Autumn in Plymouth, Massachusetts, is a season of celebration. Crisp air, vibrant foliage, and a strong sense of community make it the perfect time to explore local events and enjoy everything the South Shore has to offer. Whether you’re a longtime resident or new to the area, these fall festivals are a great way to connect with neighbors, support local businesses, and experience the charm of coastal New England.
🎉 Plymouth Fall Festival
📅 September 5–7, 2025
📍 Downtown Plymouth, MA
Enjoy live music, food trucks, artisan vendors, and family-friendly activities. This event is open to everyone and celebrates the spirit of Plymouth with seasonal flair.
🍷 Props & Hops at Plymouth Municipal Airport
📅 September 6, 2025
📍 Plymouth Municipal Airport, Plymouth, MA
Aviation meets autumn with local craft beer, food trucks, and entertainment. A fun outing for all ages.
🕯️ Pour Your Own Fall Candle – Uva Wine Bar Pop-Up
📅 September 8, 2025
📍 Uva Wine Bar, 46 Main Street, Plymouth, MA
Create a custom fall-scented candle while enjoying wine and good company. A cozy, creative experience for adults.
🧺 Hometown Handmade Fall Craft Fair
📅 November 1, 2025
📍 Plymouth North High School, 44 Nook Rd, Plymouth, MA
Shop handmade goods from local artisans and enjoy food trucks and raffles. A welcoming event for all community members.
🏰 King Richard’s Faire
📅 Weekends through October 19, 2025
📍 5 Pine Street, Carver, MA
Step into a Renaissance village with jousting, performances, and artisan markets. Open to all ages and backgrounds.
🌾 Cranberry Harvest Tours
📅 Mid-September to Early November
📍 Wareham & Middleboro, MA
Experience the cranberry harvest firsthand with guided tours and tastings. Educational and inclusive for all visitors.
🐾 South Coast Harvest Festival & Woofstock
📅 September 26–28, 2025
📍 Westport Fairgrounds, Westport, MA
Celebrate fall with live music, food trucks, and pet-friendly fun. All are welcome—two-legged and four-legged guests alike!
🍎 Apple Festival at Oakdale Farms
📅 September 13, 2025
📍 61 Wheaton Ave, Rehoboth, MA
Pick apples, enjoy hayrides, and savor fresh cider donuts. A classic New England experience for everyone.
🍂 Let’s Make This Fall Unforgettable!
Whether you’re enjoying cider donuts or considering a move to Plymouth, fall is a great time to explore your options. If you’re thinking about buying or selling a home—or just want to learn more about the local market—I’m here to help.
📞 Call Dawn Beliveau at (744) 283-2649
📧 Email: dawn.beliveau@cbrealty.com
Let’s turn over a new leaf together this season! 🍁