How Annapolis Became America's Sailing Capital


Annapolis' culture has always been tied to its maritime history. The United States Naval Academy, pictured above in 1925, is one of the city's defining nautical features. (Historia/Shutterstock)

ANNAPOLIS, MD — Boaters flock to Annapolis every summer. Vessels docked downtown last week included a superyacht from Jamaica and a lengthy sailboat from Miami.

Mariners love the nautical traditions in Annapolis, from the Wednesday night sailboat races to the annual Blue Angels air show over the Severn River.

Annapolis wasn't always the sailing capital of America, however. The city's history is inseparable from the water, but timely changes forced the town to reinvent itself repeatedly.

Annapolis started as a small colonial port and was overshadowed by a larger neighbor. The city transitioned into a seafood hub before a global war ushered in an era of modern shipbuilding. Local development and boat mass production made the town the nautical destination it is today. The focus now turns toward environmental conservation and the future of boating.

This is the story of Annapolis through the years.

Colonial Annapolis Overshadowed

It's easy to imagine Annapolis as a colonial port thanks to its narrow cobblestone streets.

The city still has more original 18th-century structures than any other American town. Construction on the Maryland State House started in 1772, making it the oldest state capitol in continuous legislative use. It's also the only statehouse to serve as the nation's capitol building.

The Maryland State House is shown here in 1786. This engraving by John Vallace is based on a painting by Charles Willson Peale. (Photo by MPI/Getty Images)

With a heritage like this, City Dock must have a storied shipping history. Right?

That's partially true, but there's more to the story.

Colonial Maryland was a tobacco giant with plantations flanking both sides of the Chesapeake Bay. That assured plenty of exports, but harvest collection ships usually went straight to the plantations and bypassed centralized ports.

Large trading ships rarely visited City Dock, Annapolis historian Jane McWilliams said. McWilliams, author of "Annapolis, City on the Severn: A History," noted that the Chesapeake did not have any bustling ports at the time.

"I don't think you can call Annapolis a major port at any time," McWilliams told Patch. "There were not major ports on the Chesapeake during the colonial period at all. If you had one, it would probably be Annapolis, but it was so easily eclipsed by Baltimore."

While writing her book, the Annapolis resident found that port activity didn't take off until the French and Indian War ended in 1763. Lawmakers, like Declaration signer William Paca, started building luxurious estates in Annapolis when the economy picked up. This led to more consumer goods flowing into the city.

Products like knives, clothing and fabrics showed up at City Dock. The town had three tanneries that cured hides along College Creek, so leather products went through the port as well.

The William Paca House & Garden, pictured above in 2021, is one of the 18th-century estates in Annapolis that sparked an influx of consumer goods. (Jacob Baumgart/Patch)

The trade of enslaved people and indentured servants is also a part of this era.

The most well-known African sold into slavery in Annapolis was Kunta Kinte in 1767. Novelist Alex Haley later traced his ancestry to Kinte and wrote about this heritage in his famous book "Roots: The Saga of an American Family."

McWilliams said 48 vessels entered Annapolis waters to sell enslaved people between 1756 and 1776. Another 317 ships brought white indentured servants during that window.

About 18,000 laborers were sold in Annapolis during that span. Ten percent of them were enslaved, McWilliams said. Most of the imported workers were indentured servants who were owned for a predetermined timeframe and then granted their freedom.

Slave trade did happen in Annapolis, but it was not the predominant use of the port.

The Kunta Kinte-Alex Haley Memorial, shown here in 2021, marks the arrival of an enslaved person in 1767 and acknowledges Annpolis' history as a slave port. (Jacob Baumgart/Patch)

Shipbuilding, on the other hand, blossomed into a major industry during the 18th century. A ship carpenter's lot opened at City Dock in 1718. In the 1770s, a 200-ton shop was built on College Creek.

A nautical economy was budding in Annapolis, but Baltimore was becoming the preferred trading port.

