The Lowell Celebrates Kerouac Festival will be held October 6-10! The October festival features tours of novelist Jack Kerouac’s Lowell places, including many sites described in his Lowell-based novels, along with panel discussions, readings, jazz and folk music, films, open mike events, a high poetry competition, book signings, and more. Kerouac fans and scholars from across the United States and around the world travel to Lowell for the festival!

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October means more magic and spectacle when the sun sets! Discover family-friendly happenings in Central MA After Dark, such as enchanting night light displays and popular venues hosting events. Adults may enjoy exploring a bevy of fall libation specials at our local wineries, breweries, cideries, cafes and farms. As always, our events calendar is jam-packed with things to do, and the Fall/Winter Visitor’s Guide will help spark ideas for your next adventure in Central Massachusetts. 

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Calling all paddlers, runners and cyclists to the annual Great River Challenge Off-Road Triathlon in Northfield on Saturday, October 8! The Triathlon will be held at Northfield Mountain Recreation Center, with registration starting at 7:30 am. 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. Register here!

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The 58th Annual Head of the Charles Regatta - the largest three-day rowing event in the world - returns to the Charles River October 21-23! The Regatta is an iconic fall event for Boston and Cambridge, an autumnal rite of passage that draws more than 11,000 athletes from across the globe, and hundreds of thousands of spectators to the banks of the Charles.

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Autumn is festival season on Cape Cod! On Saturday, October 1, enjoy crafters, kids’ activities, live music, German food and an authentic Bier Garten at Mashpee Oktoberfest. On Sunday, October 2, gather round 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 8-10, while seafood is the headliner at Wellfleet Oyster Fest October 15-16. And from October 14-31, stroll through downtown Chatham to admire the fascinating pumpkin displays at Pumpkin People in the Park. Read more of our best bets for October happenings on Cape Cod!

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Fall is foliage & Oktoberfest season in Western Mass! Stay a few days and see the beautiful fall scenery from some unique vantage points. Ride the Sky Screamer at Six Flags New England and take in the sights from 400 feet above the ground. Or hike to the Summit House atop Mt. Tom in Holyoke for a bird’s eye view. While you’re in town, enjoy Oktoberfest at The Springfield Museums, then enjoy it again with a block party at The Student Prince restaurant. Fall in Western Mass is special!

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Photo:Paradise City Arts Festival

October starts off right with the sounds of the Ron Carter Quartet at the Northampton Jazz Festival, followed by the legendary Tuck & Patti's show at Bombyx Center for Arts & Equity. Expand your sense of touch with Braille Storytime with Mary Westgate at The Eric Carle Museum of Picture Book Art, or visit Phoenix Fruit Farm for a taste of pick-your-own local flavor. Take in the smell of autumn woods on a hike up Mt. Norwottuck. Dazzle your eyes with the beauty of the Paradise City Arts Festival. October is a feast for the senses in Hampshire County!

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Double your pleasure this month — by combining a leaf-peeping tour with stops at fall festivals throughout North Central Massachusetts! From the Horseshed Fair in Lancaster to the Scarecrows in the Orchard Harvest Festival in Leominster, Westminster Cracker Festival, and Winchendon Fall Festival, there are myriad opportunities to enjoy music, great food and down home hospitality every weekend. Want to relax a bit? Check out the Historical Piano Concert on Sunday afternoons in Ashburnham. food and down home hospitality every weekend. Want to relax a bit? Check out the Historical Piano Concert on Sunday afternoons in Ashburnham.

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Photo credit: Peter Simon

Martha’s Vineyard’s October is picturesque and cozy. Fall colors dazzle, farmers markets’ harvests inspire. Serenity, solitude and beauty evoke sojourns across the Island. Still much to enjoy — beach forays, swims; trails welcome hikers with colorful carpets, cyclers rejoice, shoppers find deals! Stay at Island inns or rentals. Dine-out at Island eateries! First Friday arts event, Living Local Harvest Fest. Relax, paint, take photos, tour lighthouses, golf, fish, kayak, hike, jog, shop, arts festivals, Women in Film Festival — relaxing and fun!

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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 up on some of the fall festivals: 66th Annual Fall Foliage Parade, Ashfield Fall Festival, Crafts of Colrain, 58th Annual Festival of the Hills, 24th North Quabbin Garlic & Arts Festival, RambleFest & Mount Greylock Ramble and The Great Falls Festival aka Pumpkinfest.

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Spooky season is here and there are tons of ways to celebrate in MetroWest! On October 1, pick up the supplies for the Make Your Own Scarecrow contest at the Hopkinton Center for the Arts.  Join Ashland at their Fall Fest on October 15.. Finish the month off at the 2022 Pumpkin Walk at Choate Park on October 28!

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Photo credit: J.Greg Hinson

Nantucket’s October, prelude to the quiet season, is best enjoyed outdoors. Hiking/cycling trails, kayaks, stargazing nights, photo safaris, golfing on colorful foliage-strewn turf, sailing, fishing, shopping, beach strolling/swimming, surfing—endless possibilities. Attend the inaugural Nantucket Harvest Fair, Farmers & Artisans Market (October 1 & 8), Cobblestones & Cranberries shopping event, Annual Wet Paint, Nantucket Shorts Festival (10/9), Observatory Open Nights (Thursdays 8-9PM). Many natural and walking tours, sailing excursions, Whaling and Shipwreck-Lifesaving (open to 10-10) Museums, Maria Mitchell, and more on Nantucket Chamber event calendar! Stay awhile!

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Photo credit:  John Andrews Photography

Enjoy eleven days of agriculture, entertainment, and great food at the Topsfield Fair, happening September 30–October 10. The Cape Ann Artisans Open Studios Tour takes place October 8-9. Come explore the artisans' exquisite natural surroundings and see the fine art and craft inspired by the scenic North Shore. Then, Haunted Happenings is celebrating its 40th anniversary! Enjoy 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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Plan this year’s fall trip to historic Plymouth County. Watch jousting knights at King Richard’s Faire, take a colorful cranberry harvest tour, or grab the kids and head out to Halloween on Main Street in Downtown Plymouth. Download the See Plymouth app on your mobile device for great lodging specials, restaurants for all palates and plenty more events throughout the month of October. America’s Hometown and the entire Plymouth County region are waiting for you!

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With a crazy year leaving us feeling trapped, we could all use an escape. Southeastern Massachusetts is so close to home you’ll be here by noon. What you won’t be is looking at the same four walls, because you’ll be too busy taking a stroll by the ocean, finding that art you’ve been needing & having the freshest seafood possible...most importantly making memories that will help you escape.

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Fall in Love with the Berkshires! Fall means crisp apples, plump pumpkins, and ghoulish ghost tours! Looking for a hike amidst trees ablaze in color, a spine-tingling connection with ghosts, or warm cider and a hay maze? The Berkshires is the perfect Fall getaway! Get your haunt on with myriad ghost tours, or find your favorite pumpkin among the more than 1,500 jack-o-lanterns at Naumkeag’s Pumpkin Show. It’s sweater weather - come visit #intheBerkshires!

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