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Take a walking tour of Glastonbury's history

Previous Walking Tours

HIKING THROUGH HISTORY: A GUIDED TOUR OF THE “SOUTH GLASTONBURY TRIANGLE”
2018

This “hike through history” explored the South Glastonbury triangle of High Street, Water Street and Main Street. The guide and Glastonbury native, Howard Horton, led a walk that explored the 1930’s and 1940s era of High Street, Water Street and Main Street, including Howe's Mill, the dam on Roaring Brook with the flume that brought water to the mill, blacksmith shop, butcher shop, hay barns, pool hall, South Glastonbury Community Club, Howe's Store, Station 60 (the last trolley stop) and the old Second gas station. 


HIKING THROUGH HISTORY: A GUIDED TOUR OF THE  INDUSTRIAL REMAINS AROUND HOPEWELL MILL AND UPPER COTTON HOLLOW
2017 

This “hike through history” explored the Hopewell Mill ruins and upper Cotton Hollow. The guide and Glastonbury native, Dr. Brian Chiffer led a hike that began at the old Hopewell Mill site on Matson Hill Road. The hike explored the Hopewell Mill ruins and upper Cotton Hollow, including the industrial sites of Pratt’s Forge, Timothy Easton Mill, Hunts Forge and as far as the Old Cotton Hollow Club. This former hub of woolen clothing manufacturing is a historic explorer’s delight. 

HIKING THRU HISTORY: A GUIDED TOUR OF THE 
INDUSTRIAL REMAINS AROUND THE HISTORIC SITE KNOWN AS “SMUT”
 2016


This “hike through history” explored the industrial remains around the historic site known as “Smut.” Dr. Brian Chiffer led a hike that began at the old Hopewell Mill site on Matson Hill Road and continued upstream along Roaring Brook, crossing water at two points, the first at Slab Gut Brook, a tributary of Roaring Brook, then Roaring Brook itself at “Flat Rock”.
At the destination they explored the foundations of the mills that once existed there and viewed what is arguably the most beautiful and well-preserved historic dam on Roaring Brook. 


MAIN STREET GLASTONBURY WALKING TOUR
2015

Glastonbury boasts the nation’s 2nd largest inventory of 18th century homes and buildings with Main Street having the greatest concentration. Walkers had the opportunity to stop, admire, and learn the social and architectural history of many of the historic homes on the street. The round-trip walk started at the Museum on the Green and went as far as School Street. It featured four Town Hall buildings (former and present) and stories of the people who lived along Main Street.  Participants heard the tale of Benton’s Folly, saw “the house that turned the corner”, and found out what happens when two men build a house and don’t plan ahead. This guided walking tour is one of the best ways to take in the history and beauty the area has to offer!


Funds raised (from ticket sales) will support the mission of HSG to educate through the preservation and promotion of Glastonbury’s extraordinary historical legacy. In addition to owning, maintaining and operating multiple historic properties, HSG sponsors numerous public events; publishes books, brochures and news articles; and maintains an exceptional research library.  As a non-profit, HSG funds these activities solely by the support of members, business sponsors, foundations, donations, grants, and fund-raisers such as the Main Street Walking Tour.

Copyright © 2015 - 2025 by The Historical Society of Glastonbury


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