"As Baltimore rises, Annapolis kind of stays quiet," Annapolis historian David Gendell told Patch.

Gendell, an Eastport resident, wrote "Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon."

Many associate the 1875 lighthouse with Annapolis because it's located between the South River and Kent Island. Gendell said the lighthouse was actually built to guide ships to the more convenient Baltimore port.

Baltimore offered deeper waters, more room for storage on land and eventually better rail connections when trains debuted. The city also had moving water at Jones Falls to power mills, a luxury that Annapolis lacked. Baltimore was additionally closer to the wheat fields of Western Maryland, notching another advantage for the northern neighbor.

To protect its expanding port, Baltimore built Fort Whetstone out of soil in 1776. The federal government took over the property and erected Fort McHenry there in 1794. Fort McHenry replaced Whetstone's earthen walls with stronger bricks and added more cannons, which proved vital to Baltimore's defense in the War of 1812.

Annapolis was such an insignificant shipping port by the war that the British bypassed it in hopes of capturing the more valuable Baltimore.

Annapolis was at a crossroads, forcing it to turn the page.

Thomas Point Shoal Lighthouse, pictured above in the modern day, was built in 1875 to guide ships to Baltimore. (Shutterstock)

Watermen Take Over, Naval Academy Opens

After a slower period, the seafood industry rose to new heights. Work and fishing boats filled the harbor.

Watermen dominated the Chesapeake from the late 19th century through the early 20th century. Fishers hauled in crabs and striped bass, piling them at City Dock. Skipjacks, which are now the state boat, harvested oysters.

The building that's now Annapolis Market House opened in the 1890s as a seafood plant. Catches were processed, cooked and sold on-site. The scraps were thrown back into what's now Ego Alley across the street.

McNasby Seafood & Oyster Company moved from Baltimore to downtown Annapolis and then to Eastport in the early 1900s. Located on Back Creek, this former seafood packing facility is now home to the Annapolis Maritime Museum & Park.

"The seafood industry is always an important part of the Chesapeake," McWilliams said.

Just like seafood, the U.S. Naval Academy is another Annapolis symbol born during this period.

This 1853 wood engraving depicting the Naval Academy was etched after a drawing by W. R. Miller. The image was published in Illustrated News, New York, New York. (William Rickarby Miller/Public Domain)

Naval officers previously had no standardized training regimen. The Philadelphia Naval Asylum School was the Navy's largest at the time. There were also naval schools in New York City, Norfolk and Boston in the nation's early days.

Leaders for decades had pitched a centralized on-shore naval school. The Navy picked Annapolis for its "healthy and secluded" location to rescue midshipmen from "the temptations and distractions that necessarily connect with a large and populous city," the Naval Academy said.

Secretary of the Navy George Bancroft commissioned the Naval Academy on the Severn River in 1845. The Navy took over the Army's 10-acre Fort Severn and built the current Naval Academy Yard atop the old base.

This sparked an influx of Navy officers who were professors and administrators at the academy. These well-educated leaders came from posts around the nation, bringing a worldly culture to the growing city.

"It makes Annapolis a more cosmopolitan town," McWilliams said, noting that Navy wives in 1902 helped start what's now the Anne Arundel Medical Center.

The Naval Academy's Class of 1892 is shown above. (Edward Hart (Life Time: 1892), Public Domain)

Post-colonial waters were largely characterized by seafood and naval uses. There wasn't much recreational boating, however. It would be decades before manufacturing changes made boating the sport Annapolis knows today.

Gendell, who co-founded SpinSheet and PropTalk Magazines, said any leisurely boating in the 1800s was done in "very small, humble vessels" like homemade canoes and skiffs.

"Even the Annapolis Yacht Club started as a canoe club in the late 19th century," Gendell said. "The members would launch their canoes into Spa Creek and row them to spots up the river for swimming."

Recreational Boating Takes Off

World War II was a catalyst for the town's recreational boating.

