Autumn is festival season on Cape Cod! On Sunday, October 5, gather around the vines of Truro Vineyards for a day of American Roots Music at the Vinegrass Music Festival. Arts and crafts, rides, fireworks and live music take center stage at the Yarmouth Seaside Festival on October 11-13, while the celebrated Wellfleet oyster is the headliner at Wellfleet Oyster Fest October 18-19. PumpkinFest at the Sandwich Glass Museum on October 11-13 is an annual outdoor sale and showcase where glass artists display exquisitely hand-blown pumpkins — from tiny to life‑size — for visitors to admire and purchase. From October 13-31, stroll through downtown Chatham to admire the fascinating pumpkin displays at Pumpkin People in the Park. And on Saturday, October 18, enjoy vendors, live music, German food and an authentic Bier Garten at Chatham Oktoberfest. (also save the date for the Mashpee Oktoberfest October 4!) Explore more about Fall on Cape Cod!

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Spooky season is in full-swing in Western Mass, especially at the Springfield Museums! Witch Panic! dives into the daily lives of Springfield settlers Mary & Hugh Parsons, examining the circumstances that led to their 1651 accusation and arrest for witchcraft 40 years before the Salem witch trials! Learn about the folklore surrounding witches, like their association with broomsticks, black cats, and cauldrons, or design your own ghoulish familiar, a small creature believed to help witches. Plan to make a weekend out of it and catch FrightFest at Six Flags New England, Fear on the Farm at McCray’s Farm, and Fall Harvest Weekends at Silver Bell Farm.

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This October, the Paradise City Arts Festival showcases artisan creations over a three-day weekend, and expands to include evening concerts. Stumble onto more beauty at Easthampton’s Art in The Orchard, where a half-mile sculpture trail winds through a working fruit orchard, or during the weekly Amherst Artisan Market. Looking for a view? Don’t miss the Instagram-worthy vistas in Hadley’s Skinner State Park! And enjoy the spooky season all month long during The Great Northampton Haunt!



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Fall is in full swing across North Central MA! Enjoy a concert at Groton Hill Music Center or live music at Bull Run Restaurant. Stroll the Newton Street Festival in Ayer, wander the Davis Farmland Mega Maze, and savor Applefest at Wachusett Mountain or Flannel Fest at Red Apple Farm. Celebrate traditions at the Westminster Cracker Festival, family fun at Fall Fest at Hollis Hills Farm, spooky thrills at Leominster Frights, and Halloween magic everywhere! 



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Martha’s Vineyard’s colorful October and delightful weather are great canvases for activities and events! Fall colors peak making 200 miles of hiking and 60+ miles of cycling trails spectacular. Enjoy events like Portuguese-American Club Family Day (10/4; 1 to 4 pm); Vineyard Artisans Festival (10/11-12); Women in Film Festival (10/17-19); Morning Glory Farm Pumpkin Festival (10/18); MV Brunch Run 5/10K (10/18); Oak Bluffs Halloween (10/25); Misty Meadows Ponies & Pumpkins (10/25); Happy Haunting Edgartown(10/26); Bark & Boo Bash (10/31); and Halloween in Vineyard Haven(10/31). Stay, dine, shop!


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As the season turns to fall color in the Mohawk Trail Region, there is much to do! Take one of the famous 5 Driving Tours  for great foliage views. Check out some of the fall festivals: 69th Annual Fall Foliage Parade, Ashfield Fall Festival, 22nd Crafts of Colrain, 61st Annual Festival of the Hills, 27th North Quabbin Garlic & Arts Festival , RambleFest & Mount Greylock Ramble and 37th Old Deerfield Holiday Sample.

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Pumpkins, layers, and a bit of fear—October is officially here! Enjoy Oktoberfest at Jack’s Abby through 10/5 or take in Tick, Tick…Boom! at the Umbrella Arts Center from 10/10 to 11/23. Step into history at the WWII Battle for the Airfield, 10/11–10/12 at the American Heritage Museum. Embrace Halloween at The Hopkinton Center for the Arts if you dare enter The Haunt 10/17-10/26, Goodnow Farm’s Haunted Barn Party 10/24-10/25 or Halloween Hullabaloo at the Discovery Museum 10/25-10/26.



