Simsbury Road’s Historic Mile


Fourth Article in a Series

Thank you to the Bloomfield Journal for letting us reprint this fourth article in a series
published in Volume 32, Issue 45
Friday, November 7, 2008

Can you answer these Trivia Questions about Bloomfield?
1. When was slavery abolished in Connecticut and Bloomfield?
2. What was the occasion for the Drummer Boy statue?
3. When the Gabb Warehouse burned in 1912, how was the Town Hall next door saved?
4. What 19th century business peddled lanterns and foot warmers as far as St. Louis?
5. What Indian tribes frequented the area?


In 18th century Wintonbury, the trail that became Simsbury Road was the main route from Hartford to the Parish of Simsbury. Initially, the route went by way of what is now Juniper Road that continued over the mountain to Weatogue.  The present road over the mountain came later. (Another way to get to Simsbury was via Terry Plains Road that crossed Duncaster Road and met up with Terry’s Plain Road in Simsbury.)

The mile of Simsbury Road between West Street and Mountain Road contains many late 18th and 19th century structures and interesting history.  The mile starts at Wade’s stand and ends at the 1875 house built by one of the Burrs at the corner of Mountain and Simsbury Roads.  The old house at Wade’s was built by Grove Barnard before 1850.  At one time it was licensed for a tavern. In 1855, the Ely Brothers bought the land and used it for years as a landscape nursery, specializing in boxwood. Ron Wade’s father bought the property from a man named Miller and ran a large farm on both sides of Simsbury Road. He opened the farm stand in 1928.

Opposite Old Loeffler Road, now closed, is the Joseph Burr Home built in 1791. Mr. Burr had a linseed oil mill on Loeffler Road, called Burr Road at that time.  Linseed oil was made from flax grown in Wintonbury.

Farther east is another Burr house. The Burrs owned 215 acres known as Cold Spring Farm that included a large orchard going up toward Avon Mountain. The house east of  Cold Spring Drive, built by the Cadwells, became part of Cold Spring Farm. The farm was later owned by Levi Prosser who, in 1887, conveyed the property to the City Missionary Society, later the Children’s Aid Society, and now The Village for Families and Children. Incidentally, the Society had been started by a Bloomfield native, Virginia Thrall Smith.

Moses Cadwell and his wife were two of the original 67 members of the Congregational Church in 1738. The Cadwell family owned much of the land along Simsbury Road from the early eighteenth century to 1928.  Kenmore Road, for example, was developed on Cadwell property. Just east of Kenmore Road is the 1774 Madison Cadwell House.  Nearby across the street was the Southwest District School, a crude old wooden structure that burned down in the 1850s.  After this happened, classes were held in the home of Madison Cadwell whose daughter, Elizabeth, was the teacher. SWD SCHOOLThe new school was built of local trap rock in 1858 at a cost of $288.15, thanks in part to the labor of the town poor. The enrollment increased when the children then living on Cold Spring Farm attended the school.

Sitting on a high bank above the road is a stately old home, built in 1760 by a Cadwell. It was the principal headquarters of the Hartford-to-Westfield stage line. It was purchased by James Prosser in 1830, remodeled and named “Prosser Inn.” Mr. Prosser’s son, Levi, bequeathed $16,255.85 to the library that came to bear his name. Between 1750 and 1820, at least four houses that still stand in this mile were built by the Cadwells.

The road to what is now Auer Farm had been a right of way to wood lots on the mountain from early times. In 1910, the farm was purchased by Thomas Perkins who created a model, efficient dairy operation called Benvenuto Farm, selling its products to upscale stores and restaurants. In 1925, the farm was sold to George Auerbach of the G. Fox Company.  After his death in 1927, Beatrice Fox Auerbach took charge of the award-winning farm.  Eleanor Roosevelt was a guest there on more than one occasion.  Today most of the original land is part of the 4-H Education Center affiliated with UCONN.

by Ralph Schmoll
Wintonbury Historical Society

1. 1848
2. The U.S. Bicentennial in 1976
3. A bucket brigade from Wash Brook
4. The Filley Tin Shop
5. Agawam, Poquonock, Massaco, and Tunxis