Pleasant Cafe

This building, built in 1889, is over 100 years old, and was once home to a plethora of other businesses, including but not limited to: Cleary and Williams Dry Goods and Millinery, Jersey Butter Company, Arena and Sons Grocery, and Royal Café. Today, 36 Main Street hosts the PC we all know and love, owned and operated by the same Maynard family for over 70 years. More than just the friendly neighborhood bar, Pleasant Café is the official oldest restaurant in Maynard. The café’s website proudly boasts that it has been “serving cold beer since 1945,” but technically, a restaurant by the name of Pleasant Café operated in downtown Maynard as early as 1936. However, the former Pleasant Cafe closed during WWII. It was not until the war ended in 1945 that the café reopened at its current home at 36 Main Street, where it has remained ever since.