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Sunday, September 27, 2026
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October Awaits! Cooler, crisper fall air is here, and so are all the classic fall favorites — Football games, Apple Picking, Cider Donuts, Corn Mazes, and Fall Festivals! But that's just the beginning. No matter your fall plans, we've got plenty of options to make the season memorable.
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Boston Metro
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Cambridge Science Carnival - Cambridge
Be Curious Join scientists, engineers and more at the Cambridge Science Carnival. The celebration combines all the magic and mayhem of modern...
Sunday, Oct 4
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Monty Python’s SPAMALOT gallops into Boston’s Wang Theatre
Get ready to laugh at the musical comedy lovingly ripped off from Monty Python and the Holy Grail. SPAMALOT brings flying cows, killer rabbits, and plenty of questionable medieval logic, plus favorites like "Always Look on the Bright Side of Life" and "Find Your Grail."
October 8 - 11, 2026
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Touch-A-Truck at Hood Park Charlestown - Charlestown
Join us for Touch-A-Truck at Hood Park Explore a variety of trucks, fall activities, bites, sweet treats and more for the whole family throughout...
Saturday, Oct 3
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MIT Future Fest - Cambridge
MIT Future Fest is a five-day annual festival that opens the Institutes doors to the world. This fall, visit the epicenter of whats next...
Wednesday, Sep 30 - Sunday, Oct 4
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Somerville Fall Festival
Fall Festival is bringing ALL the vibes. Join us on Saturday, Sept. 13th from at Conway Park FREE Grab your friends to celebrate the event...
Saturday, Oct 3
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SpicetoberFest: Spice. Culture. Food. - Boston
SpicetoberFest is Bostons ultimate celebration of spice, flavor, and culture featuring fiery local food, farmers, small businesses, hot...
Saturday, Oct 3
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Harpoon Octoberfest 2026 - Boston
Oompah music. Stein hoisting. Pretzel eating. Chicken dancing. Cold beer. All the Octoberfest traditions you know and love are backplus even...
Friday, Oct 2 - Saturday, Oct 3
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The Lawn on D Fall Fest & Taylor Swift Tribute - Boston
Are You Ready for It? Dress in your favorite era and get ready to sing your heart out with Anna Daley Young from 2:00pm – 5:00pm for a Taylor Swift Tribute. Enjoy bracelet-making, face painting, and lawn games. The event is free with food and drinks available for purchase.
Saturday, October 3 from noon to 5:00pm
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Squirrel Tales Author/Illustrator Visit: Hayley and John Rocco - Boston
Join award-winning author Hayley Rocco and Caldecott Honoree John Rocco at Beacon Hill Books & Cafe for a special reading and book signing of...
Tuesday, Sep 29
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Brick-Or-Treat - Kid's Halloween Event at LEGO Discovery Center Boston - Somerville
The Minifigure Monsters are taking over LEGO Discovery Centers and theyre bringing a frightfully fun Halloween adventure with them this...
Thursday, Oct 1 - Saturday, Oct 31
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6th Annual Oktoberfest at The Tall Ship - Boston
Celebrate Oktoberfest at The Tall Ship with local craft beer tastings, live music, a Sam Adams Stein Hoisting contest, best-dressed prizes, and...
Saturday, Oct 3
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North Suburbs
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Halloween - Salem Haunted Happenings 2026 - Salem
You're invited to Salem's annual Halloween Festival It happens every year during October in the bewitching seaport of Salem, Massachusetts....
Thursday, Oct 1 - Saturday, Oct 31
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Topsfield Fair 2026 - Topsfield
Enjoy America's oldest and finest agricultural fair w/ New Englands largest carnival midway, cool demos, (ranging from beekeeping to miniature...
Friday, Oct 2 - Monday, Oct 12
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Library Lion returns to Boston this January!
Treat your family to Library Lion, the musical based on Michelle Knudsen's beloved book. Featuring a life-sized lion puppet by Jim Henson's Creature Shop, it's perfect for kids ages 4 to 10. Tickets on sale now!
January 9-24, 2027 at the Calderwood Pavilion
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NEW Jack-O'-Lantern Nights at Stone Zoo - Stoneham
Experience the magic of autumn after dark at Stone Zoo's Jack-O'-Lantern Nights, a brand-new Halloween experience transforming the zoo into a...
