Dates and details are subject to change. Check back regularly for updates.

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Community Yard Sale

May 9, 2026

Declutter, shop, and dig for hidden gems at the Downtown Middletown Community Yard Sale. Register your downtown address for $5 and get listed on our interactive Google map so shoppers can find you easily. A great way to connect with neighbors and support local commerce.

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Charcuterie Crawl

June 4, 2026 | 5:00 PM – 7:00 PM

This year's Charcuterie Crawl goes next level. Stroll Main Street and enjoy tastings from four regional wineries brought straight to downtown, plus craft beer from Volunteer Brewing Company.

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Wineries:

• Broken Spoke Winery

• Bohemia Manor Winery

• Harvest Ridge Winery

• Crow Vineyard & Winery

• DD Project Wines

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Beer: Volunteer Brewing Company

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Five pours, one walkable route, all on Main Street. We’ll also be adding  alcohol-free Mocktail tastings as an option

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Flag Day Celebration

June 14, 2026 | The Everett

A community gathering to mark Flag Day with a stage presentation on the history and significance of the holiday. Family-friendly. Free to attend.

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Our event will be on Cochran Square at 6:30pm. Join us as we celebrate with communities across the Nation.

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Family Fun Fest

July 18, 2026 | 3:00 PM – 7:00 PM

Games, activities, live entertainment, and good vibes for the whole family. Face painting, performances, and more across downtown. Join us at 19 W Green St.

Vendors welcome.

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Just Peachy Scavenger Hunt

July 18 – August 14, 2026

An extended summer scavenger hunt spread across downtown. Explore Main Street, solve clues, and discover local businesses along the way. All ages welcome.

Details and participation info coming soon.

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Lamppost Decorating

November 7 – 21, 2026

Downtown gets dressed up for the holidays. Businesses and community groups decorate the lampposts along Main Street, and the public votes for their favorites on our website.

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Christmas Tree Lighting & Caroling on the Square

November 27, 2026 | 6:00 PM

Ring in the holiday season with the annual tree lighting ceremony, live caroling, and community celebration at Town Square. Free and open to all.

Location: Town Square, four corners intersection

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Holiday Spectacular Parade

December 5, 2026 | 10:00 AM

The signature holiday event returns. Floats, marching bands, performers, and Santa Claus himself. The parade runs along South Broad Street, turns onto West Main Street, and ends at South Scott Street, with special performances at Town Square.

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Arrive early. Dress warm. Bring the family.

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The Great Middletown Cookie Crawl

December 5, 2026

Pair the parade with an afternoon cookie crawl through participating downtown businesses. Stroll Main Street, sample holiday cookies, and keep the holiday spirit going.

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Details and participating locations coming soon.

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