By the glance, Squire is also MTG card of the same name, and most of Dames and Sirs are by Boris Vallejo ( *puking smiley*).
I am kinda bored, and like actually googling art, so here it goes:
Crossroads - well, I cannot determine the author or the real location of the picture; but, the picture is ALWAYS followed by a story about how Robert Johnson sold his soul at the crossroads; so I believe it's most likely taken in Mississipi, probably Rosedale.
Duchess is an Alice in Wonderland book illustration by John Tanniel.
Fool's Gold - no idea.
Develop comes from here:
http://www.pitt.edu/~caram/plans.htmOasis - is a picture Oasis in the Libyan part of the Sahara Desert, by wikipedia user Sfivat.
Oracle - Delphic Oracle by Heinrich Leutemann.
Tunnel - I
think its a picture of a tunnel at Black Diamond Mines Regional Preserve. But it's really hard to differ it from others.
Nomad Camp - I've found a bigger picture (
http://www.michelledastier.com/sortir-de-la-zone-de-confort-par-daniella-phamphile/ ) but still no idea.
Silk Road - It's an album cover of some japanese musician..
www.amazon.co.jp/NHK特集「シルクロード」オリジナル・サウンドトラック-シルクロード~絲綢之路II~-喜多郎/dp/B00006G8VWSpice Merchant / Trader - ughh... found matching pictures, but can't determine origin.
Cache - no idea whatsoever.
Cartographer - The Geographer by Johannes Vermeer.
Highroad - Appian Way in Rome.
Ill-Gotten Gains - Treasure recovered from wreck of "Nuestra Seņora de las Mercedes" (Spanish Navy frigate, sunk 1804)
Inn - is Abigail's Hotel, located in Victoria, B.C. (Canada). (Picture possibly taken by Leslie Forsberg. ??
http://www.goworldtravel.com/travel-british-columbia-victoria-branching-out-from-its-empire-roots/ )
Mandarin - It's a cigarette card. You are supposted to find his hat on the image. Created by Major Drapkin & Co in 1926.
http://www.planetperplex.com/en/item/mandarin/Margrave - It's Charles William Frederick, Margrave of Brandenburg-Ansbach (in Prussia, I believe). I do not think the author of the portrait is known.
Stables - those are stables at Kenilworth Castle, Warwickshire, England.
Border Village - its Tmogvi, a ruined fortress in the southern Georgian region of Samtskhe-Javakheti.
Farmland - its Longsheng Rice Terraces in Guangxi.
Wow, some of these have pretty nice stories behind them
(this is whole hinterlands).