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eNRG Kayaking, Willamette Falls kayaking tour
Ithaca Janzen | 07/08/2021 | Trip Ideas

Willamette River to Main Streets: Day Trip

The Willamette River is a cornerstone of Oregon, flowing 187 miles from Eugene to Portland with many twists, turns and surprises along the way. When paired upw ith the friendly local main streets in Milwaukie, Oregon City, West Linn and Lake Oswego, you are in for a perfect day of small town charm and water delights. 

Read on for the Willamette River to Main Streets day trip itinerary, or click the image below to download the PDF itinerary - perfect for on the go!


*Before you go, check the hours of operation and note any additional considerations for each location.


1. Milwaukie

Begin your day in beautiful Milwaukie, known for its dogwood trees and 20+ vendors at the Milwaukie Farmers Market. Every Sunday from May - September you can find produce perfect for a picnic, fresh cut flowers, gift items and delicious prepared foods. We recommend picking up some breakfast here and taking it across the street to enjoy along the river at Milwaukie Bay Park. Not visiting on a Sunday? Not a problem! There are great coffee shops and cafes in town for take-out breakfast treats. We recommend Ovation Bistro or Gramma's.

Milwaukie Farmers Market Strawberries

2. Oregon City 

After filling up on breakfast it's time to adventure south along the river to Oregon City where you can rent a SUP or kayak (or join a tour) with eNRG Kayaking and paddle all the way up to iconic Willamette Falls along the Willamette River Trail. Next, head to newly opened Corner 14 Food Carts, located next door to Oregon City Brewing and Tony's Fish Market. Corner 14 has lots of outdoor seating to choose from. While in town, check out main street for shopping or maybe a ride on the Oregon City Municipal Elevator. Visiting on a weekend? Don't miss the Museum of the Oregon Territory.

Willamette Falls Panorama

3. West Linn

Time to cross the river over the Arch Bridge and head to West Linn for a relaxing glass of wine at Campbell Lane Winery, a stop on the Mt. Hood Territory Wine Trail. Wine not your preferred beverage? Check out Historic Willamette Main Street for great beer and cider options. 

Family enjoying the outdoor garden area at Campbell Lane Winery

4. Lake Oswego

Don't miss a stop at The Rogerson Clematis Garden on your way to Lake Oswego where you can stroll paths through over 850 varieties of clematis flowers, making this one of the most comprehensive clematis collections in North America. Feeling a bit peckish? There are a gunch of great outdoor dining experiences in Lake Oswego, like Pizzeria sul Lago, or opt to get dinner to go and enjoy at a nearby park. As you walk through downtown, you will find yourself in an outdoor art gallery! Admire Gallery Without Walls, a rotating series of sculptures as you make your way back to the Willamette River to end your evening riverside at Foothills Park or George Rogers Park.

Visitor Admiring Blooms at Rogerson Clematis Garden

Ithaca enjoys camping, hiking, local craft beer or just hanging out at home with her pet hedgehog, Hazel. Her role at Mt. Hood Territory includes coordinating the Tap Trail and Wine Trail and creating inspirational travel content.

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