Roton Middle School's Scavenger Hunt of Norwalk History

In celebration of America250, Norwalk Public Schools is proud to share one of its most beloved learning traditions, an engaging scavenger hunt created by Roton Middle School social studies teacher Dean Vaccaro that has inspired generations of students to explore the rich history of our city.

For years, this hands-on experience has taken students beyond the classroom and into the heart of Norwalk, where they discover stories that date back to America’s founding and the American Revolution. From the Founding of Norwalk to the Burning of Norwalk, students visit historic sites across the city—including memorials, buildings, monuments, murals, and more—bringing history to life in a meaningful and memorable way.

Now, we invite the entire community to join the adventure. Walk in our students’ footsteps, uncover Norwalk’s past, and experience the history that surrounds us every day.

• Click here to download the scavenger hunt (including maps) or follow the directions below.
• Click here to learn more from Mr. Vaccaro about how the project began.

We’d love to see you out on the hunt. Share your journey with us!

📸 Tag us:

• Instagram: @norwalkschoolsct or @rotonms_ct
• Facebook: Norwalk Public Schools or Roton Middle School

Explore more of Norwalk's revolutionary history with additional sites listed at Visit Norwalk — America 250.

The Founding of Norwalk

Site #1: Roger Ludlow Monument on Gregory Blvd., East Norwalk

The monument is located at the intersection of Gregory Boulevard and Marvin Street, on the way to Calf Pasture Beach.

1. On what date did Roger Ludlow purchase Norwalke from Chief Mahackemo of the Norwalke Indians?
2. What three things is Ludlow known for? Fun Fact: Did you know that Roger Ludlow was one of the framers of the Fundamental Orders of Connecticut (1639)?
3. What were the boundaries of the land he purchased?
4. What are two details you see in the image on the front that describe the sale? Be specific.

📸 Take a picture of yourself in front of the monument (the side with the image). POSE AS IF YOU ARE PART OF THE SCENE.

Site #2: Founding of Norwalk Sign at Mill Hill Historical Complex, Wall Street

The “Founding of Norwalk” BLUE sign is located along the sidewalk on the top of the hill at Wall Street, near the Town Green. You can park at Mill Hill, which is home to the Norwalk Historical Society, where you will find the 1835 Town House, the Little Red School House, and the Governor Fitch Law Office.

1. Find the sign and read it aloud.
2. What settlement did Roger Ludlow already own at the time he purchased the land on the east side of the Norwalke River from Chief Mahackemo?
3. What two Hartford colonists led 13 families to be the first colonists to settle Norwalke?
4. In what year did these families first settle Norwalk?
5. What two streets in Norwalk do you think are named after these two men? (Hint: Last names — You may have to use a map of Norwalk to help you.)
6. The first homes of these settlers were built on both sides of a path (near the present-day East Norwalk Train Station). Today, this path is a major street in Norwalk. Name the street.

📸 Take a picture of yourself pointing at the sign.

The Burning of Norwalk by the British 1779

Site #3: Sign of “The British Invasion” at Calf Pasture Beach, East Norwalk

The sign is located on the sidewalk along the outer parking lane. It is between the Shea-Magrath Memorial and the fishing pier, across from the softball field.

1. Find the sign and read it aloud.
2. Look out at the Norwalk Islands. It is a summer day in July, nearly 250 years ago. The British have just attacked New Haven and Fairfield. Will Norwalk be next? You look out and see a fleet of 70 British ships appear off the Norwalk Islands.
   • Pick a role. Are you a Patriot or a Loyalist? Why?
   • Assuming this role, what should you do now that you have seen the British ships?
3. Give yourself an old Norwalk name. (Think of some of the street signs you know. They might be last names.)
4. On what month, date, and year did British ships land at Norwalk Harbor and (what is today) Calf Pasture Beach? (Actually, they landed at Fitch’s Point, between the beach and Mr. Frosty.)
5. How many British and Hessian soldiers took part in the raid?
6. Describe ALL of the damage to Norwalk. (What was burned and destroyed?)

