A Step That Took 250 Years - My Family Travels
House where Grandad Matthew Lived
Wilson Castle
Family that now lives in the house in front of the kitchen.

You could say this vacation trip actually started over 250 years ago. That’s when my eighth great grandfather (Granddad Matthew) came to America. I bet you are saying…WHAT? Well, his life story was what the trip was actually about. My grandmother is a member of DAR (Daughters of the American Revolution). Yes, that’s right my eight times great grandfather fought in the American Revolution!  She had to do a lot of research to prove this. I also have a passion for history and loved listening to the stories she uncovered through her research. We (my mother, aunt, grandmother and I) decided to go on a “historical family vacation”. We wanted to find and visit some of the special places from my Granddad’s life. Our road trip carried us from Alabama to Vermont. It was a long trip but a trip full of new sights that entranced me.

Granddad Matthew started his life in America as an indentured servant to a man in Woodbury, Connecticut. Through research, we found that the actual house with its carriage barn still stood!  The family that lived there was very gracious and excited to hear our story. They invited us to tour. We actually got to see the upper room area in the carriage barn where Granddad Matthew lived for several years. However, the climb up to his quarters was quite rigorous so I was the only one of my family that actually could make it up the stairs. After 250 years, I took the same step into the room as he did. What a thrill!  Actually touching and seeing what my 8th great granddad touched and saw. Woodbury is like the setting of a fairytale. History oozes from every inch! If you love antiquing, you’ll be in heaven.

When he was in Ireland, Granddad studied printing. After the Revolutionary War, he moved to Fair Haven, Vermont and started his own newspaper because other newspapers wouldn’t publish his radical writings. We arrived to see a beautiful park at its center with a summer concert happening in the gazebo. The park was surrounded by fascinating historical buildings. You must visit the Marble Mansion Inn as well as the other B&Bs.

Granddad Matthew didn’t stay in one area very long. He traveled along dirt roadways, through wooded areas and small towns. We used HWY 7 to retrace his movements. This highway goes through the states of Connecticut, Massachusetts, and Vermont with surprises around every curve. Surprises such as the Sheffield covered bridge  called –eloquently- “Old Covered Bridge”; stately early 17th century homes; quiet tree lined city squares and my favorite stop was Wilson Castle. The castle was a jewel to behold. To be honest, the one thing that “blew us away “; a Dunkin Donuts on every corner. Where I’m from, there’s one Dunkin Donuts in the entire county.

By age 58, Granddad Matthew was a Representative of Vermont. This led us to the Vermont State Capital where his portrait hangs because he was a Vermont Congressman. The state building was made of shining elegant Vermont marble. The Usher at the Capital told us about  Leahy Library.  It had several personal items belonging to my granddad. The Librarians were very inviting and allowed us to view and hold our family member’s artifacts.

This historical trip inspired me and opened my eyes to the life of my family outside the south. I hope this inspires you to research your family’s history and visit the sites that will help you take a step that goes back 250 years.

Dear Reader: This page may contain affiliate links which may earn a commission if you click through and make a purchase. Our independent journalism is not influenced by any advertiser or commercial initiative unless it is clearly marked as sponsored content. As travel products change, please be sure to reconfirm all details and stay up to date with current events to ensure a safe and successful trip.

Comment on this article

This site uses Akismet to reduce spam. Learn how your comment data is processed.