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Here is a list of the links that I have found searching for good Chessie info on the net.

HISTORICAL SOCIETY & MUSEUM SITES RELATED TO CHESSIE:
Chessie System Historical Society:  The only Chessie dedicated society.  I am a member, and highly recommend it to anyone interested in Chessie.  They sell books online.  Lots of unique reference material.

B&O Historical Society: Good source of pre Chessie info, not alot on Chessie.  They sell books online.

B&O Museum:  Great place to visit.  Check out their site.  You need to visit if you are a Chessie fan.

C&O Historical Society: Good source of pre Chessie info, not alot on Chessie.  They sell books online.

WM Historical Society:  Don't know alot about them.  Good site.  Lots of pics.

MODELING SITES RELATED TO CHESSIE OR THE CUMBERLAND SUB:

Piedmont Sub-Division model railroad: 1970's based C&O model railroad.

Ken Miller's Cumberland to Pittsburgh model railroad:  A great site, a great railroad

Chessie Photos:    The single best source for Chessie pics on the net.  Every locomotive, every safety caboose, examples of all the types of freight cars.  It doesn't get any better than this.

Fallen Flags:  Great site.  Every B&O engine listed.  Pics of all but a few.  Plus lots of pics from railroads no longer in business.  Good easy way to find pics of other railroads cars for your Chessie layout.

SD45.com:  Great site.  Really good photographic art, more than just pictures, John Rust has an eye for beauty of the train. 

Northeast Railfan:  Good pics of all railroads from the Northeast.

WM Photo Site: Great pics of WM equipment.

Ohio Railfan:  Some good pics of Chessie stuff.

Morscher Photos:  Good pics.  Lots of them from all northeast railroads.

Randy Mower Photos:  Good pics, lots of Chessie ones specifically from Cumberland Sub.

East Penn Photos:  Some good locomotive pics.  Good images of Brunswick and Hancock.

Eddie's Michigan pics: A good site of Chessie locomotives and cabins

Michael Taylor Photos: Good pics of Chessie stuff.

B&O Railroad Network:  Good site for all sorts of B&O information.

CSX History:  Good site on general history of CSX roads, including Chessie.  Good maps, etc.

MARC Site:  Great site detailing Maryland Area Rapid Commuter system that ran passengers on the East End.

eBay:  Great place to find cheap Chessie cars, if you know what you are looking at.  Buyer beware.  There is alot of junk on eBay too.  But you can also find lots of kits that are no longer produced.