The Only Resort For Black Vacationers During Jim Crow Was in Massachusetts

Oak Bluffs on Martha’s Vineyard

Charles Shearer was born into slavery in 1854, chained in a barn by his master during the Civil War for wanting to join the Union Army. By 1912, he and his wife Henrietta had built Shearer Cottage, the first inn on Martha’s Vineyard to welcome Black guests.

Here’s the story of how this safe haven grew into Black America’s summer paradise.

The Methodists and Early Development

Methodist leaders started holding religious camp meetings at Wesleyan Grove in 1835, led by Jeremiah Pease. These spiritual gatherings grew quickly. By 1860, around 12,000 people traveled to attend these revival meetings.

At first, visitors stayed in canvas tents during these events. Families soon replaced tents with small wooden cottages. Starting with just 40 cottages in 1864, the community expanded to 500 buildings by 1880.

Baptist Revival Meetings Bring African Americans

The Baptist Association began holding its own religious meetings in East Chop during the mid-1870s. These gatherings attracted African Americans looking for spiritual connection. More Black visitors came for these events, forming the start of a lasting community.

Many first worked as servants and hotel staff in the late 1800s. Some early Black visitors bought land near Baptist Temple Park around 1890. This marked the beginning of permanent African American homes in Oak Bluffs.

The Highlands Black Neighborhood Forms

“The Highlands” (also called “The Oval”) became the first African American neighborhood in Oak Bluffs. During the late 1800s and early 1900s, Black families could only buy homes in this specific area.

The neighborhood had a unique circular layout with houses along curved streets. This design created a close community where neighbors knew each other. White landowners sold plots to freed Blacks, workers, and sailors.

These property sales helped grow a stable Black community with deep roots.

The Inkwell Beach Is Established

Oak Bluffs Town Beach got the nickname “The Inkwell” in the late 1800s. White residents created this name to mock the skin color of Black swimmers. Instead of rejecting it, the African American community claimed this name with pride.

Today, it’s the most famous example in America of turning a racist term into a symbol of strength. The beach became the main gathering place for Black families. People came not just to swim but to connect with friends and build community.

Oscar Denniston’s Arrival Changes the Community

Reverend Oscar Denniston and his wife moved to Oak Bluffs from Jamaica around 1900. Their arrival marked a turning point for the growing Black community. Denniston quickly became an important leader beyond just religious matters.

His influence helped shape the community’s direction and values. He founded Bradley Memorial Church, which served as both a spiritual and community center from 1907 to 1966. The church offered religious education and became a gathering place for social events.

Henrietta Shearer’s Pioneering Business

Henrietta Merchant Shearer started a successful laundry business in Oak Bluffs in 1903. Her business met the needs of wealthy summer visitors who wanted clean, pressed clothing.

She hired several women and became known for cleaning the fancy petticoats women wore at that time. Henrietta even provided pickup and delivery service with her own horse and wagon.

Women like Shearer led the way as the first Black business owners on Martha’s Vineyard.

The Founding of Shearer Cottage

Charles and Henrietta Shearer turned their laundry business into Shearer Cottage in 1912.

This became the first inn on Martha’s Vineyard that welcomed Black guests. Charles Shearer was born on a Virginia plantation in 1854 to a plantation owner father and enslaved mother.

Despite this difficult start, he pursued education. He graduated from Hampton Normal and Agricultural Institute in 1880. His education and business skills helped him create a safe vacation spot during the segregation era.

When High-Profile Black Guests Arrived

Composer Henry T. Burleigh stayed at Shearer Cottage every summer. He told his New York friends about Oak Bluffs, spreading word about this vacation spot. Famous guests included actor Paul Robeson and hair product entrepreneur Madam C.J. Walker.

These visitors helped build Oak Bluffs’ reputation as a premier Black vacation destination. The cottage often filled beyond capacity. The Shearers arranged overflow rooms in nearby houses and served communal meals to as many as 50 guests.

The Harlem Renaissance Comes to Oak Bluffs

Dorothy West, a writer from the Harlem Renaissance, first visited Oak Bluffs as a child. She formed a lifelong connection to the island that influenced her writing. Many other Harlem Renaissance artists and writers spent summers at Shearer Cottage.

They brought their creative energy and cultural conversations to the island. Adam Clayton Powell Jr. and his wife Isabel Washington Powell honeymooned here in 1933. Isabel had been a dancer at Harlem’s famous Cotton Club in the 1920s.

The Growth of the Black Resort Community

During the 1920s, Black homeowners began renting rooms to visitors. This created more lodging options beyond Shearer Cottage. Word spread through social networks about Oak Bluffs’ welcoming atmosphere.

Visitors came from Boston, New York, Philadelphia, and other Northeast cities. By the 1930s, Oak Bluffs had become America’s most well-known Black vacation community. Middle-class and wealthy Black families made it their regular summer destination.

Visiting Oak Bluffs on Martha’s Vineyard

You can reach Oak Bluffs by ferry from Woods Hole, Falmouth, Hyannis, or New Bedford, Massachusetts.

During your visit, tour the African American Heritage Trail (self-guided, free) with stops at Shearer Cottage, Dorothy West’s home, and the Inkwell Beach. You can also drop by the Tabernacle in Wesleyan Grove to see original gingerbread cottages.

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