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Holiday events
in Chester, MD

Discover the best Holiday events in your area and online

Holiday
Chester
Date
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Most popular events

Annapolis Chocolate Binge Festival 2025 primary image

Annapolis Chocolate Binge Festival 2025

Sun, Dec 7, 11:00 AM

53 West St

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Songs of the Season - a holiday concert and sing-along primary image

Songs of the Season - a holiday concert and sing-along

Sun, Dec 14, 7:00 PM

Eastport United Methodist Church

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Christmas With the K9s primary image

Christmas With the K9s

Sat, Nov 29, 6:00 PM

Cult Classic Brewing

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Mahjong & Mistletoe: A Holiday Mix & Match primary image

Mahjong & Mistletoe: A Holiday Mix & Match

Thu, Dec 4, 6:00 PM

Kent Island Resort

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Annual Boxwood Wreath Making primary image

Annual Boxwood Wreath Making

Sun, Dec 7, 3:00 PM

Charles Carroll House

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2025 FRA 24 Holiday Party primary image

2025 FRA 24 Holiday Party

Sat, Dec 6, 6:00 PM

Fleet Reserve Club Of Annapolis

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Autumn Harvest Brunch in Annapolis primary image

Autumn Harvest Brunch in Annapolis

Sunday at 11:30

172 Green St

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Maryland Yuletide Celebrations 2026 primary image

Maryland Yuletide Celebrations 2026

Fri, Jan 9, 6:00 PM

DoubleTree by Hilton Hotel Annapolis

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