Sat, Sun, Oct 1 - Oct 31
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Methuen Day - Methuen
Methuen Day is on October 3rd from 10 am - 3 pm. Check out - over 60 vendors, live music, food truck row, carnival games, face painting, and...
Saturday, Oct 3
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Halloween On The Hill 2026 - Beverly
An enchanting woodland hides an eerie graveyard, haunted pirate ship, stylish scarecrows, and thousands of hand-carved glowing jack-o-lanterns....
Thursday, Oct 1 - Friday, Oct 30
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Swampscott PorchFest 2026 - Swampscott
Live music all over town. Music and family fun. Rock, Indie, Country, Singer-Songwriter, Bluegrass.........all types of music. A pirate show...
Tuesday, Sep 29
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The Haunted Maze at Mahoney's Winchester - Winchester
Experience Mahoneys Haunted Maze in Winchester Sept. 26Oct. 26 Explore spooky or family-friendly paths, enjoy cider, coffee, donuts, and...
Friday, Sep 25 - Friday, Oct 30
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Manhattan Short Film Festival - Rockport
The Manhattan Short Film Festival is a unique experience, extending beyond its headquarters in New York City by inviting participating venues...
Sunday, Sep 27 - Sunday, Oct 4
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Brick or Treat's Minifigure Monsters are back! - Somerville
Join the ghoulish gang for Halloween at LEGO Discovery Center Boston this October. Expect frightfully fun build activities, spooky creative workshops, and the return of the 'Great Monster Chase' 4D movie.
Boooook Now!
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Magic In Medford
Get ready for Magic In Medford Enjoy a free, family-friendly evening of jaw-dropping illusions and tricks featuring eight local magicians at...
Monday, Sep 28
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Marblehead Fall Fair
Annual Fall Fair on Saturday, October 3rd from 10:00am - 3:00pm at the Jeremiah Lee Mansion Garden in Marblehead, MA. Hosted by Discover Marblehead...
Saturday, Oct 3
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Medford Craft Fair
Join us for a craft fair with 25 unique vendors AND tables selling baked goods, jewelry and raffles that benefit the Medford Senior Center directly....
Saturday, Oct 3
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South Suburbs
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King Richard's Faire: THE New England Renaissance Festival - Carver
Escape YOUR reality at New England's largest and longest-running Renaissance festival nestled in the enchanted woods of Carvershire... one day,...
Sat, Sun, Sep 5 - Oct 25
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Boo in the Barnyard at Weir River Farm - Hingham
Its Halloween at Weir River Farm Wear your costume and meet Petunia the pig, Betty the sheep, Pepper the goat, and many more barnyard friends...
Every Saturday, Oct 3 - Oct 31
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Monty Python’s SPAMALOT gallops into Boston’s Wang Theatre
Get ready to laugh at the musical comedy lovingly ripped off from Monty Python and the Holy Grail. SPAMALOT brings flying cows, killer rabbits, and plenty of questionable medieval logic, plus favorites like "Always Look on the Bright Side of Life" and "Find Your Grail."
October 8 - 11, 2026
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NEW DATES South Coast Harvest Festival - Westport
South Coast Harvest Festival returns September 2527 to Westport, Massachusetts, featuring stunning fall gardens, 70+ artisan vendors, local...
Friday, Oct 2 - Sunday, Oct 4
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Playing with a Purpose with Miss Tammy - Plymouth
Join PACE Child Care Works and Miss Tammy at Lakeville Public Library for a free 5-week interactive play and learn series for babies and kids...
Every Wednesday, Sep 23 - Oct 7
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Quincy Food Truck & Music Festival - Quincy
Enjoy live bands, kids entertainment, dozens of food trucks, dessert trucks, and axe throwing at Quincy's free annual festival on Coddington...
Saturday, Oct 3
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West Suburbs
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Maynard Fest
Dozens of sidewalk sales, over 100 vendors and free family entertainment. It is sure to please both young and old, including free children's...
Saturday, Oct 3
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Lexington's East Village Fair - Lexington
Celebrate Fall by joining us for the 185th Annual East Village Fair This family-friendly festival features our signature Flea Market, childrens...
