Selena Wilkes did not set out to buy a barbershop, a diner, and a stretch of Main Street. She set out to buy back her family's farm.
When Wilkes moved home to Williamsport, she bought the farm back from the developer who had it and turned the property, barn and all, into a bed and breakfast and wedding venue. A building owner in town noticed. He was selling his own place and told her he thought she should buy it too, that she had the vision to turn the town around. That conversation is, by her own account, how Port 44 started. Wilkes and her sister Lettie brought in three more local residents and began buying up buildings that needed work.
Since then, Port 44 has purchased 22 buildings in downtown Williamsport. If you have walked Potomac Street or the block around Conococheague and noticed new paint, new signage, or a storefront that used to sit empty, there is a good chance you were looking at one of theirs.
What's Already Open
The businesses that have actually opened their doors are a specific list, not a vague trend. Cindy's Old Thyme Country, Get Right Barbershop, Lotus Moon Cafe, and Still Smokin' BBQ all located downtown as part of this wave, alongside Mama Lu Lu's Diner, whose grand opening drew Maryland Commerce officials out to Williamsport to mark it. That is on top of the businesses that were already anchoring downtown before Port 44 existed: Cushwa Brewing Company, founded in January 2017 by homebrewers Marcus Thomas, Scott Coleman, and Garrett Chambers, and its co-located Rad Pies kitchen, both tucked into the back of the development on Governor Lane Boulevard. Tony's Pizza has been a few blocks from the canal since 1985. China 88 sits near the lift bridge at mile marker 99.5, the point where the towpath crosses into the Cushwa Basin, a short walk from the C&O Canal Grill & Pub.
Walk that stretch today and you are covering ground that includes a working brewery, a barbecue joint, a diner, a barbershop, and a cafe, all within a few blocks of each other. Several of those storefronts were the empty buildings Port 44 started with.
What's Still Coming
Not everything Port 44 has announced has opened yet, and it is worth being precise about which is which. According to Maryland Commerce's own account of the group's plans, the pipeline still in progress includes a rooftop restaurant and bar, a bicycle shop, a combined coffee and ice cream shop, a health hub, an interior design store, and an outdoors store. Above the ground-floor commercial space, the plan calls for luxury loft apartments, meant to put more people living downtown rather than just visiting it.
That is a meaningfully different kind of project than a facade grant or a ribbon cutting. It is a bet that Williamsport can support a rooftop bar and a bike shop at the same time, on the same block, before either one exists yet. If you have been waiting to see what fills a particular storefront, that waiting is not accidental. These builds take time, and Wilkes herself has described the progress so far as something the community has noticed and responded to, with residents pitching in alongside the money Port 44 has already put into the buildings.
Where the Public Money Actually Went
It is easy to assume that a downtown this changed got that way through some state program. That is only partly true, and the part that is true is smaller than you might expect.
Williamsport earned its Main Street Maryland designation years ago, one of several communities recognized under a state program built to strengthen local business districts. Kathryn Gratton, a main street specialist with the Maryland Rural Development Corporation and Williamsport's former Main Street manager, said that as of spring 2025, more than $343,000 had been invested in the community over the prior two years through private contributions and the state's Community Legacy Program, with local officials hoping to add roughly $150,000 more. That money is real, and it shows up in retaining walls, sidewalks, porches, and other street-facing improvements across town.
But that figure is facade money. It pays to make an existing building look better from the sidewalk. It does not buy the building. The 22 properties in Port 44's portfolio are a separate, private transaction entirely, funded by the five people who formed the group and whatever partners they have brought in along the way. The state helped dress up what was already there. The people who decided what would go inside those buildings, and who took on the risk of buying them in the first place, were Wilkes, her sister, and three other local residents.
There is a third piece to this that predates both of the others. The Chesapeake and Ohio Canal National Historical Park relocated its headquarters to Williamsport in the fall of 2024, a $15 million project led by the Maryland Economic Development Corporation with support from Washington County, the town, and the state, bringing more than 50 jobs within walking distance of Main Street. The park as a whole draws more than 5 million visitors a year across its full 184.5 mile length, and in 2021, more than 480,000 of those visitors spent time specifically in Williamsport, generating nearly $15 million in the local community that year. That is the foot traffic Port 44 is building toward. The headquarters landed first. The storefronts came after, and they are still catching up to what the visitor numbers suggest the town can support.
Reading the Block Correctly
If you live here, the practical version of all this is simpler than the funding breakdown. The new lunch spot on Potomac Street and the barbershop that replaced an empty storefront are not isolated openings. They are pieces of a single, still-unfinished project being run by five people who live in this town, financed privately, and only partly supported by the public money most residents assume is doing the heavy lifting.
It also means the next round is not speculative. A bicycle shop, a coffee and ice cream shop, and a rooftop bar are specifically what Port 44 has said it plans to bring downtown next, on top of apartments above the storefronts meant to keep people living in the district year round. Whether that timeline holds is worth watching the same way you would watch any local project with a lot of moving pieces. The businesses that have already opened are proof the group follows through. The ones still coming are the test of how far that follow-through goes.
For a lower-stakes version of the same story, Deliteful Dairy, a seventh generation working farm on the edge of town, runs an on-site fall festival each year with a tractor ride, live music, and a field full of local vendors. It is a smaller example of the same pattern playing out downtown: a family business that has been here for generations, adapting to bring people in rather than waiting for them to show up on their own.
Steve Powell has spent 26 years watching Washington County towns go through exactly this kind of change, and tracking which of these shifts actually stick is part of what informs the pricing and positioning work his team does for owners in Williamsport and across the Tri-State region. If you are curious how a changing Main Street affects what your own property is worth, Steven L Powell offers a private home valuation with no pressure attached.
