Insurance in Holliston, MA

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Why our insurance agency loves Holliston!

Holliston, Massachusetts is a town of nearly 14,000 residents located on the southern tip of Middlesex County. It is the only town that borders both Worcester and Norfolk Counties. It is generally considered part of the MetroWest area, a suburban section of the state to the west of Boston.

Holliston covers 19 square miles and is located 21.6 miles west of Boston. While Route 495 and the Massachusetts Turnpike are both easily accessible from town, the town itself does not have direct access to these major roads or the Charles River. Residents must also drive to other towns to take advantage of the extensive MBTA network. It is bordered by Sherborn, Millis, Medway, Milford, Hopkinton, and Ashland.

The town’s history spans over 300 years, during which time a number of distinct districts have developed. Some of these include:

  • Braggville
  • East Holliston
  • Gooch Corners
  • Metcalf
  • Mudville
  • Thomas Hollis Historic District

Insurance Holliston, MA


Like much of Massachusetts, the area that would become Holliston was first used and lived on by Native Americans. In 1659, the Massachusetts Bay Puritans arrived in the area and began settling along Pout Lane (now Route 16). It was part of Sherborn until 1724, when it was incorporated as a town in its own right, and named for Thomas Hollis, a benefactor of Harvard University.

The major industry in Holliston was shoe manufacturing. At one time, it was the largest shoe manufacturer in the nation, with companies like the Goodwill Shoe Company boasting several factories in town. Today it is largely a residential community, and these factories have been turned into artists’ studios.

There are a variety of historical buildings that can be seen throughout the town. The Bullard Farm was established in 1652, and run by the Bullard family until 1916. Today it is a preserved homestead showing one of the first that was built in the town. Fiske’s General Store is the longest running business in town, founded in 1863 which still does a robust business.

Famous residents from or having lived in this town include:

  • Mike Grier, hockey player
  • P. Rockwood, one of the early founders of the Latter Day Saints
  • John Sencio, television personality
  • Mark Sweeney, baseball player
  • Kevin Systrom, founder of Instagram
  • Jeff Taylor, founder of

Insurance Holliston, MA

The Balancing Rock and Local Lore

A historic and interesting attraction in Holliston is the Balancing Rock. 20 feet long, 10 feet wide, and 6 feet thick, this 5 ton rock is balanced upon a granite ledge. Dating back to before the Revolutionary War, this landmark is now part of a residential community. Legend has it that George Washington led his soldiers through Massachusetts along this route, and when they arrived at the rock, the soldiers and General Washington himself tried to tip this rock over, to no avail. Despite many attempts over the years, the Balancing Rock has held firm.

Holliston’s Mudville village area also has a claim to fame. Ernest Thayer, author of the famous poem “Casey at the Bat” has family ties to the area in the form of a woolen mill near Mudville. Residents believe they are the Mudville in which the poem was set. However, Stockton, California, also tries to claim this honor, with an on-going friendly rivalry.

Holliston is a picturesque residential community in the heart of Eastern Massachusetts. Its convenient location leads many to come here, taking advantage of the quiet scenery and historic setting for living, working, and playing.

Holliston, MA Insurance

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Insurance Coverages

Personal Insurance

  • ATV
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Business Coverages

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Business Coverages

  • Hazmat Truck
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  • Restaurant
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  • Tow Truck
  • Tree Service
  • Valet
  • Workers Compensation