The Dude

Summers—and the enclaves in which they’re enjoyed—hold a special place in the hearts of families, especially in New England, where winters can be long and unforgiving. While researching for a family that has summered in West Falmouth for over a century, we uncovered a piece of local history too charming not to share.

Today, the ultra‑wealthy might hop on a helicopter or private jet to avoid Cape traffic, but in 1884, the dedicated summer crowd had a different solution: they booked a season ticket on The Dude.

From June to October, up through the summer of 1916, The Dude Train—also called the Dude Flyer or the Flying Dude—carried Boston’s Gilded Age elite from the city to Woods Hole at remarkable speed. The trip took just 1¾ hours, a full hour faster than regular service. Onboard were the era’s most notable names: John Parkinson; members of the Forbes, Winsor, and Beebe families; Brigadier General Charles Paine; and even President Cleveland. Many of these surnames still mark local roads and landmarks today.

But beyond the glamour and the speed, The Dude represents something more relatable. The determination to reach their families and summer sanctuaries as quickly as possible. The schedule made that devotion possible. A 7:40AM departure from Woods Hole got them to Boston by 9:25 for a (modest) day’s work, while a 3:10 PM train returned them to the shore in time for cocktail hour—and more importantly, walking barefoot in the sand.

Sadly, the Dude is long gone, but the impulse behind it isn’t. Whether we’re inching over the Bourne Bridge, racing to catch a ferry, or tapping a rideshare to the airport, the goal is the same as it was in 1884: to get to the people and places that make summer feel like summer.

Does your family gather in one spot each summer? Reach out, because that house definitely has a story to tell.