The Portland area transforms during the winter months, bringing cozy markets, dazzling light displays, festive train rides, cultural celebrations and plenty of family-friendly fun to explore. Whether you’re searching for a classic holiday tradition, a creative outing or a chance to discover something new in your community, there’s something for every kind of winter wanderer.
We’ve rounded up some of the most fun happenings and included dates, details and links so you can start planning your winter adventures! And these events are all accessible by TriMet! Plan your trip at trimet.org 🚌
Bundle up in your TriMet holiday sweater, grab a warm drink, and check out the fun winter events taking place around the region ✨
*Most descriptions come from event organizers.
⛸️ Ice Skating at Lloyd Center
Lloyd Center, 2201 Lloyd Center, Portland
Glide into the holiday spirit at Lloyd Center! Their seasonal ice rink transforms the mall into a winter wonderland perfect for families, friends and anyone looking to experience a bit of festive magic indoors. Lace up your skates and enjoy a cheerful, active outing.
Prices vary with discount nights available.
More info and tickets to ice skating
🐘 ZooLights
Through January 4
Oregon Zoo, 4001 SW Canyon Rd., Portland
See the zoo in a whole new light! Check out the magical meadow light show, along with a variety of interactive displays. Hop on the zoo train and see dozens of life-size animal lanterns along the route. Walk through vibrant tunnels of glittering lights and take in the glowing festive atmosphere.
On-site parking fills fast and early. Skip the lots and get to the lights faster and easier by taking TriMet. Bonus: Your ZooLights ticket is your TriMet fare!
More info and tickets to Zoolights
🚂 Columbia Gorge Model Railroad Club Holiday Open House
Nov. 15-Dec. 7
2505 North Vancouver Ave., Portland
The Columbia Gorge Model Railroad Club is celebrating 78 years of model railroading with its annual Holiday Open House shows.
Tickets start at $12 for Adults (12+), and $5 for Youth (3-11).
More info and tickets to the open house
🎨 Portland Art Museum Free Admission Days
Nov. 20-23
Portland Art Museum, 1219 SW Park Ave., Portland
Join the Portland Art Museum for four days of free admission, activities and events as they celebrate the grand opening of their Museum transformation!
Free admission will be available for walk-up visitors from 11/20 to 11/23 on a first-come, first-served basis.
More information and tickets to Portland Art Museum
🛍️ Gem Faire
Nov. 21-23
Westside Commons, 801 NE 34th Ave., Hillsboro
Gem Faire is a large gem, jewelry and bead show! You’ll discover fine jewelry, costume jewelry, precious and semi-precious gemstones, millions of beads, sparkling crystals, gold and silver, jewelry tools, supplies and boxes all under one roof!
Admission is $7 at the door for the entire weekend, but check out their website for free admission options and 2-for-1 special pricing.
More information about Gem Faire
🛍️ Portland Flea
Saturday, Nov. 22 and Sunday, Nov. 23 • 11 a.m.-4 p.m.
The Redd, 831 SE Salmon St., Portland
Come to the gathering place for creators, curators and collectors! Join “Decked Out” — their festive holiday market all about getting yourself ready before the season kicks into high gear!
Admission is free.
More information about Portland Flea
⛸️ OMSI on Ice
Nov. 22-Dec 31
OMSI, 1945 SE Water Ave., Portland
Put on your skates and take to the rink this winter at OMSI on a unique indoor synthetic ice rink. Experience all the joys of ice skating together while comfortably indoors in OMSI’s auditorium turned winter wonderland.
$10 Adults (14+), $9 Seniors (63+), $8 Youth (5-13)
More information about skating at OMSI
🎄 Hillsboro Holly Days and Downtown Tree Lighting
Saturday, November 22 • 2 p.m.–7 p.m.
Historic Downtown Hillsboro
Celebrate the season at the annual Hillsboro Holly Days Celebration in Historic Downtown!
Artisans showcase their best handmade work at this bustling market, while carolers, live music, and activities for all ages abound. Downtown merchants will also be open for business with a variety of in-shop activities and promotions.
