This Was Then: Welcome to Glenwood

Psst — wanna buy some land on Martha’s Vineyard?


Martha’s Vineyard has long been known for its beaches and cliffs, its harbors and bluffs, its ocean views and stony shorelines. The Island’s interior, on the other hand, was long notable for being, well, not very notable.

A new visitor to the Island, headed from Holmes Hole Harbor to the Camp Meeting in Oak Bluffs in the summer of 1865, described his trip across town as “dusty road and sterile ridges, in whose loamless sand subsist only a few stunted shrubs, coarse grass, and moss that crumbles like ashes to the touch.” Another visitor, writing for the Atlantic in 1859, chronicled his journey into the interior of West Tisbury: “The road lay through what would have been an oak forest, except that none of the trees exceeded some four feet in height.” 

“Oaks, great and small, are the principal constituents of our forests,” wrote historian Charles Banks, “and the great plain land is a dense jungle of the ‘scrub oak.’” The tens of thousands of acres of monotonous scrub in our interior went largely undeveloped for centuries.

But after the Civil War, fashionable Cottage City burst onto the scene, making the Vineyard a social nexus for the first time. Geologist Nathaniel Shaler, writing for an 1874 edition of the Atlantic, scoffed at the explosive growth of the new town. “Oak Bluffs,” he wrote, “where oaks and bluffs are both on the average less than 10 feet high, has grown to be a pasteboard summer town capable of giving bad food and uneasy rest to 20,000 people.” But Shaler was mesmerized by the vast forest that covered so much of the interior of the Island. “There has come an amazing variety of oaks … From the saddle or carriage seat the eye ranges above their tops for miles over a billow sea of the deepest green … In one direction we may journey through the woods for 10 miles without a trace of habitation or culture. Through it runs a maze of old paths … There is an indescribable charm in the monotony of these woods; an acre would be tiresome, but the whole has the charm which comes from the limitless. In our drive of half a day, we did not meet man or woman, and passed but one house, and that was a deserted ruin.”

Real estate in Cottage City during the frenzy of the early 1870s fetched increasingly more outrageous prices. In 1874, a 60-by-40-foot lot in Oak Bluffs reportedly sold for $2,600 — an astonishingly high figure at the time. Meanwhile, lands in the Island’s interior typically sold for just a few dollars per acre. Town officials often didn’t even bother to take the time to tax it.

Charles W. Smith of Boston was the first to try to turn our scrubby interior into a hot commodity, banking on a prediction that folks charmed by the idea of affordable lots “on Martha’s Vineyard” might not ask too many questions as to where, exactly, they were located. He bought a series of large tracts in the remotest parts of West Tisbury, bisected by Dr. Fisher Road. In 1874, he named his first lot the Vineyard Improvement Co., and subdivided it into 858 cottage lots. Two adjacent lots became the Tisbury Improvement Co. and the Old Colony Land Co. The following year he named another tract near the Edgartown border the Narragansett Land Co. He subdivided them into nearly 3,000 cottage lots in total.


Following Smith’s lead, in 1876–77 realtor Thomas Wells of Boston bought a pair of adjacent tracts off Old County Road in West Tisbury, naming one Oakland Grove and the other Glenwood. His son Webster drew up some rushed plans, still on file in Edgartown.

But the mid-1870s were not a good time for developers, as the country fell into an economic recession known as the Long Depression. Wells declared bankruptcy in 1878, but his son Joe (who later became a distinguished architect) soon acquired his father’s land and business plan.

Richard Pease’s 1876 “Guide to Martha’s Vineyard” includes a striking half-page notice, reading, “A WORD OF WARNING. Those who are solicited to purchase lands on Martha’s Vineyard, having never visited the island … would do well to remember this friendly warning. Lands on the Vineyard, in the midst of scrub oaks, miles distant from all places of summer resort, have been purchased by designing men at their full value — one dollar per acre — laid out, on paper only. Unwary persons have found themselves owners of lands wholly unknown to the assessors, and not worth taxing, and have learned by bitter experience what it is to be the victims of a swindler.”

An 1882 Boston Globe exposé titled “Phantom Purchases” claimed that 5,000-square-foot lots were selling for $200, $300, and one at $850 (which they calculated to be a 600,000 percent profit for the seller.) The location was typically just described as “Martha’s Vineyard … which is very vague, and the nonresident who only knew of Cottage City would be likely to think that the location was near Oak Bluffs.” Many of the lots were used as barter. The Globe described land selling for “harnesses, watches, or anything of value which could be obtained for something with no intrinsic worth.”

A few hapless buyers tried to visit their new property. “It is entirely useless to attempt to find any one lot,” wrote the Globe reporter. “It would be a difficult matter to get through the thick scrub brush even if they knew where to go, and one trial is usually sufficient to deter them from making a second attempt.” The paper described one buyer’s adventure: “After a drive of 12 miles through the most desolate and uninteresting part of the island, he came to a thicket which was, if possible, more barren of beauty than the locality through which he had ridden.”

None of the lots were ever built upon. But some were used by Boston criminals to dupe marks. In an 1889 Globe story titled “Suckers Are Always With Us,” Boston Police reported that a group of con men twice borrowed $200 from their victim, securing it each time with deeds to 5,000-square-foot lots in the Narragansett Land Co. in West Tisbury. In a similar story in 1892 (“Land Called Valueless”), a Boston man was charged with exchanging a lodging house and an active business for three of the worthless lots. 

Dozens of registered purchases can be found at the Dukes County Registry of Deeds (although many more went undocumented). Louis Payette of Worcester took out a hefty mortgage to buy two lots of the Vineyard Improvement Co. in 1875 for $450. (He sold them both 20 years later for less than $50.) Annie Chesley, a farmer’s wife from Effingham, N.H., bought four lots in Glenwood in 1880, paying $500 in all. (Nearly 50 years later they would be valued at about one dollar, total.)

Naturalist Susan Whiting recalled, in a 1976 report, tales of deeds changing hands “for revolvers, jackknives, or given away with the purchase of goods from Vineyard Haven stores.” A 1959 AP article describes Vineyard land being given away with a pound of tea or a $2 purchase at a department store. A New Bedford theater owner reportedly paid $500 for 5,000 acres, giving out deeds with his theater tickets as a promotion.

Just after the turn of the 20th century, a 100-acre tract near the Edgartown–West Tisbury Road in Edgartown was purchased by the Flint Remedy Co. of New Bedford and subdivided into 2,345 lots. Named Island Heights, these are usually referred to as the “Medicine Lots,” as 25-foot x 75-foot lots were given away with the purchase of one of 500 bottles of Dr. Flint’s Quaker Bitters (“a vegetable tonic for the stomach and blood,” which was more than 22 percent alcohol). Some of these lots were taken by the county about 1958 for the expansion of the Martha’s Vineyard Airport, and the owners who could be found were paid $5 per lot. The remaining set of medicine lots were finally acquired by the Nature Conservancy in 2013. 

In 1925, the commonwealth took thousands of acres abutting the Heath Hen Reservation, primarily by eminent domain, to create the State Forest, including all of Smith’s and Wells’ 1870s developments. State officials faced a daunting task clearing the titles. Commissioner Bazeley of the Massachusetts Department of Conservation told a Globe reporter at the time, “The question of land titles on Martha’s Vineyard is about as mixed up as anything can be.” Land owners who responded to the state’s claims received only about 25 cents for each 5,000-square-foot lot (or a little over $2 an acre). Our State Forest was born.