Q:

How do we roll a ball along a street from A to B?

This question is a follow up to この道をまっすぐ行ってください。Why “を” and not “で”? posted earlier.
If:

道で転ぶ = fallover on the road
ボールが道を転がる = a ball rolled along the street
〜を転がす = roll something (他）

How do we say:

"I rolled a ball along the street from the police station to the second traffic lights?"

Is it:

道沿い／道に沿って交番から二番目の信号までボールを転がした

？
[I want to capture the movement along the direction of the street and we can't have two をs. I have only just remembered the expression に沿う]

A:

"I rolled a ball along the street from the police station to the second traffic lights?"

Let's make it clear that along is a preposition(前置詞) in this sentence, not an adverb(副詞). 

"rolling along the street (道を転がる）"

rolling along the street would be better translated as 「道に沿って転がる」 rather than 「道を転がる」.　「道を転がる」 is a shorter version of 「道の上を転がる」. So it means "rolling onto the street". 
And with this phrase, the subject is a thing that actually rolls by itself such as a ball. (e.g. The ball rolled along the street.) On the other hand, the subject of 「ボールを転がす」 is not a ball but a person or a kind of force that rolls the ball. (e.g. The wind/I rolled the ball.)
「転がる」 and 「転がす」　are different kind of verbs. The former is an intransitive verb(自動詞) which does not require an object(目的語). On the other hand, the latter is a transitive verb(他動詞) and requires an object(目的語). 
So "道をボールを転がす", which sounds really odd to the natives, appears that "ボールが道の上を転がる" and "私がボールを転がす" are said at once in one clause of a sentence.