📸 Take a picture/video of yourself LOOKING OUT AT THE BRITISH SHIPS. (A Patriot will look terrified. A Loyalist will be waving at the ships.)

Site #4: “Grumman’s Hill” D.A.R. Monument at Norwalk Inn, 99 East Avenue

The Daughters of the American Revolution (D.A.R.) erected a monument in front of the present-day Norwalk Inn to mark the area where the British general (General Tryon) watched Norwalk burn from high atop (what once was) Grumman’s Hill. From that hill, he could see the town burning along both sides of the Norwalk River (today, East Ave. and West Ave.).

1. Find the monument and read it aloud.
2. It is July 10, 1779. You rode your horse from the spot where you first saw the British ships. You are heading towards the Town Green. You look to the right and see the British general sitting in a rocking chair on top of Grumman’s Hill (where the Inn is).
   • Why do you think he is sitting there (on top of the hill)?
   • What will you do? (Think about whether you are a Patriot or a Loyalist from Q #10.)
3. What does the monument say?
4. In what year did the D.A.R. erect this monument?
5. Where do you think he got the rocking chair from? (Hint: Look to the left—towards the flagpole.)

📸 Take a picture/video of yourself next to monument, pointing towards the old hill, SHOUTING: “GENERAL TRYON! WE SEE YOU!” Patriots — You are taunting him because you want to lure him into the “trap” – the Battle of the Rocks.

📸 Take a picture/video of yourself on the sidewalk in front the Grumman-St. John House next door, PRETENDING YOU ARE THROWING BUCKETS OF WATER ON THE BURNING HOUSE. (Part of this 265-year-old house survived the Burning of Norwalk!) Extra credit: Bring a bucket!

Site #5: “Battle of the Rocks” D.A.R. Monument at France Street & Adams Avenue

The Daughters of the American Revolution erected a monument to commemorate the area known as “the Rocks”, where Norwalk Patriots fought off the British on July 11-12, 1779. How do you find it? Drive past the Town Green on Park St., which turns into France Street (France St. becomes West Rocks Rd.) It is on the left, on the corner of France Street and Adams Avenue.

1. Find the monument and read it aloud.
2. You ride your horse from Grumman’s Hill north, past the Town Green to the area of high elevation known as “the Rocks." You see many of your fellow Norwalkers evacuating the town and heading to “the Rocks” for safety. Look north and you’ll see “the Rocks” area. From this area, Norwalk & local Patriots fought off the British, forcing them to return to their ships.
   • How do you think the high ground help the local militias fight off the British?
3. What does the monument say?

📸 Take a picture/video of yourself in front of the monument, arms up in the air YELLING OUT: “HUZZAH! HUZZAH! HUZZAH!”

Extra Credit

Site #6: British Cannonball and “Flax Hill Monument” (D.A.R.) at 7 Hillside Place, S. Norwalk

Located on the stone wall of the house on the corner of Hillside Place and Elmwood, behind the former Ben Franklin School (Crystal Theatre). Go down Flax Hill, take a left on Taylor Avenue and the first right on Hillside Place. This monument marks the site of a battle between Norwalk militia and the British on July 12, 1779. There is a cannonball from the battle that is in the monument. The cannonball was found on the battlefield 100 years later by the Daughters of the American Revolution. Hint: Look for the steps.

1. What does the monument say?

📸 Take a picture of yourself in front of the D.A.R. monument, POINTING AT THE CANNONBALL (BUT DON’T TOUCH). This monument lies on someone’s property, so please be respectful!

TEMPORARILY REMOVED — Site #7: “Founding of Norwalk Monument” (D.A.R.) on East Avenue, East Norwalk

Located in East Norwalk (the “cradle of Norwalk”) on East Avenue by the East Norwalk Railroad Station, across from the intersection of Fort Point St. and East Ave. It is located across the street from the empty lot by East Ave Pizza. Park at the Train Station across from the empty lot.

