CAMBRIDGE — Just past the Choptank River Bridge and slightly to the right lies the future of Cambridge: Sailwinds Park and a large neck of waterfront property.

The 35-acre parcel on the edge of the Choptank River hosts a state-run visitor center, playgrounds, parking lots, beaches and waterfront access, along with the University of Maryland Shore Medical Center facility. Now, Cambridge has a grand vision to transform that entire plot into a waterfront villa and public park with improved outdoor amenities.

That could enjoin with residential units and housing, as well as commercial space, such as restaurants and hotels, in what is expected to be a nearly $300 million dollar project.

The city’s master plan is not complete and subject to change. The blueprint so far envisions a substantial overhaul of the waterfront property, most of which is already known — but several interviews with city officials, private property owners and interested parties, along with pages of documents collected by The Star Democrat and Dorchester Star for the first time, reveals a long road ahead for Cambridge as it works to transform the waterfront under an ambitious timetable.

The property has the potential to put Cambridge back on the map, making it an attractive tourism destination akin to St. Michaels or Ocean City.

“This takes Cambridge from one level to the next,” said Mayor Andrew Bradshaw. “Success and investment begets success and investment — every good thing that happens here leads to good things elsewhere.”

Cambridge Waterfront Development Inc., the nonprofit set up by city hall to manage development of the waterfront, recently acquired 11 acres of property and is seeking a deal to acquire the nearby hospital site.

Meanwhile, Dorchester County and other private property owners in the area are fleshing out plans to develop the land they own in anticipation of the waterfront development.

Some in Cambridge are also resistant to the idea of commercial space and housing sprouting up at Sailwinds Park, a popular public access area for many residents. And the park sits in a low-level area and is one of a number of locations in Dorchester County that will be most impacted by sea level rise.


According to a May 2021 master plan, Cambridge is ambitious with this development. At its core is that CWDI proposes a large waterfront park along 16 acres of land.

Eleven acres, including the port and gateway property on the water’s edge, is owned by the city. Currently, it consists of parking lots, fields and a walkway on the water, along with the Governor’s Hall, a restaurant and event space.

The state of Maryland owns the Dorchester County Visitor Center and roughly two acres of land. Dorchester County owns another two acres — a playground, amphitheater, beach and parking lot space.

Sandra Tripp-Jones, CWDI executive director, said the state will keep ownership of the visitor center, while the county and city parcels will connect into an improved beach stretching from the visitor center to the other side, near the port.

Dotted along the waterfront are plans for a public bath house, a 1,500 square foot pavilion, outdoor dining and a boat launch with 13 trailer parking spaces.

Plans also call to build a marina office with canoe and kayak rental huts and a 20,000-square-foot boutique hotel; a 10,000-square-foot restaurant is planned for construction close to the Governor’s Hall.

Several acres of land near Byrne Street are slated for future development and could consist of both housing and more commercial amenities.

Tripp-Jones estimates it will be mid-to-high range housing, given it’s waterfront property, but said it will be in keeping with Cambridge’s architecture.

“We want it to feel like the rest of the city,” she said.”But what is the rest of the city? We have bungalows, Victorian homes, and mixed-use housing. It’s quite a range of styles. Overall, it will have a maritime, industrial feel.”

Tripp-Jones championed the idea of a mixed-use development, for which the area is zoned, because 15 million cars travel across the Choptank River Bridge every year. The city expects a large waterfront park and commercial hub directly off the bridge will attract tourists heading to Ocean City every summer.

She said it will also be a splendid feature for locals.

“Our intention and our goal is to be attractive — not only to visitors, but an attractive site used by the locals who use this now,” Tripp-Jones said. “We want it to be welcoming, so people don’t look at this and say, ‘I don’t belong there.’ It will be welcoming to everyone.”

In anticipation of increased traffic, the city will build out four gateway entrances into the waterfront villa at Byrne Street, Hayward Street, Maryland Avenue and Aurora Drive. No traffic study has been completed.

One key obstacle is the UMMS hospital system has not yet transferred its 19-acre property to the city, a parcel of land that makes up the bulk of the master plan for the development. Negotiations are ongoing.

The city said it will need to spend half a million to demolish the hospital buildings and wants to acquire the property for free because of the demolition cost.

The hospital system said in a statement through communications director Trena Williamson that it is nearing the completion of a $53 million new facility in the heart of Cambridge off U.S. Route 50 and is committed to finalizing a deal.

“As we plan to transition to the new UM Shore Medical Center and Pavilion at Cambridge, we have made a commitment to negotiate exclusively with Cambridge Waterfront Development Inc. (CWDI) in order to safeguard the community’s vision for the redevelopment of the hospital’s property on the Choptank River,” Williamson wrote. “We remain determined to reach an agreement with CWDI, allowing the realization of this exciting revitalization project for the benefit of Dorchester County and the greater Eastern Shore.”

CWDI anticipates a 10-year buildout, hiring a master developer to build out the entire parcel of land, which would maintain consistency across the mixed-use property.

Bradshaw said it could cost $150 million to $250 million to develop the entire property. Grants will help, but a large portion of the development will be paid for by the master developer, who would then have control of the property after development.