The streets will be full of holiday cheer and excitement leading up to the awe-inspiring tree lighting at 6:00 p.m.
More info about Hillsboro Holly Days
🎄 Downtown Portland Annual Tree Lighting Ceremony
November 28 • 5:30 p.m.–6:45 p.m.
Pioneer Courthouse Square, 701 SW 6th Ave., Portland
A joyful community sing-along led by Portland’s own Thomas Lauderdale of Pink Martini with many of Portland’s finest musical artists and chorale singers. Portland’s Tree Lighting Ceremony is the highlight of the holiday season in downtown. Join in this holiday tradition as Santa Claus ‘flips the switch’ to illuminate nearly 10,000 colorful lights on our City’s Tree that will shine bright throughout the holiday season.
More info about the tree lighting at The Square
🏒 Portland Winterhawks vs. Regina Pats
Friday, November 28 • 3 p.m.
Veterans Memorial Coliseum, 300 N Ramsay Way, Portland
Make it a night out with friends or bring the family for a winter tradition! A Winterhawks game is one of the season’s best ways to warm up.
Tickets start at $39.
More info about Winterhawks games and tickets
🎄 Forest Grove Tree Lighting
Friday, November 28 • 6 p.m.
College Way & 21st Ave., Forest Grove
Join a magical evening as Forest Grove kicks off the holiday season with the annual Holiday Tree Lighting Celebration! Enjoy caroling, cookies, family activities and a visit from Santa as the community comes together to celebrate.
More info about the Forest Grove Tree Lighting
🍿 Jurassic Park at Cinema 21
Friday, Nov. 28 & Sat. Nov. 29
Cinema 21, 616 NW 21st Ave., Portland
Experience the iconic original classic, this coming Thanksgiving weekend at Cinema 21! During a preview tour, a theme park suffers a major power breakdown that allows its cloned dinosaur exhibits to run amok.
Tickets are $12.25 online.
More info and tickets to Jurassic Park
🎪 Cirque Nutcracker with the Oregon Symphony
Nov. 29–30
Arlene Schnitzer Concert Hall, 1037 SW Broadway, Portland
The awe-inspiring talents of Troupe Vertigo join the Oregon Symphony with their unique hybrid of cirque, dance and acrobatic art backed by Tchaikovsky’s beloved holiday masterpiece, The Nutcracker. This festive and family-friendly concert is sure to have you and yours jumping for joy!
Tickets start at $35.
More info and tickets to Cirque Nutcracker
✨ The Grotto – Festival of Lights
Friday, Nov. 28 through Tuesday, Dec. 30
The Grotto, 8840 NE Skidmore St., Portland
You’re invited to experience one of the Northwest’s premier Christmas celebrations! See millions of Christmas lights across the sanctuary grounds, plus a robust music program in the Chapel of Mary (cathedral-like acoustics), sweet treats, children’s events and more!
The Grotto offers a shuttle bus from the Parkrose/Sumner MAX Station. Additionally, two bus lines stop nearby: Line 12 and Line 72.
Buy online ahead of time: General admission $16.95, Youth $7.95
Buy at the gate: General admission $18.95, Youth $8.95
More info and tickets to The Grotto
⭐ 15 Days of Decemberville Winter Window Walk
Nov. 29-Dec. 13
Taking place at over 40 businesses in Sellwood–Moreland.
Something new is coming for this Decemberville— It’s the 15 Days of Decemberville Winter Window Walk!
This year, neighborhood brick and mortars are getting in the winter spirit by decorating for a window display competition! That’s right— the neighborhood gets to enjoy a festive 2 week long celebration and vote for their favorite displays in a variety of categories.
More info about Decemberville in Sellwood–Moreland
🚂 Holiday Express at ORHC
Nov 28–Dec 28
Oregon Rail Heritage Center, 2250 SE Water Ave., Portland
Join Santa and his elves for a magical ride behind one of our famous steam locomotives. Vintage passenger coaches transport you along the Willamette River in the heart of the city.
