You're here. Now what do you do? Here's a sure path to not missing out on those Portland moments that might come along only once a year.

Summer

Roll to Rosé

Day trips and weekend getaways to the Willamette Valley wine growing region come in all forms, but it’s hard to beat a summer tasting tour by bike. A loop from Dayton through the Eola-Amity Hills sub-AVA (that’s American Viticultural Area) can include a shady break at Grochau Cellars (pictured above).

Park Yourself

Portland Parks & Recreation has indoor pools open year-round, often with waits of 30 minutes or more for weekend open-swim sessions. In the summer, there’s plenty more splashing to go around when the gates are finally unlocked at outdoor pools at Peninsula Park, Sellwood, Pier Park, Wilson (with its meandering channel and giant frog), and others. Parks & Rec also runs concert series, movie nights, free kids’ lunches, and other activities all summer long. (Don’t need a government agency to tell you how to have fun? Go rogue and start your own picnic club.)

Get Pickled

At Walker Stadium in Southeast’s Lents Park, college baseball players spend their summer on the Portland Pickles, part of a wood-bat league that includes the Port Angeles Lefties and the Walla Walla Sweets. The level of play sure ain’t MLB, but the games are a folksy blast, with wacky promotion nights (like 2017’s Twin Peaks Sheriff’s Department beanie giveaway), cheap beer and food, and the most accessible mascot in amateur sports. If you don’t leave with a picture of Dillon the Pickle (even if he’s just photo-bombing you), there’s something wrong.

Feast on Festivals

For about 10 days in early September, it feels like the eyes (and ears and stomachs) of the world are turned our way. The Portland Institute for Contemporary Art’s Time-Based Art Festival, or TBA, brings performance and experimental artists from around the globe to local stages. It overlaps with the Rose City ComicCon, a three-day pop culture extravaganza at the Oregon Convention Center, and the sprawling culinary festival Feast Portland. Can a human do all three? We’re not sure, but it would be fun to try.

Concert Campout

Every August, a bucolic Happy Valley farm plays home to Pickathon, a three-day music fest that began as an intimate bluegrass affair 20 years ago. These days, attendees number in the thousands, and artists span the musical spectrum—2018 highlights include Broken Social Scene, Shakey Graves, Tinariwen, and the Blind Boys of Alabama. People camp among the trees, spread out blankets underneath the stars, and head-bang in a barn. In short, it’s a music festival for people who don’t like music festivals.

Go by Bike

Not even the occasional June-uary can slow down Pedalpalooza, a volunteer-driven bike fest in which anyone can propose and lead a ride. Organizing themes might include tacos, musical showdowns (Bowie vs. Prince, Run DMC vs. Beastie Boys), and nudity—including the always well-attended World Naked Bike Ride, which certainly ups local demand for pasties and body paint. One Sunday a month from May through September, the city’s transportation bureau closes streets in a different part of town for Sunday Parkways, huge family-friendly two-wheeled rolling community fairs.

Fall

Harvests and Hayrides

Join the steady ribbon of cars headed to Sauvie Island pumpkin patches on October weekends. If the crowds or the lack of a passing lane are too much, make a weekday excursion to this island in the Columbia River, home to the metro area’s densest collection of activity-packed, visitor-friendly farms. Or look a little farther afield: Portland’s urban growth boundary means the city is ringed with working farms in places like Helvetia and Boring. In the fall, you’re never far from a corn maze and a hayride. (Same goes in the summer for berry-picking.)

Bird Ballet

At Northwest Portland’s Chapman Elementary, September is back to school not just for students but for visiting Vaux’s swifts, who dazzle with a twilight aerial bird ballet before plunging into the school’s chimney each evening for a week or two during their southerly migration. Picnicking crowds gather nightly to cheer them on. (According to the Audubon Society of Portland, Chapman hosts the world’s largest roost of migratory swifts.)

Get Lit

November’s one-day Portland Book Festival (formerly Wordstock) brings acclaimed writers—Ta-Nehisi Coates, Maria Semple, and Colson Whitehead are among recent attendees—to town to share panels, talks, pop-up readings, and book signings with some of the best local literary talent. Related shenanigans (with added intoxicants) might include a bar-hopping Lit Crawl, the occasional burlesque performance, and a Sci Fi Karaoke Comedy Horror Bingo Night.

Say Prost!

In the beer year, September is Oktoberfest season. (It can extend into October, too.) Be on the lookout for lederhosen at Oaks Park, Occidental Brewing in St. Johns, McMenamins’ Edgefield, and the blowout fest in Mount Angel, a town 40 miles south of Portland that goes all-in on its Bavarian theme. Similarly timed fresh hop festivals happen in Portland, Hood River, Sisters, and Yakima, Washington.

Catch the Spirit

Home Trail Blazer games are buoyant, loud affairs whether the team is winning or not. Grab some grub at the arena’s local-centric stalls (Bunk Bar, Sizzle Pie, Cha Cha Cha!) and hope for star point guard Damian Lillard to sink one of his patented last-minute game winners. Pregame at Spirit of ‘77—named for the Blazers’ sole championship year—or  quaff a German-style ale at Pints in Old Town, then hop the MAX to the Rose Garden (that’s what old fans call the renamed Moda Center).

