Road Trippin’

Time Period
1877 to 1924
1925 to Today
Domestic Life

A Holladay family photo album contains images from a summer vacation. Here new automobiles travel through old Virginia dirt. (MSS1 H7185h 376) 

There’s just something about a summer in Virginia—and nothing captures the carefree spirit of the season like a road trip. Since its beginnings, the automobile has represented entertainment as much as practicality. It brought new excitement to the summer vacation as well, enabling revelers to enjoy all Virginia had to offer with new ease. 

On Roads 

By 1900, Virginians were revved for the automobile, but the commonwealth’s infrastructure wasn’t. Dirt roads turned to mud pits in a summer storm, impassable for new driving machines, and bumpy country paths served horses better than motors and tires. As infrastructure caught up, early twentieth-century road trips were fascinating moments where old met new. Massive road-building efforts in the 1910s and 1920s, however, gave Virginians even more reason to take a summer vacation. 

Car Troubles

The car radically changed the way Americans got around, bringing new joys—and frustrations—to the travel experience. In the same way car problems plague modern travelers, the earliest automobiles were prone to overheating and other mechanical malfunctions.


A map of Tidewater, Virginia.

One summer road trip in August of 1924 ended in a familiar frustration. A family member wrote to Mollie McLaughlin of Richmond regarding a road trip misadventure:

“Dear Mollie, Liz and I made it after much cussing and discussing, but  Oh! what a trip . . . had to stop about every two miles and fill up with water and then it would boil going down hill. . . . I must have lost two or three hours, and also my religion.” (August 7, 1924, MSS1 M2225a)

For all the excitement the automobile brought, it added a little of that hair-pulling, tire-kicking irritation not unfamiliar to twenty-first century drivers.

Enjoying Virginia 

New highways systems made Virginia’s treasures more accessible than ever before. A pamphlet promoting the Tidewater region boasted: 

"The state of Virginia, with her historic shrines, seaside resorts, mountains, caverns, and other natural wonders, presents to the tourist a charm and interest not to be surpassed anywhere. A fine road system enables one to get from place to place, by motor, with utmost ease." 


Watermelon seeds glued to the pages of the Gilkeson diary (MSS1 G3973a) 

Early twentieth-century Virginians enjoyed summers in many of the same ways we do today. Richmond teen Helen Gilkeson recorded in her diary a June filled with fishing and camping trips, dips in the creek, and parties on cool nights. Though in 1908 she still relied on older means of transportation (for example, horse drawn carriage), she marveled at a first ride in an automobile. 

Henry Wise used the summer of 1938—and his automobile—to explore Civil War battlefields (MSS1 W7547a 6,701). His account of how he “sped along on hard surfaced roads” but encountered an “endless number of automobiles” will sound familiar to current travelers. 

By the postwar era, cars were everywhere and more reliable than ever. Jane Allen Hall recorded her Virginia travels in the mid 1950s, when she enjoyed visiting Williamsburg, the Shenandoah Valley, and even the Virginia Historical Society (today, the Virginia Museum of History & Culture). 


Jane Allen Hall filled this massive scrapbook from her statewide travels. (MSS 5:7 H1443.1)