The monument is on the sidewalk of a busy street. Be careful. Do not cross the street here. Do not stand in the street to take the picture.

1. What does the monument say?

📸 From the sidewalk, take a picture of yourself next to the sign, POINTING ACROSS THE STREET AT SITE OF THE FIRST NORWALK HOMES AND CONGREGATIONAL CHURCH. (The actual site of the first meetinghouse was probably where the recently closed Penny’s Diner is today.)

This monument has been temporarily removed while the East Norwalk Train Station is undergoing a major renovation as part of the CTDOT WALK Bridge Replacement Project (as of 5/3/26).

Site #8: The mural “The Purchase of Norwalk” in City Hall, 125 East Ave. (City Hall is not always open on weekends.)

Located in the first floor atrium, on the left side of the elevators.

1. What does the text box in the painting say?

📸 Take a picture. Make yourself part of the painting! Be a Roger Ludlow or Chief Mahackemo.

Site #9: The 1951 DAR marker for the famous Norwalk Oak Tree. It was purported to be the second largest oak tree in the United States at 190 Martin Luther King Dr., South Norwalk

Located in front of the UPS building on Dr. Martin Luther King Drive.

It was considered the second-largest Oak Tree in the U.S. The DAR dedicated the marker during a well-attended ceremony on August 26, 1951, as part of Norwalk’s 300th anniversary celebration. At that time, it was about 90 feet tall and 85 feet wide. The tree was removed in the 1970s after falling into decay, living to be about 300 years of age! This means it was there 100 years before the U.S. became a nation at the signing of the Declaration of Independence in 1776.

One if its descendant trees, named the “Legacy Oak,” is thriving today, just to the left of the UPS entrance. The marker was buried, covered over, and lost to history for decades. It was rediscovered and cleaned up in August 2017. They are considering building a commemorative park called “Legacy Oak Park.”

1. What does the monument say?

Some of the oak trees in this area today are descendants of the original tree. Park at UPS and explore. Find the descendant “Legacy Oak.” When you pick up some of its acorns… When you hold up one of its fallen leaves... you are beholding the legacy of that original, famous Oak Tree. When you touch the tree, you are touching hundreds of years of Norwalk history! Be a part of “living history!"

📸 Take 2 pictures: One pointing at the marker and another picture next to the “Legacy Oak.”

Special Extra Credit

Site #10: East Norwalk Historical Cemetery

Located near the intersection of Van Zant Street and East Avenue. This is where many of Norwalk’s founding families are buried. Park in the parking lot of the East Avenue United Methodist Church, located across from Sweet Ashley’s on Van Zant St., and walk your child across East Ave. Here you will find the First Settlers monument and the Rev. Thomas Hanford tombstone.

Visit the “First Settlers of Norwalk Monument" — This monument contains the names of the first (Puritan) settlers of Norwalk, who moved from the Hartford Colony.

1. In what year did these first families settle Norwalk?
2. How many were there? (Count the names.)
3. Streets in Norwalk were named after most of these first settlers, using their last names, with some spelling changes (i.e. Sention was changed to St. John.) Name at least 3 streets in town that are named after these settlers. (You may have to use a map of Norwalk to help you.)

📸 Take a picture of yourself in front of the monument pointing to a last name that is a street name that is near your home or that speaks to you.

Visit the “Reverend Thomas Hanford Tombstone” — Rev. Thomas Hanford was the first (Puritan) minister of Norwalk, in 1652. The first “meetinghouse” (Congregational Church) was located near the recently closed Penny’s Diner on East Avenue. From 1652 to 1694, Hanford was the religious leader, town/civic leader, and schoolmaster for the children.

(Hint: Enter across from Sweet Ashley’s. Take 50 steps on a left diagonal, towards the center. It is down low and has a black stone on ground in front.)

1. What does his tombstone say?

📸 Take a picture of yourself in front of the monument paying special tribute to Rev. Hanford.