by Bobby Blair
Like its rarely seen counterpart, the cow tunnel on Bullard Street, the Highland Street Rail Tunnel is hard to access – harder actually, unless you’re willing to take a long walk or tumble down a huge hill. In a recent conversation someone even asked, “Where is the Highland Street Tunnel?” With trees and bushes all but obscuring the downward view, the tunnel itself cannot be seen from Highland Street even in the treeless winter, as it is directly below the street.
Part of the construction of the railway through town in the 1840s, by predominately Irish immigrant laborers, the building of this tunnel through the Phipp’s Hill Cut fell into bankruptcy no less than three times. A natural spring flows through the granite blocks of the tunnel, creating water filled trenches along the abandoned rail beds. With the coming of the bike trail, the tunnel will finally get the attention it has deserved for the past 150 years.
The Littlefield Tavern stands next to a swamp not far from Weston Pond. Located on the corner of Washington Street and Paul Road, the tavern (now a private residence) is said to have served a mug of beer to the father of our country George Washington. The mug resides at the Holliston Historical Society.
The tavern, built with add-ons, was supposedly built around the early 1700s and was a local watering hole for the town’s revolutionary militia who resided in that portion of town. Recent new owners of the tavern have given it a complete new outside makeover worthy of its history. That suits the wonder that it has survived 300 years.
John Greendale sent us the Highland Street Tunnel nomination and Town Clerk Jackie Dellicker personally nominated Littlefield Tavern.