Historic Oakwood: A Tour of Raleigh's Victorian Architecture

Raleigh’s Historic Oakwood neighborhood is like a living museum of 1800s architecture and Southern charm. On this walking tour, you’ll find out how Oakwood went from Sherman’s Union Army campground to a fashionable suburb with gas-lit streets and horse-drawn streetcars, before falling into decline and then saved through passionate community preservation efforts.

The tour starts at the official residence of the state’s governor, the 1891 North Carolina Executive Mansion, whose clay bricks were handmade by indentured laborers. You’ll explore tree-lined streets filled with lovingly preserved Victorian, Queen Anne, Second Empire, and Craftsman homes, each with its own character and story. Along the way, you’ll discover how many of these grand homes were once divided into apartments during hard economic times before being restored to single-family residences.

As you meander through the neighborhood, you’ll hear the remarkable story of Vallie Henderson who helped save Oakwood from demolition, and see a controversial modern home that sparked a legal battle. The tour ends at the iconic Krispy Kreme on North Boundary Street, home to the famous charity race.

On this 75-minute walking tour, you’ll have a chance to:

• Admire the whimsical ‘Halloween House’ with its year-round T-rex sculpture
• Visit the Thompson-Anderson-Allen-Robertson House, Oakwood’s largest and second oldest home, which was meticulously restored after a devastating fire in 2012
• See the former home of Leonidas L. Polk, North Carolina’s first Commissioner of Agriculture and founder of Progressive Farmer magazine
• Peek at Pullentown, a small enclave built by philanthropist Richard Stanhope Pullen, who donated land for NC State University and Pullen Park
• Spot the quatrefoil attic vent that’s become Historic Oakwood’s official symbol
• Discover the historic Tucker House, carefully relocated and preserved as a community meeting space
• Learn about remarkable women like Anna Ball Stronach Thomas who supported their families by operating businesses from home
• Stroll past architectural treasures like the Second Empire-style Heck-Lee and Heck-Wynne Houses, both built around 1874

This tour invites you to step into Oakwood’s storied past, while exploring the vibrant community that continues to honor its unique heritage.