At the corner of Southwest Sherwood Boulevard and Third Street, a lot just under an acre has sat empty since 2007, when the city tore down a two-story schoolhouse built in 1911 after engineers flagged it as a seismic risk. On May 19, the Sherwood City Council voted unanimously, 7 to 0, to adopt a plan that finally settles what goes there: a public plaza.
That would give Old Town three paved gathering spaces within a few blocks of each other, joining Robin Hood Plaza and Cannery Square. Community Development Director Eric Rutledge has said the goal isn't more square footage, it's visibility. Drivers passing through on Highway 99W or Tualatin-Sherwood Road often have no idea Old Town exists just off the main route. "Like do you even know it's here?" he asked during a council presentation on the plan. Stacking civic gathering space that close together turns a handful of quiet blocks into something a driver actually notices.
Two Plazas Already Set the Pattern
Robin Hood Plaza came first, built in 2023 for about $1.5 million on the former site of the Robin Hood Theater at Pine and First. Kodiak Pacific handled construction, with input shaped by Lango Hansen, the design firm behind Cannery Square a few blocks over. Cannery Square, next to the public library, runs on a different rhythm. Its water feature operates from Memorial Day weekend through September 30, which means the splash pad shuts off for the season this week. The Sherwood Saturday Market, held in the same square every Saturday from May through September, 9 a.m. to 1 p.m., has also just closed out its run for the year.
Each space does different daily work:
- Robin Hood Plaza anchors the Robin Hood Festival and the Cruisin' Sherwood car show, and doubles as a parking lot the rest of the year.
- Cannery Square carries the farmers market and splash pad season, plus community events like the Christmas tree lighting.
- The proposed third plaza would work as an arrival point, the first visual signal to a driver turning off the highway that they've reached Old Town.
The Corner That's Been Empty Since 2007
The Sherwood Boulevard and Third Street site sits at what's currently a three-way stop, the kind of intersection most drivers pass through without registering. Rutledge has called it "a key corner property" where the plan calls for open space, likely paired with a mixed-use or commercial building next door. No construction timeline exists yet. The city still has to decide whether it develops the site itself or brings in a private partner, and that decision comes before any design work starts.
The Plan Has Three Jobs, Not One
Planning Manager Sean Conrad broke the strategy into three pieces when he presented it to the council: business health and growth, sense of arrival, and infill and development. The plaza covers the second piece. The other two show up in less visible ways.
On infill, the most concrete near-term step is the vacant pad directly in front of the Sherwood Center for the Arts on Pine Street. The city plans to issue a request for proposals for the roughly 4,500-square-foot site, retaining ownership but leasing to a developer, with a feasibility and design study due by the end of 2026. Rutledge has floated a single or two-story building with room for more than one tenant, possibly a restaurant or event space that complements the arts center next door. Two years before the council's vote, Cooper Mountain Ale Works had already opened a Sherwood location attached to that same arts center building, alongside its main brewery and pub in Tigard, a sign the city sees the location as viable before it's even settled on a tenant for the empty lot beside it.
On business health, the city is weighing non-financial incentives, like a staff liaison who walks new owners through the permit process, alongside financial ones such as system development charge waivers and permit-fee relief, pending future council approval. Old Town already carries a higher share of small, locally owned businesses than the retail strips along Highway 99W, and the plan is built to protect that ratio.
Why the Recruitment Pitch Keeps Circling Back to Wine
The plan singles out food, drink, and wine businesses specifically. Sherwood sits on the route drivers take from the Portland side of Washington County into the Willamette Valley's wine country, and the city wants Old Town to register as a stop along that drive rather than a pass-through. In July, a group of local business owners formed a new alliance aimed at branding Sherwood itself as a wine destination, built around joint marketing and agritourism, a move that lines up with the city's own recruitment goals rather than working against them.
Old Town already has pieces of that identity in place. Symposium pours Stumptown and Coava coffee alongside a full bar of whiskey and gin. 503 Uncorked serves wine flights a block over, often with live music. Blakeslee Vineyard Estate hosts a First Thursdays live music series. BearKat Brewing Company runs a weekly music bingo night. Clancy's has served Sherwood's home-cooked classics long enough that its Tuesday trivia night reads as an institution rather than a promotion. None of these needed the strategic plan to open. What the plan adds is a formal push to bring more of them in, faster, with less friction at City Hall.
The Curbless Streets Are Part of the Same Idea
One detail in the plan is easy to miss because it's literally underfoot. Old Town's streets are built without traditional curbs, a design the city plans to extend further, specifically so tents and crowds during street events don't create a tripping hazard where a curb line would otherwise sit at the edge of a closed road. Rutledge has pointed to the Robin Hood Festival and Cruisin' Sherwood as the events that make the case: when Pine Street closes for a weekend, a flat surface means strollers, wheelchairs, and folding tables move across what used to be a curb without anyone planning around it.
That's a small piece of infrastructure, but it runs on the same logic as the plaza decision and the business recruitment push. The city keeps making choices that only pay off if people are walking Old Town's blocks on foot, closer together and more often, rather than driving in for one stop and leaving.
The vote on May 19 approved the strategic plan itself, not construction funding for the third plaza. The feasibility study for the Pine Street pad in front of the arts center is due by the end of this year. A separate study is looking at whether Columbia Street could extend to connect with Oregon Street, an idea Mayor Tim Rosener has pointed to as a new entry point into Old Town, though it still has to work its way into the city's broader transportation plan before it goes anywhere. The corner lot at Sherwood Boulevard and Third has a direction now. It doesn't yet have a shovel in the ground.
If you're watching how these changes might shape what it's like to own along Pine and Columbia in the next few years, TK Real Estate Group is keeping an eye on it too. Reach out anytime to talk through what we're seeing on the ground in Old Town.