Adults – $34.00
Children (3-13) – $25.00
Children (2 and under) – Ride free on lap
Family (2 adults and 2 children) – $105.00
Senior – $31
Military – $31
More info and tickets to the Holiday Express
Winter Village @ Orenco Station
November 30, 2025 – January 11, 2026
Jerry Willey Plaza at Orenco Station, 943 NE Orenco Station Loop, Hillsboro
Find seasonal cheer at this outdoor ice-skating rink. Winter Village is a beloved Hillsboro event. Bring your friends and family to a skate session, take an ice skating lesson, or rent the rink for your private party. Don’t miss exciting special events and skate days!
More info about Winter Village
🎄Winter Festival Presented by Rockwood Market Hall
Sunday, November 30 • 3 p.m.–6 p.m.
Rockwood Market Hall, 458 SE 185th Ave, Portland
Kids can get creative with a craft session (FREE for all kids!) At 5 p.m., the Rockwood Market hall will light up their Christmas Tree. The market’s local vendors will be open for holiday shopping.
More information about the Winter Festival at Rockwood Market Hall
🎶 Ben Folds with the Oregon Symphony
Tuesday, December 2 • 7:30 p.m.
Arlene Schnitzer Concert Hall, 1037 SW Broadway, Portland
Ben Folds is widely regarded as one of the major music influencers of our generation. The genre-bending, multi-platinum selling artist joins the Oregon Symphony to perform everything from beloved fan-favorites to exciting new music.
Tickets start at $46.
More info and tickets to Ben Folds
🏀 Rip City Remix Games
November through March
Chiles Center, 5000 N Willamette Blvd., Portland
The Rip City Remix are a professional basketball team in the NBA G League based here in Portland, and are affiliated with the Portland Trail Blazers. Whether you’re a die-hard hoops fan or just looking for a fun night out, a Remix game is the perfect mix of Portland pride, big-talent basketball and good-time energy.
TriMet riders get 25% off single-game tickets – discount is automatically applied
⭐ The Benson
Tuesday, December 2 • 6 p.m.
The Benson Hotel, 309 SW Broadway, Portland
Each year, The Benson transforms into a wonderland of holiday magic — and this year promises to be truly unforgettable. Guests of all ages are invited to enjoy live music, children’s activities, a hot chocolate station and a surprise visit from Santa, all surrounded by the sights, sounds and scents of the season.
While this year’s gingerbread creation remains a carefully guarded secret, whispers from the kitchen suggest a theme filled with heart, courage and a touch of magic. Whatever it may be, you can expect another breathtaking display that captures the imagination and spirit of the holidays.
⛵️ Christmas Ships Parade
December 4–21
Columbia River and Willamette River waterfronts
Since 1954, the Christmas Ships Parade has been a beloved Pacific Northwest tradition that brings joy, wonder and holiday spirit to families across the region. It’s free to attend, family-friendly and there’s multiple viewing locations. Bundle up and attend one or more of the 15 nights in December.
More info about the Christmas Ships Parade
✨ Beaverton Winter Lights
Friday, December 5 • 4-8 p.m.
Beaverton City Park, 12500 SW 4th St., Beaverton
Get ready to kick off the 2025 winter season at the Beaverton Winter Lights & Tree Lighting. Bring the whole family for an evening of festive fun, featuring live performances by local musicians, special guests and activities for all ages.
More info about Beaverton Winter Lights
🩰 The Nutcracker at Keller Auditorium
Dec. 5-24
Keller Auditorium, 222 SW Clay St., Portland
A sparkling winter tale set to Tchaikovsky’s festive score. When Marie’s mysterious godfather gives her a magical Nutcracker that comes to life, Marie and her Nutcracker Prince set off on an unforgettable Christmas Eve adventure to the Land of Sweets.
Tickets start at $35.
