As Connecticut’s oldest town, Windsor is full of astonishing architecture, incredible landmarks, and fascinating stories. Strolling through this picturesque place is a treat — especially if you’re a history lover. The stories behind the oldest town in Connecticut are truly fascinating.

Settled by a group from Plymouth in 1633, Windsor's history is long and rich.
John Phelan/Wikimedia Commons
For thousands of years, the area was largely inhabited by the Pequot and Mohegan tribes. In the early 1600s, however, the two nations were at war. In order to create a buffer between the two tribes, Podunk leaders invited Plymouth settlers to settle between them. This small group of European settlers created a home near the gorgeous Farmington River.
From 1633 to 1637, more settlers slowly arrived to the area.
Dr_Bill_Corcoran/TripAdvisor
The original settlement was named Dorchester. But in 1637, the colony changed the name to Windsor after the town in Berkshire, England.
During the summer of 1640, Windsor faced a difficult decision: Should they side with Connecticut or Massachusetts?
F.T. Merrill, Engraver/Wikimedia Commons
In this trying summer, European settlers experienced a grain shortage. William Pynchon, the founder of Springfield, attempted to negotiate grain prices with natives. After much back and forth, Pynchon returned empty-handed.
After Pynchon's unsuccessful attempt, citizens of Windsor and Hartford were livid. In order to get their desperately-needed grain, Hartford sent famous fighter John Mason to Springfield.
MoonWaterMan/Wikimedia Commons
John Mason stormed Springfield and threatened the natives with violence if they refused to share the grain. The natives eventually agreed, and Mason rushed back to Hartford. However -- Mason refused to give any of this valuable grain to Springfield, and he even insisted on an additional tax on their ships.

Related Stories

The Breathtaking Scenic Drive Through Connecticut That Runs Along The Long Island Sound

The Breathtaking Scenic Drive Through Connecticut That Runs Along The Long Island Sound

 The Magnificent Lakefront Airbnb In Connecticut That Is Perfect For A Spring Retreat

The Magnificent Lakefront Airbnb In Connecticut That Is Perfect For A Spring Retreat

 It's An Epic New England Adventure On This Lighthouse Cruise Tour In Connecticut

It's An Epic New England Adventure On This Lighthouse Cruise Tour In Connecticut
Rather than sticking with Connecticut through the conflict, Springfield sided with the Massachusetts Bay Colony. Windsor, thanks to its close proximity to both colonies, remained neutral. They had a decision to make.
Daderot/Wikimedia Commons
Windsor decided to take Connecticut's side and remain part of its settlement.
Chrissypan/Wikimedia Commons
Much of Windsor's intriguing past lives on. To experience some of the town's most impressive places, venture to Palisado Avenue.
John Phelan/Wikimedia Commons
The photo above features the Horace H. Ellsworth House, an impressive structure completed in 1872.
You can also enjoy a relaxing stroll through Palisado Green, a peaceful park full of historic monuments.
John Phelan/Wikimedia
Take a closer look at Connecticut's founders at this charming old town. There's so much to discover.
Daderot/Wikimedia
To learn more about this incredible town, visit the Windsor Historical Society's website here.

What’s your favorite fascinating place in Connecticut? If you need some ideas for your next outing, check out these 10 amazing historic landmarks in Connecticut.

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

Related Articles

Featured Addresses
Windsor, CT, USA