Although the Rose City is attractive all year round, the peak season from June to August is the best time to visit Portland. It shows sunny weather, clear blue skies, and street fairs galore. Explore the Oneonta Gorge or take part in the World Naked Bike Ride—a bevy of outdoor activities are here for you. Just make sure you book your room in advance. The fall sees a gradual drop in temperatures and tourist flow. September in Portland still can be quite busy, but October is pure heaven for bargain hunters. Winter in the city means the weather at its chilliest and rainiest but also excellent deals on accommodation. Choose White River West Sno-Park if you’re a passionate winter sports lover. Pack some layers and rain gear if you’re coming to Portland in spring as it comes with rising temps and occasional rain. March through May also means fantastic flower blooms, so don't miss Wooden Shoe Tulip Fest in Woodburn.