Saturday, Oct 3
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The Lawn on D Fall Fest & Taylor Swift Tribute - Boston
Are You Ready for It? Dress in your favorite era and get ready to sing your heart out with Anna Daley Young from 2:00pm – 5:00pm for a Taylor Swift Tribute. Enjoy bracelet-making, face painting, and lawn games. The event is free with food and drinks available for purchase.
Saturday, October 3 from noon to 5:00pm
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Wayland Festival - Wayland
Join us at Wayland Town Center for the Wayland Festival - a full day of community, culture, and fun for all ages. Enjoy live music and performances,...
Saturday, Oct 3
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Annual Harvest Festival at Verrill Farm - Concord
Join us for our annual Harvest Festival to support Pediatric Care at Emerson Hospital. A day of family fun featuring games and prizes, live music...
Saturday, Oct 3
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CultureFest at Bellforge - Medfield
Bellforge Arts Center partners with Medfield Together for CultureFest, a free annual celebration of global music, dance, food, and cultural traditions...
Saturday, Oct 3
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Winnie the Pooh 100th Birthday Party @ Ten Trees Books - Natick
Celebrate a century of honey-loving fun at Ten Trees Books in Natick for Winnie the Pooh's 100th Birthday Party featuring storytime, cupcakes,...
Saturday, Oct 3
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Hayfest - Newton
Join us celebrate autumn with Historic Newton at the annual Hayfest Enjoy live music, historic crafts, children's games, pumpkin decorating,...
Sunday, Oct 4
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Library Lion returns to Boston this January!
Treat your family to Library Lion, the musical based on Michelle Knudsen's beloved book. Featuring a life-sized lion puppet by Jim Henson's Creature Shop, it's perfect for kids ages 4 to 10. Tickets on sale now!
January 9-24, 2027 at the Calderwood Pavilion
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Kids Corner with Little Beats - Sudbury
Sudbury Plaza invites families to enjoy Little Beats, a fun music & movement class featuring singing, dancing, and rhythm activities. Ideal for...
Tuesday, Sep 29
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Central Mass
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Oktoberfest at Wachusett Mountain - Princeton
Eat, drink and be merry, German style Enjoy beautiful foliage, tasty beer and comraderies among friends Raise your steins and toss the empty...
Saturday, Oct 3 - Sunday, Oct 4
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Fairies Aglow at New England Botanic Garden - Boylston
Fairy Hollow at New England Botanic Garden becomes even more mesmerizing with dazzling light displays and illuminated fairy houses. The family-friendly...
Fri, Sat, Sep 19 - Oct 23
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Seasonal Guides
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October Activity Highlights The school year begins and Boston shines brighter than ever while bustling with festivals and celebrations to satisfy every taste. There is also Fall foliage to admire, fitness events, and a plethora of fun and oft free things to do. September is full of events guaranteed to offer a memorable start to the Fall season!
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Ultimate Guide to Boston Fall Fun Fall in Boston brings a season packed with family fun and adventure. From crisp hikes to vibrant foliage, apple orchards, pumpkin patches, and harvest festivals, there's something for everyone.
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Pumpkin Festivals and Jack-o-Lantern Displays Near You New England is usually chock full of fall festivals dedicated to pumpkins, jack-o-lanterns, scarecrows and spooky fun: the icons of fall and of course Halloween.
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Apple Picking Near Boston
There is no apple that tastes better than the kind that you pick yourself. Local orchards invite visitors to pick-your-own apples just as the leaves begin to change their hue. Find an orchard near you and start planning a fun fall activity. Call ahead, as some may require reservations.
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Hayrides for Kids of all Ages
Hayrides are a fall tradition for many families. Depending on the age of your child, you might be in search of a farm themed jaunt through fields or a spine-chilling adventure that sparks spooky Halloween excitement. Here's a handy list to get you started!
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Corn Mazes Near You
Fall is upon us and autumn weather calls for outdoor fun. Here's a great list of Corn Mazes near Boston with cool themes and family friendly activities for all ages to enjoy.
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Things to Do in Boston on a Rainy Day - Boston When it rains in Boston, it's helpful to know about fun things to do indoors, so you can still enjoy the day. Rainy day activities can actually be great option on any day - but sometimes the weather just calls for indoor activities.
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Stacey Sao, Managing Director
BostonCentral.com
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