The city has already invested some money on the property and is expected to spend millions more. Nearly $8 million will be spent on infrastructure alone, while $4 million will be spent on the demolition of buildings, including the hospital grounds and the venue space at Governor’s Hall.

About $400,000 will be spent on planning and acquisition and another $210,000 on broadband.

The city is hoping the property will be attractive for businesses and tourists, which could also connect to downtown Cambridge. Investment could lead to a steady source of property tax revenue if the city becomes a larger tourist destination.

“Where Cambridge is strong, it gets to be unique, it gets to be itself,” Bradshaw said. “Cambridge grows organically and can be its own location instead of six versions of the same thing. The (waterfront) will draw some of the folks that go to St. Michaels or Easton.”


Plans to develop Sailwinds Park and the waterfront stretch back to the ‘90s. The waterfront property was used as a large port since the time of the city’s original settlement in 1684. In the 19th century, it was home to a massive seafood operation with oyster packing houses scattered across the city.

Phillips Packing Company opened up across from the waterfront at the turn of the 20th century and ushered in a whole new era of operations out of the port. More than a million oysters were shucked annually in Cambridge during its heyday. But the plant closed in the 1960s following a decline in the seafood industry.

The Cambridge Port officially opened in the 1970s as a deepwater port meant to revitalize the maritime and seafood industries. It remained the second largest port in Maryland until it closed in 1991.

In 1993, the Maryland Port Administration took over the property. MPA leased the property to a nonprofit, Sailwinds Park Inc., which eventually redeveloped the land into a visitor center, playground and beach area.

In 1995, an old fish plant and warehouse on site were converted into the Governor’s Hall, which became a popular entertainment venue that continues to attract the county’s largest events today.

At the time, the state planned to create a large mixed-use development with a hotel and restaurants, similar to what is proposed today. The $36 million plan was supported by then-Gov. William Donald Schaefer.

“Sailwinds Park will be the showcase of Cambridge and Dorchester County, much as the Inner Harbor is the heart of Baltimore’s revitalization,” he said in a guest column in The Star Democrat in 1996. “It will be the key to Cambridge and Dorchester County’s future.”

Hundreds of thousands of dollars were poured into the project, mostly through state grants. The visitor center and surrounding beach and play area were built by the end of the decade.

Further plans to develop the area failed to materialize, and it became evident that Sailwinds Park Inc. had fallen into serious debt. In the early 2000s, the city stepped in to help the nonprofit organization manage the property and its debt.

In 2009, the state and MPA announced plans to sell the property to the highest bidder. Cambridge, however, stepped in at that time to suggest they hand the property back to the city in order to redevelop it into the mixed-use harbor it had long planned to develop. The state agreed and extended a lease of the property.

A few years later, in 2014, the state transferred the 12-acre port property to the city, under the condition that it be developed within 15 years. Cambridge already had plans to renew redevelopment of the waterfront and began installing light fixtures and renovating the port property in anticipation of new development.

CWDI was formed in 2018 to oversee the redevelopment of the waterfront. This time, the city organization, made up of seven members in the county, city and state agencies, along with one Sailwinds Park Inc. member, promised to do it right.

“CWDI is currently working with the city to green up, clean up and make the site shovel ready,” promised Frank Narr, a member of Sailwinds Park Inc. and a board member of CWDI, during a county promotional release.


Some private property owners already have a stake in the development, while one business owner says local businesses are threatened by the city’s waterfront plans.

Governor’s Hall, the entertainment space that first opened in 1995, is a vocal opponent of the Sailwinds Park redevelopment. Inside the entertainment venue is a small bar and restaurant, which is currently run by Grady Wilson, the president.

Cambridge leases the property to Wilson, but the city has been honest about demolishing Governor’s Hall as officials prepare for incoming development. That means Wilson will have to pack up and leave one day, but Wilson insists he has nowhere else feasible to go in Dorchester County when that happens.

Governor’s Hall hosts events such as the Seafood Feast I-Val and large weddings. People in Dorchester have come to rely on the large waterfront venue.

“There’s no place else for the community to go with ample space and parking,” he said. “There’s no place in Dorchester County that will hold what this place will hold.”

Cambridge is working to convert the old Phillips packing plant into a larger venue space, but Wilson and Vice President Jerome Jackson are skeptical that it could ever be as attractive as the waterfront property.

“This waterfront property is part of the attraction,” Jackson said.

Meanwhile, the city has not renewed the lease for Governor’s Hall, which is up in January. Wilson and Jackson said they have lost more than $11,000 in pre-event bookings because they don’t know if they will have a home there this winter.

“If you don’t have the common courtesy to come to us, and say, ‘We’re going to give you another year’s extension or two years’ — I mean, it’s common courtesy,” Wilson said. “We’re stuck in limbo.”

Tripp-Jones said the Governor’s Hall has been slated for demolition since 2016, and the business is aware of that.

Other businesses in the area hope to expand and include themselves in the future vision of Sailwinds Park.

Yacht Maintenance, which has been operating its ship repair business on five acres of land next to the port property since the ’70s, plans to create an immersive experience for guests to watch boats being hauled, lifted and repaired from an observation deck.