More info and tickets to The Nutcracker ballet at Keller Auditorium
🎄 Portland Holiday Brew Fest
Dec. 5 & 6
Pioneer Courthouse Square, 701 SW 6th Ave., Portland
The Portland Holiday Brew Fest is back, featuring 30+ holiday/winter beers and ciders from around the Northwest, music, food and more!
Tickets start at $36.
More info and tickets to Holiday Brew Fest
🎉 City of Tualatin Light Parades
Dec. 5–7
Various Locations
The Tualatin Light Parades are back!
Friday, December 5 – North Parade (Includes neighborhoods around Community Park and Jurgens Park)
Saturday, December 6 – South Parade (Includes neighborhoods around Ibach Park and Tualatin High School)
Sunday, December 7 – East Parade (Includes neighborhoods around Atfalati Park, Fox Hills, and Marquis)
More info about the Tualatin Light Parades
🎄 Gresham Spirit of Christmas
Saturday, Dec. 6 • 8 a.m.–9 p.m.
Downtown Gresham
Kick off the holiday season with a full day of family-friendly activities for the whole community to enjoy.
Join this beloved community gathering with music, free treats, pictures with Santa and more.
More info about Gresham Spirit of Christmas
🛍️ My People’s Market
Dec. 6 & 7
Oregon Convention Center, 777 NE Martin Luther King Jr Blvd., Portland
Join My People’s Market for a weekend of live music that’ll get you moving, art that inspires, and food that hits every craving. Plus, shop and support over 150 amazing local small businesses!
Admission is free.
More info about My People’s Market
🎄 Milwaukie Umbrella Parade & Tree Lighting
Saturday, Dec. 6 • 4:30 p.m.
Downtown Milwaukie
Join the Milwaukie holiday tradition of decorating umbrellas and parading through downtown ending with the lighting of the tree. Yes, there has been a MAX Umbrella in the past.
Anyone can join!
More information about the Milwaukie Umbrella Parade
🎄 Laurelhurst Winter Bazaar
Sunday, Dec.. 7 • 10 a.m.–4 p.m.
Laurelhurst School, 840 NE 41st Ave, Portland
Step into the magic of the season at the Laurelhurst Winter Bazaar, a cozy neighborhood tradition that brings together makers, neighbors and holiday cheer. Find handcrafted gifts, and one-of-a-kind treasures made by local artisans.
Follow Laurelhurst Winter Bazaar on Instagram for updates
🎶 Live Wire
Thursday, December 11 • 7:30 p.m.–9:30 p.m.
Revolution Hall, 1300 SE Stark St. #203, Portland
An evening of conversation and music featuring Hari Kondabolu, Reverend Billy, the Stop Shopping Choir and Edna Vázquez.
General admission tickets are $43.76.
More info and tickets to Live Wire
🎻 Merry-achi Christmas
Wednesday, Dec. 10 • 7:30 p.m.
Arlene Schnitzer Concert Hall, 1037 SW Broadway, Portland
Eight-time GRAMMY-nominated Mariachi Sol de México de José Hernández brings holiday cheer with its “Merry-achi Christmas” tour, celebrating the Christmas season with a dazzling blend of mariachi and holiday classics.
Tickets start at $34.
More info and tickets to Merry-achi Christmas
🍿 Dr. Seuss’ The Grinch Who Stole Christmas at Cinema 21
December 12-18
Hollywood Theatre, 4122 North East Sandy Blvd., Portland
On the outskirts of Whoville lives a green, revenge-seeking Grinch (Jim Carrey) who plans to ruin Christmas for all of the citizens of the town. This movie will be shown in 4K restoration for the 25th anniversary!
General admission tickets $12, senior/student/child $10.
More info and tickets to The Grinch
🎶 12th Annual Great Figgy Pudding Caroling Competition
Friday, Dec. 12
Pioneer Courthouse Square, 701 SW 6th Ave, Portland
The 11th Annual Great Figgy Pudding Caroling Competition, hosted by KGW’s Drew Carney, is a fun, festive and joyful competition bringing hundreds of carolers to a ten-block radius the surrounds the Square. Carolers perform in front of Downtown’s favorite nearby shops, restaurants and hotels with the top three caroling groups holding a “carol-off” at The Square.
