Autumn is festival season on Cape Cod! On Saturday, October 2, come to the Mashpee Commons Village Green for a day of merry-making at Mashpee Oktoberfest! Enjoy crafters, kids’ activities, stein races, German food and an authentic Bier Garten featuring live music. On Sunday, October 3, gather round the vines of Truro Vineyards for a memorable day spent listening to American Roots Music at the 7th annual Vinegrass Music Festival. Arts and crafts, rides, food, fireworks and live music take center stage at the Yarmouth Seaside Festival on October 9 and 10. From October 15-31, take a stroll through Kate Gould Park in Chatham to admire the fascinating pumpkin displays at Pumpkin People in the Park. And on Saturday, October 23, be mesmerized by shimmering, handblown glass pumpkins (all for sale) at the 10th annual PumpkinFest at Sandwich Glass Museum!

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Six Flags New England transforms into the Scare Capital of New England this October when FrightFest returns to Western Mass! With over 20 haunted experiences and live shows featuring roaming monsters, zombies and ghouls, it’s a scary good time! Running weekends and select weekdays through October 31st. 

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Celebrate all things autumn in Hampshire County, where fall foliage takes full form in October. And there is so much more to see and do while leaf peeping. If music, art, culture or theater is your thing, then check out the Northampton Jazz Festival or any of the 10 other performances this month at the Academy of Music Theater. Get your drink on at any of our many craft breweries or experience the New England Noir – New England’s first multi-cultural wine festival.  Maybe a fall harvest is what excites you. If so, pick you own apples or choose the perfect pumpkins at Park Hill Orchard or Phoenix Fruit Farm. Looking for what’s next? Then be sure to explore Greater Amherst for even more fun. The other side of MA awaits you!

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Photo credit: John Burk

Photographers, start your engines — and head out on the back roads of Johnny Appleseed Country to capture the breath-taking beauty of foliage season! From picturesque town commons to rolling hillsides, the region is aflame with Nature’s seasonal magic. Spend a sunlit afternoon savoring the brilliant scenery — then stop by a local winery or brewery for a bit of refreshment, or a farm or farm stand to stock your pantry for the holidays. Looking for a different perspective? Add a stunning perspective to photos on the region’s waterways!

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Let's Go Out on Martha's Vineyard! Martha's Vineyard businesses offer ample reasons to keep going out this fall too, and none are more delectable than our local restaurants and culinary offerings. Savor the flavors of the changing seasons with deliciously curated food and drink experiences and unique happenings to keep you working up an appetite, and satisfying it too. October’s sunny days and cool nights are perfect for outside activities, too. Hiking, cycling, kayaking and touring, and fun activities such as Oysterfest, LadyFest, Fall-on-the-Farm-Weekends, MV-Film-Festival, Vineyard-Artisans Festival and Women in Film Festival. The Vineyard’s fall colors and gilded sunlight welcome you! 

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Photo: Williams College Museum of Art

The art doesn’t stop at the gallery doors. The Northern Berkshire Art Outside self-guided tour includes some 30 works stretching across 10 miles of country roads.

An initiative of The Clark, Mass MoCA & Williams College Museum of Art, this online walking & biking tour showcases outdoor art in Williamstown and North Adams. Explore the route on Google Maps!

In addition to Martin Puryear’s Big Bling, the trail includes Walter Fähndrich’s Music for a Quarry & Klaas Hübner & Andrew Schrock’s Corrugarou in North Adams, Louise Bourgeois’ Eyes and Thomas Schütte’s Crystal in Williamstown, and more.

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The Franklin Downtown Partnership is excited to host the Harvest Festival in downtown Franklin in the center of the Cultural District on Saturday, October 2! Please come out and enjoy this family fun, community event that will feature local businesses, entertainment, foods from local restaurants, kids' activities, shop specials, and arts & crafts. Over 160 vendors, crafters and food booths! Rain date of Sunday, October 3.

