Sherwood Old Town | First Forty Feet

Old Town Strategic Plan

Sherwood, Oregon | 2024-2026

Robin Hood May Be the Legend, But Old Town is the Real Treasure

In 1891, Robert Alexander suggested the name “Sherwood” because the surrounding Oregon woods reminded him of England’s Sherwood Forest. That identity lives on through the Robin Hood Festival, which continues to bring people, activity, and tradition into Old Town.

Old Town is Sherwood’s historic, civic, and cultural heart. Its walkable streets, local businesses, gathering places, and strong community identity provide the foundation for a more active and connected town center.

First Forty Feet worked with the City, residents, business and property owners, and technical partners to create an action-oriented strategy for the district’s next chapter. The plan brings community priorities, market realities, infrastructure needs, and development opportunities together in a five-year roadmap focused on access and arrival, business health and growth, and coordinated infrastructure and redevelopment.

What route would you walk or bike to Old Town?

What types of businesses are missing in Old Town?

What attracts you to Old Town?

Finding the Way to Old Town

Old Town is close to major streets, neighborhoods, parks, and trails, but limited visibility and fragmented routes can make it difficult to find. The plan establishes a hierarchy of gateway, directional, and destination signs to guide people from Sherwood’s primary corridors into the heart of the district.

Connecting the Community

Existing paths already connect Old Town with parks, schools, neighborhoods, and regional trails. By filling key gaps and organizing these routes into a series of walk, bike, and roll loops, Sherwood can make everyday trips clearer, safer, and more inviting.

Focus Investments Where it Matters

The plan concentrates infrastructure and redevelopment efforts along SW Pine and SW Columbia Streets. Extending Pine Street’s curbless design, activating vacant sites, and creating a new front door along Columbia Street can support new businesses, housing, and public life while strengthening Cannery Square and Old Town’s existing destinations.

Reconnect Old Town Across the Tracks

A pedestrian crossing at Washington Street would restore a direct link between the Arts Center, public parking, Railroad Street, and neighborhoods south of Old Town. The plan positions the City to work with ODOT Rail, the railroad owner, and operator to explore a safe crossing and a future rail-trail connection.

A New Northern Gateway

At SW 3rd and Pine Streets, Sites A and B can establish a more visible northern entrance to Old Town. New mixed-use buildings would frame both streets, bring active ground-floor uses to the corner, and create a public gathering space that complements Robin Hood Plaza and Cannery Square.

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Activate First & Pine

Site C occupies one of Old Town’s most prominent intersections at SW 1st and Pine Streets. The plan envisions a building oriented to both streets, with an active retail ground floor and housing or offices above—adding activity, reinforcing the street edge, and supporting the historic commercial district.

A Five-Year Roadmap from Vision to Action

The Old Town Strategic Plan turns community priorities into a coordinated set of near-term actions. Thirteen actions organize the work around arrival and connectivity, business health and growth, and infrastructure and development; giving the City clear steps for advancing projects, partnerships, policy changes, and investment.

Together, these actions create a practical path for honoring Old Town’s character while making room for new businesses, homes, public spaces, and connections. The result is a roadmap for keeping Old Town at the heart of Sherwood’s civic, cultural, and economic life.