Tag Archives: Coastal Living

Boston waterfront, South Coast harbor, and Provincetown views representing a Massachusetts coastal bucket list

A Coastal Massachusetts Bucket List: Boston, Cape Cod & the South Coast

Coastal Massachusetts is a region of remarkable variety. Historic city streets give way to working harbors, quiet villages, open beaches, protected landscapes, and some of New England’s most recognizable coastal destinations.

In Boston, centuries of history meet a modern waterfront and an internationally known arts and cultural scene. Along the South Coast, maritime cities, village centers, farms, vineyards, and natural spaces reveal a less-traveled side of Massachusetts. Across Cape Cod, each town brings its own character, from lively harbors and village Main Streets to sweeping dunes and Atlantic beaches.

Together, these destinations offer far more than a seasonal escape. This Coastal Massachusetts bucket list highlights memorable things to do in each region, with links to our complete local guides for deeper exploration.

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What Connects a Law & Order Star and a Supreme Court Justice?

Originally published September 2016. Updated August 2026.

What do Law & Order’s Sam Waterston and former Supreme Court Justice Oliver Wendell Holmes Jr. have in common?

No, it’s not that they both spent a lot of time in the courtroom. Although they did… if you count the TV courtroom.

And while it’s true that both men were Ivy League educated, Holmes at Harvard and Waterston at Yale, that’s not the connection that binds them either. Continue reading