The Board gives no reason for this decision; it's a geographical mystery. There are myths and theories, of course, one being that apostrophes will look too much like they're indicating a formation in the topography. Their own website suggests the reason is "ownership of a feature is not in and of itself a reason to name a feature or change its name." I reckon they take that possessive thing seriously.
If you're still intrigued, check this out: In the last 118 years or so, only five natural features have been approved by The Board to use apostrophes. Martha's Vineyard was allowed the use of an apostrophe after the residents fought for it in 1933. The other apostrophe recipients seem to rightfully deserve one as it may change the way it's read: Ike's Point, John E's Pond, Carlos Elmer's Joshua View (overlooks a stand of Joshua trees), and Clark's Mountain (referring to the importance of the Clark of Lewis and Clark fame). Pikes Peak does not contain an apostrophe on maps or signs either.
So, if you're typing or writing the location, Deals Gap, I wouldn't worry so much about the apostrophe. Grammatically you'd be correct in saying that it was Mr. Deal's gap in the mountains and geographically you'd be correct if you left the apostrophe out. Seems the The Board just doesn't want to allude to Mr. Deal owning the gap but will acknowledge that people call it his gap.
To learn more about the history of the Dragon at Deals Gap, see our special features here. Our interviews with Doug Snavely are more about how motorcycling evolved there than grammatical details, I promise!
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