Portlanders love a good festival, particularly if it celebrates beer, bikes, music, or that favorite local pastime—devouring delicious treats. If you don’t mind the rain, November, December, and January are great times to secure cheap hotel rates and catch seasonal attractions. Following the rainy months, ski season is often at its height between January and March.

In the zoo after dark, colored lights make up animal shapes like a hippo and crocodiles.

Each winter the Oregon Zoo celebrates the holidays with festive lights. Photo © Sam Churchill, licensed Creative Commons Attribution.

Coastal Storm-Watching

Whether you head to the Columbia Gorge or the Oregon Coast, you’re not far from some pretty spectacular storm-watching. Come January and February, there’s nothing like holing up behind a grand picture window by a warm fire while Mother Nature puts on a show.

Fertile Ground Festival

This annual festival of new works, which is held in January, is a fine example of why Portland is becoming a launch pad for creative and exciting new plays.

COST: Free

All right, so January in Portland isn’t exactly a “showcase” month. Tourism is down, the skies are gray, and the weather is, at best, unpredictable. It’s tempting to sulk about the house, but frankly, a whole month indoors is just not natural for most Portlanders. Thank goodness this city is full of creative folks who are not willing to give up on January. Thanks to them, the city suddenly has a reason get out of its collective pajamas and experience something truly original. In 2008, Portland launched its first citywide performing arts festival devoted entirely to new works. More than two years in the making, this ambitious 10-day event unites more than a dozen performing arts groups to present a series of world premiere productions. Portland has always been a “fertile ground” for playwrights and premiere performances, so it’s no surprise that so many companies are consistently able to develop their seasons around the idea of producing something new and groundbreaking during this event. —p.132, Festivals and Events, Moon Portland

The Grotto

More than half a million lights illuminate the National Sanctuary of Our Sorrowful Mother, a Catholic sanctuary that is more commonly called The Grotto. It’s a breathtaking sight that you don’t have to be Catholic (or celebrate Christmas) to enjoy.

8840 NE Skidmore St., 503/254-7371
COST: $9 adults, $4 children ages 3–12, free parking

For more than 20 years now, The Grotto, a 62-acre Catholic shrine and botanical garden, has hosted the Festival of Lights, which is open nightly from around Thanksgiving through December 30 (except for Christmas Day). The spectacle features 150 musical performances, more than 500,000 lights, petting zoos, puppet shows, carolers, family entertainment, and more. Local choirs perform at the Chapel of Mary, a remarkable cathedral constructed of rock quarried from a cliff; it’s an awe-inspiring display of polished marble, magnificent statues, and beautiful murals, and the acoustics are said to rival some of Europe’s finest cathedrals. During the festival, The Grotto is open nightly 5–9:30 p.m. ——p.127, Festivals and Events, Moon Portland

Holiday Ale Festival

Toast the dark, cold month of December at the only beer festival in the Northwest to be held outdoors in Pioneer Courthouse Square. There are usually 30–40 beers on tap, all of which are special-edition winter ales.

Pioneer Courthouse Square
COST: $30

Who says you can’t have a beer festival in December? The Annual Holiday Ale Festival features some of the season’s best craft beers (with names like Auld Nutcracker, Lumpa Coal, Ebenezer, and Sled Crasher). Held at Pioneer Courthouse Square, the event manages to get pretty heated, despite the chilly temperatures. A large, clear tent keeps patrons dry but allows views of the city. Beer lovers sample robust brews, listen to seasonal music, and warm themselves by the gas heaters that surround the city’s enormous holiday tree. Don’t miss the third annual Brewers Brunch (tickets can be purchased on the website), where breakfast and local and imported beers not otherwise available at the festival are served. ——p.134, Festivals and Events, Moon Portland

New Year’s Eve with the Portland Winterhawks

At the turn of every year, Portland’s hockey team hosts the Seattle Thunderbirds in what can easily be categorized as a civil war. The game starts at 8 p.m. and is a good way to ring in the new year with the family.

Memorial Coliseum, 300 N. Winning Way, 503/238-6366
The Portland Winterhawks are a major junior ice hockey team that plays in the Western Hockey League, which is based in Western Canada and the Pacific Northwest. It is one of three leagues that make up the Canadian Hockey League, the highest level of non-professional hockey in the world. Most home games are played at the Memorial Coliseum, though typically a few games each season are also played in Rose Garden Arena. ——p.142, Recreation, Moon Portland

The Nutcracker

Every year, Portlanders know that the holiday season has begun when the Oregon Ballet Theatre begins dancing The Nutcracker. The production is a holiday tradition that families flock to every year and is the only West Coast production of George Balanchine’s version of the famous ballet.

