Photo: J. Coutre

Nantucket’s "Second Summer" arrives cloaked in cool breezes, crimson beach sunsets and harvest moons. Guided walks, sunset sails, science field trips, oyster farm tours, astronomy nights, history and nature tours, live music at Cisco Brewers, The Rose & Crown, The Chicken Box, or The Brotherhood of Thieves, so much to discover. Whaling and Shipwreck Museums offer cultural and historical perspectives. Unwind; enjoy magnificent cuisine, and moonlit harbor strolls. Daytime, explore Coskata Coatue and 200+ gorgeous trails, cycling paths, or take a stroll through ‘Sconset. Mark your calendars for Cobblestones & Cranberries weekend (10/7-10/9) and the Fall Fashion Show (10/7)! Nantucket Island Fair (9/24), an island tradition, celebrates approaching autumn. Spend a few nights at one of Nantucket’s magnificent hotels, bed & breakfasts, or inns. Adventure awaits!

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Join us for the 39th annual Gloucester Schooner Festival, August 31-September 3, an event put on by Maritime Gloucester! Schooners from all over travel to Gloucester to race and show off their beauty and grace both under sail and as a dock-side attraction. Begin your Essex County adventure with Trails & Sails September 15–24! Be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds.

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There is no shortage of quintessential New England activities happening in this historic region as we turn the page from Summer to Fall this month. Head to ultimate Renaissance Festival, King Richard’s Faire, opening September 2nd! Celebrate the official state berry of Massachusetts with an authentic Cranberry Bog Tour! Tours run from late September through early November. Come See Plymouth County with friends and family!

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Have you been looking for that dream destination wedding location, but care about travel costs? Southeastern Massachusetts has a lot to offer. Historic locations and scenic views are all around. We’re close enough to have all of those important people share your best day ever.  Less than an hour from Boston and minutes away from Providence. Your escape is here waiting for you in Southeastern Massachusetts

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Take a deep breath and inhale the inviting scent of apples! September means apples of all kinds, ready for you to pick (due to late spring freeze selections may be limited this season),or bagged and waiting for you to take that first, juicy bite! Visit the Berkshires to find its farms and orchards also making delicious, cold cider, and stocked with fresh late-season veggies. Head to the bakery counter for sugary, warm cider donuts and pies. You can even taste a fresh-pressed hard cider, or locally-made, award-winning wine. Bring the whole family for an abundance of fall flavors, and then enjoy a trail hike or walk in the warm fall sunshine. It’s all so good you’ll want to do it again the next day!

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From the crossroads of Science, Technology, Engineering, Art and Mathematics comes the racing spectacle Lowell Kinetic Sculpture Race, to be held on Saturday, September 16 in downtown Lowell! Kinetic sculptures are human-powered, all-terrain sculptures made from new and repurposed materials and engineered to race over streets, water, mud, and sand. The race is open to all ages and works with students, artists, engineers, bike enthusiasts, and anyone with a spark of creativity and a sense of adventure. This free, family-friendly event that included not only the race, but kids’ activities, live bands and food trucks.

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Central Massachusetts is buzzing with excitement this September! Join us for Worcester County Day at Fitton Field, a day filled with family fun and baseball action. For history enthusiasts, "Secrets of Swordplay" offers a thrilling glimpse into medieval combat techniques. Music lovers can catch the talented Riley Green in concert, while the LGBTQ+ Pride Celebration at NEBG promises a vibrant and inclusive experience. And don't forget the 15th Anniversary Plaza Party & Season Kick-off – a fantastic way to celebrate and kickstart the fall season. Discover more at event. Your September adventure awaits!

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The 174th Franklin County Fair will be held September 7-10 at Franklin County Fairgrounds in Greenfield! The oldest continuously running fairgrounds in the United States is back. The Franklin County Fair offers fun for everyone in the family, with live entertainment, craft beer, rides, pig racing, power wheel demonstrations, competitive exhibits, craft shows, demolition derbies, and all the fair food stands that Franklin County is famous for! Find out more and buy tickets here.

