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Not a road that rolls, but a road for rolling.

In the areas of Colonial America where Tobacco was grown1, roads were generally terrible. The only feasible way to get around, and to transport agricultural products, was by raft or boat.

Now, this still left the tobacco farmer the problem of getting tobacco to an entry port. After the tobacco was harvested2, huge barrels called "hogsheads", 8 feet in diameter and 10 feet high, would be built3, and then packed3 full of tobacco.

That's a mighty big barrel to haul by wagon. So special roads were built3 from the tobacco plantations down to the entry ports, an extremely gentle grade, downhill all the way. At harvest time, the hogsheads would be rolled, either pulled by oxen or manually pushed3 all the way.

Rolling roads were the first decent roads in places like Maryland and Virginia. Some of them grew into the first turnpikes, while others simply hung around. The courses of several old rolling roads are followed by heavily-traveled roads today. "Rolling Road" in Catonsville was used to roll hogsheads down to the tobacco port near present-day Relay, Maryland.
1Pretty much everywhere, this being the only thing that factors in back in Mother England would pay for.
2Not by the planter, of course, but by his indentured servants, or even more economically, slaves.
3See note 2. Frequently.

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