North Main Street

Windsor, VT
Difficulty: Easy
Special Features: Architectural, Historical
Walking Conditions: Pavement
Duration: 1:00
Season: May-Oct


A stroll through Windsor’s Downtown.


From either Exit 8 or 9 off Rte. 91, take Rte. 5 to Windsor. Turn west onto State Street at the traffic light and within a few hundred feet, park either in the lot for the Episcopal Church on the left at the corner of State Street and Dunham Avenue, or park on State Street.

Clues and Map

Click here to view/print the clues and map for this quest.


Up on the bandstand, look around,

Old Town Hall and Library can be found,

Walk down the hill, find the site

Of the Old Court House, then left at the light.


Along the way, some shops you’ll see,

All played a part in Windsor’s history.

A 100+ years—Go back in time,

And you’ll understand the rest of your rhyme.


Coming from Boston or Montreal,

This “house” was the place to have a ball.

You could get a meal, you could get a room,

Presidents and guests could arrive soon!


Next is a home of retirees,

Once the home of railroad executives.

Dinner for 400 was the norm.

Guests caught the train for the return trip home.


Walk along and you will find

The Mansions of Windsor­—count them—five,

Granite fence posts will lead the way

As you look and dream of yesterday.


(It’s not a mansion, but it’s pretty as can be,

The yellow brick road is a favorite to me.)


Move along and you will see

The birthplace of Vermont history

Once was just a tavern in 1777

A signed constitution sealed its place in heaven.


Back up and cross at the crosswalk,

Look to the right

House of brick, porch of white.


Keep on walking, find the first steeple,

Goes to the church that has no people

In 1846 it was built as a church

Now you can go in and buy a shirt!


In front of the church, look in the sky,

A legal eagle you will spy.

Today this building sends out mail.

yesterday it was Federal Court and jail.


Look around and you will see

More of Windsor’s history.

Step on a crack and break your back

Follow the signs to the railroad tracks.


On the corner, take a break in the park.

Read the message on the history rock.

On to the Depot and hear the sounds

1849 brought guests from all around.


Back up to the corner, don’t turn right,

Cross the street—at the light.

Walk to the bandstand, take a look,

Cross over to the house of books.


Continue up the road and you will see

What was once the oldest U.S. prison in history.

In 1975, it ceased to be.

Now it is a home for the elderly.

(Go PAST the Davis House.)


In this “village” you will find

Benches and flowers to boggle the mind.

A little wooden box, attached there in a tree

Tells the rest of our town’s history.


Read the stories, stamp your book,

Walk around and take another look.

Hope you enjoyed 4-Parker’s Quest.

There are more! Do the rest!


Created by Linda Parker's 4th grade in 1999

Other Adventures

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