Your Guide to Fall Festivals in MetroWest Massachusetts and Beyond (2026)
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.
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, 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, 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, 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 returns for 17 days of food, entertainment, and classic fall fun. Explore the Avenue of States, catch big-name concerts and live shows, browse exhibits and vendors, and make room for plenty of over-the-top fair food and longtime favorites.
Natick Days, Natick, MA (Sept 19): One of Natick’s favorite community traditions takes over the Common with a lively day of family-friendly fun. Enjoy local food, live entertainment, activities and exhibits, and the always-popular touch-a-truck area for kids, all while connecting with local organizations and celebrating the Natick community.
Johnny Appleseed Arts & Culture Festival, Leominster, MA (Sep 19): Downtown Leominster comes alive for this longtime celebration honoring hometown legend John Chapman, better known as Johnny Appleseed. Browse more than 200 vendor booths, enjoy live entertainment, family activities, local food, and plenty of apple-inspired treats throughout the day.
Old Fashioned Harvest Fair, Holliston, MA (Sep 20th): Step into a classic New England fall tradition at the Holliston Historical Society’s Old Fashioned Harvest Fair. Browse a juried selection of handcrafted textiles, pottery, artwork, and other artisan goods, enjoy seasonal treats, and don’t miss the homemade apple pies that have become a favorite part of this charming community event.
GrotonFest Fall, Groton, MA (Sep 26th): A beloved community tradition since 1979, GrotonFest Fall brings Legion Field Common to life with local vendors, artisan crafts, homemade baked goods, live music, family-friendly activities, and plenty of small-town New England charm.
North Quabbin Garlic and Arts Festival, Orange, MA (Sep 26–27th): A lively, community-rooted celebration of local creativity, sustainability, and all things garlic. Browse juried art and handcrafted goods, sample inventive garlic-forward foods, enjoy live music on two stages, and take in demonstrations, family activities, and the relaxed rural atmosphere that makes this festival a favorite fall tradition.
Topsfield Fair, Topsfield, MA (Oct 2–12th): A beloved New England tradition and the country’s oldest continuously running county fair, the Topsfield Fair brings together agriculture, entertainment, and classic fall fun. See prize-winning livestock and exhibits, watch the famous giant pumpkin weigh-off, enjoy live shows and midway rides, and indulge in plenty of favorite fair foods along the way.
Apple Fest Family Day, Sudbury, MA (Oct 3rd): The Wayside Inn Foundation’s signature fall celebration draws thousands to the historic property for a full day of family-friendly fun. Enjoy hayrides, a petting zoo, craft and artisan vendors, seasonal activities, food, and the beautiful autumn setting of one of Sudbury’s most treasured landmarks.
Douglas Oktoberfest, Douglas, MA (Oct 3rd): Downtown Douglas turns festive for this annual community celebration featuring live music, a lively beer garden, a classic car show, local vendors, food, and plenty of family-friendly fun. Kids can enjoy rides and activities while adults take in the entertainment and small-town Oktoberfest atmosphere.
MaynardFest, Maynard, MA (Oct 3rd): A favorite downtown tradition since 1993, MaynardFest fills Main and Nason Streets with more than 120 vendors, local businesses, sidewalk sales, food, and free family entertainment. Spend the day browsing, shopping, and enjoying the lively small-town atmosphere in the heart of Maynard.
Wachusett Mountain’s 42nd annual AppleFest, Princeton, MA (Oct 17th, 18th, 24th & 25th): One of Wachusett Mountain’s most popular fall traditions returns for two weekends of seasonal fun. Sample apple-inspired favorites ranging from sweets and baked goods to festive cocktails, browse vendors and activities, and take in spectacular autumn scenery from the mountain. With its mix of food, entertainment, and sweeping views of the foliage, AppleFest is a quintessential New England fall outing.
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Murphy Insurance2025-09-17 11:28:352026-08-14 13:06:3027 Reasons to Work with Murphy Insurance AgencyAbout Us
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.
