Friendly and ultra-relaxed, the city of Portland, Oregon makes for a cozy vacation destination. Though the city’s metro area is growing, it feels more like a small town, especially since the highly walkable downtown boasts funky coffee shops and independent bookstores. Moreover, the excellent MAX public transit can easily take visitors to almost every corner of the city. Although Portland has a reputation for rain, the weather can actually vary considerably throughout the year. Before booking a stay at one of many unforgettable Portland vacation rentals, check out the things to do and special events available during each season. This can help you decide what to pack to stay comfortable when you go biking across the Steel Bridge in November, or kayaking down the Wilamette River in July.

Visiting Portland In The Summer

Portland defies its rainy reputation in the summer. From June through August, days hover in the 70s and 80s, and the weather is largely dry. The fantastic weather brings out the locals, and the city buzzes with festivals and outdoor events. Check out the Portland Rose Festival, Portland Beer Week, and The Big Float. Summer is also a great time to explore the city’s surprising urban wilderness. Hike the Green Trail in Mount Tabor Park, see the woods in full bloom on the Maple Trail in Forest Park, or rent a kayak from Portland Kayak Company to paddle through downtown on the Willamette River. Light, breathable clothes can keep you dry on outdoor adventures, and a light rain shell is a great idea for cooler days and the occasional rain storm. Book your vacation rentals well in advance, particularly if you’re coming on a holiday or a festival weekend.

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Visiting Portland In The Fall

Portland is tucked into forested hills that burst with color in the fall. The city is beautiful and comfortable this time of year, with mild temperatures that slowly drop from the 70s in September to the 50s in November. Expect plenty of rain, particularly in late October and November, but don’t worry; stay dry by packing water-resistant shoes, a great raincoat, and an umbrella. Follow the locals’ example and explore the city’s fantastic bike trail system with a bike from BIKESHARE or a rental from Waterfront Bicycle.

Fall is a great time for Portland’s booming arts scene. Catch a touring Broadway show at the Keller Auditorium, or check out the Oregon Ballet Theatre’s fall production. If you’re into sports, head to a Portland Trail Blazers basketball game. Other local events include the Portland Film Festival, the Corn Maize on Sauvie Island, and the Portland Fresh Hops Fest, a beer-lover’s dream.

Visiting Portland In The Winter

If you want to feel like a Portland native, winter is a great time to visit. Crowd levels drop, but the city continues to hold festivals and fun holiday events such as the Holiday Ale Fest and the Great Figgy Pudding Caroling Competition in Pioneer Courthouse Square. Downtown Portland comes into its own in the winter. Cozy breweries and welcoming shops glow enticingly along the streets, giving the area a charming, small-town vibe that’s surprising for a city of its size. Temperatures usually sit in the 30s and 40s, and rain is frequent, but the MAX light rail makes it easy to get around. Alternatively, you can do as the locals do: flip up your hood and enjoy the walk. Stay comfortable and dry with a warm, water-resistant jacket and boots, as well as a hat, gloves, and umbrella.

After Christmas and New Year’s, Portland continues the festivities. Experience the wild Lunar New Year celebrations in January, take an illuminated bike ride through the light-bedecked city during the Portland Winter Light Festival in February, or head indoors during February’s Portland Jazz Festival.

Visiting Portland In The Spring

For lovers of natural beauty, spring is one of Portland’s most spectacular seasons. Pops of color lie around every corner as the cherry trees, roses, and azaleas start to bloom. This is a fantastic time to visit the Portland Japanese Garden and the International Rose Test Garden. The weather is unpredictable, with rain showers and bursts of sun happening in the same hour. Rain gear is a must, and it’s a good idea to pack warm clothes for temperatures that sit in the 40s and 50s. As May approaches, you can often get away with a light jacket.

In March, experience Portland’s world-class dining scene with Portland Restaurant Month, or see the tulips bloom during the Wooden Shoe Tulip Festival in nearby Woodburn. May brings the exciting Cinco de Mayo Fiesta, when Tom McCall Waterfront Park comes to life with traditional Mexican music, dancing, and food.

When Is The Best Time to Visit Portland?

The lovely weather and low rainfall in June, July, and August make summer the best time to visit Portland. In fact, the season is one of the Pacific Northwest’s best-kept secrets; locals come out en masse to partake in the sunshine and the summer festivities, giving you the chance to join in the fun, offbeat culture. The summer months also make it easy to take advantage of Portland’s unique urban wilderness environment. Spend your days hiking in Washington Park, watching the animals at the Portland Zoo, or biking along the Willamette River in the sunshine.

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