Keller Auditorium, 222 SW Clay St., 503/227-0977

Oregon’s premiere classical dance company, Oregon Ballet Theatre (OBT) was the product of a 1989 merger of Ballet Oregon and Pacific Ballet Theater. At the time, James Canfield, a former dancer with Joffrey Ballet, served as artistic director, and under his direction, the company repertoire grew to comprise over 80 ballets, from evening-length works to contemporary pieces. Every holiday season, the company performs the West Coast production of George Balanchine’s The Nutcracker, which includes OBT’s full company and nearly 100 students from the OBT School. ——p.122, The Arts, Moon Portland

Portland Jazz Festival

The city of Portland has a long and vibrant jazz history. This annual multi-venue festival features headlining talent such as Wayne Shorter, McCoy Tyner, Dianne Reeves, Regina Carter, Tom Grant, and Eddie Palmieri, along with a number of free showcase performances highlighting regional talent.

COST: $15–130

Held every February, the Portland Jazz Festival showcases local talent, as well as widely known performers like Branford Marsalis, Esperanza Spalding, Bill Frisell, and Charlie Hunter. Spread out over various venues around the downtown area, the festival offers a unique look at both the future and history of jazz. It’s not uncommon to see up-and-coming musicians take the stage with the legends who inspired them in the first place. Ticket prices for the headliners can run about $30–60, but there is something in it even for jazz fans on a budget. The festival always offers a number of free and low-priced music performances, jam sessions, films, lectures, and exhibits. ——p.134, Festivals and Events, Moon Portland


If you see hundreds of Santas parading the streets of Portland singing, shouting, and behaving badly, you have stumbled upon Santacon. This guerilla-style pub-crawl/march is all about creativity, spontaneity, and a little bit of harmless debauchery.

COST: Free

If you are visiting Portland in December, and you happen to see a large gathering of people dressed like Santa, don’t be alarmed. You are simply witness to one of the city’s most mysterious and talked-about events: Santacon. Each December in Portland, revelers dress up as Santa and engage in a day-long pubcrawl that takes them to several bars, a few parks, and the occasional stop for (relatively) innocent mischief. The event is so popular, it has spawned a number of copycat events. As such, the details of when and where the Santas meet is kept very much a secret until right before the event. Joining the crawl isn’t hard if you do your research and make sure you are following the right event. While you are there, be sure to behave yourself in a manner befitting a true Portland Santa (don’t be a jerk, bring cash, and above all, be nice to the city and your fellow Santas). ——p.135, Festivals and Events, Moon Portland

Ski Season

Oregon has the longest ski season in North America thanks to all that precipitation. Putting up with a little rainfall in the city means an opportunity to carve some serious powder on the slopes of Mount Hood.

Mt. Hood Skibowl (87000 E. Hwy. 26, Government Camp, 503/272-3206, Mon.–Tues. 3–10 p.m., Wed.–Thurs. 1–10 p.m., Fri. 9 a.m.–11 p.m., Sat. 8 a.m.–11 p.m., Sun. 8 a.m.–10 p.m.) is one of three major ski resorts on Mount Hood, and America’s largest night-skiing area. With the highest lift at 5,027 feet and the base lodge at 3,600 feet, it ranks lowest in elevation but still has some of the steepest terrain on the mountain, with vertical drops of 1,500 feet. There are no high-speed lifts at Skibowl, but it keeps things laid-back and serves to keep the mountain from getting overly crowded. ——p.209, Excursions from Portland, Moon Portland

ZooLights Festival

This annual holiday event is a delight. Each winter, the Oregon Zoo comes alive with thousands of lights, hundreds of musical groups, and the brightly lit Zoo Train. Stroll through after dark and see how active the animals are in the chilly night air.

Oregon Zoo, 4001 SW Canyon Rd., 503/226-1561
COST: $10 adults, $8.50 seniors, $7 children, free for children under 3

Every evening (except Christmas Eve and Christmas Day) from November 28 until December 28, the Oregon Zoo transforms into a holiday fairyland for its annual Zoolights Festival. It’s a spectacular event for the entire family. Decorated with nearly a million lights, this winter wonderland is a more whimsical display than your traditional holiday light show, with swinging monkeys instead of snowmen, slithering snakes instead of nodding reindeer. Sip some cocoa from the Zoo Café or ride the special Christmas train, brightly decorated and aglow with lights, as it winds through the zoo. ——p.135, Festivals and Events, Moon Portland

Excerpted from the Second Edition of Moon Portland.