Central Oregon's Winter PrideFest began with just 150 participants in 2018. By 2023, that number had swelled to 1,400. This year's celebration includes group rides on Mount Bachelor, dance parties, drag bingo, comedy from trans activist and stand-up Ren Q. Dawe, and, of course, a blowout ball headlined by RuPaul’s Drag Race alum Miz Cracker. 

Southern Oregon's chocolate extravaganza hits its 22nd year, with chocolate creations from across the West Coast and no shortage of chocolate-themed events. Beyond demos and talks on the history of chocolate, the science of cacao blending, and how to pair wine with chocolate, expect a bevy of chocolate and confectionery vendors, chocolaty meals and happy hours, and chocolate trivia.

Tryon Creek hosts a full day of lectures, activities, and guided hikes centered on Oregon's owls and their habitats. Participate in arts and crafts, dissect an owl pellet, and learn about the owls that live in this forested ravine in Southwest Portland.

SheBrew's 11th annual festival highlights the work of more than 40 women in the local craft beer and cider industry, drawn from the likes of Wayfinder, Von Ebert, Baerlic, and Bauman's Cider. This year marks the festival’s first foray into spirits,  with the inclusion of Jamie Bones, head distiller and beverage director at Kachka and at the vodka-focused distillery and bar Kachka Fabrika. A separate home brew competition features quaffs from amateur brewers; sample them all and then vote for your favorite. Proceeds benefit the Human Rights Campaign, the country's largest LGBTQ+ lobbying organization, and the Oregon Brew Crew, a home-brewing club headquartered in Portland.

This competitive fundraiser returns to Mt. Hood Meadows to benefit a variety of organizations focused on cancer research, awareness, prevention, and hospice. Teams of five compete for prizes in an alpine downhill race that “rewards consistency and teamwork rather than individual speed.” Each day of skiing concludes with a party—a social bash the first night, with a dinner and auction, and a Monday-night awards ceremony.

Kurt Braunohler, Mia Jackson, Chris Gethard, and Mohanad Elshieky headline the sixth iteration of this comedy festival on the coast. Events take place at the 1920s-era Coaster Theatre, which began its life as a skating rink.

Goofiness is the name of the game at Hoodoo’s decades-old winter extravaganza. The lifts will be open 9am–9pm, but no lift ticket is required for a long slate of alternative activities, including disc golf, axe throwing, musical chairs, three-legged obstacle races, and contests in archery, Hula-Hooping, pie eating, and snow sculpture (the last, alas, appears limited to Hoodoo employees). Don’t miss the Dummy Downhill contest, in which participants send homemade dummies down the slope and over a jump to see whose can withstand the impact. Also on deck: a special dinner, a torchlight descent, and professional fireworks.

Start stretching. The city’s longest-running (get it?) foot race offers options ranging from the one-mile Leprechaun run for kids to a half marathon. Don your best green duds, and don't forget about the post-run party, with a beer garden—participants get their first one free.

Tulip time is among the best times. Grab a good pair of walking shoes and get your camera ready for this annual flower fest, where you’ll find 40 acres of fields blooming with more than 100 varieties, not to mention cutout boards for silly photo ops. Other activities include wooden shoe–making demonstrations, duck races for the kids, and hot-air balloons (if weather allows). For a tipple among the tulips, sip through a flight at the tasting room of Wooden Shoe Vineyards. Dates are currently tentative—tulips can be temperamental—so check the website before setting out.

Whale alert! After wintering in the balmy lagoons of Baja, Mexico, thousands of gray whales are on the move north to Alaska, and for about a week they can be spotted up and down the Oregon Coast. Volunteers will be posted at more than a dozen state parks to help visitors spot these majestic mammals, understand their migration patterns, and record their numbers.

Though there’s no official event commemorating the arrival of the cherry blossoms at Waterfront Park, do take time to amble through the aisle of pretty pink trees. Peak bloom varies depending on the weather, and the display only lasts a few weeks, so expect tons of foot traffic and lots of families and couples posing for photos. (We recommend a weekday visit.)