6:34 PM / Sunday March 26, 2023

6 Jun 2015

Cambridge, Maryland, “Heart of the Eastern Shore”

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June 6, 2015 Category: Travel Posted by:

By Renée S. Gordon

“A ship, like a human being, moves best when it is slightly athwart the wind, when it has to keep its sails tight and attend its course…” —Chesapeake

From the first European sighting of the Chesapeake Bay area, by Spanish explorers in the 1520s, the region has been lauded for its beauty and abundance of wildlife and fish. Mid-16th century maps show that they called the bay Santa Maria. The earliest documented foreign visitor, Captain John Smith, arrived 82-years later and it is from his journals that we gather information on the geography, native population and culture. The Native Americans referred to the water as the “great shellfish bay,”  “Tschiswapeki,” which to English ears became Chesapeake. The major tribes in the region were the Nantaquak (Nanticoke), Pocomoke-Assateague and Susquehannock. You can follow the Captain John Smith Chesapeake National Historic Trail.

Waterways were our first roads and this made the 200-mile long Chesapeake Bay Estuary, the largest in the nation, accessible and lucrative land upon which to settle. More than 100,000 creeks, rivers and streams wind through the watershed. The first permanent settlement in the area was a trading fort established in 1631 by William Claiborne on Kent Island. He purchased and named the island after his homeland and began to trade with the Susquehannocks. Three-years later George Calvert, Lord Baltimore, received 10-million acres and founded the colony of Maryland. Dorchester County, “The Heart of the Eastern Shore,” was founded in 1669 and named to honor the Earl of Dorset. It has more miles of shoreline than any other county in the sate.

The Choptank River, the largest on the Delmarva Peninsula, is named after a tribe and is said to mean a “stream that separates.” Cambridge, one of Maryland’s most picturesque and historic gems, owes much to its location on the river’s southern shore. It was platted in 1684 and quickly became an important river town with its prosperity based on water-based occupations. It is the only deep-water port on the eastern shore of Maryland, the second deepest port in the state and was incorporated in 1693. The Cambridge Historic District was placed on the National Register of Historic Places in 1990.

Visits should begin with a stop at the Dorchester County Visitor Center in Sailwinds Park. This architecturally awesome structure replicates a skipjack, its 100-ft. sails billowing in the wind, moored at the eastern end of the bridge spanning Route 50 and the Choptank River.

High Street Slave Cabin

High Street Slave Cabin

The center features area information, facilities, a fully equipped playground and two levels of exhibits on regional history and culture. There is a brief orientation film, interactive exhibits and interpretive displays showcasing the Underground Railroad, Harriet Tubman, Annie Oakley and local water-related industries. A two mile boardwalk offers a fishing pier, beach and walking and cycling path. The Harriet Tubman Underground Railroad Byway begins at Sailwinds and continues for 125-miles to the Delaware State Line.

Just as the city began with the water, so too should our exploration of Cambridge. Long Wharf Park is today a public marina and its serenity and panoramic vistas do not give visitors a hint of its historic importance. The area is situated on a man-made land because until the mid-1800s there was a 600-ft. wharf that extended into the water because of a huge sandbar. Trading vessels, including slave ships from Africa and the Caribbean, docked here until 1808 when the Trans-Atlantic slave trade became illegal and once the soil was depleted and large numbers of slaves were no longer needed it was used as a port to transport slaves to other regions. “Black Jacks,” African American mariners arrived on merchant vessels bearing news for the local black population and they, as well as white abolitionists, assisted escapes using the maritime UGRR route from this port. This area was known as Chesapeake Station and is a prime example of the cooperative efforts of captains, pilots, dockworkers and ordinary citizens in the UGRR.

Long Wharf was begun in the 1800s and was completed as one of Roosevelt’s initial WPA projects because it was needed as a location to dock the presidential yacht. Roosevelt visited on October 26, 1935 to dedicate a bridge and a monument on the wharf memorializes his visit. It is the actual elevator, encased in a smokestack, used by the president on the U.S.S. Potomac.

