‘New Canaan There & Then’ is sponsored by Brown Harris Stevens Realtors Bettina Hegel, Joanne Santulli and Dawn Sterner.
In the spirit of former New Canaan resident David Letterman, we present the “Top Ten Things About The Perambulation Line”:
10. What was the Perambulation Line?
The Perambulation Line was a formal, straight, generally north/south property line established by royal surveyors in 1685 that officially delineated the boundaries between Norwalk and Stamford prior to New Canaan’s incorporation in 1801. This followed decades of disputes between the two future cities, each of which sought to tax landowners on both sides of the Line. The surveyors started at the mouth of the Five Mile River, and following a south-to-north course established a border ending at the Connecticut colony line, which at that time was situated within present-day Westchester County.

One of the last remaining stretches of the Perambulation Line exists in the woods east of New Canaan High School. What was once Stamford was on the left of this stone wall; on the right was Norwalk. (Terry Dinan photo)
9. Where was the Perambulation Line located specifically?
The Perambulation Line entered New Canaan at what is now Brookside Road, then ran across South Avenue past the intersection of Route 106 at Park Street, then through Mead Park, across Elm and Weed Streets, and finally thence more-or-less parallel to West Road. For those with a more refined expertise in geography, the Perambulation Line ran 37 ½ degrees west of north in a straight line for twelve miles from Darien. The effect of the Line was to put two-thirds of Canaan Parish in Norwalk and one-third in Stamford, giving a solid financial win to our forebearers to the east.
8. Why is the Perambulation Line important today?
It’s not, other than as an interesting historical anomaly. New Canaan is today a very separate, and very different, entity from Stamford and Norwalk. Since the Perambulation Line was all about taxes (shocking), this is best exemplified by the disparate 2025 mill rates amongst the three municipalities (a mill being equal to $1.00 of tax for each $1,000 of assessment): Stamford, 27.17; Norwalk, 32.00; and New Canaan, 16.69. [note to reader – this is where the author started running out of fascinating historical things to say about the Perambulation Line].
7. What does “perambulate” mean?
“Perambulate” means to travel over or through an area, especially on foot. A secondary definition is “to make an official inspection of a boundary on foot.” Perambulate is essentially an Old English, highfalutin term for walking. Thus in another world we could have had such pop hits as “Perambulate This Way,” “These Boots are Made for Perambulation’” and of course the heartstring-tugging “You’ll Never Perambulate Alone.”
6. Can you actually see the Perambulation Line?
Yes, a rebuilt portion of the Line can be seen in the Bristow Bird Sanctuary. In addition, isolated remnants of the original Line – mostly weathered and crumbling stone walls – can be seen here and there along its route. In this way it is not unlike the current New Canaan Advertiser.
5. Can you parkour the Perambulation Line?
Technically yes, although it is not advisable for safety reasons, owing to the presence in certain places of thick forestry and undergrowth, poison ivy and sumac, wild animals, domestic pets, and roving packs of luxury SUV carjackers.
4. Is there a Darien Perambulation Line?
As mentioned earlier, the Perambulation Line started at the Five Mile River, but it never had the impact it had in New Canaan because there were no tax disputes at issue. Interestingly this is not the first time that Darien has come up short vis a vis New Canaan: for example, it has no Waveny Park analogue, no scenic downtown unburdened by the past, and no First-Team All Pro NFL player.
3. Speaking of professional football, will the New York Jets ever stop being dysfunctional?
It’s tough to say. If the baseline for “functionality” is being able to find 53 random guys willing to put on a uniform, collect a small weekly paycheck, and go through the motions on national television on route to a 4-13 season, then possibly yes.
2. Speaking of television, who is David Letterman?
David Letterman is a legendary comedian who spent 33 years hosting top-rated late night shows for so-called television “networks” CBS and NBC (just Google them). Letterman lived on upper North Wilton Road in New Canaan from 1983 to 2002, and was well known for driving his very flashy and very fast foreign cars around town (yes, he once got a speeding ticket here). He currently volunteers as a Civil War reenactor.
1. Speaking of the Civil War, will this winter ever end?
Unfortunately, probably not. The latest long-range forecast for New Canaan is cold weather and snow, followed by even colder weather and even more snow. If Punxsutawney Phil lived in New Canaan, he probably would have found a nice quiet burrow near the Perambulation Line and stayed holed up there until 2027.