Winter

Head for the Hills

You may have noticed that large mountain looming just east of town. That’s Hood, né Wy’east, and winter turns it into a wonderland. Maintained sno-parks can connect you to sledding hills and Nordic trails. (For downhill, get to know Hood’s ski resorts.) Buy a day or annual sno-park pass (required between November 1 and April 30) at the DMV, Bi-Mart, or most major sporting goods stores before you head out. Warm your bones on the way home with roaring fires and mac and cheese at Zigzag’s Skyway Bar & Grill. (No car? The $2 Mt Hood Express bus from Sandy can take you all the way to Timberline.)

Hole Up at Home

On the off chance it snows in town, new residents might be shocked at locals’ inability to deal with a small dusting of the white stuff: schools seem to close at the first sign of a flurry, drivers abandon their cars on the highway.... Be a pro by having a snowpocalypse plan in place. Check the location of your nearest sledding hill (the Rose City Park Golf Course is a Northeast mainstay). Know which corner bars have staff who live nearby and can get there to open up no matter what. Own a pair of boots with some decent traction or get crafty with some DIY crampons, so you can get there, too.

Escape the Gray

The chill and rain might eventually take their toll. At some point, you’ll want to get out of town. It’s still winter there, but Central and Eastern Oregon promise more sun than you tend to find west of the Cascades. Or hop a direct flight to warmer climes: PDX has winter nonstops to Palm Springs, Puerto Vallarta, Maui, Los Cabos, and plenty of other places with vitamin D to spare.

Stay Strong

Northwest winter is a great time to adopt a new indoor exercise routine: take up boxing at the storied Knott Street club inside Matt Dishman Community Center, enroll in Body-Positive Weightlifting 101 at Liberation Barbell, or dance it out with Rock Your Body at Northwest Dance Project. Or embrace what’s going on outdoors on the Worst Day of the Year Ride, held on a Saturday close to February 8, chosen because it held historical records as both Oregon’s wettest day and Oregon’s coldest day. (Yes, the bike ride’s been canceled before due to weather.)

Catch a Flick

February brings a fantasia of film fests. The Portland International Film Festival presents 80-plus features and dozens of shorts in languages from Finnish to Farsi at various cinemas around town. The Cascade Festival of African Films packs a whole continent onto screens at Portland Community College and the Hollywood Theatre, and admission is free! The Hollywood also hosts the Portland Black Film Festival, which highlights local talent and brings in legends like Pam Grier for Q&A sessions. (Or have your own film festival on your couch with a stack of DVDs from SE Belmont Street’s Movie Madness, one of the last, best video stores on the planet.)

Spring

Fix Everything

Want to feel like one of those “creative class” Portlanders you keep hearing about? Grab a jaunty scarf and a cool Euro notebook and hit April’s Design Week, a series of mostly free or cheap workshops, exhibits, and discussions that broaden the idea of what “design” is, and what kinds of problems it can tackle, from gender inequality to homelessness to refugee displacement. (See, we were kidding about the jaunty scarf and cool notebook. Well, mostly.)

Flower Up

No need to wait for the Rose City’s bizarrely traditional Rose Festival (parades, a midway, elephant ears, the crowning of a local high schooler as queen) to get your flower fix. Just outside of Woodburn, the Wooden Shoe Tulip Fest starts the last week of March, luring locals to trudge around in the mud and ogle the bulbs planted in rainbow stripes (weekend bonus: bouncy house, pony rides, etc.).

Get Rolling

More into bruises than blossoms? Spring is especially action-packed for the Rose City Rollers roller derby league, which holds bouts between teams like the Break Neck Betties and the Heartless Heathers. Be warned that you might get hooked and find yourself trying out for a team (or it could happen to your daughter: the Rollers also run junior programs for girls as young as 7). Should that occur, get some skating practice during a regular session (or a karaoke night, or a fitness class, or a date) at the old-school rink at Oaks Park.

Soak Up Sun, Suds

Every year in Portland, there’s that first Friday, usually in April, when the sun is shining and it’s just warm enough to skip out on other responsibilities and sit on a patio with a drink. Try to snag a seat at known (and thus sometimes crowded) quantities like White Owl, Wayfinder, Produce Row, and Rontoms in the Central Eastside; downtown’s Momo; or the rooftop of 10 Barrel Brewing in the Pearl. Or find your own secret patio somewhere, and tell no one.

Watch Spring Get Sprung

By May, drink in wildflower views on hikes in the Columbia River Gorge—try Mosier Plateau on the Oregon side for an easy ramble, or Washington’s Dog Mountain for a real quad burner. (The 2017 Eagle Creek fire still has some Gorge trails closed. Check gorgefriends.org for reopening dates and info on required parking passes.)

Visit Soccer City

Is everyone downtown suddenly wearing a matching scarf? They’re probably on their way to Providence Park. Pro soccer’s Timbers and Thorns both start their seasons in March (schedules for both teams at timbers.com). Every men’s game has been sold out since the Timbers joined Major League Soccer in 2011, and the Thorns (who defend their second league title this year, led by Canadian national team legend and University of Portland alum Christine Sinclair) consistently draw one of the largest (and loudest) crowds for the women’s game in the world.

Top: Grochau Cellars (photo by Isaac Lane Koval)