It Happened in Windham: Once upon a time there was a tavern

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Back in Windham’s early days, when carriages and buggies were the primary means of transportation, there were a number of taverns scattered throughout our town. One of the most popular in the crossroads area of Windham Hill at the corner of Ward and Windham Center roads. It has gone through several different nomenclatures, but is best known as Webb Tavern.

Major Edward Anderson began  construction of the building in the early 1800s. It was meant to be his private residence, but he died in 1804 before it was completed. By 1857, it had become a tavern owned by George W. Davis and named Windham House. During this time, Windham Center Road was a major thoroughfare between the White Mountains of New Hampshire and the port of Portland. The tavern was a popular stop for coaches carrying passengers and teamsters taking goods to market.

Local legend has it that during Civil War, the tavern was a stop on the Underground Railroad. Dr. Charles Parsons, a Windham Hill resident, was a teacher at the Abyssinian Meeting House in Portland, a northern hub of the railroad. Some believe he hid runaway slaves at his residence and took them to the tavern to be transported up north to Canada.

In the 1870s, Jason Webb assumed ownership of the business and changed the name  to Webb Tavern. He had the reputation of being a genial proprietor and his popularity helped him win election as a state representative. According to a story in the Oct. 7, 1986, edition of the Courier Free Press, a vice consul from England summered at the tavern one year during World War I. Townspeople enjoyed watching his black limousine drive by as he made his daily trip into Portland to conduct business.

For a short while during the 1900s, the building took on an unusual purpose. It was purchased by Charles Smith to house people suffering from mental illness.
These unfortunate individuals were kept in the basement of the building. Bars
were installed on the basement windows during this time.

In the 1920s and 1930s, the property changed hands again to become the
spectacular Crossroads Gladiola Farm owned by Demas Burgess. The grounds
were a sight to behold with thousands of gladiolas filling the gardens. One worker
on the farm recalled planting 2,300 gladiola bulbs in just one day and 1,100 a day
later. The resulting lavish landscape made this a favorite place for many Windham locals.

The private residence we see nowadays is much different from the building we
would have seen in the days when it was a tavern. Back then, there were three stories facing out on Windham Center Road. Some believe there was a fire on the third floor at some point, resulting in the design we see today. The four gables on the second floor and the large front porch could have been part of this renovation.

There are still some original architectural elements present on the property,
however. There is an early red barn next to the house and on the Ward
Road side of the house itself, there are beautiful period mouldings and a lovely
transom window over the door. I wonder how many weary travelers passed
through that door in the days of long ago, days when Jason Webb would be there
to welcome them with a warm bed, a hot meal and some good old-fashioned
conversation.

Haley Pal is a Windham resident and active member of the Windham Historical Society. She can be reached at haleypal@aol.com.

Pal
Back in Windham’s early days, when carriages and buggies were the primary
means of transportation, there were a number of taverns scattered throughout
our town. One of the most popular was situated in the crossroads area of
Windham Hill at the corner of Ward and Windham Center Roads. It has gone
through several different nomenclatures, but it is best known as Webb Tavern.
Construction of the building was begun by Major Edward Anderson in the early
1800s. It was being built to be his private residence, but he died in 1804 before
the structure was completed. By 1857, it had become a tavern owned by George
W. Davis. He called the establishment Windham House. During this time,
Windham Center Road was a major thoroughfare between the White Mountains
of New Hampshire and the port of Portland. The tavern was a popular stop for
coaches carrying passengers and teamsters taking goods to market.
Local legend has it that during the American Civil War, the tavern was a stop on
the renowned Underground Railroad. Windham Hill resident, Dr. Charles Parsons,
was a teacher at the Abyssinian Meeting House in Portland, a northern hub of the
Railroad. Some believe he hid runaway slaves at his residence and took them to
the tavern to be transported up north to Canada.
In the 1870s, Jason Webb assumed ownership of the business. He changed the
name of his public house to Webb Tavern. He had the reputation of being a genial
proprietor and his popularity helped him win election as a state representative.
According to a story in the October 7, 1986 edition of the Courier Free Press, one
year during World War I, a Vice Consul from England summered at the tavern.
Townspeople enjoyed watching his black limousine drive by as he made his daily
trip into Portland to conduct his business.
For a short while during the 1900s, the building took on an unusual purpose. It
was purchased by Charles Smith to house people suffering from mental illness.
These unfortunate individuals were kept in the basement of the building. Bars
were installed on the basement windows during this time.

In the 1920s and 1930s, the property changed hands again to become the
spectacular Crossroads Gladiola Farm owned by Demas Burgess. The grounds
were a sight to behold with thousands of gladiolas filling the gardens. One worker
on the farm recalled planting 2,300 gladiola bulbs in just one day and 1,100 a day
later. The resulting lavish landscape made this a favorite place for many Windham
locals.
The private residence we see nowadays is much different from the building we
would have seen in the days when the structure was a tavern. Back then, there
were three stories to the building that faces out on Windham Center Road. Some
believe there was a fire on the third floor at some point in time and this resulted
in the design we see today. The four gables on the second floor and the large
front porch could have been part of this renovation.
There are still some original architectural elements present on the property,
however. There is an early red barn that sits next to the house and on the Ward
Road side of the house itself, there are beautiful period moldings and a lovely
transom window over the door. I wonder how many weary travelers passed
through that door in the days of long ago, days when Jason Webb would be there
to welcome them with a warm bed, a hot meal and some good old-fashioned
conversation.
Photo caption: An early photo of Webb Tavern. Photo courtesy of the Windham
Historical Society.

An early photo of Webb Tavern.

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