Portland Summer Picks | The Benson Hotel

Portland Summer Picks

Summer in Portland may be one of the world’s best-kept secrets. Days are long and dry, temperatures are comfortably warm, and the city makes the most of these conditions with outdoor celebrations and exciting things to do running well into September. From cars to craft beer, contemporary art and music, to the internationally acclaimed culinary scene, Portland packs the sunniest season with festivals and events that celebrate the best of the Rose City. Here’s our top picks for things to do, see and experience during a summertime visit to Portland.

May 26 – June 11
Portlanders and visitors alike are invited to celebrate Portland’s floral heritage and community spirit with the return of the annual Rose Festival. Time-honored traditions include the Grand Floral Parade, Starlight Parade, Junior Parade, Rose Festival Court and Queen’s Coronation. CityFair is considered the “hub” of the annual Rose Festival, with carnival rides, concerts, food and fireworks for multiple weekends at Waterfront Park.

June 2-4
The Oregon Brewers Festival is one of the nation’s longest-running and best loved craft beer festivals, and is considered a craft beer destination. On a sun-soaked afternoon, there’s no better place to sip independent craft beers, cider & wine with friends along the banks of the Willamette River, with the Portland skyline as the backdrop.

June 8-12
Since the very beginning of the Rose Festival back in 1907, visiting ships and other fleet-related elements (like submarines) have been making their way to Portland’s waterfront for Fleet Week. The City of Portland is known to be a favorite port of call for military (and non-military) visitors — and citizens enjoy making these visitors welcome! The greatest purpose of Fleet Week is to celebrate and thank our active, reserve and veteran military personnel. The Benson Portland, Curio Collection by Hilton, is offering military discounts in honor of Fleet Week. Learn more here.

June 10
The brunch-time party of the year returns for year #5 at the Bloody Mary Festival. Don’t miss PDX’s best Bloody Marys & more – all under one roof – for one day only! Unlimited tastes of creative Bloody Marys, craft spirits, artisan food samples and live music. Age 21+.

June 24
Check out hundreds of “Lowrider” cars transformed into cultural expressions and the dedicated aficionados who make and drive them at the Lowrider Super Show.

June 30 – July 2
The Portland Craft Beer Festival at the Fields Neighborhood Park features the broadest selection of local beers, ciders and wine, all crafted within the city limits of Portland. Enjoy various genres of fabulous offerings from Portland-based food carts too!

June – August
Portland’s cycling culture peaks during summer’s multi-week Pedalpalooza, featuring 200+ local-led, themed rides, all open to the public.

July 1-4
The Waterfront Blues Festival is Portland’s largest and longest-running music celebration. Feel the energy and experience over 100 acts on 4 stages, over 4 days.

July 15-16
The Portland Pride Festival attracts thousands of visitors to Portland each year and brings significant visibility for our region’s LGBTQ+ community. Pride Northwest is particularly committed to providing the Pride celebration in order to create a safe and celebratory environment for our young people. Not only do things get better, Pride is what better looks like!

July 15-16
Rose City Vintage Market teams up with Left Coast Revivals to presents the finest vintage dealers in the west, indoors and outdoors at the Portland Expo Center for two spectacular days of hunting and gathering home decor, fashion, accessories and other collectibles. Featuring antiques, Midcentury, Americana, and a whole lot more.

August 3-6
The Pickathon Music Festival is an annual three day music festival located just outside of Portland in Happy Valley, Oregon on Pendarvis Farm. Occurring every August since 1999, the festival has featured a variety of artists and genres including: Indie, Rock, Rap, Folk, and Bluegrass.

August 5
Join the Oregon Chinese Coalition for the 2023 Chinese Festival in the Square. Celebrate Chinese American culture and enjoy nonstop entertainment, delicious Chinese food, authentic arts and crafts, and much more.

August 26
The 6th Annual Taste of Motorsports Experience is a day filled with fast cars, fine food, fantastic scenery and fabulous friends. The art of motoring will be celebrated by the automakers, dealers, clubs and enthusiasts. Celebs and motorsports royalty will mingle with fellow enthusiasts on and off the track.

Make the most of Portland’s epic summer season right in the heart of the city. The Benson Portland, Curio Collection by Hilton offers you comfort, luxury and proximity to your best summertime picks. Take advantage of early savings on your summer getaway here.

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