At one point in time there was a thread here that had some (or most) of the Christmas Town music. From that, here's what I have in my current Christmas Town playlist.
Entrance
----------
Spirit of the Season -> Alan Silvestri
England
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Star Carol -> Rutter, John
Scotland
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O Holy Night -> Celtic Woman
A Highland Carol -> Michael W. Smith
O Holy Night -> Michael Crawford
Bells Over Belfast -> The Irish Rovers
Ireland
----------
Ding Dong Merrily on High -> Celtic Woman
Greensleeve -> California Guitar Trio
France
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Au Royaume du Bonhomme Hiver -> Marie Myriam
C'est l'hiver -> Marie-Elaine Thibert
The Twelve Days of Christmas -> New York Philarmonic
New France
----------
Christmas Cookies -> George Straight
Here Comes Santa Claus -> Joey Miskulin
Let It Snow -> Roy Clark
Joy to the World -> The Clarke Family
Auld Lang Syne -> Columbia River Group Entertainment & The Clarke Family
Bridge between New France and North Pole
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La Det Sno -> Scandinavia
On the River -> Frank Chacksfield Orchestra
La Det Snow, La Det Snow, La Det Snow -> Kine Therese Ludvigsen (Kine)
North Pole
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Father Christmas -> Harry Gregson
Seeing is Believing -> Polar Express
The Bells of Christmas -> Loreena Mckennitt
Oktoberfest
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Freu dich! -> Kristina Bach
Herbei, O Ihr Glaubigen (O Come All Ye Faithful) - Engel Bringen Frohe Kunde (Gloria In Excelsis Deo) - Kommet, Ihr Hirten - Ganz Leise Bluht Eine Blume Auf -> Hella Heizmann
Lasst uns froh und munter sein (Medley) -> Peter Alexander
Hier kommt der Weihnachtsmann -> ??
Ich glaube noch immer an den Weihnachtsmann -> ??
Bridge between Oktoberfest and Italy
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Let There Be Peace on Earth - The Boys Choir of Harlem
Veni, veni Emmanuel (arr. A. Delmoni) -> Arturo Delmoni, Alexander Romanul, Nathaniel Rosen & Katherine Murdock
O Sanctissima (arr. A. Delmoni) -> Delmoni, Arturo
Miracles
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I Believe (Edit) -> Nikki Yanofsky
Main Title from Home Alone (Somewhere in my Memory) -> John Williams
Light the Fire Within -> LeAnn Rimes
Angels -> Jim Brickman
Christmas Canon -> Trans-Siberian Orchestra
Ordinary Miracle -> Sarah McLachlan
Holiday Hills
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Baby its Cold Outside -> Johnny Mercer
A Marshmallow World - Dean Martin
All I Want for Christmas (Is My Two Front Teeth) -> Nat King Cole Trio
Santa Claus Got Stuck in My Chimney -> Ella Fitzgerald
It's Beginning to Look A Lot Like Christmas -> Bing Crosby
The Man with the Bag -> Kay Starr
Christmas Island -> The Andrews Sisters
If It Doesn't Snow on Christmas Day - Gene Autry
Polar Pathway
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Another Answer Came -> Yanni
After the Sunrise -> Yanni
Misc
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A Holly Jolly Christmas -> The Fireside Singers
God Rest Ye, Merry Gentlemen -> Mannheim Steamroller
Angels Among Us -> Alabama
Driving Home For Christmas -> Chris Rea
Updates/corrections are appreciated.