The Choptank Lighthouse is a replica of a lighthouse that replaced the lightship LV-25 in 1871. The ship indicated the entrance to the Choptank until an iron screwpile lighthouse was constructed. The wooden lighthouse was hexagonal in shape with six screwpiles and four fenders to protect the foundation. In 1918, ice floes destroyed the lighthouse and a pre-existing one was relocated 100-miles to the Choptank River. The current lighthouse is a replica of the second structure. It sits on a 60-ft. platform and was completed in 2012 on Pier A.  Self-guided tours and a museum are located inside.

One of Cambridge’s most unique adventures is a sail aboard the authentic 65-ft. Skipjack Nathan of Dorchester. The skipjack, Maryland’s official state boat, is named after species of fish noted for their speed. The boats date from the 1890s and are noted for shallow drafts and maneuverability. They are the only working sailboats remaining in the country and are still used to dredge oysters in the Chesapeake. One and three-hour narrated, heritage tours leave from Long Wharf on a regular schedule.

Long Wharf is nestled at the foot of High Street and walking tours of the historic street begin there. High Street is so well preserved that it served as a model for one of James Michener’s cities in “Chesapeake.” The homes arrayed along High Street represent architectural trends from the late 1700s to the early 20th-century. Styles include American Foursquare, Colonial Revival, Georgian, Gothic Revival and Queen Anne. Two of downtown Cambridge’s three sites listed on the Harriet Tubman UGRR Byway, Long Wharf and the Dorchester County Courthouse, are located on High Street.

Notable aspects of the 100 and 200 blocks of High Street are the individual properties with original outbuildings that served as offices during colonial times. Josiah Bayley’s 1796 wooden law office is the oldest extant office building in the city. Bayley was the state’s 10th attorney general. His home, the oldest in the city, is also on High Street and is featured on ghost walks.

The Church of England founded thirty parishes in 1692 in Maryland and an Anglican Church was built in Great Choptank Parish in Cambridge by the following year. The 3rd and current Christ Episcopal Church is situated on the site of the first structure. It is a High Victorian Gothic church built of granite with a slate roof and adjoining cemetery used for internments since the church’s founding. Four of the state’s governors are buried there.

Directly across High Street stands the Italianate Dorchester County Courthouse designed by Richard Upjohn. The original courthouse burned in 1852 and was replaced in 1854. Slave sales were held on the courthouse steps and a number of significant cases were held in the courthouse.

Samuel Green was born a slave in 1802 in Dorchester. He obtained his freedom in 1832 and became a highly regarded lay minister, abolitionist and farmer. He was suspected of assisting fugitives and shortly after returning from visiting his son, who had fled to Canada, he was accused and his home was searched. No real evidence was found but he was arrested for possessing a copy of Harriet Beecher Stowe’s “Uncle Tom’s Cabin.” The court appointed a lawyer, a local slaveowner, and a two week trial began in April of 1857. He was convicted and sentenced to 10-years of hard labor. There were protests over the sentence and some local whites raised $2000 to try to free him.

On March 26, 1862, a hearing was held and Governor Augustus Bradford pardoned him on the condition that he leave the state within 60 days. He was freed on April 21, 1862. Because he was now penniless he gave speeches along his route to Canada. In New York he met Stowe and while in Massachusetts when asked what he wanted he is said to have requested a copy of “Uncle Tom’s Cabin” because he had never finished the book.

The courthouse played an important role in the saga of Harriet Tubman. She hired a lawyer for $5 and sued for her freedom based on the fact that her mother was to have been freed upon the death of a prior owner and she therefore would have been born free. Her second, more incendiary interaction took place in December 1850. Harriet’s niece Kessiah Bowley and her two children were to be auctioned on the courthouse steps. John Bowley, Kessiah’s free husband bid on his family and won. When payment was called for they were gone. Tubman had arranged their escape on the Chesapeake to Baltimore and then further north.

