5 Charming Small Towns Within a 2-hour Drive of Big Cities

Brewster, Massachusetts

Near: Boston
Population: 9,820

Even though Cape Cod has no shortage of charming small towns, Brewster stands out for its long history. It was established in 1659 and has dramatic architecture and wide-open natural preserves.

With many miles of secluded bay-side beaches and over 5,000 acres of conservation land, including 80 sparkling kettle ponds originating from glaciers, it’s considered the area’s prime eco-tourism destination.

The charming small town is also a fantastic stop for bike lovers, with the Cape Cod Rail Trail that links Brewster to five towns. Overall, for folks who love the great outdoors and being in nature, Brewster is a terrific place to live in and visit.

Once known as “the sea captain’s town” due to the large number of rich ship captains who lived here, this town is still striped with lovely waterfront estates, many of which now operate as lodgings.