Shady Side Holiday events

Holiday events in Shady Side

Discover the best Holiday events in Shady Side! From festive Christmas markets to New Year's Eve fireworks displays & Holiday Bazaar, we have something for everyone. Explore the Shady Side's winter attractions and make lasting memories with friends and family. With so much to do in Shady Side, you'll never have a dull moment this holiday season.

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Holiday events in Shady Side

Holiday events in Shady Side

Sun, 07 Dec, 2025 - 12:30 PM

Tea with the Sugarplum Fair and the Nutcracker Prince

1418 EW Shady Side Rd, Shady Side, MD, United States, Maryland 20764
Sun, 14 Dec, 2025 - 12:30 PM

Tea with the Sugarplum Fairy and Nutcracker Prince

1418 EW Shady Side Rd, Shady Side, MD, United States, Maryland 20764

4+ Interested

Holiday events from nearby cities

Sun, 14 Dec • 12:00 PM

40th Annual Cookie Tour of Historic Homes

Union Square

30+ Interested

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USD 25
Sat, 13 Dec • 12:00 PM

🌟 🎄 2nd Annual Holiday Craft Fair & Toy Drive! 🎁 🎅

iLove Events Center

Free
Fri, 05 Dec Onwards

A Christmas Carol for Edgar Allan Poe

Motor House

5+ Interested

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USD 50
Sat, 29 Nov Onwards

Holley Jolly Holiday Crafting Event

Baltimore County Public Library - Pikesville Branch, Reisterstown Road, Pikesville, MD, USA

4+ Interested

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USD 20
Sat, 13 Dec • 12:00 PM

Canton’s Biggest Santa Bar Fest

1021 S Linwood Ave

Newly Added

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USD 10
Sun, 14 Dec • 05:00 PM

Toys for Shelter Pets – Second Annual Christmas Charity Event

Hotel Hive

Newly Added

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USD 15
Sat, 13 Dec • 12:00 PM

The Worthington's Bad Santa Day Party

2900 O'Donnell St

Newly Added

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USD 15
Wed, 24 Dec • 09:00 PM

MATZOBALL® WASHINGTON DC XMAS EVE ages 21-49 December 24, 2025

Decades DC

Newly Added

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USD 40
Sun, 14 Dec • 01:00 PM

Winter Wonderland Fest

Seneca Valley High School

63+ Interested

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Free

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