Photo credit: Kyle Klein

Fall in Boston is always unique. As the leaves start to turn and the air becomes brisk, the blue skies remain crisp and there’s just nothing like it. Energy is everywhere: students returning, activity along the Charles, apple-picking and pumpkin-themed parties, performing arts back on stage, holiday celebrations and commemorations, the return of home games at TD Garden and Gillette Stadium, and, if we are lucky, postseason baseball at Fenway Park.  

In any year, this lineup of events makes Boston the place to be in autumn. This year, however, is unlike any other, and we invite you to fall for Boston like never before. From the Marathon to the Regatta, and the Laver Cup, we have much more than just Oktoberfests on tap!

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The Fall season, also known as our Second Summer, is the perfect time to explore Cape Cod! Enjoy farmers' markets, New England's best golf, walking trails, beautiful beaches and fun-filled seaside festivals. At the Harwich Cranberry & Music Festival on September 18-19, shop for paintings, jewelry, photography and other works of art from local artisans, while enjoying a wide variety of live on-stage entertainment. The annual Tennesse Williams Theater Festival takes place September 23-26 in Provincetown, where Williams spent several summers working on his classic plays. And experience the best in craft beer at the annual Cape Cod Brew Fest on September 18 at Cape Cod Fairgrounds in Falmouth. Sample from 50+ breweries and over 200 styles of beer!

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The Basketball Hall of Fame honors the Class of 2021 on September 11 in Springfield, the birthplace of the sport. This year’s class includes one of the winningest coaches in NBA history Rick Adelman, two-time NBA champion Chris Bosh, 10-time NBA All-Star Paul Pierce, the first Black NBA head coach Bill Russell, four-time NBA Defensive Player of the Year Ben Wallace, five-time NBA All-Star Chris Webber, two-time NCAA national champion Villanova coach Jay Wright, seven-time WNBA All-Star Yolanda Griffith and seven-time WNBA All-Star Lauren Jackson. Tickets to the ceremony are available here.

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The final days of summer are here and a fun time to visit Hampshire County! During Labor Day weekend, come enjoy the 3 County Fair – the country’s longest running continuous agricultural fair with great entertainment and thrilling rides. September is also the perfect time to experience Park Hill Orchard, where you can pick your own fruit or buy it at the farm stand. You’ll also see Art in the Orchard, a walking sculpture trail that winds through the open fruit gardens. This year’s exhibit features the works of 30 sculptors. Visit soon!

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Leap into harvest season with three days of music, art, and abundant food at the Appleseed Country Fair on Labor Day weekend! Sip cold craft beer or cider while listening to bands performing on three stages. Bring the whole family to Red Apple Farm in Phillipston, and enjoy tractor rides, apple picking and games for the kids! Visit farm animals. Watch a chain-saw sculptor. Plan ahead for the holidays with gifts from talented crafters and artists. Welcome autumn in Johnny Appleseed Country!

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Photo credit: Marnely Murray

Vineyard magic swells in September—harvests and fall colors remind us autumn is near! Fall for the Arts’ lectures, outdoor concerts, classes, and more mean more reasons to return or just stay longer! Flea markets, Felix Neck kayaking/SUPs, WT Farmers Markets, Historic Walking Tours, Cape Poge/ Edgartown Lighthouse Tours, Arboretum Tours, Labor Day Vineyard Artisans Festival, Sculpture Trail, live music, MV Striped-Bass-Bluefish Derby (through October 16), harvests, fresh seafood abound at island restaurants-farms. Don’t forget MV International Film Festival, Wind Festival and MV Playhouse Art Space!

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Nikolai Astrup (Norwegian, 1880–1928), Marsh Marigold Night, woodblock, before 1915; print, c. 1915. Color woodcut with hand coloring on paper, 16 1/16 x 18 9/16 in. (40.8 x 47.1 cm). Savings Bank Foundation DNB / KODE Art Museums and Composer Homes, Bergen

Head to the Clark Art Institute in Williamstown for your last chance to see "Nikolai Astrup: Visions of Norway" before this critically acclaimed exhibition closes on September 19. The New Yorker, The Wall Street Journal, and The Boston Globe all agree that now is the time to discover the color and magic of Astrup’s remarkable paintings and prints. The Clark is the only U.S. venue for this remarkable introduction to the work of an exceptional, but little-known, artist.

