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Highland Beach on the Chesapeake Bay: Maryland’s First African American Incorporated Town

Feb 15, 2017 09:00AM ● By Cate Reynolds

Anniversary Article Series: We revisit a few of our favorite articles from the 20-year archive of What’s Up? Media

This month, we offer excerpts from Highland Beach on the Chesapeake Bay, a book released in 2008 from which our magazine had the privilege of publishing a portion of the text. The book offers a history of Maryland’s First African American Incorporated Town, located five miles southeast of Annapolis. “It’s been a labor of love,” enthused Margo Dean Pinson at the time, one of three authors. Due to the efforts of Ray Langston and co-authors Jack E. Nelson and Pinson, the story of the community founded by Charles (the youngest son of Frederick Douglass) and Laura Douglass came to print. The 160 page book, illustrated with 230 historic photos, traces the town’s history from 1892 to 2007. “Each of us was responsible for different chapters,” explained Langston. “While we have common experiences we each have different perspectives and these different viewpoints check and balance each other.”
Croquet was a popular recreational activity in the early 1900s. Photo courtesy of Highland Beach Historical Collection.
Annapolis Community Bank and the Annapolis Rotary Club provided funds to sponsor the project and the trio of authors selected Dunning Publishing to publish the book, initially being printed in a limited run of 1,000 copies. Profits from the sale of the $50 hardbound books were donated to the Highland Beach Historical Commission, which maintains the Frederick Douglass Museum and Cultural Center and sponsors outreach and cultural programs for the community.

Excerpted from the book released in 2008 for publication and written by Jack E. Nelson, Raymond L. Langston, and Margo Dean Pinson

Highland Beach marked the 115th anniversary of its founding on April 10, 2008.

Established as a summer colony for African Americans at the end of the nineteenth century, it has endured and prospered over the years as a vibrant community. It is, today, forging ahead into the twenty-first century, continually adapting to a very changed environment from which it was created.

Strategically situated between the bustling Bay Ridge Resort and Amusement Park and the emerging development of Arundel on the Bay at Thomas Point, Charles Douglass, son of the irrepressible and renowned abolitionist, orator, publisher, and diplomat Frederick Douglass, astutely saw the potential to develop the Brashears family site into a vacation community for blacks: a place where they could enjoy the pleasures of Bay life while allowing an escape from the repressive grip of racial segregation in America.

It had been just over a quarter century since the end of the Civil War at the time Charles Douglass transacted the deal with the Brashears descendants. While the nation was now at peace, the oppression of black Americans continued in earnest with the advent of the Jim Crow era. Despite passage of the Thirteenth Amendment in 1865 that granted full citizenship rights to all black people, the Jim Crow laws that were enacted across many parts of the nation in the late nineteenth century ensured that the antebellum state of bondage would simply be replaced with near-peonage status for most black Americans. The year 1892 had the ignominious distinction of being the high water mark for lynchings, reaching a historical peak of 161 for the year. But in spite of various measures and acts of oppression against blacks since the earliest days of the Republic, there always existed a cadre of competent and able individuals who persevered and excelled despite all odds. W. E. B. DuBois referred to them as the “talented tenth.” Charles Douglass explains in a letter to his father on May 15, 1893, that he chose the name Highland Beach because “the land at that point is higher than either side of me on the beach.”

With the exception of Bay Avenue, Douglass drew upon the surnames of famous African American personages of that era to name the streets. Douglass Avenue was named for his famous father Frederick Douglass; Langston Avenue for John Mercer Langston, U.S. congressman from Virginia, founder of the Howard University School of Law, and minister to Haiti; Bruce Avenue for Blanche K. Bruce, U.S. senator from Mississippi; Lynch Avenue for John R. Lynch, U.S. congressman from Mississippi; Pinchback Avenue for Pinckney Benton Stewart (P. B. S.) Pinchback, governor (acting) of Louisiana; and Wayman Avenue for Rev. Alexander Walker Wayman, the influential bishop of the African Methodist Episcopal Church in Baltimore and eulogizer at the funeral of Frederick Douglass.
Authors Jack E. Nelson, Margo Dean Pinson, and Ray Langston stand outside the Highland Beach Town Hall. Photo by Tony Lewis, Jr.
All of them were legal and political giants of the nineteenth century and were outspoken, if not outright militant, advocates of justice and equality for black Americans. With the exception of Langston and Wayman, they were also all former slaves. They would be memorialized by having their names lent to designate the thoroughfares of this new summer enclave where blacks could escape the oppression of Jim Crow America.

Haley Douglass, twelve-year-old son of Charles Douglass, wrote to his grandfather, Frederick Douglass, on August 17, 1893:

I am down on the Bay spending the summer. I go out fishing and crabbing almost every day. I have learned how to swim real well and I can swim over a hundred yards without stopping to rest.

Perhaps this was the first of many youthful expressions yet to come of the grand times to be had at the summer wonderland that was to become “the Beach.”
Highland Beach founder Major Charles R. Douglass (1844–1921), the youngest son of Frederick Douglass. Photo courtesy of Highland Beach Historical Collection.
Highland Beach was in many respects Charles Douglass’s Field of Dreams. He appears to have been motivated by the same message that was so central to the movie: “Build it and they will come.” Until well into the twentieth century (1948) there were often restrictive covenants on deeds that prevented the sale of real estate to blacks and other minorities. Charles Douglass opened up an opportunity for blacks to freely purchase beach property in the heart of the burgeoning Annapolis Neck Region of Anne Arundel County, with convenient access from both Washington and Baltimore.

To purchase a copy of the book, check availability through the Frederick Douglass Museum and Cultural Center located at 3200 Wayman Avenue, Highland Beach; also reached by phone at 410-268-2956 and online at