June 5—7

Ring in the season

According to us, summer starts the first day of June—calendar and lingering rain be damned! To kick off yet another glorious Portland summer, begin with a spin through the First Friday art walk, the east side’s grittier answer to First Thursday. Start in the light-filled Gallery at the Jupiter, then stroll over to Redux to ogle local handmade jewelry and art. Finish up at One Grand Gallery on Burnside before assuming your post at Le Pigeon’s famed chef’s counter for a well-earned feast. Saturday brings the Rose Festival’s Grand Floral Parade—but if you’d prefer solitude, hightail it to Pechuck Lookout, a savior of spontaneous summer adventure perched 4,338-feet up a fir-bristled hill in the Table Rock Wilderness, 60 miles southeast of town. The lone surviving stone fire lookout in Northwest Oregon, Pechuck sits at the end of a trail lined with blooming rhododendrons in June, and the tower’s compact size belies its vast rewards: panoramic views and a planetarium’s worth of stars each night. (And it’s first come, first served for hopeful campers, so get there early!) Head home via Estacada and drop in to Fearless Brewing Company, home to one of the state’s best burgers and a fine Scottish ale. Back in the city, celebrate the Rose Festival your own way, with an aromatic evening stroll through Washington Park’s always-lovely
International Rose Test Garden.

June 11—14

Get loud & be proud

This year, the Portland Pride Festival kicks off Thursday night with a white-hot burst: Portland Monthly’s own Flare, featuring Spinderella (yes, that one!) on the turntables, glowing geodesic domes, and the city’s finest cocktails. And if you dance like we hope you do, you’ll need a touch of fresh air and open space to revive you on Friday. Stretch those legs out on the scenic 12-mile bike loop around Sauvie Island, that agricultural oasis just 10 miles northwest of downtown. Point your wheels toward Collins Beach at its northern terminus, where you can elect to either strip down to your birthday suit in the nude section (it is Pride, after all), or play it safe and keep that bathing suit on. For an après-beach treat, swing by Bella Organic farm to pick a few pints of strawberries at their peak—paired with a bit of rhubarb, they’ll fuel the ultimate early-summer pie. Come Saturday, the Portland Fruit Beer Festival descends upon the parking lot at Burnside Brewing Co. Sunday is a day for low-key thrills, and there’s no better place to indulge than Oaks Amusement Park, where bumper cars, mini golf, and vintage carnival games offer a sweet dose of youthful nostalgia.

June 19—21

A celebration of light!

An “immersive rave” with the world’s largest wading pool, a hookah lounge, and electronic music out in the Gorge, basking in the shadows of Mounts Hood and Adams? Well, sure! What The Festival’s fourth year should bring more of the artistically inclined, light-on-the-land, carnivalesque brand of fun that’s already lofted WTF to international acclaim on the festival circuit. Plus, showers and yoga and tea! But because a full weekend of raving in the sunshine can be, well, overwhelming, we won’t judge you for departing early to observe the summer solstice from the quieter sanctuary of your home on Sunday. We recommend jumping aboard a midmorning kayak tour with Alder Creek, which launches you from the Eastbank Esplanade on a three-mile paddle around Ross Island, where you’re likely to spot a good few of the 100 species of migratory birds that summer here, including bald eagles and great blue herons. Finish your splendidly chill day with a cold one in hand at the recently revived Skyline Tavern, where Ping-Pong, horseshoes, a DIY grill, and verdant views over the canopy of Forest Park offer the perfect punctuation for the longest day of the year.

June 25—28

Highbrow, lowbrow & everything in between

This weekend starts early, with Thursday evening’s LitHop PDX, a (you guessed it!) literary barhop with 54 mini-readings at six different downtown venues. Keep that high-minded fun swinging into the weekend with a stroll through the 

Portland Art Museum, where the fourth Friday of every month is not only free but also likely to contain rowdy photo booths and a pop-up pub. Continue your classy evening about town at Summer Splendors, NW Dance Project’s annual collaboration with Chamber Music Northwest at PSU’s Lincoln Performance Hall. But still, the night is young! Lest you forget, Friday night is that Portlandiest rite of passage, the World Naked Bike Ride, and if you’re not riding you must at least seek out the singular awkwardness of watching as thousands of bikers cruise by in the buff. On Saturday, skip town for the Lincoln City Summer Kite Festival, where the skies fill with futuristic flying objects, followed by a jaunt over to Cape Meares via the Three Capes Scenic Route, where Big Spruce and the Octopus Tree offer arboreal inspiration. Sunday brings a bit of park-hopping: first, the International Beerfest in Holladay Park, and then Peacock in the Park, the heavily sequined, family-friendly drag extravaganza at the Washington Park Amphitheater.