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The Ashland Dragonfly Festival on Saturday, September 18 is free, family-friendly and open to the public! Organized by Arts! Ashland Alliance, the festival features seasoned musicians, dance performers, children's entertainment, artisans and food vendors. Festival runs from 1 to 5 pm at the Ashland Historical Society, which abuts Mill Pond and the Sudbury River, a natural habitat for the dragonfly and The Corner Spot. Find out more!

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Photo credit: Nantucket Sustainable & Farmers Market

Warm weather sticks around on September’s Nantucket! Gilded light, burnished sunsets, changing leaves and island harvests tell us fall is coming. Warm waters still invite the full spectrum of recreation entreats with their beauty. Island lodging welcomes relaxing stays for quiet beach days, al fresco dinners, and new memories. Museums, galleries, boutiques welcome all, cycling paths, golf courses and conservation trails beckon with their beauty, sightseeing and whale/seal tours still running. Nantucket’s near, and planning is easy with visit widget!

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Join us for the 37th annual Gloucester Schooner Festival, an event put on by Maritime Gloucester. Schooners from all over travel to Gloucester to race and to show off their beauty and grace both under sail and as a dock-side attraction! Newburyport Maritime Days, September 10-12 hosted by Custom House Maritime, will feature themed dinners, live music, treasure hunts, and more. Begin your Essex County adventure with Trails & Sails September 17-26. Be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds.

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King Richard’s Faire celebrates its 40th season at King Richard’s Fairgrounds in Carver! The New England Renaissance Festival is a place where visitors can travel back in time and escape their reality on 80 acres of enchanted woods. Stages pounding with song and dance, handsome knights jousting for the King’s favor, jugglers, fire and sword swallowers, wacky wenches, minstrels, frolicking faeries, talented dancers and artisans, and an amazing new pirate stunt dog show. Weekends and holidays, September 4–October 24. Gates open 10:30 am & close at 6 pm.

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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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Photo credit: Jay Miller

This fall, ArtWeek Berkshires will celebrate the indelible spirit of creativity with a 10-day, county-wide festival bringing art, music, dance, theater, craft, and more to residents and visitors of the Berkshires. From September 16-26, art lovers can enjoy a colorful palette of gallery shows, open studios, craft demonstrations, special events, and more hosted by local creators. ArtWeek Berkshires is a collaboration of Downtown Great Barrington, Lenox, North Adams, Pittsfield (Upstreet Cultural District), and Williamstown. #creativityliveshere, come and see for yourself. 

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The much-anticipated final phase of Concord Museum’s decade-long $16 million renovation project will culminate with the opening of 10 new permanent galleries and a public celebration starting on Labor Day, September 6 through September 12. This last installation marks the completion of the redesign of the entire Museum and over 20,000 square footage of space. The ten new galleries opening in September include a renewed focus on Concord’s famous Transcendentalists Ralph Waldo Emerson and Henry David Thoreau, Louisa May Alcott, the women who led the effort to abolish slavery, and African Americans who lived in Concord before and after the Civil War.

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Photo credit: Tower Hill Botanic Garden

It’s the season of festivals & special events in Central MA – mark your calendars so you won’t miss the fun! Kids will love pony rides at Sunflower Farm Fest and circus acts during KidsFest at Wachusett Mountain. Brighten up your evening plans at the Southwick’s Zoo Festival of Illumination, Tower Hill’s Autumn Illuminated, and HYPERGLOW "America's Largest Glow Party” at the Palladium. For sardonic wit, join David Sedaris at The Hanover Theatre on the 27th!

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 The 172nd Franklin County Fair will be held September 9-12 in Greenfield! This year's theme is "Franklin County Fair: It's the Bee's Knees." One of the oldest continuously operating fairs in the country, this large agricultural fair features livestock, exhibits, demonstrations, crafts, music, a midway, demolition derby and lots of food. Opens on the Thursday after Labor Day and runs for four days. For more information visit fcas.com or call 413-774-4282.

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