Members of the public can participate in this FREE event by registering to perform with a caroling group or by visiting performing caroling groups to vote for your favorite.
More info about the caroling competition
🛍️ Portland Bazaar
Dec. 13 & 14 • 11 a.m.–4 p.m.
Dec. 20 & 21 • 11 a.m.–4 p.m.
1715 NW 17th Ave, Portland
The flagship holiday shopping experience shines a spotlight on Portland’s most skilled artists, makers and small businesses. There will be be 160+ vendors selling their goods! Join us for TWO weekends this holiday season!
Free and open to all ages.
More info about Portland Bazaar
🎶 The Nutcracker at The Reser
Dec. 13 & 14
The Reser, 12625 SW Crescent St, Beaverton
The Oregon International Ballet Academy’s highly-acclaimed rendition of The Nutcracker delivers pure seasonal joy in their performances again this year at the Patricia Reser Center for the Arts. This is a beloved favorite with fresh surprises every year.
Tickets are $43.50.
More info and tickets to The Nutcracker at The Reser
🎄 West Linn Annual Holiday Parade
Saturday, Dec. 13 • 5 p.m.
Historic Willamette Main St., 1754 Knapps Alley, West Linn
Join a magical evening at the “Jolly Gingerbread Jamboree” Holiday Parade in historic downtown Willamette! This joy-filled celebration will light up the streets with festive floats, cheerful music and the spirit of the season.
Bring your family and friends to enjoy the sights and sounds of the holidays.
More info about West Linn Annual Holiday Parade
🎶 34th Annual Tuba Christmas Concert
Saturday, Dec. 13 • 1:30–3:30 p.m.
Pioneer Courthouse Square, 701 SW 6th Ave., Portland
This iconic, quirky and heart-warming holiday musical tradition is back! Experience the mighty sounds of big brass as nearly 300 tubas play in harmony while the crowd is invited to sing along.
This live performance is one of the largest in the country with tuba participants travelling from all points of Oregon to join in this festive event with a crowd of thousands. Attending this seasonal performance is FREE for the public.
More info about the Tuba Christmas Concert
🛍️ Winter in Willamette Holiday Market
Saturday, Dec. 13 • 10 a.m.–5 p.m.
Historic Willamette Main St., 1754 Knapps Alley, West Linn
Visit West Linn’s Historic Willamette Business District for a fun-filled holiday market!
More info about the Willamette Holiday Market
🍿 Home Alone: CineWhimsy – An Immersive 4D Holiday Extravaganza at Tomorrow Theater
Saturday, Dec. 13 • 6 p.m.
Tomorrow Theater, 3530 SE Division St., Portland
Think you know Home Alone? Or are you thirsty for more? Home Alone: CineWhimsy transforms this holiday classic into an immersive, prop-infused holiday adventure.
Become part of the experience as you cheer Kevin on, clap along to surprise renditions of popular holiday classics and reenact iconic hijinks as you set off “booby traps.” With live hosts, call-and-response antics, reenacted skits, and mischievous surprises, this isn’t just a movie night—it’s stepping inside Kevin McCallister’s snow-dusted, trickster-infused universe. Laughter, lighthearted mayhem and pure holiday delight guaranteed!
Tickets are $35 for this “4D” experience!
More info and tickets to the Home Alone immersive experience
⭐ Earl Sweatshirt: 3L World Tour
Monday, Dec. 15 • 8 p.m.
Crystal Ballroom, 1332 W Burnside St., Portland
Rapper Earl Sweatshirt will play Portland’s iconic Crystal Ballroom in support of the his new album, “Live Laugh Love.” The celebrated artist shines brightly on his own and has collaborated the Odd Future, Frank Ocean and RZA.
More info and tickets to Earl Sweatshirt
🎶 The Fab Four: The Ultimate Tribute to the Beatles
Thursday, Dec. 18 • 7:30 p.m.
