2020 Halloween Activities Guide

All things Halloween in the Rutland area

By Catherine Heatley, Publisher Mom, Macaroni Kid Rutland-Windsor VT October 13, 2020

Halloween looks a little different this year due to the pandemic, but there are plenty of options for safe family fun. Trick-or-Treaters will be taking to the streets on Saturday, October 31st, and there are plenty of other activities going on to make Halloween 2020 memorable!

Check back often, as events and ideas are being added daily.

Know of something we missed? Submit an event HERE!

Beginning  October 1st

🎃 Oct 1 - 31: Guess Gertrude the Pumpkin's Weight and win a prize!

🎃 Oct 1 - 31: Saturday Night Halloween Movie at the Vermont State Fair Drive-In Movie

🎃 Oct 1 - 31: Saturday Night Halloween Movie at the Jack McKernon Drive-In Movie

🎃 Oct 1 - 31: Saturday Nights! Moonlight Madness at the Hathaway Farm Corn Maze

🎃 Oct 1 - 16: FREE Pumpkin Voucher while supplies last

🎃 Oct 1 - 18: Enter to win a FREE BOO Bag from Macaroni Kid Rutland - Windsor

Saturday, October 10th

🎃 Trails and Treats

🎃 Fall Craft Fair

🎃 Fall Festival

Wednesday, October 14th

🎃 Register for Rutland Rec Department's Costume Stroll

Beginning October 17th

🎃 Oct 17 - 31: The Great Pumpkin Story Walk - Rutland

Beginning October 19th

🎃 Enter to BOO or BE BOO'd in Brandon. Sponsored by the Brandon Area Toy Project and Macaroni Kid Rutland - Windsor VT

🎃 Oct 19 - 24: Delivery to Macaroni Kid Rutland - Windsor BOO Bag winners!

                            Didn't win this year? You can still get in on this pay-it-forward movement by surprising your own friends with FREE printable instructions HERE

🎃 Oct 19 - 31: Halloween Scavenger Hunt - Rutland

Beginning October 23rd

🎃 Oct 23 - 31: Shocktober Virtual Haunted House

Sunday, October 25th

🎃 A Family Halloween at Billings Farm and Museum

🎃 Halloween Fun Run (pre-registration required)

Halloween Week

🎃 Oct 24 - 31: Halloween Windows on Parade - Rutland

🎃 Oct 26 - 31: Spooky Nature Scavenger Hunt - Rutland

🎃 Oct 29 - 30: Smith Street Haunted House - West Rutland

🎃 Oct 30: Spooksville Trunk or Treat - Brandon

🎃 Oct 31: Pumpkin Carving Contest - West Rutland

🎃 Oct 31: Halloween Farmers Market - Rutland

🎃 Oct 31: Kinder Way Trick or Treat - Benson

🎃 Oct 31: Costume Stroll - Rutland (pre-registration required)

🎃 Oct 31: Trunk or Treat Treasure Hunt - Poultney

🎃 Oct 31: Drive Through Trunk or Treat - Pittsford

🎃 Oct 31: Drive Through Trick or Treating - West Rutland

🎃 Oct 31: BOO-M! A Halloween Fireworks Spectacular - Rutland

Did we miss an event? Please CLICK HERE to submit an event or email me at

*Please follow all state, local, and venue guidelines. Practice social distancing and other safety protocols. We always recommend verifying event information with the venue before heading out to participate in an event.

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