It Happened in Windham: South Windham roared in 1920s

Dow’s Drug Store in 1924. It was located at the corner of Depot and Main streets in South Windham.

When driving through South Windham today, we see a sleepy little hamlet with a post office, a fire station and not much in the way of foot traffic. But back in the 1920s, the streets were alive with activity and the village was a thriving business center.

It was a pleasant place to live and to grow up, and hearing about it makes one a bit nostalgic for those bygone days when life was busy, but so much simpler.

Virginia Ridlon grew up in what would become the Little Falls section of town, and what follows are some some of her recollections about what it was like living in South Windham in the 1920s. These are paraphrased from an article she wrote in December of 1990 for The 302 Times. Thank you, Virginia, for giving me such a lovely memory to share with the people who live here in Windham today.

There was a pulp mill and a woolen mill in South Windham in those days and both were operating at full capacity. There were also two boarding houses that accommodated the mill workers.

There was a trolley service to Westbrook and Portland every hour from 6 in the morning until 11 at night. The waiting room for the trolley was over Sawyer’s Store where there was a long settee where people would sit and wait for the trolley’s arrival. If you wanted a treat or a soda before hopping aboard, you could buy an ice cream or a pop downstairs.

There were two doctors, Dr. Harper and Dr. Parker, and both made house calls whenever they were needed. Milk was delivered daily to homes by Oakhurst Dairy and meat was peddled door to door by horse and wagon by Peter Smith, a local man who made meat deliveries for years.

The railroad was still very busy at that time and carried goods to and from the mills as well as passengers. There were four grocery stores, a drugstore and a bank in town back then. One of the grocery stores was an A&P, where the children enjoyed running errands because the proprietor allowed them to roller-skate through the store while doing their grocery shopping. What could be more fun than roller-skating to the store and then being able to roller-skate down the aisles? To picture it, it’s like taking an up-close glimpse at a Norman Rockwell painting.

People would dress up to come downtown to do their shopping and their banking, and it was a usual sight to see women in their pretty dresses with matching heels and hats walking down the street with dapper gentlemen at their sides.

Some of the popular shops in town were Dow’s Drug Store and Arthur Facto’s store, where in addition to groceries, you’d find the best selection of penny candies anywhere in town. It was very hard to decide between a penny’s worth of spearmint leaves, chocolate babies or a lollipop. If you wanted some delicious roasted peanuts, you’d visit Lizzie Reid because she was famous for them.

The hottest entertainment place in town was Oriental Hall. Children enjoyed presenting their school plays on the stage there and it was a popular meeting place of the Community Club, which would often put on shows to entertain the locals. It was also a movie theater for a while.

Although the area was thriving in the 1920s, life proceeded at a quieter pace than today. There were still horses in town, so there was a blacksmith shop and livery stable. You’d see sleighs on the streets after a snowstorm and on summer Sunday afternoons, you’d see families on their porches reading the newspaper or involved in conversations with their neighbors.

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

Dow’s Drug Store in 1924. It was located at the corner of Depot and Main streets in South Windham.

Oriental Hall as it looks today. It was the entertainment center of town in the 1920s.