Innkeepers & History

Welcome to Oak Grove Plantation Bed & Breakfast

The Innkeepers

Pickett Craddock

Innkeeper Pickett at Oak GroveOak Grove Plantation has been occupied by my family since 1820. I enjoy telling visitors stories about the plantation’s past, its founding by Virginia legislator Thomas Easley, the impact of the Civil War, the heyday of tobacco growing and the farm’s conversion to pine trees in recent years.

In winter, I teach preschool at Amazing Life Games in Washington, D.C., and reside in Arlington, Va. As an avid hiker, I have walked the C&O Canal in Washington, the Camino de Santiago in Spain and areas around San Francisco, but I find the hiking on our five miles of trails the best of all. I’d love to lead you on a hike.

Mike Doan

Mike, the Phantom Husband of Oak Grove Plantation B & B

I am a transplanted Californian who loves the slower pace and the warmth of Southside Virginia. I retired in 2009 after 46 years as a journalist in Washington, D.C., for The Associated Press, U.S. News & World Report, the Kiplinger Washington Editors and other publications. I am an avid cyclist, skier, singer, actor and jazz pianist. I have appeared in five Summer Theater productions with the Prizery in South Boston. I would enjoy going on a bike ride with you.

Niko and India

bonnie and new puppyOur 7-year-old and 2-year-old standard poodles love to walk the trails with us every day and watch over our 400 acres from the front porch. They play well together but are looking for other dogs to come and cavort with them.

Family in Civil War

William H. Easley of Halifax County, Va., was inspired to military service by the gallantry of his older brother, Thomas Easley, a West Point graduate who died in the Mexican-American war in 1835.

When war came, the younger Easley was captain of Virginia’s Black Walnut Light Dragoons, which served as cavalry in the Peninsula Campaign near Yorktown. But Captain Easley, at age 29, caught typhoid fever in November, 1861, and he was returned to his home in Cluster Springs, Va.

When it become apparent that he was about to die, he told a member of his company: “Tell all the boys farewell.” Though he felt he had not been too strict, he said, “Tell them if I have hurt their feelings, forgive me. Remember me. I remembered them to the last.” The family farm is still intact, now operating as Oak Grove Plantation Bed & Breakfast by Pickett Craddock, a direct descendant of William Easley..

Source; Col. George B. Davis,  Librarian, Virginia Military Institute.

Oak Grove Plantation Front Yard

Oak Grove Plantation: A Virginia Family’s History

Early Years

Tobacco farmer Thomas Easley built Oak Grove in 1820 in Cluster Springs, a stop on the stagecoach line before South Boston became a town. Easley, who served a term in the Virginia legislature, built a home that was two rooms wide and one deep, with woodwork and mantels in the federalist style. The house was built with heart of pine wood cut from the farm and bricks made on the farm. Easley and his wife, Harriet, had 10 children.

Wars and Tragedy

Education was important to the family, and the oldest son, Thomas, went to West Point but was killed in the Mexican-American War. Son William, who went to Virginia Polytechnic Institute, was Captain of the Black Walnut Calvary Dragoons in the Civil War’s Peninsula Campaign but got sick and came home to die in 1861.


When Thomas and Harriett’s youngest child, Mary Bailey Easley, married Dr. John Craddock in 1853, they moved to Oak Grove with her mother and expanded it. They widened the front hall, put a second story over the dining room and added a one-story, two-room rear addition with Greek revival mantelpieces and no wainscoting. They also added a Greek Revival front porch with latticework columns, sidelight surrounds, double doors and a hipped roof. With the tobacco business thriving, John Craddock had 29 slaves.

Turn of the Century

The Craddocks’ 10th child, Edward Branch Craddock, married Mary Douglas Easley in 1897, and moved to Oak Grove in 1897. He was a stock farmer, worked for the family’s Craddock-Terry shoe company and was appointed Halifax County sheriff in the late 1920s. Oak Grove was also a dairy operation and shipped milk to Lynchburg by train daily.  When Edward’s wife, Mary Douglas Craddock, died in the 1918 flu epidemic, he married Fannie Barksdale Vaughn, who contracted tuberculosis. The cure for the era was fresh air, and after two sun porches were built around 1920, she was in good health again.

Bed and Breakfast

Nine years after her father, E.D. Craddock died in 1979, Mary Pickett Craddock opened Oak Grove as a bed and breakfast in 1988. Along the way, she has added two bathrooms, a handicapped ramp, hand rails on exterior stairs, some insulation and central air conditioning and heating.

The little house is a rental house and has been renovated. Farming operations ceased, and most of the 400 acres were planted in pine trees under a conservation program.

In perhaps the biggest change in over a century, Oak Grove has added solar panels for electricity to keep the main house in use all winter. And in 2016, we added an electric car charging station.