The Annapolis Yacht Yard, which built wooden boats in Eastport, won a contract to build naval vessels for the Allied powers in the 1940s. The shipyard built over 100 of these warships, including torpedo boats and minesweepers.

Around 400 people worked at the yacht yard, leaving an abundance of skilled boat manufacturers after the war. These workers then applied their skills to build leisure yachts at the property, which became Trumpy Boatyard, until it closed in 1974.

"That was the beginning of our marine industry," Gendell said. "We went from a sleepy town patching holes in your crabbing skiff to being able to build wooden boats of high quality at speed."

This 1904 map charts the Chesapeake Bay from the South River to Kent Island. (Granger Historical Picture Archive/Shutterstock)

Residential development around the city picked up in the 1960s and 70s. The most desirable neighborhoods had a community pier along the water.

Fiberglass boats outpaced wooden vessels. Fiberglass is a cheaper material that was easier to mass produce and maintain.

These factors made boating more accessible to the masses.

"You don't have to be extraordinarily wealthy or born into it," Gendell said. "It opened up yachting now to a bigger community ... It was suddenly more affordable."

The Annapolis Sailing School was founded in 1959, making it the nation's first adult sailing school.

The school designed its own training vessel, the Rainbow 24, to simplify sailing for beginners. Gendell said the school opened branches in California, Florida and Missouri. It even set up shop in the U.S. Virgin Islands.

The school has taught thousands to sail, and Annapolis is an ideal place to learn.

The current isn't overly strong. The wind isn't overpowering. And the shores aren't rocky.

Sailboats fill the Annapolis harbor in late May with Greenbury Point in the background. (Jacob Baumgart/Patch)

A growing population of experienced boaters made Annapolis a nautical hub.

The U.S. Sailboat Show recognized this flourishing culture and held its first exhibition in the city in 1970. This was the country's first in-water sailboat show.

The Annapolis Boat Shows eventually expanded to have four annual events, with two each year for sailboats and powerboats.

"Now, people come from all over the world to go to those boat shows," Gendell said. "The marine industry all turns up in Annapolis to exhibit at those shows. And those shows also did a lot to advance the popularity of recreational boating and Annapolis' spot within it."

What's Next For Boating?

Gendell, McWilliams and Marylanders all agree that boating isn't going anywhere.

Gendell, a sailor and a powerboater, has noticed a shift toward motorboats in recent years. He attributes that trend to consumer preferences for turn-key vessels ready for quick trips and dock bar visits.

"I always believe Annapolis will deeply be a sailing town .... but what I'm seeing in terms of trends is COVID really accelerated small boats," Gendell said, pointing to pandemic spikes in canoeing and kayaking as well.

Personal vessels like these require public water access. Gendell thinks there is a demand for more launch points where anybody can park their car for a day and paddleboard around local waterways.

City Dock, pictured above in May, was once a seafood packing hub. Now, it's a recreational boating destination lined with restaurants and shops. (Jacob Baumgart/Patch)

Gendell is proud of the Chesapeake Bay conservation efforts in Maryland, but he thinks there is room for improvement in the more distant states of the watershed.

"As a community, that awareness leads to action on the individual level," Gendell said. "Now, we need to work on upstream things."

Annapolis is a waterfront town through and through.

The city is narrated boat tours from Watermark Journeys. It's cruises from nonprofits like Chesapeake Region Accessible Boating and the Valhalla Sailing Project. It's nautical restaurants like the Severn Inn, water taxi rides to Eastport, tugs-of-war over Spa Creek and fireworks in the harbor.

Annapolis is the water, and the water is Annapolis.

"Will it change?" McWilliams wondered. "No, I don't think so. As long as people are willing to buy the boat for enormous amounts of money and go out and sail, ... they're going to do it."


The Annapolis harbor is consistently filled with personal dinghies and lavish yachts like the ones shown here last week. (Jacob Baumgart)
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