Photo: John Andrews Photography

Enjoy eleven days of agriculture, entertainment, and great food at the Topsfield Fair, now through October 9th. Cape Ann Artisans Open Studios Tour takes place October 7-8. Come explore the artisans exquisite natural surrounding and see the fine art and craft inspired by the scenic North Shore. 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 ahead, 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! In Ipswich, explore Marini Farm’s 7-acre corn maze, open weekends in October. This maze is not your typical walk through the stalks. It is educational and interactive with 18 stations placed throughout the maze with answers to your game sheet given at the start.

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Head to Plymouth County this October for an unforgettable weekend getaway by the sea, an incredible Autumn dining experience or fully immerse yourself with a week-long stay and explore this historic region at your leisure! Enjoy a great evening out with First Fridays Plymouth on October 6. Get scared in Duxbury at the Alden House Historic Site Haunted House on October 20 and 21. And cap the month off with the Heavenly Spirits Halloween Dinner at Uva Wine Bar!

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The summer weather has started to cool down, sending a cool welcoming breeze to Southeastern Massachusetts. Soon, the foliage will be a blaze of red, yellow and orange. Grab your favorite sweater and enjoy the phenomenal views. You can listen to live music while having the freshest seafood possible. A beautiful escape for a couple, or an incredible exploration for a family. It’s all about making memories that will help you escape.

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ArtWeek Berkshires is back! This annual celebration of local creativity is sure to delight art lovers of all kinds. Showcasing the creative skills and wares of residents across the Berkshires from October 14-22, the event invites the public behind-the-scenes for a glimpse into the artistic space and process. Come see handmade jewelry, oil and watercolor painting, and sculptures. Participate in dance performances, song and poetry writing, or meditation exercises. ArtWeek Berkshires is coordinated and supported by Berkshire County’s five Cultural Districts: Downtown Great Barrington Cultural District, Lenox Cultural District, North Adams Cultural District, Upstreet Cultural District in Pittsfield, and Williamstown Cultural District.

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"El Encuentro: The Latino Film Experience" will be shown on October 13-14 at 7 pm in the Richard and Nancy Donahue Theater at Middlesex Community College in Lowell. Each evening will consist of 90 minutes of original films by an underrepresented group of filmmakers who deserve to be heard. Enjoy a Salsa Dance performance with live music before each show. Tickets for this exciting event are $15, and $10 for MCC Students. Find out more here!

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October is filled with festivity in the region, as World Smile Day brightens up Elm Park, and festivals liven up the likes of Stowe Farm, Wachusett Mountain, Polar Park, Douglas Orchard & Farm and Sturbridge Town Common. All the while, New England Botanic Garden at Tower Hill sees Myths, Magic, and Monsters, as Old Sturbridge Village uncovers eerie tales at Phantoms by Firelight and hosts a cattle show of yore at their Agriculture Fair Weekend.

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The Great River Challenge Off-Road Triathlon will be held October 7, with registration starting at 7:30 am, at the

Northfield Mountain Recreation Center. Calling all paddlers, runners and cyclists to the annual Great River Challenge Off-Road Triathlon in Northfield! Grab your boat, sneakers, and mountain bikes and head upriver for an incredible race that has challenged and delighted athletes of all levels for many years. There is no better time of year to come out and enjoy the wilds of Western Mass! Learn more and register here.

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Photo: Kyle Klein

On Friday, September 29, Friends of James Beard Benefits (FOJBB) is bringing together top chefs from across Boston to host a once-in-a-lifetime dining experience at Fenway Park. This year’s Stadium Chef Series culminates at the Green Monster, home of America’s oldest operating MLB ballpark, and will feature a cocktail reception with local chefs, five-course family-style dinner overlooking the Red Sox’s stadium, and chance to a walk onto the warning track for photo opportunities.

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Autumn is festival season on Cape Cod! On Sunday, October 1, 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 7-9, while seafood is the headliner at Wellfleet Oyster Fest October 14-15. From October 14-31, stroll through downtown Chatham to admire the fascinating pumpkin displays at Pumpkin People in the Park. And on Saturday, October 21, enjoy vendors, kids’ activities, live music, German food and an authentic Bier Garten at Chatham Oktoberfest. Read more of our best bets for October fun on Cape Cod!

