The past meets the future in this 1905 view of Phillips Avenue, as a horseless carriage approaches a horse-drawn one. By 1905, Phillips Avenue had been home to a schoolhouse, two hotels and a number of summer cottages. But just 50 years earlier, the land it occupies was still mostly pastures and woods. The 1888 book, History of the Town of Rockport, tells how Phillips Avenue came to be:

About the year 1855, Mr. Eben B. Phillips purchased at Pigeon Cove, of John W. Wheeler and others, a large tract of pasture and wood-land, and soon commenced to lay out and construct avenues over the same. He also added to his first purchase until it included Andrews and Halibut Point. There are now over this territory miles of good smooth road, by the line of which are many pleasant and attractive summer cottages. These avenues taken in connection with that over Sunset Hill, and others over the Babson Farm constructed during these later years by the Misses Babson and Gaffield, constitute as pleasant a drive as can be found anywhere within our good old county of Essex. On one side in the near distance is the broad Atlantic in full view; on the other, trees and shrubbery in great variety. In fact we think it would be hard to find a more pleasant drive than that from the Gloucester line at Folly Cove, over the main street to Sunset Hill, then over Phillips’ Avenue to Granite street, through Pigeon Cove to Beach street, to Main through Sandy Bay, then over Mt. Pleasant and South streets, to the Long Beach.

Even today, it would be hard to find a more pleasant drive. Here is another telling of the origins of Phillips Avenue, this one from the 1873 book Pigeon Cove and Vicinity:

Since the purchase of Andrews’ Pasture and the extensive adjacent grounds, by Eben B. Phillips and George Babson, these proprietors have improved their tract by laying it out with broad avenues and winding walks. These avenues and walks are nicely graded and gravelled. From the hotels into the principal avenue, — that is, Phillips Avenue, — it is but a step. The mile’s walk of this wide and smooth road is circuitous, partly through groves of oaks and pines, and partly over open grounds, fragrant with sweet ferns, bayberry shrubs, and wild roses, and affording fine views of the sea from Thatcher’s Island to Agamenticus, and a view of the long coast to this mountain in Maine, from Ipswich Beach and Plum Island.

As noted above, Phillips Avenue was once home to a schoolhouse, a two-story building constructed in 1857. Although not the first school in Rockport, it was the first school to be built by the town in its corporate capacity.

This 1905 postcard was published by The Rotograph Co. of New York and printed in Germany.