Leaves, Laughs & Haunted Paths: A Month of Fall Events

Acton:

• Halloween Hullabaloo: Saturday, October 29th and Sunday October 30th, Discovery Museum, 177 Main Street.  Join the Discovery Museum as they celebrate Halloween weekend! Dress for the occasion and give your Halloween costume the chance to spook, sparkle, and shine. Challenge yourself to a few holes of Pumpkin Putt Putt and other outdoor games with a frightfully fun twist. Use your powers of observation on a Spooktacular Scavenger Hunt and expect other ghostly surprises to pop up around the Museum! Some outdoor activities will be weather-dependent. 

Ashland:

• Fall Fest: The Corner Spot, Saturday, October 18^th 3-6pm. Celebrate the season with an afternoon of fall fun, food, drinks, music, and games. Enjoy bites from Joey D’s Wingz & Things, Dulce D Leche, and Refreshin’ Concessions, plus seasonal beer and wine from Wine Empire.  Hit the Bus Band will be bringing the tunes and Imagine That Face Painting will be on hand for the kids.

Bellingham:

• Halloween Trunk or Treat Stroll: Saturday, October 25, 5:30pm – 7:30pm, Bellingham Town Common

Blackstone:

• Cider Fest at Daniels Farmstead: Sunday, October 5th 11am-3pm, 286 Mendon St. Join Daniels Farmstead for the first ever Cider Fest featuring local flavors, live entertainment and a festive atmosphere.

Concord: 

• Taste of Concord: Tuesday, October 21, 6pm-8pm.  Nashawtuc Country Club.  Don’t miss this one-of-a-kind evening of food, wine, rare spirits and community!

Framingham:

• Framingham Fest: Saturday, October 4th, 2025, 11am-3pm, Framingham Centre Common.
• Oktoberfest: Jack’s Abby from Saturday, September 27th – Sunday, October 5th.  Join Jack’s as they bring a little bit of Munich to Framingham with different events celebrating Oktoberfest happening throughout the week.

Holliston:

• Oktoberfest: Friday, October 17th, 6:30pm-10pm.  Join Holliston Historical Society for an authentic German dinner with beer and wine. There will be laughing, singing and polka dancing!

Hopkinton:

• Hopkinton Center for the Arts – Carnival at Deadwoodville: Friday and Saturday, 10/17, 10/18, 10/24 and 10/25 at 6, 7, 8 and 9pm. Kid friendly haunt 10/20 and 10/27 at 5, 6, 7 and 8pm at YMCA Outdoor Center 45 East Street.  For two uncanny weeks, Deadwoodville comes alive with the sights, sounds, and spirits of a dark carnival like no other.  Imagine strolling beneath tattered big-top tents, where ghostly jugglers toss flaming skulls and skeletal acrobats soar through the fog. The air is thick with the scent of sour candied apples… and something far more mysterious. Every booth, game, and shadowed corner hum with anticipation as the living and the departed prepare for a union that defies the grave.

Hudson:

• RecFest: Saturday, October 4th, 12pm – 4pm Guidotti Park, 120 Chapin Road.  Includes carnival style games, pony rides, face painting, inflatables, touch-a-truck, and live entertainment.
• Downtown Trick or Treat: Thursday, October 30th, Downtown Hudson, Main St.  Hudson’s Downtown Trick or Treat is a beloved tradition where local businesses hand out treats to costumed kids. Streets are closed to ensure safety, and the event attracts around 2,000 children. Look for pumpkins in windows to identify participating businesses.

Medway:

• Autumn Night Out: Medway Community Farm, Saturday October 25^th, 7 – 10pm.  A Farm to Fork event featuring a delectable assortment of appetizers prepared by local Medway caterers Aliquot’s.
• Pumpkin Walk: Friday, October 24th, 7pm-9pm, Choate Park.  Pre-registration will be required. Registration for Medway Residents will open on Monday, August 11 at 9am. Non-Resident registration will open on Monday, October 6th at 9am.  Medway Community Farm will be selling concessions this year (Hot Cocoa, Popcorn, snacks). The playground will also not be accessible during the event.  Please remember flashlights as this is a dark event. They will be handing out glow necklaces/bracelets.

Mendon:

• Southwick Zoo: The Great Jack O’Latern Journey, September 26^th – October 31^st, 5pm to close. Explore one of the most popular Halloween Festivals in New England.  Shows, entertainment and family fun surrounded by hundreds of glowing, carved pumpkins showcasing animals, super heroes, and more!

Natick:

• All About Bats: Broadmoor Wildlife Sanctuary, Friday October 17th, 6:30pm – 8pm. There’s so much more to bats than their spooky reputation! Search for bats in the evening sky as we enjoy a walk-through sanctuary fields and forest. Learn about bat behaviors, habitat and how they communicate as we track their sounds using our Wildlife Acoustics’ Echo Meter, which picks up and records their ultrasonic sounds that we cannot hear!
• Tractors & Treats: Lookout Farm, Saturday, October 25^th, 4:00pm-6:00pm. Trick or Treating, Monster Mash DJ Dance Party, Crafts, Games and Spooky Fun.

Southborough:

• Heritage Day: Monday, October 13^th, 10am-1pm at St. Mark’s Field Rt. 30 and Rt. 85 Intersection. Enjoy a parade, artisan booths, and food trucks.

Sturbridge:

• Old Sturbridge Village: Phantoms by Firelight – The Grand Finale Season – Fridays, Saturdays and Sundays October 10 – 26, 2025 from 4:30pm to 9pm.  As nightfall cloaks the Village in darkness, the line between past and present fades, and history’s shadows come alive. Wander fire-lit paths and step inside historic buildings, gather by the crackling bonfire for eerie tales, and revel in the dazzling spectacle of fire dancers, soaring acrobats, and haunting melodies. Step into a world of flickering lanterns, whispered secrets, and the magic of Halloween like you’ve never experienced before.

Sudbury:

• Wayside Inn: Jerusha’s Halloween Ball, Friday, October 24^th 6pm – 10pm.  Pre-party Tarot, Costume Contest, Music and Dancing, Whiskey & Wine Pull.  Ticketed event/21+.
• Goodnow Farms Halloween Barn Party: Friday and Saturday, October 24^th and 25^th, 6pm, 7pm, or 8pm. 80 Goodnow Road, Sudbury.  Their barn was built over 200 years ago, and over the years a bewildering number of spooky creatures have taken up residence.  They usually behave themselves, but on one special night per year (just before Halloween!) they all appear at once to terrorize the mere mortals who have the misfortune to cross their path.
• Musicians of the Old Post Road – Brillant Borrowings: Saturday, October 25^th, 4pm, First Parish, 327 Concord Road.  Witness the magic of inspiration and influence among Baroque luminaries! Program includes one of Telemann’s Corelli sonatas, Chedeville’s reimagining of Vivaldi’s Four Seasons, a Handel work inspired by Telemann, a string concerto by Avison after Scarlatti, and the premiere of the ensemble’s arrangement for chamber ensemble of Bach’s Italian Concerto.

Wayland:

• Wayland Festival: Saturday, October 4^th, 11am-6pm, Wayland Town Center, 4 Elissa Drive.  This event features a combined multicultural pavilion and artists’ marketplace, Touch-a-Truck, food/beverage/ice cream trucks, a Rail Trail parade celebrating the nation’s 250th Birthday, and live music!

Westborough:

• Main Street Trick or Treat: Tuesday October 28^th, 4pm to 7pm.  Downtown Westborough (Main Street, East Main Street, Milk Street & South Street).