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Foliage season is peaking soon in Western Mass. Looking for unique ways to enjoy everything Mother Nature has to offer this fall? Check out the changing leaves from 400 feet onboard the SkyScreamer at Six Flags New England – then stay for Oktoberfest and FrightFest! Hike to the top of Mt. Tom or around the beautiful Quabbin Reservoir. Kayak with Zoar Outdoor and see it all from the water or zipline through the foliage with Berkshire East. There are so many ways to enjoy fall in Western Mass, you’re going to want to stay a few days.

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An autumn tradition returns when the Paradise City Arts Festival comes to Northampton, showcasing hundreds of artists, jewelers, and furniture makers over a three-day holiday weekend. Explore more one-of-a-kind creations at Easthampton’s Art in The Orchard, where a half-mile sculpture trail winds its way through an apple orchard with mountain views (be sure to grab a cider slushie after your stroll). Or simply enjoy nature’s own artistry with the spectacular foliage on view at the Silvio O. Conte National Wildlife Refuge. Beauty abounds in Hampshire County!

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What do apples, cannoli, and garlic have in common? In Johnny Appleseed Country, these flavorful favorites are all highlights of autumn festivals! And they’re just the beginning. From cute and cuddly alpacas to Oktoberfest beer gardens, local communities and farms offer terrific reasons to celebrate the season. Wachusett Mountain Ski Area is hopping with weekend festivals, and Winchendon and Westminster will be rocking with community fairs. Take a break from your foliage-peeping to enjoy great music, food and family fun!

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Martha’s Vineyard’s October is vibrant, colorful with many exciting happenings! MV Striped Bass Bluefish Derby (through 10-14), 35th MV Big Golf Fore Kids Tournament (10-1); West Tisbury Farmers Markets (Saturdays 10/14-28); JAWS-Creating Amity at MV Museum; Gay Head 10K Road Race (10/1); 26th Annual Manhattan Short Film Fest (10/1) and Women in Film Festival (10/13-15). Cycling and hiking trails in fall technicolor, shops’ end-of-season prices, restaurants’ fall-dining, Inn-B&B-Hotel stays, Harvest & Pumpkin Fests, Felix Neck Kayak/SUP Quests and more! Enjoy Fall for the Arts, seasonal Martha’s Vineyard arts celebration — galleries, open studios, courses, filmmakers, live performances!

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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. 67th Annual Fall Foliage Parade, Ashfield Fall Festival, Crafts of Colrain, 59th Annual Festival of the Hills, 25th North Quabbin Garlic & Arts Festival, RambleFest & Mount Greylock Ramble, and the 35th Old Deerfield Holiday Sample.

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October is a great month for festivals in MetroWest Boston! October 7-8 brings an amazing WWII re-enactment to Hudson’s American Heritage Museum. Ashland’s Fall Fest on October 14 offers games, food, and live music. Goodnow Farms’ Haunted Barn Party on October 21 celebrates with food, drink, ghouls, and award-winning CHOCOLATE! Sweet Pea’s October Fest on October 22 includes vendors, live music and trunk or treat. View the unique scarecrows at Hopedale’s Scarecrow Fest October 20-November 2. Find event details here!

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Photo: J. Greg Hinson

In October, Nantucket is more lovely than ever! Turning leaves, soft fall light, and the return to serenity make for memorable visits. Bay scallops mean great eats at island restaurants,

Sankaty Light tours 10/7 (Register 10/2); AAN Wet Paint Weekend (10/6-8); Cobblestones & Cranberries (10/6-9), Fall Fashion Show (10/7), Nantucket Shorts Festival (10/8), live music at Cisco Brewers calendar and Nantucket Half Marathon (10/8), Batacular Fall Fun Day (10/29). As fall arrives, enjoy the colors on island walking and cycling trails; beachcomb, kayak, SUP, hike and bike. Spend a weekend, shop fall sales, fish, golf Siasconset and Miacomet courses, many activities at Maria Mitchell.

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