George Robinson, the owner of Yacht Maintenance, is expecting to host “the largest travel lift between Virginia and New Jersey.” The shipyard currently uses a railway system and a 60-ton travel lift in the water, which hauls boats out of the water and into the maintenance yard.

But a 45-foot tall, 200-ton travel lift could haul even taller ships like the Pride of Baltimore. Yacht Maintenance would construct a building with an observation deck for the public to watch the hauls.

“We envision being able to haul some of these vessels on Saturdays,” Robinson said, “and make it a kind of an event that will generate interest in Cambridge and the maritime industry.”

Design plans and preliminary reports are only 60% finished; the business does not have an estimate on the price tag for the project, although it’s expected to be a “fairly costly venture,” according to Robinson.

He expressed optimism in the waterfront park. Robinson bought Yacht Maintenance five years ago, around the time CWDI was formed and approached him with the Sailwinds Park redevelopment. He said he immediately envisioned the travel lift.

“If this is done correctly — and there’s no reason it’s not going to be — this will be a boost for everyone in the area,” Robinson said.

Another business slated to move in is RAR Brewing, which has plans for a 25,000-square-foot taproom and brewery.


Cambridge residents want to see less commercial space and more public waterfront access.

In a survey released earlier this year, which asked for public input on the waterfront redevelopment, Cambridge residents suggested the city retain more public and water access than build out housing and commercial units.

The survey collected 1,500 responses from December 2020 to January 2021. Overwhelmingly, residents asked for public waterfront access and amenities including walking trails, exercise stations, improved beach access and green infrastructure like rain gardens and tree plantings.

Boat ramps and outdoor activities, as well as a larger promenade and entertainment space, were also favored.

Residents were mixed on whether they wanted to include housing at the Sailwinds Park. About 16% asked for no housing on the property, while 19% asked for rentals only.

About 80% of the survey respondents were more in favor of mixed-use developments that host commercial space on the bottom and residential units on the top.

In dozens of comments posted in the survey, Cambridge citizens gave approval to the idea of a waterfront park open to the public, but expressed concerns about condos or other expensive housing units popping up at Sailwinds Park.

Residents questioned why the city would sell the plot to a developer, instead asking for them to lease it to property owners. Others asked for the space to be city-run with the entire park open to the public.

Dallas Brooks, who lives in downtown Cambridge, said he was concerned about “housing getting in the way.”

“Once you get houses on that, it will be no trespassing. I just would like it to be open to the public,” he said. Brooks uses the parkland now for recreational activities. “It’s a nice place to relax, eat crabs.”

Kayla Babes, who also lives in downtown Cambridge, often takes her son to the park. She also pushed to keep the property more publicly available than privately owned for the benefit of children.

“Kids want things (like Sailwinds Park) instead of just being on the streets,” she said.

Babes said she would like to see more recreational activities built there, such as basketball courts.

Wilson, the owner of Governor’s Hall, questioned the push for housing and commercial space, which he fears will be the focus of the development.

“What is benefitting Dorchester County by building (homes)?” he asked.


Another hurdle is developing a property situated just above the Choptank River. A number of residents have raised the alarm about sea level rise — the Chesapeake Bay is expected to rise about two feet by 2050.

In a 2008 report from Maryland’s Department of Natural Resources, researchers found that Dorchester County will face some of the worst effects of sea level rise on the Eastern Shore. Nearly 60% of the county lies in a floodplain and half of Dorchester is below the elevation of 4.9 feet.

While bulkheads raise the Sailwinds Park well above the Choptank River and Choptank Creek, the area still lies in a floodplain and is subject to flooding, according to DNR researchers, who predicted that Sailwinds and seven other parks in Dorchester will experience the worst effects of sea level rise.

“Period flooding and permanent inundation (will) affect these parks,” the authors wrote.

The study called for preventive measures to protect the areas but suggested that waterfront communities will become a thing of the past, especially in the low-lying Dorchester County.

“There will come a point in time where waterfront property will no longer be desirable due to its liability and short-life expectancy,” the authors concluded in the study. “Government finances based on property tax assessments will be faced with making adjustments in tax rates when people stop coveting waterfront properties. Government budgets will experience serious economic declines.”

CWDI acknowledged the waterfront lies in a flood-prone area. Tripp-Jones said they can address the issue with stone pavements, which they already have out on the shoreline, and large, open, green space that can absorb some of the flooding.

Still, some residents have called for a living shoreline to help offset the effects of sea level rise. In that case, however, some of the beach area may be lost. That could put a dent in the city’s plans for a waterfront park.

Bradshaw is less concerned about the Choptank and its impact on the development. He said the city would hire a responsible developer with “a green outlook.” The mayor plans to work with the large waterway in a sustainable way.

“We see the Choptank as our gem,” he said. “It’s our history and our heritage, but also our future.”

Bradshaw said Cambridge has one shot to revitalize the city and transform it into a premier destination on the Shore.

“I’m excited to finally get this done. It leaves a legacy,” said Bradshaw. “We have to get it right — if you get it wrong, there’s no turning back from that.”

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