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Back by popular demand Boston Lights: A Lantern Experience returns for its fourth year at Franklin Park Zoo. Running through October 29, visitors can explore the wonder of over 55 illuminated displays comprised of hundreds of beautifully crafted lanterns. Spanning the 72-acres of Franklin Park Zoo, Boston Lights features a dazzling array of experiences that will impress and delight guests of all ages.

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Soak up Fall on Cape Cod, also known as the Cape's Second Summer! After Labor Day, visitors can expect fewer crowds, warm temps, a chill vibe and fun outdoor adventures all the way through October. Visit Cape Cod and celebrate the seasonal contrast of vibrant blue ocean, shimmering gold foliage, and crimson cranberry bogs. Fall is also festival season on the Cape! Click here for a preview of our upcoming autumn fests – at the end, enter to win a $100 American Express gift card!

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A visit to Western Mass is a great idea anytime, but coming to the region in September is a whole different experience. The Big E runs from September 15-October 1 and celebrates each of the six New England states and everything they’re famous for, including food, crafts, travel information and more!

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It’s a musical month in Hampshire County! Catch Leonard Cohen tribute The Secret Chord at Luthier’s Co-op in Easthampton. Grammy nominated folk and blues singer Maria Muldaur performs at The Drake in Amherst, while fiddle lovers won’t want to miss Brittany Haas and Lena Jonsson at The Parlor Room in Northampton. Looking to play? Explore workshops and classes at The Parlor Room’s School of Music, where you can learn clawhammer banjo, songwriting, or blues guitar from the pros. Close out September with the must-see Max Roach Centennial Celebration at the Northampton Jazz Festival!

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Fall is a fabulous season in Johnny Appleseed Country — and a great time to visit farms, fields and hillsides to celebrate the bounty, talent, and agricultural roots of the region. There are festivals highlighting produce, from garlic to pumpkins; crafts, from blacksmithing to fine jewelry; and foods, from cannoli to pierogi. And don’t forget the apples! From Wachusett Mountain Ski Area to Sholan Farms, apples reign over fun-filled fall festivals! 

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Photo: George Bekris

Martha’s Vineyard’s September "Second Summer" evokes fall’s magic, serenity, uncrowded beaches, open spaces. Hints of fall colors, cool nights, warm days. Plus a happening cultural and social scene — new exhibit "JAWS: Creating Amity"; Chilmark Flea Market; Vineyard Artisans 26th Summer Fest (Sundays-9/5-9/10); 18th Annual MV Int’l Film Fest (9/5-9/10); Oak Bluffs Open Market Sundays/Live Music; West Tisbury Farmers Market (Saturdays to 9/30); Tuesday Karaoke at The Ritz (Tuesdays to 9/26); 78th MV Striped Bass Bluefish Derby (9/10-10/14); MV Legacy Breakfast Club & Black Symposium (9/14). Stay, dine, shop, explore, savor, cycle, hike, relax, get a facial, spa treatments.

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The 47th Old Deerfield Fall Arts and Crafts Festival will be held September 23-24 from 10 am to 4 pm. Held on the lush and beautiful grounds surrounding Memorial Hall Museum in Deerfield. Stop by and browse the creations of 100+ artisan crafters!

Pottery, woodworking, jewelry, glass, apparel, fine art, mixed media, specialty foods, live music, craft demonstrations & more Admission is adults $7, children 12 & under free.

Also, mark your calendar for the 35th Old Deerfield Holiday Sampler November 18-19!

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Kick off fall with the Northborough Applefest September 7-10, a full weekend of family fun including BBQ, fireworks, parade and more! History buffs won’t want to miss the flying demonstrations at the American Heritage Museum’s World War I and Aviation Weekend September 16-17 or the Sudbury Colonial Faire and Fife & Drum Muster September 30th at historic Longfellow’s Wayside Inn which includes dozens of colonial and craft vendors and 25 fife and drum corps.

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