Your Guide to Fall Festivals in MetroWest Massachusetts and Beyond (2026)

August 14, 2026||inCommunity|autumn, community events, metrowest, personal insurance

There’s something about the upcoming autumn in New England that makes you want to slow down and enjoy the fantastic weather. The air turns crisp, the leaves put on their annual show, and towns in MetroWest Massachusetts and beyond fill their calendars with harvest fairs, craft markets, apple picking, hayrides, and community festivals on the town common.

Your Guide to 2026 Fall Festivals in MetroWest Massachusetts and Beyond Blog Post
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Soon it will be the season for pulling on a flannel, grabbing a cider donut, and spending a wonderful day wandering a fairground or a farm with the people you love.

At Murphy Insurance, we’ve called this community home for a long time, and we like to show up for it, not just insure it. That’s why we put together this event list, kicking off with the Bolton Fair this weekend. We rounded up some of our favorite fall festivals happening around MetroWest and across the state, so you can plan your weekends and make sure you don’t miss out on the fun. See you there!

Bolton Fair Logo

Bolton Fair, Lancaster, MA (Aug 14–16th): For a taste of true New England tradition, head to the Bolton Fair at The Fairgrounds at Lancaster, 318 Seven Bridge Rd, Lancaster, MA. A beloved local institution since 1874, this classic agricultural fair brings together everything that makes a small-town fair special: livestock competitions, midway rides, fair food, and live entertainment. Don’t miss the demolition derby, a crowd favorite and a weekend highlight. Whether you’re bringing the kids to see the animals or looking for a fun night out, the Bolton Fair offers a nostalgic, down-to-earth escape worth it. Estimated attendance: over 10,000.

King Richard's Faire Logo

King Richard’s Faire, Carver, MA (Sep 5–Oct 25th, weekends): Step back in time at New England’s largest Renaissance faire, where an 80-acre wooded village comes alive with knights, royalty, performers, and colorful characters. Watch thrilling jousting tournaments, explore artisan shops, enjoy live music and entertainment, and feast on classic faire favorites. Costumes are encouraged, making this family-friendly fall tradition an immersive day of medieval fun, fantasy, food, and festivities. Attendance is projected at roughly 120,000 visitors across the fair’s eight-weekend run, or about 15,000 per weekend and is located at 5 Pine Street, Carver, MA 02330.

Pride Worcester Festival

Pride Worcester Festival, Worcester, MA (Sep 12th): Celebrate community, creativity, and inclusion at one of the region’s largest cultural festivals in downtown Worcester. The day brings together more than 200 artisan makers, local organizations, food vendors, and community groups, along with live music and performances throughout the event. A dedicated youth and family zone offers activities for all ages, making Pride Worcester a lively, welcoming celebration of connection, self-expression, and local pride. Organizers are xpecting 30,000 visitors at the Worcester Common Oval 455 Main St. Worcester, MA 01608, from 2:00pm to 7:00pm.

  • The Big E, West Springfield, MA (Sep 18–Oct 4th): New England’s largest fair, with the Avenue of States, big-name concerts, and 17 days of classic fair food.
  • Natick Days, Natick, MA (Sept 19th): Natick’s biggest annual town celebration on the Common, with food, entertainment, and a touch-a-truck area for kids.
  • Johnny Appleseed Arts & Culture Festival, Leominster, MA (Sep 19th): A downtown celebration honoring Leominster native John Chapman, with over 200 vendor booths and apple-filled treats, just outside Clinton.
  • Old Fashioned Harvest Fair, Holliston, MA (Sep 20th): A juried craft fair from the Holliston Historical Society featuring handmade textiles, pottery, and homemade apple pies.
  • GrotonFest Fall, Groton, MA (Sep 26th): A community tradition since 1979, with local vendors, baked goods, live music, and artisan crafts on Legion Field Common.
  • North Quabbin Garlic and Arts Festival, Orange, MA (Sep 26–27th): A community-rooted celebration of local art and garlic-forward food, with juried crafts and music on two stages.
  • Topsfield Fair, Topsfield, MA (Oct 2–12th): The country’s oldest continuously running county fair, known for its giant pumpkin weigh-off and classic midway.
  • Apple Fest Family Day, Sudbury, MA (Oct 3rd): The Wayside Inn Foundation’s signature free event, drawing thousands for hayrides, petting zoos, and craft vendors.
  • Douglas Oktoberfest, Douglas, MA (Oct 3rd): A downtown street fair with live music, a beer garden, a classic car show, and rides for the kids.
  • MaynardFest, Maynard, MA (Oct 3rd): Maynard’s downtown street fair since 1993, with over 120 vendors, sidewalk sales, and free family entertainment on Main and Nason Streets.
  • Wachusett Mountain’s 42nd annual AppleFest, Princeton, MA (Oct 17th, 18th, 24th & 25th): Is your ticket to both, featuring every apple-flavored treat from candy to cocktails, and one of the most unique bird’s-eye views of Fall foliage in Massachusetts. Extended to two weekends due to popularity!

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Murphy Insurance Team

Murphy Insurance is one of the largest family-owned, independent agencies in Massachusetts. We handle all types of personal, business and financial insurance. We work with over 25 insurance carriers and have access to over 100 more allowing us to develop customized plans to meet our clients’ specific needs. Over our 85 years in business, we’ve changed to meet the needs of our clients and keep pace with the ever-changing demands of the insurance industry. We’ve grown to 6 locations in Bolton, Groton, Harvard, Hudson, Marlborough and Medway, and serve clients across the state and beyond. Our greatest achievement is maintaining our focus on what’s most important, which is taking care of people. We invite you to learn more about us and hope that we’ll have an opportunity to assist you.