By Brittany Amalfi

In 1926, Ashland was a small but growing mill town of just 2,521 residents. That year, 592 passenger cars and 88 commercial vehicles were registered—numbers that hint at a community beginning to embrace modern life while still firmly rooted in its 18th- and 19th-century past.

About a century later, Ashland has grown to an estimated 19,391 residents, according to the U.S. Census Bureau’s July 1, 2024 population estimate. While the town’s size and pace have changed dramatically, many of its most familiar landmarks continue to anchor Ashland’s identity.

A Changing Streetscape

Walking down Main Street in 1926, the town would have looked exponentially different. Between Myrtle Street and Homer Avenue, only a handful of buildings still stand today:

• The Ocean House

• The mill buildings

• The house at 100 Main Street

• The Federated Church (expanded over time)

• Town Hall (modified)

• James Jackson’s house (now part of Ashland House)

• Lunker’s (formerly the Ashland News Store)

• Stone’s Public House (formerly the Ashland Hotel)

On Front Street, between Main Street and the library, just three original structures remain: the Ray Building (48 Front Street), the Greenwood Building (52 Front Street), and the library, though all have seen changes over the decades.

At the town’s center, Gordon A. Green Square continues to honor Ashland’s war veterans, just as it did in 1926—though the square itself has expanded to reflect the town’s growth.

A Family Business That Spans Generations

Not many businesses depict Ashland’s continuity better than Main Street Wine & Spirits, which has remained family-owned for more than a century.

The story began around 1917, when John Goldberg lent his brother-in-law, Sam, money to purchase a small neighborhood market near today’s location. The store sold everyday necessities such as meat, produce, and baking goods—and by 1919, John became a full partner. Together, they ran the business for 32 years.

After a devastating fire in 1949 destroyed the neighboring building, John purchased the current property and constructed a larger, modern store, opening in 1951. At the time, it was the largest market in Ashland and featured the town’s first self-service, pre-cut packaged meat department.

In the early 1960s, John’s twin sons, Allan and Marvin, took over, eventually shifting focus as supermarkets replaced small grocery stores. Despite big-box competition, the store remains rooted in community support and customer service.

The Ocean House: From Colonial Home to Historical Anchor

A staple in Ashland’s Main Street stands the Ocean House, a building whose history predates Ashland itself. It was built in 1748 by Colonel John Jones and is the house that sits on land originally owned by Savil Simpson, widely regarded as Ashland’s first settler. Jones married Simpson’s daughter and later inherited the property, which included mills and dams near today’s Mill Pond on Myrtle Street.

An addition built around 1763, recognizable by its distinctive Beverly jog, expanded the home for Jones’ growing family. For 170 years, the Ocean House remained in the Jones family or their descendants before being sold in 1918.

After passing through several owners during the 20th century, the Ocean House found its permanent role in 1991, when it became the home of the Ashland Historical Society. A barn was carefully relocated and reconstructed, and modern additions, including a library and meeting room, were designed to tie in with the original structure.

Today, the Ocean House preserves Ashland’s story. As one might wonder, if Colonel Jones could walk through its doors now, what would he think of the town that grew up around his home?

Some say he never left.

A Town That Remembers

In 1926, runners gathered for the 30th Boston Marathon, while Ashland residents went about their daily lives in a town that felt worlds away from today’s busy community. Yet even as Ashland has grown nearly eightfold, the buildings, businesses, and institutions that remain remind us that the past is never far away.

A century later, Ashland stands as a town that has grown substantially while maintaining clear ties to its past.

Sources: Ashland Historical Society (Cliff Wilson), Main Street Wine and Spirits website