J.M. Clayton Company is the oldest working crab house in the world. The family-owned company, established in 1890, gives tours to groups of 15 or more. An on-site retail store sells their Epicure™ Crabmeat, prepared naturally without chemicals, additives or preservatives. 108 Commerce Street.

In 1913, Annie Oakley, the award-winning sharpshooter, and her husband constructed the Colonial Revival bungalow and garage for their retirement in Cambridge. They chose the area because it was beautiful, rural and wild game was abundant. The house was designed for the couple and retains many of its original features including floor-to-ceiling trophy cases in the living room and a kitchen crafted for a 5-ft. woman. Annie was known to climb out the upstairs windows and shoot ducks in the water from her roof. She penned her first autobiography in this residence. Annie’s husband, Frank Butler, said that Annie was a “rotten housekeeper” and it appears she was an equally unhappy housewife. In 1917 they came out of retirement and returned to show business and living in hotels. The house, 28 Bellevue Ave., now a private residence, was listed on the National Register in 1996.

Cambridge is filled with both historic structures and contemporary shops and the dining options are spectacular. In the heart of the downtown area there are no chains and each eatery puts a special spin on seafood dishes using fresh ingredients that are locally sourced.

A gastropub is a casual and cozy restaurant that serves creative dishes and has an extensive selection of brews and wines and the High Spot Gastropub in Cambridge provides the perfect experience. The dishes to try here are the Zombie Meltdown, any of their numerous pizza selections and crapple, a combination of crabmeat and scrapple.

Jimmie & Sook’s Raw Bar and Grill is open daily for lunch and dinner with the added attraction of live entertainment from Thursday through Sunday. Patrons select from indoor or patio seating.  The emphasis here is on Eastern Shore seafood and the featured dish is the crab dip served in a warm bread bowl, the winner of the Taste of Cambridge Crab Cook-Off People’s Choice Award. The restaurant is named after the common terms used for a male blue crab, a Jimmie, and a mature female crab, a Sook.

Stoked Wood-Fired Eatery is the trendy choice of locals and visitors alike. The menu is huge and showcases local ingredients, fresh baked breads and homemade desserts with seasonal dishes prepared with a special twist. More than 60 specialty wines and beers are on offer.

The luxury Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina , completed in 2002, provides ideal accommodations for a destination stay, a family vacation or a hub from which to visit sites and attractions in the area. The resort offers all the standard amenities plus Camp Hyatt for children, a kennel for your pet, a golf course, a 150-slip marina and a program of daily activities all in a bucolic setting. Most of the 400 rooms have balconies and water views.

One of the most wonderful things about Cambridge is the fact that much of the landscape looks as it did over 100 years ago and teems with wildlife. This is what Harriet Tubman would have seen and our final stop on this part of the journey, and first stop on the Harriet Tubman Trail, is the 28,000-mile Blackwater Wildlife Refuge, the “Everglades of the North.” The refuge is a stop on the Atlantic Flyway and is home to the largest breeding population of American bald eagles north of Florida. Visitors can access the area by land or water and a four mile Wildlife Drive, complete with pull-offs, is a great option for families. Eagle sightings, up close and personal, are practically guaranteed. Fugitives are known to have hidden in these marshes when making an attempt to be free.

Cambridge is a 2.5-hour leisurely drive from Philadelphia. Next week we will follow Harriet’s journey to Philadelphia. You can plan a trip to Cambridge using tools available online.

I wish you smooth travels!


This summer, visitors to the Chesapeake Bay area have a unique opportunity to take a Waterman Heritage Tour led by a working waterman. Tours range from participating in the daily activities to land-based shore programs. The variety of opportunities is stunning and they are offered for all ages and ability levels at locations throughout the Chesapeake region.

The world’s largest rubber duck, 61-ft. tall and weighing 11-tons, is due in the Delaware River to join the festivities during the Tall Ships® Philadelphia Camden 2015. The 4-day festival, featuring an international array of 12 Tall Ships® and a host of other activities, will open on June 25th. Tickets and information are available online.

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