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Holiday events
in Oakland, MD

Discover the best Holiday events in your area and online

Holiday
Oakland
Date
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Most popular events

Breakfast or Lunch with Santa and his Reindeer! primary image

Breakfast or Lunch with Santa and his Reindeer!

Sat, Dec 12 • 10:30 AM

DiMarco's Bistro & Cantina

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FRIGHT NIGHT (HALLOWEEN) primary image

FRIGHT NIGHT (HALLOWEEN)

Sat, Oct 31 • 8:30 PM

801 E Park Ave

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An Evergreen Christmas primary image

An Evergreen Christmas

Sat, Nov 14 • 1:00 PM

Evergreen Heritage Center

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Nemacolin Castle Ghost Tours 2026 primary image

Nemacolin Castle Ghost Tours 2026

Friday • 6:00 PM + 89 more

136 Front St

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GROW WEST FALL FEST primary image

GROW WEST FALL FEST

Sun, Oct 18 • 12:00 PM

1812 Brewery

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Haunted Halloween Tales: Stories of the Ligonier Valley primary image

Haunted Halloween Tales: Stories of the Ligonier Valley

Sat, Oct 24 • 6:30 PM + 11 more

Compass Inn Museum

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Compass Inn Museum by Candlelight: Celebrating the Yuletide primary image

Compass Inn Museum by Candlelight: Celebrating the Yuletide

Sat, Nov 28 • 4:00 PM + 31 more

Compass Inn Museum

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Bonfire Celebration: An Old English Tradition primary image

Bonfire Celebration: An Old English Tradition

Sat, Nov 7 • 3:30 PM

Compass Inn Museum

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