The first settlers in the Caine Woods area were probably Native Americans who moved their village to the coast during the summer months. The area formerly known as “Yellow Banks,” directly across the Fenwick Ditch from Caine Woods, was once an active site, and many arrowheads and tools were found there prior to the bulldozing for the development of what is now Nantucket Point.

Probably the first white visitor was Col. Henry Norwood, who in 1649 was set ashore and abandoned by his mutinous crew at the Fenwick Inlet, located just north of where the lighthouse stands today. Local Native Americans guided him back to Virginia.

The Fenwick Inlet existed until about 1791, offering access to pirates who used Cedar Island in Little Assawoman Bay as headquarters. Capt. Louis Guillar made Pirate Islands, located west of Caine Woods, his headquarters. There are rumors that treasure was buried in both sites.

The first summer settlement in the area began with a camp meeting in a grove of oak trees about 300 yards from the ocean. Called Fenwick’s Camp Meeting, it was located on what is now 141st Street near the present-day Phillips Restaurant. About 50 cottages were built around a circle, and there were usually three services during the day, followed by a bonfire on the beach in the evening. Getting there meant walking on a long boardwalk over the marsh and cranberry bogs. On occasion, the cranberries were picked to take home.

Because there were no roads along the coast, a trip to downtown Ocean City meant driving west and then south to Berlin, then following old Route 346 east. The road to Bethany was built in the early 1940s, and the road south to Ocean City was opened soon after.

Often confused for the Mason-Dixon Line, the border between Maryland and Delaware is actually the Transpeninsular Line. It was surveyed in 1750-1751 by four men (two from Maryland and two from Pennsylvania) and runs 69 miles due west to Delmar, where it meets the north-south line surveyed by Charles Mason and Jeremiah Dixon in 1760.

The marker at the Fenwick Lighthouse came over from England as ballast on the ship Betsy Lloyd. The lighthouse, built in 1859, is 87 feet tall and, along with the tender’s house, cost $23,748.96. At the time it was built, a fresh-water pond measuring one-quarter mile long by 50 to 100 yards wide was located between the lighthouse and the ocean.

The Fenwick Ditch, which separates Caine Woods from the mainland, is really not a ditch, but more of a flowing saltwater river. It was said to have been cut during the late 18th century to prevent cattle that were being raised along the coast from wandering away.

In the 1800s, Ziporiah (Zippy) Lewis built her home near Caine Woods from parts of schooners that had wrecked along the coast. She furnished it with ships’ furniture that had washed ashore. It is rumored that her treasure is still buried here, or hidden in the hollows of old trees. Zippy lived out on the end of the marsh and had a number of children. She is said to be the grandmother of many of the Buntings.

Another colorful character was “Lady Gale” Eckert, who was 75 to 80 years old when the marshland of Caine Woods was being pumped out. On moonlit nights, workers reported watching Lady Gale do her naked dance on the Fenwick bridge. She lived in a little shack alongside the bridge and made a lasting memory for everyone who met her.

During World War II, a total of 11 ships — a destroyer, three freighters, five tankers and two barges — were sunk by German submarines off the Delmarva coast. The concrete towers found up and down the Delaware coast were erected to provide information for target settings on surfacing German submarines.

In the late 1960s, James Caine, an Ocean City realtor and developer, owned all of the bayside property and much of the oceanfront from the Carousel Hotel at 118th Street to the Delaware line. In 1971, he conceived the idea of the Montego Bay Mobile Home Park to occupy the entire bayside. Concerned that the area might be too big for the mobile home park market, he laid out residential lots for the northernmost section. That is how Caine Woods was born.

At that time, the Town of Ocean City ended at 42nd Street. Caine found it next to impossible to obtain financing to develop land north of the town’s limits. The banks refused to invest under any circumstances. So Caine proceeded by borrowing from individuals and paying them back in six months with 100 percent interest.

Unfortunately, funds to complete the development ran out. After the streets and underground utilities were in place, Caine divided the residential lots into smaller units, which were sold to different developers. Some areas were dedicated as well-sites and parks.

Development continued in the 1970s, and some real estate agents offered quite a lot to prospective buyers. For example, agents told some buyers of an interior lot that they would also get a boat slip in the deal. The agents even took those buyers to a boat yard, where Harpoon Hanna’s is now located, and pointed out which boat slips would be theirs. However, the proprietors of the boat yard were unaware of this arrangement!

Some buyers were told that Caine Woods was limited to single-family homes, but they soon learned that no such protection existed. At this time, waterfront lots sold for $18,500; interior lots were $6,500.

On Sept. 2, 1981, residents Steve and Arlene Johanson, George Pleat, Fred Witt, George “Bud” Weszka and Charlie and Joan Burger met at the home of Richard Thobe. They developed bylaws and planned a neighborhood social event to be held at the Burger home.

Weszka was elected president; Cooper, vice president; Joan Burger, secretary, and Thobe, treasurer of what was then called the Parker Estates Community Association. (Gene Parker, another local developer, had purchased a number of lots from Caine. Parker then developed the Tiburon complex and other parts of Caine Woods; hence, the name Parker Estates.) The organization was incorporated in October 1981.

In January 1983, the Parker Estates Community Association changed its name to the Caine Woods Community Association.