A lot of the hiking we do is to historic places in the Hilltowns especially from when the first settlers came..here is some #hilltownhistorywp-15891106897107532485374594268730.jpgSmall Pox Cemetary in Montgomeryfb_img_15865585364643992802426961068196.jpgHiram’s Tomb in Chester20200410_1259538836266321500200299.jpgHiram’s Tomb in Chester

Huckleberry Trolley Line in Huntington

Courtesy of Debbie Daniels….The Huckleberry Line was opened in stages, finally all the way through to Huntington in the summer of 1917. This is borne out by the printed page above–the first car ran on August 15, with the manager’s 16-year-old daughter at the controls a lot of the way! What my book said was that the line operated for the remainder of that season, but closed a few months later as it couldn’t be economically kept running in winter. By the following year, 1918, wartime conditions (inflation and a labor shortage) had badly affected the Berkshire Company, and the company applied for a subsidy from the towns that the route passed through. Facing pressure of their own, the towns declined to pay. As a result, the company didn’t operate the line that year, and the following year, as automobiles proliferated and roads improved, the decision was made to abandon the route. That was the beginning of the end for the Berkshire Company in general, along with all the other streetcar lines.Although the Berkshire Company reached Huntington, and the same town was served by streetcars coming up from Springfield, the rails were never linked. If you wanted to make a through journey, you had to walk a few blocks. I wonder if anyone ever made the whole trip, in the short period when it was possible.This is from the “Electric Railway Journal” for October 1918:Will Abandon Forty-four Miles. When the new tariff of the Berkshire
Street Railway, Pittsfield, Mass, referred to elsewhere in this issue, goes
into effect on Nov. 12, service will be discontinued for the present at least on
the “Huckleberry” line from Lee to Huntington and from Great Barrington
to Egremont and from Great Barrington to Canaan, Conn. By this order 44
miles of track will be abandoned as follows: From Lee to Huntington, 24
miles; from Great Barrington to Egremont 7 miles; from
Great Barrington to anaan, 13 miles. This order will probably mean giving
up the power station at Sheffield and transferring the operating base to
Housatonic. It is the hope of the management that it will not be necessary to abandon
and scrap any of the company’s property, but for the present at least, it is
proposed to discontinue service up on the lines south and west of Great
Barrington and upon the line from Lee to Huntington. This is necessitated in order that the company may continue a going concern and not be forced to
discontinue service essential to the communities from Great Barrington to the
Vermont State line. The management says that without the increase in
revenue coupled with economies to be obtained by a discontinuance of service
Now operated at a loss, the property can no longer be run so as to give the
required service to this more densely settled portion of the county.


Chester and Becket Railroad in Becket


English Grass Cave in Montgomery

“the Regicides,” two English political fugitives who hid out in a cave, according to legend just south of Mount Shatterack during the 1660s.

Probably some early settlers explored the wilder regions, and according to one of many legends connected with Tekoa and the surrounding hills, two fugitives from the wrath of King Charles II, the “Regicides,” hid out in a cave there for as long as a year during 1660s.

This is the most dubious of Tekoa’s legends, although the English Grass Cave exists-so named, according to tradition, because the approaches were once grassy and the fugitives were English. During that time period, of course, nearly all the region’s settlers were English, indicating the cave was named later, probably much later, casting further doubt on the story.

The cave is little more than a large fissure in a granite outcropping. Located in a forested area of Montgomery near the Russell bound ary, a few miles northwest of Tekoa and just south of Mount Shattuck, it’s hard to find and well suited to serve as a hideout. A jumble of boulders conceals the low, narrow entrance, which opens into a chamber about 12 feet across and four to six feet high. To the rear a passageway three feet in diameter leads upward to a smaller room.

The story of the regicides, William Goffe and Edward Whalley.


Garnet Hill War Memorial in Peru

Homer Crosby Stone in Blandford

Chester Roundhouse and Coal Tower

Palmer Cemetary in Russell

Railroad Builder Rock in Montgomery

Railroad History


Hilltown Mining

Granite Works

Saw and Grist Mills

Falley’s Armory in Montgomery

There is much more Hilltown History information here on our Blog!