for certain events, while many have free admission. Visitors should check specific event pages or organizers for detailed guidance on tickets, parking, accessibility, and pet policies.

Background and context

Autumn in Massachusetts has long been associated with agricultural fairs, harvest celebrations and local traditions that highlight regional produce and outdoor activities. Many events combine entertainment, competitive exhibits and vendor marketplaces to support local businesses and community groups. The seasonal schedule typically concentrates activity in September and October, with a few events beginning in late August and some continuing into mid-October.

Quick reference table

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Additional Resources

• AOL: 7 Best Fall Festivals in Massachusetts
• Telegram: Applefest and Massachusetts’ Best Fall Festivals
• Mommy Poppins: Fall Festivals and Fairs for Boston Kids and Families
• Boston.com: Best Fall Events in Boston and New England
• Patch: Wayland Fall Guide
• Wikipedia: Fall Festival
• Google Search: Fall festivals in Massachusetts
• Google Scholar: Fall festivals Massachusetts
• Encyclopedia Britannica: Festival
• Google News: Fall festivals Massachusetts

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