Oktoberfest at Rapscallion

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An annual tradition marking the release of their O-Fest seasonal, a traditional German Marzen, along with live music all weekend and a bratwurst special on the food truck! Big Jon Short, Boogie Chillin' and Matt Soper play the tap room! Also check out apple picking, disc golf, hay rides and more. +discover

Great Pumpkin Nights 

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When: October 12-14, 19-21, 26-28 

Where: EcoTarium, 222 Harrington Way, Worcester, MA

Celebrate Halloween at the EcoTarium’s annual family-friendly Great Pumpkin Nights! Wander the EcoTarium grounds to see striking funkin displays of dinosaurs, safari animals and more. Inside, enjoy the museum’s fascinating exhibits while also getting to trick-or-treat. Don’t forget your costume!  +discover 

Harvest Festival at The Farmer's Daughter 

When: October 13, 2018 from 10 AM - 4 PM 

Where: The Farmer's Daughter, 153 Millbury Street, Auburn MA

Visit the cows and their newborn babies, take a wagon ride, get your face painted, try a sack race and leave with a pumpkin!  +discover 

Free Family-Friendly Jazz Festival 

When: October 13, 2018 from 12 PM - 6 PM 

Where: 455 Main Street, Worcester MA

It’s fall! And that means beautiful autumn weather and festivals to enjoy. Set on the grounds of Worcester Common, this new event is bringing award-winning musicians, food trucks, vendors, and kids activities to the city. You’ll want to bring your friends and whole family to gather together and celebrate the joy of music. +discover 

Sturbridge Annual Harvest Festival 

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When: October 13-14, 2018

Where: Sturbridge Town Common & Publick House, 277 Main Street, Sturbridge, MA

The 29th Annual Harvest Festival on the Sturbridge Town Common and grounds of the Publick House Historic Inn is a family fun tradition. The event includes countless local crafters, artisans, live music, specialty food vendors and farm fresh harvests. +discover 

Fall Fest Weekends at New England Botanic Garden at Tower Hill

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When: October 11-14, October 20-21, Oct. 28

Where: New England Botanic Garden at Tower Hill, 11 French Dr, Boylston, MA

If you are in search of a classic New England fall experience, look no further than Fall Fest at New England Botanic Garden at Tower Hill. These special weekends will be jam-packed with fall-themed fun including an "October Oddities" exhibit of unusual and weird gourds, pumpkins and strange vegetables; an apple themed flower show; and a "dogs in costume" parade on October 28. +discover 

Old Sturbridge Village Apple & Agriculture Days

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When: October 13 - 14, 2018 

Where: Old Sturbridge Village, 369 Main St., Sturbridge

Celebrate the harvest in the beauty of the fall color. Learn how food made its way from farm to table in the 1800s by costumed interpreters. They'll be harvesting apples and potatoes and demonstrating the use of root cellars, gardening, and the shelling of corn and beans. Watch the old way of making cider in the ox-powered cider mill. On Sunday October 14, attend the Celebration of Cider and Music Festival from 11 AM - 6 PM where you can enjoy hard ciders and tunes in a historic village setting. +discover

Wachusett Annual Apple Fest

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When: Sat. Oct. 13 - 14, 2018 from 10 AM - 5 PM

Where: Wachusett Mountain Ski Area, 499 Mountain Rd., Princeton 

Cost: Adult $11 - $14, Child $0 - $9 

AppleFest features over 125 craft fair & farmers' market booths, family entertainment, scenic foliage skyrides to the summit, comedy and live music, apple pie eating contest, Irish step dancing performances, roaming entertainment and more! +discover

Food Truck Fright Fest 

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When: October 20, 2018 from 12 PM - 5 PM  

Where: Green Hill Park, 50 Skyline Dr., Worcester MA

Over 20 food trucks are taking over Worcester's beautiful Green Hill park for an epic Halloween bash! Children under 12 free admission. Trick or treat for the kids 4pm to 5pm... from the food trucks! Discounted admission for attendees in costume. +discover 

Fall Festival at Ski Ward 

When: October 27-28, 2018 from 11 AM - 5 PM 

Where: Ski Ward, 1000 Main Street, Shrewsbury MA

This family-friendly festival is hosted by Ski Ward. Enjoy fall-flavored ice cream, Oktoberfest brews, bounce houses, caramel apples and more. +discover