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Winter solstice
100

Elvis Presley sings about this kind of Christmas.

What is a Blue Christmas?

100

This can be deadly if you eat it. (But a kiss can be even deadlier if you mean it.) 

Mistletoe.

100

This 2003 rom-com movie features 9 intertwined stories and many big stars of the day including Hugh Grant, Keira Knightly, Liam Neeson, Emma Thompson, and Alan Rickman. 

Love, Actually. 

100
Alvin wants this for Christmas.
What is a Hula Hoop?
100

This word means "Sun Stands Still."

Solstice.

125
Frosty's nose is made of this.
What is a Button?
125
This popular drink is only available around Christmas.
What is Egg Nog?
125
George Baileys guardian angel
Who is Clarence?
125
This reindeer helps Rudolph fly at the reindeer games.
Who is Clarice?
125

We don't know who built it, but this monument aligns with the winter solstice.

Stonehenge. 

150
All I want for Christmas is two of these.
What is My Two Front Teeth?
150

Santa's original name is this.

Kris Kringle.

150
The movie White Christmas takes place in this state.
What is Vermont?
150

This gentleman sings the most popular version of Rudolf the Red Nosed Reindeer.

Gene Autry.

150

The turning of mid-winter into longer days was marked by this ancient Roman holiday.

Saturnalia. 

175
It's fun to ride in this as we jingle all the way.
What is a one horse open sleigh?
175

This company was the first to use Santa Claus in an advertisement.

Coca-Cola.

175
The name of the rabbit in the magic hat in "Frosty the Snowman"
Who is Hocus Pocus?
175

This cartoon character brings a sad, tiny, little tree to his friends to decorate.

Who is Charlie Brown?

175

During the solstice, everything north of this circle's line sees no sun rise above the horizon for a full day.

The Arctic Circle.

200

On the eighth day of Christmas, my true love sent to me?

8 maids a milking.

200
The gingerbread house came from this country.
What is Germany?
200

This 1988 action movie features Bruce Willis taking on terrorists during his ex-wife's office Christmas Party. 

Die Hard. 

200
The Grinch stole all of the presents from this town.
What is WhoVille?
200

The winter solstice always falls between these dates?

Dec. 20th-23rd.