Top 10 Cities in Clackamas County to Consider for Your Next Move

If you’re looking to move to Clackamas County, you’ve probably realized something quickly: it’s huge, and every town has a completely different personality. From riverside history to rural acreage, there’s no single “best” spot—just the spot that fits your life best.

Here are 10 cities (in no particular order) that offer a distinct slice of Pacific Northwest living, to help you build your shortlist.

1. West Linn

Set on the hills overlooking the Willamette River, West Linn is known for its established neighborhoods, winding roads with views, and extensive parks.

• Vibe: Quiet, green, and scenic.

• Best for: People who love river recreation and a purely residential feel without a loud nightlife scene.

2. Oregon City

The end of the Oregon Trail is having a major moment. With a revitalized Main Street, the historic municipal elevator, and Willamette Falls, it mixes grit and history with trendy new dining.

• Vibe: Historic, proud, and community-focused with a quickly growing downtown scene.

• Best for: Buyers who want walkability and character rather than a cookie-cutter subdivision.

3. Lake Oswego

Famous for its private lake (accessible to certain easements) and a very walkable, flower-basket-lined downtown area featuring high-end shopping and dining.

• Vibe: Polished, manicured, and resort-like in the summer.

• Best for: Those who want a “village” feel with upscale amenities close to Portland.

4. Wilsonville

Sitting right on I-5, Wilsonville is a gateway between Portland and Salem. It feels planned and organized, with diverse housing stock, tech jobs, and the WES commuter rail.

• Vibe: Modern, convenient, and active.

• Best for: Commuters who need easy freeway access and love well-maintained community parks.

5. Canby

Separated from the metro sprawl by a buffer of farmland, Canby feels like its own independent town rather than a suburb. It hosts the County Fair and is surrounded by nurseries.

• Vibe: Small-town agrarian roots with a strong independent streak.

• Best for: People who want a slower pace and a true “hometown” feeling.

6. Happy Valley

One of the fastest-growing areas, known for newer large-scale construction, sweeping valley views, and convenient shopping centers.

• Vibe: New, spacious, and master-planned.

• Best for: Buyers looking for modern homes, reliable utilities, and predictable layouts.

7. Milwaukie

Just south of Portland, Milwaukie has excellent MAX light rail access and a riverfront that’s being rediscovered. It has a bit of an “Old Portland” feel—unpretentious and green.

• Vibe: Retro, approachable, and connected.

• Best for: Commuters who want a quick trip to downtown Portland without the price tag of inner neighborhoods.

8. Molalla

Further south, Molalla is the gateway to the Cascade foothills. It’s known for the Molalla Buckeroo Rodeo and affordable access to acreage.

• Vibe: Rural, rustic, and wide-open.

• Best for: Those seeking land, horse property, or a genuine country lifestyle.

9. Sandy

Perched on the way to Mt. Hood, Sandy is where the suburbs truly give way to the mountains. It famously has its own high-speed fiber internet utility (SandyNet).

• Vibe: Mountain-town rugged meets high-tech connectivity.

• Best for: Remote workers who love skiing, hiking, and trees.

10. Estacada

Located along the Clackamas River, Estacada has transformed from a timber town into an arts and recreation hub.

• Vibe: Artistic, outdoorsy, and tucked away.

• Best for: Kayakers, artists, and anyone wanting to be away from the I-5/I-205 traffic corridor.

Keeping it real (estate): No such thing as "perfect"

Every city on this list has trade-offs—commute times, price points, or noise levels. The best way to choose? Don’t just look at online stats. Go have coffee in the downtowns, drive the commute at 5:00 PM, and see which vibe actually matches you.

Fair Housing Note: As a real estate professional, I don’t steer buyers toward or away from communities based on demographics, nor do I label areas as “good” or “safe.” My job is to help you identify the lifestyle factors that matter to you—commute, lot size, amenities—and find the location that delivers them.