Walk to the foot of Cannon Street on a Saturday morning, coffee in hand, headed for the farmers market at Fountain Park, and you pass the same chain-link fence you've been passing since 2022. Behind it sits a condemned building that used to be the 98 Cannon Riverfront Grille, closed since a fire tore through it that January. For four years it's been the one piece of downtown that never changes while everything around it does.
That's finally starting to shift, but not into the building most people expected.
What was supposed to go there
In February 2024, Chestertown's mayor and council heard from Donald Urgo Sr., president and CEO of Bethesda-based Urgo Hotels & Resorts, who told them he had the property under contract for $899,000 and planned to demolish the old structure and rebuild. His pitch was ambitious: a mid-priced restaurant serving Chesapeake Bay to table seafood and steaks, paired with an inn large enough to hold 40 to 50 guest rooms. Urgo told the council he and his wife had gone looking for a place to eat on the water in Chestertown and come up empty, and that the surprise of it stuck with him.
Mayor David Foster's response at that meeting captured how long the town had been waiting. He said he wanted a restaurant badly enough that he'd love to be able to tell visitors there was a room for them right down the street.
The plan that got smaller as it got real
Two years of engineering and cost estimates later, the project that's actually moving toward construction looks different from the one Urgo described in 2024. By December 2025, according to reporting in the Chestertown Spy, the guest room count had dropped from the original 40 to 50 down to just 10, stacked on a second floor above the restaurant. Foster attributed the shrinkage to the rising cost of building on pilings in a floodplain, telling the Spy that Urgo would need more than a restaurant alone to recoup what he's spending on foundation work, but that the numbers no longer supported anything close to the original scale.
The timeline since then has moved in fairly regular public steps.
| Date | What happened |
|---|---|
| January 2022 | Fire closes 98 Cannon Riverfront Grille |
| February 2024 | Urgo tells town council he has the site under contract, describes a restaurant and 40 to 50 room inn |
| January 7, 2026 | Historic District Commission approves demolition of the condemned structure |
| March 4, 2026 | HDC gives conditional approval to architect John Hutchison's design for a restaurant and 10-room inn |
| May 2026 | Planning Commission reviews site plan and civil engineering documents |
| August 2026 | Preliminary final site plan and a resident opposition letter both filed with the town |
As of this fall, the project is still working through Planning Commission review rather than under construction. A letter to the editor in the Spy in February 2026 pointed to a target of summer 2027 for opening, though that's one resident's read on the timeline rather than a commitment from the developer or the town.
What the building will actually look like
Hutchison's design, presented to a packed HDC meeting on March 4, calls for a two-story structure with decks on each level. The ground floor holds the restaurant and conference rooms. The 10 guest rooms sit above. The whole building will be raised on pilings, with the finished floor elevated to just under 10 feet to meet the site's FEMA floodplain elevation requirements, a detail that matters on a lot that Hutchison told the commission is slowly sinking into the river in its current form.
The new footprint will be modestly larger than what's there now, about 15 feet wider and just short of 34 inches deeper than the existing 120-foot building. On height, Hutchison pointed commissioners to two nearby reference points: the Custom House at Washington College, which stands about 36 feet, and the Scott's Point townhouses along Wilmer Park, at roughly 34 feet. The proposed building falls in that same range. He also noted that 98 Cannon sits 250 feet from its nearest neighbor, compared to the 40 to 45 feet of typical spacing elsewhere in this part of town, which is part of why the design leans modern and open on the river-facing side rather than trying to mimic a historic facade.
Not everyone is on board
Public comment at the March meeting ran mostly in favor, with residents pointing to four years of a vacant, fenced-off waterfront lot as reason enough to move forward. But a February 2026 letter to the Spy raised more pointed concerns, questioning whether the project's scale fits what the writer called Chestertown's 320-year-old best interest and asking the HDC to weigh height and river-view impacts more carefully before final approval. Online comments on the Spy's coverage split along familiar lines: some residents asked what harm 10 rooms and roughly 20 guests at full occupancy could really do to a town used to much larger tourist weekends, while others worried about flooding risk at that exact spot or about the view from across the street once a second story goes up.
Why the town cares this much about one lot
The stakes here go beyond one restaurant. The town spent millions rebuilding the adjacent Port of Chestertown Marina in 2014, and Foster has said publicly that not having a restaurant at the water's edge has hurt the marina's own viability ever since. A working restaurant and a handful of rooms at 98 Cannon would give boaters, marina visitors, and Washington College guests a reason to walk down to that stretch of the water again, something the town lost the moment the fire closed the old Grille.
What's already filling in around the empty lot this fall
None of that waits on a building permit. The Farmers and Artisans' Market runs every Saturday from 8 a.m. to noon at Fountain Park, a few blocks up from Cannon Street, the same rhythm it's kept for years regardless of what's happening at the waterfront. First Fridays bring extended hours and gallery openings to the shops downtown once a month. And the biggest weekend of the season lands right next door to the vacant lot: Sultana Downrigging Weekend runs October 30 through November 1 this year at the Chestertown Marina, the largest annual gathering of tall ships in North America paired with a bluegrass music lineup in the Music Village. Friday and Saturday require a ticket for the Music Village, but Sunday is Community Day, free to walk in.
So for one more fall, the crowds at Downrigging will sail and dock and wander past 98 Cannon exactly as they have since the fire, past a fenced lot with a set of approved plans and a rebuilt marina next door still waiting for the restaurant it was rebuilt to support.
If you're curious how projects like this one move through Chestertown's Historic District process, or what it means for a property near the water when flood elevation requirements come into play, that's the kind of local detail Tina Brown Homes tracks closely for clients thinking about the Chestertown waterfront. Reach out anytime you want a straight answer on what's actually happening at a specific address.
