If you have lived in Sherwood for more than a couple of years, you already know Old Town runs on a small set of familiar addresses: Clancy's, Symposium, the library, the splash pad at Cannery Square. What has shifted in 2026 is not the addresses. It is the city's intent for what can open next to them, and the first businesses that have actually followed through.
The short version: Old Town is being deliberately reshaped into a walkable food-and-wine district, and the retail energy along Tualatin-Sherwood Road is now doing something noticeably different from what is happening on Pine and 1st. Here is how to read the summer as a resident.
The plan that just changed what can open where
On May 19, 2026, the City Council adopted the Old Town Strategic Plan, aligning it with Sherwood's 2040 Comprehensive Plan and focusing it on preserving historic character, supporting local businesses, and improving public spaces. That vote turned a years-long conversation into policy.
The specifics matter for anyone who walks these blocks. Community development director Eric Rutledge has said the city is targeting food, drink, and especially wine businesses as Sherwood establishes itself as the gateway to wine country and is surrounded by local wineries in the Willamette Valley. On the ground, the most concrete move is a search for a tenant on the vacant pad in front of the Sherwood Center for the Arts on Pine Street. Rutledge described it as a 4,500-square-foot space that could accommodate multiple tenants, with a feasibility and conceptual design study due by year end.
Read that as a signal. If you have wondered why the city has been quiet about parking meters and loud about wayfinding signage, this is why. The plan leans on non-financial incentives such as fast-tracking building permits, a staff liaison for future entrepreneurs, and possible system development charge waivers or permit-fee relief if the council approves. Cheaper, faster paperwork for the kind of tenant they want.
OLEA on 1st Street is the first visible proof
The clearest evidence that the plan is working showed up on July 8, when the Sherwood Area Chamber of Commerce held a ribbon cutting for the OLEA Vineyards tasting room at 16017 SW 1st St, described as Old Town's latest addition.
This is not a new label. Olea Vineyards, located at 17406 SW Parrett Mountain Rd, specializes in Estate Grown Pinot Noir from the Chehalem Mountains AVA, and the estate has always been by appointment. The Old Town room is a downtown extension of a Parrett Mountain producer, which is exactly the type of tenant the strategic plan named on paper. If you have not been up to the estate, the winery was founded by Tom and Melinda Melillo as a creative extension of their indie record label Olea Records, with private seating indoors and out and a patio firepit that looks toward Mt. Hood across the vineyards. The 1st Street room brings that idea into a walking radius of the library.
Cooper Mountain, the arts center, and the anchor problem
If OLEA is the newest proof, the working prototype is Cooper Mountain Ale Works. Two years ago, Cooper Mountain Ale Works opened a Sherwood location attached to the Sherwood Center for the Arts, a venue that complements the business' main brewery and pub in Tigard. That single lease showed the city that a beverage-forward operator paired with the arts center could hold weekend traffic in Old Town after 5 p.m.
That is the anchor Rutledge is now trying to replicate on the Pine Street pad. He has been direct about the visibility problem, asking whether motorists on Highway 99 or Tualatin-Sherwood Road even know Old Town is here. The bet is that clustering wine tasting, brewing, and arts programming gives someone driving past a reason to turn.
"We really want Old Town to be a walkable and vibrant place… We want it to be a destination for local residents." — Eric Rutledge, Sherwood community development director
Saturday mornings still belong to Cannery Square
None of this changes the rhythm of the market. The Sherwood Saturday Market runs Saturdays, May through September, 9 a.m. to 1 p.m., at Cannery Square, 22622 SW Pine St, next to the library. If you are new to the schedule or trying to plan around it, a few practical notes:
- Farm vendors must grow or produce 70% of their product, which is why the produce table looks like a farm stand rather than a resale operation.
- The market is closed on Cruisin' Sherwood and Robin Hood Festival weekends, so plan accordingly.
- The market runs a Young Entrepreneur Youth Booth program that gives school-age vendors a place to try selling. Worth a stop with kids.
- Cannery Square itself has a water feature the kids can play in, grass and covered benches, and a low water bowl for dogs.
For context on the summer calendar around it, the Robin Hood Festival ran July 17 to 18, 2026, in Old Town, a continuous tradition since 1954. That is the weekend the market takes off. August largely belongs to the car-show crowd at Langer's on the other side of town.
Meanwhile, the Langer's corridor is doing something else
The retail action along SW Langer Farms Parkway is telling a parallel but different story. On June 20, 2026, the first Stella's Ice Cream franchise in Oregon opened in Sherwood at the Langer's shopping center, run by owner Jenifer Nelles. The menu leans local where it can. Alongside the standard flavors, there are Oregon-themed pours like duck pond, Oregon trail, beaver dam, and Sherwood forest, plus dairy-free and gluten-free options. Address, for the record, is 21650 Southwest Langer Farms Parkway.
That opening was one of a cluster. KinderCare, Stella's, and Oregon Pediatrics fill out the 36,000-square-foot Parkway South Retail Center, and Komo Sushi relocated to Parkway South from the Sherwood Plaza Shopping Center, which then allowed the Sherwood Liquor Store to expand. The counter-story: Killer Burger, the Portland-grown gourmet chain, closed its Sherwood location on Nov. 15 after opening in 2015, in a market with at least 10 other Sherwood restaurants offering similar fare.
Put those side by side and a pattern emerges. Old Town is being steered toward independent, wine-adjacent, walk-up operators. The Langer's corridor keeps absorbing regional chains, medical tenants, and family destinations. Neither is worse. They serve different Saturdays.
How to string a Saturday together as a resident
If you want to actually use what has changed this summer, here is a sequence that respects the walkable geometry the city is trying to build:
- 9:15 a.m. Park once near Cannery Square. Coffee at Symposium, which features Stumptown and Coava Coffee Roasters and Steven Smith Teamaker.
- 9:45 a.m. Walk the market. Grab produce first, flowers last so nothing wilts.
- 11:30 a.m. Lunch at Clancy's, in the center of Sherwood's historic Old Town shopping and arts district, serving home-cooked classics and daily specials.
- 1:30 p.m. Book an afternoon slot at OLEA's 1st Street room, or drive up to the estate at 17406 SW Parrett Mountain Rd if you want the Mt. Hood view. The tasting fee is $20 per person, waived with any wine purchase.
- 5:00 p.m. Cooper Mountain Ale Works before an evening event at the Sherwood Center for the Arts.
- 8:30 p.m. Detour to Stella's on Langer Farms on the way home. Try the Oregon Trail; the owner has said it is her favorite.
That is six stops, one parking maneuver in Old Town, and one on the Langer's side. It uses the district the way the plan assumes you will.
What to watch next
Two things worth tracking as a resident. First, the Pine Street pad. Rutledge has said the building could be single-story or two-story, flex space or retail, possibly a restaurant or events center, and is meant to complement the arts center. The feasibility work is meant to wrap by year end, which puts a real tenant conversation into 2027.
Second, the utility question. Undergrounding overhead power lines along Southwest Pine Street has been discussed as a way to make Old Town more attractive, though burying those lines has historically been cost prohibitive for property owners. If that changes, expect the streetscape to look different in photos a year from now.
For homeowners here, the practical takeaway is simple. The district you walk on Saturday morning is being shaped on purpose, and the businesses that opened in the last six weeks are the first legible chapter of that plan.
If you are curious how these Old Town changes are showing up in what buyers ask about your street, or what your home would be worth against the current Sherwood backdrop, the team at Ty Lankheet is happy to walk you through it. Get a Free Home Valuation whenever you are ready.
