Definitely! In fact, instead of Middlebury Gap why not back it up to Brandon Gap and go all the way to Appalachian Gap, making the trip all of Long Trail Division 7 and most of Division 8. The section between Lincoln Gap and App Gap is the "Monroe Skyline" and is an incredible ridge walk.
I have some pics from Lincoln Gap as far as Mt. Ellen
here, to give you an idea.
This would be around 38-39 miles.