Walk the northwest corner of Southwest Sherwood Boulevard and Third Street and you'll find grass, a chain-link fence, and not much else. It has looked this way since 2007, when the city tore down the two-story schoolhouse that had stood there since 1911 because engineers flagged it as a seismic risk. For nineteen years it has been the kind of lot people in Old Town stop noticing. That's about to change.
This spring, Sherwood's city council took up a resolution to move forward with the Old Town Strategic Plan, and the corner sits at the center of it. The plan calls for turning that not-quite-acre into a public plaza, possibly with a mixed-use or commercial building next to it. If it happens, Old Town would have three plazas within a few blocks of each other along Sherwood Boulevard and Pine Street: the new one, plus the two that already anchor foot traffic today, Robin Hood Plaza and Cannery Square.
That detail matters more than it sounds like it should. A third public gathering space isn't cosmetic. It's the city admitting something specific about what's been missing, and what hasn't.
Two Plazas Already Work. The City Is Building a Third.
Robin Hood Plaza and Cannery Square already do real work for Old Town. They're where the Sherwood Robin Hood Festival has staged its parade and archery match against Nottingham's Sylvan Archers rivals since 1954, where the Winter Art Walk sets up artist tables, where the holiday parade routes through every December. These aren't underused spaces. They're the two places in town that reliably pull a crowd.
So when Eric Rutledge, Sherwood's community development director, calls the schoolhouse corner "a key corner property" and says "the plan calls for an open space or a plaza," he's not describing a fix for a dead zone. He's describing a bet that a third plaza, positioned between the other two, will stitch together a stretch of Old Town that currently asks people to walk past a fenced lot to get from one part of downtown to another.
Rutledge was blunt about why visibility matters here. "If you are on Highway 99 or Tualatin-Sherwood Road, how visible is Old Town? Like do you even know it's here?" That's the actual problem the plan is trying to solve. Not a shortage of things happening downtown, but a shortage of people driving past on 99W realizing there's a downtown to turn into.
The Real Obstacle Was Never Foot Traffic
The plan's other two moves are less visible than a plaza, and more telling. The city is looking at fast-tracking building permits for new Old Town businesses, assigning a staff liaison to walk entrepreneurs through the process, and considering system development charge waivers or permit-fee relief. It's also talking about undergrounding the overhead power lines that run along Southwest Pine Street, something property owners have historically avoided because burying those lines has been cost-prohibitive.
None of that addresses whether people show up. It addresses whether a business owner can afford to open the door in the first place. Rutledge said the city's focus is on Pine and Columbia streets specifically, the "two corridors central to access and activity in Old Town." Old Town already has a higher concentration of small, locally owned businesses than the strip malls along Highway 99W and Tualatin-Sherwood Road. What it hasn't had is an easy path for the next one to open.
Cooper Mountain Ale Works is a useful data point here. The brewery opened a Sherwood location attached to the Sherwood Center for the Arts two years ago, a spot that complements its main brewery and pub in Tigard. That's the kind of expansion the strategic plan is trying to make more common: an established local business choosing Old Town as a second location, not because the foot traffic wasn't already there, but because the path to opening was clear enough to take.
What Old Town Actually Runs On Right Now
If the plan's premise is that Old Town has activity but not enough visibility or ease of entry, the current calendar backs that up. This isn't a downtown waiting for something to happen. Clancy's, sitting in the center of Old Town's historic shopping and arts district, runs Old Town Trivia every Tuesday night at 7. BearKat Brewing Company runs Music Bingo. The Sherwood Bookstore anchors a weekly trivia book club and sponsors the community events calendar that tracks all of it, alongside Ziggi's Coffee. Blakeslee Vineyard Estate hosts First Thursdays Live Music. The Sherwood Center for the Arts runs its own rotating schedule of classes, gallery exhibits, and Movies in the Park.
The Dog Stop is a smaller but telling example of what's already working near Old Town. Owned by Cindy Smith and located near Langer's Entertainment Center, it offers boarding, daycare, grooming, and training, and the city spotlighted it this month for American Business Women's Day. Smith's advice to other women considering opening a business was to "take the chance in yourself and always offer the best to your customers." It's a small business that opened, found its footing, and is now the kind of local fixture the strategic plan is explicitly trying to make easier to replicate on Pine Street.
None of this reads like a downtown short on activity. It reads like a downtown with a full weekly rhythm that a lot of people outside Sherwood have never had a reason to notice, because the highway view of Old Town is a fenced lot and some overhead wires, not a plaza.
What to Watch This Fall and Winter
The most immediate marker of where the plan stands is small and easy to miss. The city opened a short call for local artists to table at the 2026 Old Town Sherwood Winter Art Walk, set for Tuesday, December 1. That call closes September 30, so if you've been meaning to apply, this is the window. It's not directly tied to the plaza project, but it's the same instinct at work: using Old Town's existing streets as the venue rather than waiting for new construction to make the case for people to show up.
Longer term, the things to watch are the ones that don't come with a ribbon-cutting. Whether the power lines along Pine Street actually come down. Whether a builder or the city itself breaks ground on the schoolhouse corner. Whether the permit fast-track and staff liaison turn into something a new business owner can point to when they're deciding whether Old Town is worth the paperwork. Those are the changes that will tell you whether the strategic plan reshaped Old Town or just renamed a vacant lot.
The corner at Sherwood Boulevard and Third has been empty long enough that most people who live here have stopped seeing it as anything other than background. The plan on the table would change that, and it would do it by admitting the quiet part out loud: Old Town Sherwood was never short on reasons to visit. It was short on an easy way in.
If you're curious about what a changing Old Town could mean for property values or timing a move in Sherwood, that's a conversation worth having early. Chandler Willcuts has been tracking Sherwood's Old Town plans alongside the rest of the local market and is glad to talk through what it might mean for your own plans, whenever you're ready.