Newmark Theater, 1111 SW Broadway Ave., Portland
This acclaimed Beatles tribute features an all-new stage show celebrating the band’s second film, HELP! They’ll also perform other Beatles hits from the band’s various eras. How good is the band? They’re so good, you’ll think you’re watching the real thing, and they won an Emmy to prove it.
More info and tickets to The Fab Four
🎄 Peacock Lane – Portland’s Christmas Street
December 15-31
SE Peacock Ln., Portland
It’s the most wonderful time of the year, and the residents of Peacock Lane are happy to share that they will be displaying their lights from December 15 to December 31. Take TriMet so you don’t have to battle traffic!
For 2025, the Pedestrian-only nights will be December 19 and 20. Mark your calendars!
🛍️ Mississippi Avenue Third Thursdays
Thursday, December 18 • 5 p.m.-8 p.m.
Mississippi Avenue
Eat, sip and shop with your favorite local spots on the Ave while enjoying special sales, pop-up vendors, giveaways and more. It’s the perfect way to get into the holiday spirit and support small businesses along Mississippi Ave! ❤️🔥
More info about Mississippi Third Thursdays
🍿 The Muppet Christmas Carol at Tomorrow Theater
Saturday, Dec. 20 • Doors 3:30 p.m.; Event 4 p.m.
📍Tomorrow Theater, 3530 SE Division St., Portland
Pull on your coziest sweater and bring the whole gang for a merry, music-filled screening of The Muppet Christmas Carol: a warm, wonderfully weird holiday classic that mixes genuine heart with full-throttle Muppet mayhem. Watch Michael Caine bring unexpected gravitas to Scrooge while Kermit, Miss Piggy and the rest of the gang turn Dickens’ tale into a tuneful, family-friendly joyride. Perfect for longtime fans and first-timers alike!
Tickets are $15.
More info and tickets to The Muppet Christmas Carol
🍿 ELF in Concert
Dec. 20-21
Arlene Schnitzer Concert Hall, 1037 SW Broadway, Portland
Nobody spreads Christmas cheer quite like Buddy the Elf! This holiday season, relive this heartwarming holiday classic on a giant screen as every note of John Debney’s wonderful score is played live to picture in Elf in Concert!
More info and tickets to ELF in Concert
🎶 Portland Cello Project Holiday Show
Tuesday, Dec. 20
Put on your mittens and scarves and join Portland Cello Project for The Reser’s Winter Holiday show! This full-band program featuring singer Sarah Clarke includes beautiful orchestrations of your favorite festive tunes, as well as the true “classical” classics that have stood the test of time. Come to the hall decked out in your coziest (and/or ugliest) sweaters and celebrate the official beginning of Winter.
Tickets start at $45.
More info and tickets to the Portland Cello Project’s Holliday Show
🎄 A Charlie Brown Christmas Live On Stage
Saturday, Dec. 27
Keller Auditorium, 222 SW Clay St., Portland
Peanuts’ timeless holiday television special comes to life with the national tour of A Charlie Brown Christmas Live On Stage, coming to Portland this December. This critically acclaimed holiday celebration that the whole family can enjoy brings Charlie Brown, Snoopy, Lucy, Linus and the rest of the Peanuts gang together live on stage as they uncover the true meaning of Christmas and perform songs from the unforgettable musical score of legendary composer Vince Guaraldi.
The Broadway-style production complete with immersive sets, lighting, choreography and colorful costumes!
More info and tickets to A Charlie Brown Christmas
🏠 Pittock Mansion Home for the Holidays
Through January 31
Pittock Mansion, 3229 NW Pittock Dr., Portland
Enjoy a special “decades” tour theme and a new art exhibit at Pittock Mansion.
Admission for the holiday season is $17 for adults, $15 for seniors, $13 for youth and children five and under.
More info and tickets to Pittock Mansion
Need the right fit for the holidays?
Grab a limited-edition TriMet Holiday Sweater and get compliments all winter long! We’ve also got train and bus squishies, plus t-shirts that make great gifts! Shop the TriMet Gear Store.
