Accessing land and commercial real estate is a critical factor that significantly impacts the growth and sustainability of Black businesses. In Maryland, where legacy landowners predominantly control the land, this can create a challenging environment for emerging entrepreneurs. This limitation not only restricts physical expansion but also hampers the ability to build equity and wealth, perpetuating economic disparities.
The challenges Sharon and Quinton Wilder, owners of the luxury bed and breakfast inns The Oaks and The Oaks Annapolis, have faced while seeking expansion space on which to develop a large-capacity event venue in Montgomery County present a revealing case study.
The Oaks: Breaking Down Barriers
Sharon Jackson Wilder, Esq. grew up in Montgomery County. She went to elementary, middle, and high school here before going north to college and then coming back to settle.
As she was growing up, her mother owned The Foxes Den in Silver Spring, the first Black-owned beauty shop in Montgomery County. Sharon started working in the salon at about 12 years old, having the spirit of entrepreneurship ingrained in her from that early age.
“I said to myself, ‘One day I too will have a business in the County.’” A few years later she would leave behind the love of her life to come back here.
Sharon and Quinton Wilder met at the University of Massachusetts/Amherst. The vision for The Oaks was born in the late 1980s on one of their trips to Cape Cod. On that trip, they stayed at a fabulous bed and breakfast inn and said to each other that, “One day we’d like to own one of these.” Sharon was 19 years old at the time.
But Sharon came home from UMass to go to Georgetown University Law School, and as it happened she stayed. So the couple broke up and didn’t meet up again for 27 years. Quinton remained in Boston. But, Sharon says, “I had always wanted to be back in D.C., in MoCo.”
They each built lives with other people, and the idea of a BnB faded into the background.
“It was a dream that was only possible with him,” Sharon said.
But nearly three decades later, they found each other again. On a quick trip they took back to one of the bed and breakfast inns they had enjoyed at the Cape, they remembered the dream. Quinton said: “You still want to do that?”
“That would be awesome!” Sharon replied. And that was that. They held a spontaneous business meeting on the beach at Martha’s Vineyard.
Back home in Cabin John, Maryland, Sharon went into her parent’s basement and retrieved the trunk she had taken with her to college. In it were letters she and Quinton had written to each other during college – including a draft business plan for a bed and breakfast.
Three weeks later, Quinton made plans to move to D.C.
The couple would open their 7-room bed and breakfast as a short-term rental space in Bethesda on December 1, 2020.
Sharon’s mother, also an interior designer, designed the rooms. They lived on Laurel-Oak Drive – hence the name: The Oaks. Then they named all the rooms after their other love: oak-barreled wines.
Expansion: The Oaks Annapolis
With the success of The Oaks, the Wilders wanted to expand. Sharon has long had a vision for an event space – there is no Black-owned or operated event space in Montgomery County large enough to hold an event of 300-500 people or more. Nor is there even one in the entire state of Maryland. Yet Black organizations in Maryland spend millions of dollars each year on large events.
The Wilders are determined to change that. The problem is getting the land.
In the hunt for opportunities to expand, they were directed to an available venue in Annapolis called the Blue Heron Inn. One of the owners passed away, and the spouse couldn’t keep up with it on his own.
The Wilders bought it, and opened The Oaks Annapolis as the only Black-owned bed and breakfast in Maryland’s capital. It opened for business on December 1, 2023 – three years to the day after opening their first property.
The Annapolis location blends historic charm with modern luxury. It’s just a short walk from the U.S. Naval Academy, City Dock, Main Street, and Maryland Avenue, right in the middle of the capital’s famed historic district.
Wildly popular from the day it opened, The Oaks Annapolis is booked through most of 2025.
The Hunt for an Event Space in Montgomery County
Now, the Wilders are looking for a new property in the county large enough to be an event space.
Sharon and Quinton are members of multiple civic and fraternal organizations that need space, among them Delta Sigma Theta Sorority, Inc., The Links Incorporated,The Society, Inc., and the National Coalition of 100 Black Women for Sharon, while Quinton is a member of Kappa Alpha Psi, Inc. and the Batchelor-Benedict Organization where he serves on the foundation board. Sharon has served, or is serving, in a board capacity for each one of her organizations, and knows that they are always having large fundraisers to fulfill their service missions.
She has now been looking for a couple of years for the right location. Yet the barriers have not yet fallen. Even with their success, they find themselves stymied by the commercial real estate challenge.
One of the problems is the difficulty of getting information. Although Montgomery County is known as business-friendly, when they started during the pandemic it was very hard to get advice. They had run other businesses but hadn’t needed to involve themselves with the County. They found a challenge getting County officials to understand their concept.
“It was complicated!” Sharon said. “What kind of license to get? How do we get it? How do we get registered? It was just challenging, and no one could understand what I was doing when I said a ‘hospitality group that focuses on small inns.’”
In 2023, Sharon was appointed to the Montgomery County Permitting Service Advisory Board by the County Executive, Marc Elrich. She accepted the appointment so that she can influence the permitting process and be in a position to advise other Black-owned businesses on commercial real estate zoning laws and other land use laws and regulations.
Land Use Issues in Montgomery County
The other big problem the Wilders still face is that most of the land in the county is owned by old, established families that have held onto their property for many years. It’s a close-knit society and when land transfers, it’s usually offered to friends before it’s put on the public market. They found the same environment in Annapolis and were simply lucky to find their opportunity.
Today, they’ve got their eye on the old Sears building in White Oak. Sears went bankrupt years ago but the building has been sitting vacant ever since, occupying that large piece of land. The spot would be an ideal match for their concept. They have talked to Friends of White Oak, but find a very high barrier to entry when it comes to funding and being viewed as a valued partner in the business growth and development of underserved areas within the county.
The Wilders find that owners don’t want to give up or share their property, which could increase not only land values but hope and jobs for underserved communities. The developer still has a lease and won’t free up the White Oak land. Sharon points to numerous such buildings in parts of Silver Spring, particularly in the Tech Road area near Briggs Chaney where vacant office buildings just sit unoccupied.
“Entrenched developers have no incentive to rent or sell these properties. They use them as tax deductions. Meanwhile, this does nothing for the County. No tax dollars. No new investment and no local jobs,” said Sharon. “It’s really a shame.”
“I’d like to partner with Montgomery College’s hospitality program and give those students and residents of White Oak on-the-job training and internship opportunities. So many young people in the area could use that kind of leg up.”
Despite these challenges, Sharon and Quinton are holding tight to their vision.
They want to create something big. Something that can be not only a top-tier event space, but can double as a hub for their many nonprofit organizations, and be safe, community-oriented transformational spaces where residents feel a sense of belonging rather than a sense of being pushed out.
And they want to break the lock on land ownership by generational companies that were started in the 1800s. It’s time to share resources so that other hard-working, long-time residents of Montgomery County can create opportunities not only for their own families but also for new and future generations of Montgomery County residents.
Advocating for Change in Land Use Policy
As the Wilders’ story illustrates, land use issues, including barriers presented by policies and practices governing commercial real estate leasing, shape the landscape for many Black-owned businesses striving for growth and success in a competitive market. This underscores the importance of business owners proactively educating ourselves about local land use policymaking.
Individual businesses find it very hard, if not impossible, to create policy change on their own. But when more small and local business owners engage with county and state government offices and agencies, we can advocate for the adoption of policies that not only support small businesses but also contribute to the expansion of the tax base within the county. It's through such informed and active participation that small business owners and entrepreneurs can influence a more inclusive and supportive regulatory environment, fostering opportunities for growth and greater economic equity.