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Nantucket’s cool, colorful October offers fun events and stunning fall colors island-wide! Restaurant Week (through October 5); En Plein Air (6 October); (10/6, 3 to 4:30 pm); Fall Fashion Show (October 10); Cobblestones & Catwalks (10-13 October); ‘Sconset Tour (3 pm Thursdays through October 10); Coskata-Coatue Wildlife Refuge Walkabout (10/6-8-12PM); Stargazing at Loines Observatory (10/1-3-8-10-17-24-31); Tour Sankaty Lighthouse (10/11;10 am-3 pm); 14th Nantucket-Half Marathon + 10k (10/12-8AM); Scalloping Field Trip (10/1-11/19). Now time to relax, stay, dine, sip, shop, cycle and hike, It's all here!

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Photo: Holly Perry

Enjoy eleven days of agriculture, entertainment, and great food at the Topsfield Fair  October 3–October 13. Haunted Happenings is the largest celebration of Halloween in the world! Visit Salem for the parties, parades, vendor fairs, walking tours, museums, attractions, and special offers. Plan your trip, put on your costume, and join in a month that is steeped in history, haunts, and a bit of magic. There is something for everyone!

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On October 3-5 and October 10-13, be part of an up-close cranberry harvest among an intimate group of fewer than 25 (choose either 9:30 am or 1:30 pm.) Purchase tickets here! In October, a star-studded array of talent is lined up at Plymouth Memorial Hall. Check out the line-up here! Looking for spooky Halloween Events? Browse the See Plymouth October events calendar for over a dozen hairy scary experiences.

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Photo credit: Andy Ryan @andy_ryan_photography/Buzzards Bay Brewery Corn Maze

Southeastern MA

Fall in Southeastern Massachusetts is packed with excitement—food truck festivals, chowder cook-offs, Oktoberfest, and more. Take part in unforgettable experiences like Trick-or-Treating on a battleship, or enjoy family-friendly activities all month long. For the full lineup of October events, visit the Southeastern Mass Visitors Bureau. It’s All Here and All Near!

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Fall is the perfect time to enjoy the Berkshires. The Berkshire Botanical Garden is changing up its annual Harvest Festival to include even more family fun on October 11-12. If you didn’t get a chance to visit Tanglewood this summer, no worries! It is now offering an exciting new fall-through-spring music festival at the Tanglewood Learning Institute. In the mood for something a bit spookier? Then be sure to take part in a ghost tour at The Mount - there are even special tours for the younger kids! No matter what you are in the mood for this fall, the Berkshires has you covered.

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Join us in celebrating the grand opening of the brand-new Revolutionary Valley Visitor Center in Lowell on Wednesday, October 15 from 11 am to 1 pm! This milestone marks a bold new chapter for the region, offering visitors an inspiring gateway to explore our history, culture, and communities. The event will feature local leaders, special guests, and a ribbon-cutting ceremony welcoming all to experience Revolutionary Valley. The Revolutionary Valley Visitor Center is located at 115 Merrimack Street in Lowell.

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Photo: SIX comes to Hanover Theatre 10/14-19.

It's the busiest month of the year in Central Massachusetts: cultural and fall festivals, haunted happenings, a killer live music and theatre lineup, plus family favorites at DCU Center: Hot Wheels Monster Trucks, Disney on Ice, and Bluey visits Worcester Railers opening weekend! October marks the 175th Anniversary of the First National Women's Rights Convention, held at Worcester's Brinley Hall in 1850. Learn more about that celebration, and see our full shortlist of October events.



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The Ashfield Fall Festival returns on October 11 -12 from 10 am to 5 pm! Nestled in the hills of Western MA, this charming annual event features handmade crafts from jewelers, woodworkers, painters, and more. Indulge in seasonal treats like fresh pumpkin donuts, maple sno-cones, and hearty eats, including chili and chicken pot pie. The kid-designed midway offers fun games for all ages. Celebrate autumn with local food, art, and entertainment in beautiful Ashfield! Learn more here.

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Photo: Kyle Klein

The Head of the Charles Regatta, the world’s largest three-day rowing event, returns to the Charles River October 17–19! Watch more than 11,000 athletes from around the globe compete in races that wind through Cambridge and Boston. Beyond the riverbanks, enjoy lively hospitality tents, local food vendors, and riverside festivities that make this iconic regatta a celebrated fall tradition.



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