18th Annual "Scarecrown Contest"
Sep
28
to Oct 17

18th Annual "Scarecrown Contest"

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Eighteenth Annual “Scarecrow Contest” - Main Street Middletown will provide you with the scarecrow kits. They can be picked up at town hall beginning September 28th. Kits are a limited number and they go fast!

There are 2 categories for entries: family/individual and business/organization.

Scarecrows must be returned to town hall by October 16th.

The March of the scarecrows (judging) is on the 17th.

Prizes are awarded for 1st, 2nd, 3rd, & Burgess’ Choice in the two categories. Get creative and enjoy an event that is a local favorite!

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Middletown Lions Club Halloween Parade
Oct
24
5:00 PM17:00

Middletown Lions Club Halloween Parade

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Dress in costume and march in Middletown’s annual Halloween parade. The parade begins at 5:00pm, beginning at Martha Mason Drive, will come down Green Street, and end at the town hall with candy & refreshments. Participants are to be at the school grounds at 4:30. Sponsored by the Middletown Lions Club and the Town of Middletown.

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Christmas in the Valley
Dec
5
4:00 PM16:00

Christmas in the Valley

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  • Google Calendar ICS

We invite you to join us in celebrating the holiday season at  Middletown’s annual Christmas in the Valley on Saturday, December 4, 2026 at 4:00 PM. 

Festivities include caroling, roasting marshmallows, the lighting of the Town Christmas tree, a visit from Santa Claus with treats for the kids, story time with Mrs. Claus and then Christmas music at Zion Lutheran Church. 

After the show join us for punch and Christmas cookies in the church social hall.  Those mischievous elves will be hiding in our business’s windows for the month of December – be sure to participate in the elf hunt!

Santa Claus will also have a mailbox in front of Town Hall for those letters to Santa!

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