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Photo credit: Jamie Holmes

Nantucket’s gentle October relinquishes summer slowly. Hot days cool, sultry nights’ breezes tease. As Nantucket surrenders greens-for-reds, oranges and ochres, gilded sunlight warms autumnal days. Two-by-two walks among blushing leaves inspire. Cool evenings evoke appetites for chowders, seafood stews at island eateries. Inns, B&Bs and hotels provide breathing-room to play, nap, read, knit, journal. The living island in transition reminds that all are in transition … Nantucket’s gentle nudge is welcome. #ShopNantucket during Cobblestones & Cranberries October 8-11 for chances to win! Planning your Nantucket getaway is easy with the Nantucket visit widget!

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Enjoy eleven days of agriculture, entertainment and great food at the Topsfield Fair October 1-11. Cape Ann Artisans Open Studios Tour takes place October 9 & 10. Come explore the artisans exquisite natural surrounding and see the fine art and craft inspired by the scenic North Shore! Enjoy Haunted Happenings, a festive celebration of Halloween and fall in Salem, October 1–31. There is something for everyone, from family fun events to haunted history and much more! 

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Each Friday in October, the Hingham Historical Society welcomes little historians to enjoy books read aloud by a ‘colonial’ character, followed by a related craft, light snack, and refreshments. Weather permitting, we will gather outside at the Hingham Heritage Museum. Recommended for ages 2-5, but all are welcome! Adults and children 1 year old and under are free; participating children ages 2 and up are $10/Non-Member Child and Free/Member Child. Reserve your spot here!

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ESCAPE is something we could all use. Especially after last year, am I right? Escape is closer than you think when you travel to Southeastern Massachusetts. Less than an hour from Boston and minutes away from Providence. We have some stunning views, incredible food, and plenty of things to, or NOT do when you want focus on fun, relaxing and do NOTHING at all. Your escape right here waiting for you.

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During these unprecedented times, it is more important than ever to show one another kindness and compassion. Be Kind Berkshires, a campaign brought to you by 1Berkshire and the Norman Rockwell Museum, aims to inspire empathy. So when you are packing up your bag for your next Berkshire vacation, be sure to include some kindness!

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Saturday Artisan Markets at Fruitlands Museum are back through October 30 from 10 am to 4 pm. Included with Museum Admission, find vendors spread throughout the Fruitlands Campus, offering safe, socially distant opportunities to shop high quality handmade local crafts. Jewelry, pottery, glass, wood, fiber arts, photography, mixed media and more! On Saturday, October 9, co-founder of The Beach Boys Brian Wilson will take the stage with special guests Al Jardine and Blondie Chaplin at Lowell Memorial Auditorium. Tickets on sale here!

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Fall Foliage at Wachusett Mountain.

Spooky season commences in full force, with Oktoberfest and Apple Fest at Wachusett Mountain, followed by Harvest Fest in Sturbridge. Worcester Public Library hosts HorrorFest, while Old Sturbridge Village features Phantoms & Fire and Douglas Orchard & Farm howls with its own Halloween festivities. For the sports fans, the Railers and Ice Breakers Tournament kick off the season, while the musically inclined Escape to Margaritaville or immerse themselves in the beautiful movement of Shen Yun.

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The annual Crafts of Colrain Studio Tour is back with a Pop-up preview October 9-10 and a Studio Tour November 13-14 from 10 am to 5 pm! Twenty artisans, from fine art furniture to artisanal beer, will be opening up their doors to visitors from near and far! See the flying sparks of iron on the forge and admire winter accessories woven from the fibers of animals grazing right outside the studio where the yarn was spun. Colrain's pastoral landscape is the off-the-beaten-path backdrop for all this creativity. Details here!

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Two iconic sporting events return to Boston this October, with the Boston Marathon occurring on Monday, October 11 and the Head of the Charles Regatta over the weekend of October 22-24. For the first time ever, the world’s most famous Marathon will take place against the backdrop of beautiful fall foliage, while the banks of the Charles always offer the autumnal flair that makes the Regatta in Boston so special!

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