From the June 6, 1941 edition of the Gazette:

Surfaced automobile roads cross and recross the Vineyard in this day, and if it should chance that thaw or frost should cause a crack to appear in the smooth, black surface, it is a safe bet that some disgruntled motorist would contact the state superintendent of highways and register a complaint. Not that it occurs often, because the superintendent and his gang are always on the job, but such things occur often enough to indicate the frame of mind of the modern Vineyard public.

When roads or ways of any sort first came into being on the Vineyard no one can actually state. Records, such as they are, and notes in private journals, break out abruptly with references to certain “wayes” or “paths” in a manner that takes it for granted that all who read, or who might read later, would know exactly what was indicated.

A few of the older ways in Edgartown have been preserved through their eventual development into town streets, and this we have Pease’s Point Way and Planting Field Way. There are others, known and recognized through tradition, such as the Mill Path, connecting Edgartown with West Tisbury, while others or traces of others, may be found elsewhere about the Island.

Here and there, where the old stone walls stand unscathed, may be found narrow openings, wider than is necessary for the passage of a pedestrian, but far too narrow for any wheeled vehicle. The person who discovers one of these will possibly wonder why the unusual width of the passage. The answer is that some forgotten Vineyard way once passed through this opening and in that time it was wide enough for the passage of such traffic as employed the Island roads.

It is significant that the first actual move to better road conditions, outside of the actual village streets, came as the result of bicycles and their riders. Not only was the development of paths by the side of roads encouraged, but the road themselves came in for some real repairs in many places. It is interesting, too, to note that the late John L. Tilton of Chilmark proposed a plan to grade the town ways, then all of dirt construction, and illustrated his idea on a stretch of the North Road just west of the West Tisbury line. The result of his effort, all performed with a pick and shovel, produced a dirt highway exactly like what is now produced by means of the popular road-scraper. Such machinery was not known then, at least on the Vineyard, and Tilton’s scheme was rejected as being impractical. Yet he lived to see it adopted wherever dirt roads existed.

The rubber tire had come to stay, however, and as each succeeding year brought more and more of them to the Island, road work began to increase and improve. The automobile had not yet made its appearance, but the bicycles had greatly increased in number, and the carriages with rubber tires, pneumatic and solid, had become common. Macadam road was constructed, and highway traffic speeded up accordingly, but the lumpy, dusty sort of highway would seem poor indeed to the motorist of the present.

That continued improvement to the road surface would have naturally followed is quite probable, for the Vineyard was definitely sold on the idea of good roads. Although the automobile has been credited with causing the present road system to develop, that seems doubtful in view of the public sentiment that prevailed long before cars came to the Island. What this vehicle actually brought about was simply the widening and straightening of many of the roads, but not the other improvements.

No, Martha’s Vineyard had jolted and bumped over rocks and holes, had been splashed with muddy water and stuck in drinking places for horses for generations. When, therefore, an opportunity to ride in greater comfort presented itself, the Island was ready to grasp it, and the automobile, while adding impetus, without doubt, did not inspire the action.

It is interesting, therefore, to one who has followed the development of the high roads and the low of Martha’s Vineyard, to ride or walk today along the smooth, black highway, and think a trifle grimly, perhaps, of what lies beneath. The deposits of sand that were always deep and feathery, in which wheels sank halfway to the hubs and horses strained to move their loads; the never-dry mudholes, deep and treacherous, where wheels plunged down with a thud to snap axles or spokes and heave a black jet of muddy water high in the air; the well known boulders, of which only a small portion appeared, right in the wheel-rut where every wheel bumped them, and which were so huge that no road surveyor dared to attempt excavating them because of the expense for labor; and finally the hills so difficult to climb either on foot, by bike or with a carriage, but now graded to a pleasant and smooth incline. Yes, the Vineyard highways could tell some real tales of themselves, if they could speak.

Compiled by Hilary Wallcox