It goes without saying that Westerly, RI, is one of South County’s top holiday destinations. After all, you can book a vacation rental in beautiful oceanfront communities like Watch Hill, Misquamicut, and Weekapaug and spend your entire trip lounging on the beach and enjoying the town’s laid-back vibe.

Westerly also has an incredible amount of history, as the area was first settled in 1661, incorporated in 1669, and played a central role in the American Revolution. It was also a shipbuilding center during the War of 1812 and a transportation hub through the country’s early days.
For years, it was assumed Westerly was named after its location since it’s Rhode Island’s westernmost town. However, relatively new information on John Crandall, one of the town’s founding residents, puts that information into question.
Here’s a dive into Westerly, Rhode Island, and how it really got its name.
The Traditional Name Story
For centuries, people believed Westerly received its name because it was the westernmost area in the Colony of Rhode Island and Providence Plantations. The reasoning makes a lot of sense, too, because the community sits right on the Pawcatuck River and borders Connecticut.
When European settlers first set up in present-day Westerly in 1661, they knew the land on the other side of the river was part of the Connecticut Colony, so they couldn’t venture any further west.
However, that explanation ignores some vital information regarding John Crandall. For a long time, it was believed Crandall came from Chepstow, Monmouthshire, Wales, before crossing the ocean and settling in Rhode Island. Further research puts Crandall’s hometown into doubt, though, and could change what we know about Westerly’s origins.
Where John Crandall is Really From
In reality, there isn’t much data putting Crandall in Chepstow at all. We don’t know why it was believed he came from the town, although there’s a chance the information came straight from him or that he lived there for a period before departing for the American Colonies.
There’s a good chance Crandall spent at least some time in Wales because he grew up nearby, but records show his ancestors living in England as far back as 1539. Chepstow sits right on the River Severn and borders England, which could be one reason for the confusion.
So, what does that have to do with Westerly and its name? Well, there’s a town in South Gloucestershire, England, called Westerleigh that’s only 15 kilometers from Chepstow. There’s also a baptism record for a John Crandall in Westerleigh, England, for around the same period Westerly, Rhode Island’s Crandall was born, making it very likely Westerleigh was his hometown.
When Crandall settled in present-day Westerly in 1661, he was an elder at the First Baptist Church in Newport, giving him significant power. As the townspeople incorporated in 1669, it’s possible, and perhaps likely, that Crandall spoke up and asked them to name it Westerly after his birthplace in England.
A Piece of Rhode Island History
The name Westerly seems to fit this community because it’s South County’s westernmost town. However, knowing what we now know about Crandall means the town’s name could have a double meaning, adding another layer to its story.
No matter the reason for naming this community Westerly, it has remained one of Rhode Island’s top getaway destinations for decades. You can easily reach the beach, head west to Connecticut, or venture up to Providence in a matter of minutes from this central location, giving you plenty of motivation to book a vacation rental in town.
Start planning your next vacation to Westerly, and take advantage of this historic and vibrant community on the Rhode Island shoreline.