Road trips · Massachusetts

Massachusetts road trips & hidden gems.

The stops worth changing a travel day for in Massachusetts — crowd-voted gems, events worth traveling for, and the public golf you can actually book. Curated by Roamward, the scenic road-trip planner.

World Cup 2026

June 11 - July 19, 2026 · U.S., Mexico, and Canada host cities, 11 U.S. host cities

Barely two dozen marquee events hit the whole country in a year — and Massachusetts has one this June. Roamward builds the trip around it: the scenic route in, the detours worth a slack day, and when rooms sell out.

What locals say you shouldn’t miss.

Crowd-nominated in the Gem Hunt. Add yours and vote the finalists into the app.

Dr. Seuss Sculpture Garden

Over thirty bronze Seuss characters, from the Cat in the Hat to the Lorax, scattered across a free downtown courtyard honoring Springfield's hometown author.

Quabbin Reservoir Lookout

A stone tower and overlook gaze across the water that drowned four entire towns in 1938 to slake Boston's thirst — an eerie, beautiful view and lost-town history in central Massachusetts.

Glacial Potholes at Shelburne Falls

Fifty smooth pools carved into riverbed rock by 14,000 years of swirling ice-age meltwater, paired with the adjacent flower-covered trolley bridge in this artsy northwestern village.

Hammond Castle Museum

A genuine medieval-style stone castle built by an eccentric inventor, perched on cliffs above the crashing Atlantic in Gloucester, with a great hall and pipe organ.

Dogtown and the Babson Boulders

An abandoned colonial settlement in the Cape Ann woods where Depression-era stonecutters carved sayings like "Help Mother" and "Never Try Never Win" into giant boulders.

Bash Bish Falls

In the far southwest Berkshires, the state's tallest waterfall splits around a jutting rock into a twin cascade before dropping into a serene pool — a stunning, leaf-season favorite.

Events that put Massachusetts on the calendar.

Get the scenic route, the stops, and the timing.

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