Note: Reader Theo Hathaway Saner offered this guide to Madison South when I asked for your views on Portland’s coolest neighborhood after TimeOut ranked Kerns among the coolest in the world.
Madison South is one of Portland’s most unique neighborhoods, offering a vibrant mix of open spaces, great food, diverse culture, and plenty of hidden gems.
Note: The neighborhood is just north of I-84 and west of I-205.
Here’s why it stands out:
Open Space and Nature
Madison South boasts among the most open space of any neighborhood in Portland, making it a haven for nature lovers. There are panoramic city views from Rocky Butte's lookout and serenity at The Grotto, a 62-acre sanctuary for reflection and peace.
For outdoor activities, Gateway Green is a favorite spot for mountain bikers and hikers, while Glenhaven Park offers a top-notch skatepark.
Food and Dining Hotspots
Madison South is home to Ki’ikibáa, crowned Portland’s 2023 Restaurant of the Year by the Oregonian for its Yucatecan dishes and inviting atmosphere. Also, Pho Oregon serves up some of the best Vietnamese food in the city.
Hidden Gems
Tucked away on Northeast 85th and Fremont, The Shopeteria is Madison South’s secret bodega with unique snacks and quirky offerings. It’s one of those spots you might miss unless you’re in the know.
Community and Nightlife
Misfits, a LGBTQ+ friendly bar, is a welcoming space for everyone and contributes to the inclusive spirit of the community. (Note: The neighborhood is also known for having one of the highest concentrations of sex workers in Portland.)
Sports and Social Activities
For those looking to stay active, The People’s Courts offers a dedicated pickleball spot that’s become a hit with locals. And for those who enjoy a bit of nostalgia, Rose City Golf Course isn’t just for golfers — it’s a legendary spot known for high school keggers and its role in local history.
