Local Events & Happenings

13231 SE Sunnyside Rd, Clackamas (10 min drive)

The Happy Valley farmers market hosts a family-friendly Halloween special at Sunnyside on October 31, with trick-or-treating among market vendors, seasonal produce, and festive fun for kids. About 10 minutes from Milwaukie.

13231 SE Sunnyside Rd, Clackamas (10 min drive)

A special harvest edition of the Happy Valley Farmers Market featuring seasonal produce, artisan gifts, baked goods, and live music, about 10 minutes from Milwaukie. A great way to stock up for Thanksgiving and support local vendors.

Eight farms across Clackamas County (10–25 min drives)

A free, month-long farm-trail program from Clackamas County's Mt. Hood Territory tourism group. Pick up a free Harvest Trail Passport at any participating farm, then collect stamps by visiting corn mazes, hayrides, and pumpkin patches across eight local farms. Complete any five activities to earn a prize. A fun way to explore the region's farm country close to home.

Spoke & Word Books, Milwaukie

A monthly crafting circle at Spoke & Word Books (10863 SE Main St) in downtown Milwaukie. Bring your knitting, crochet, embroidery, or any portable craft project. Coffee, tea, and conversation provided. A cozy way to meet neighbors.

Oregon Convention Center

The Pacific Northwest's premier anime and Japanese culture convention, held each year at the Oregon Convention Center in Portland. Artist alley, cosplay, panels, gaming, and vendors celebrating anime, manga, and Japanese pop culture. A 20-minute drive from Milwaukie.

Harmony West, Clackamas Community College, Milwaukie

A free evening of live jazz performed by the Clackamas Community College jazz band and combo at Harmony West on the college’s Milwaukie campus. Reservation required via Eventbrite. A polished, close-to-home way to enjoy the area’s music scene.

Osterman Theatre, Niemeyer Center, Oregon City (15 min drive)

Clackamas Community College theater presents Sarah Ruhl's acclaimed modern retelling of the Orpheus myth, directed by Alison Moon. Performances Thursday through Sunday evenings with weekend matinees at the Osterman Theatre on the Oregon City campus, about 15 minutes from Milwaukie.

St. Helens, OR (40 min drive)

The beloved Halloweentown celebration takes over the St. Helens riverfront at Columbia View Park with the iconic great pumpkin float, costumed characters, family activities, and festive set pieces. Runs weekends from September 26 through November 1, 11:00 AM – 9:00 PM. A can't-miss fall tradition about 40 minutes from Milwaukie.

8703 SE 43rd Ave, Milwaukie (5 min drive)

A beloved Milwaukie Halloween tradition, the Davis Graveyard is a huge hand-built backyard display at 8703 SE 43rd Ave, free to visit nightly through October 31. Animatronics, fog, sound, and themed scenes run from dusk to 10:00 PM (until 11:00 PM on Fridays and Saturdays), with extra special effects on Friday, Saturday, and Sunday nights. A can't-miss stop for families, and it is right in the neighborhood, minutes from home.

Oaks Park, Sellwood, Portland (15 min drive)

Oregon's largest Halloween event takes over historic Oaks Park, about 15 minutes from Milwaukie. Multiple haunted houses, scare zones, rides after dark, and an artisan vendor market run Thursday through Sunday nights through November 1. Best for older kids and adults; not recommended for children under 12.

14601 Arndt Rd, Aurora (20 min drive)

A classic Clackamas County farm festival at Fir Point Farms in Aurora, about 20 minutes from Milwaukie. A five-acre corn maze, cow train, giant slides, pumpkin walk and painting, bounce houses, hay rides, petting zoo, and warm apple cider donuts make it a full day of fall family fun.

Downtown Oregon City (15 min drive)

Downtown Oregon City's family-friendly Halloween tradition along Main Street, with local shops and businesses handing out candy to costumed trick-or-treaters. A festive, walkable outing just 15 minutes from Milwaukie.

Stronger Indoor Skate Park, 6102 SE King Rd, Milwaukie (5 min drive)

An all-ages Halloween celebration at Stronger Indoor Skate Park in Milwaukie, fun for all wheels and abilities. Pizza and candy are included, along with a costume contest and mini skate jams, making it a lively, family-friendly way to celebrate right in the neighborhood.

1847 Food Park, 1925 E Scott St, Milwaukie (5 min drive)

A free, family-friendly Halloween bash at Milwaukie's 1847 Food Park with a rooftop DJ, costume contest, pumpkin coloring, palm reading, and scary tattoos. A festive way to spend Halloween evening with food carts and neighbors close to home.

2029 SE Jefferson St, Milwaukie

A retrospective exhibit celebrating five decades of craft, community, and legacy at Toolbox Gallery in Milwaukie. Browse original artwork from local makers and stop by gallery events to support the neighborhood's arts scene. Free and open during gallery hours.

Downtown Milwaukie

An enchanting winter art walk through downtown Milwaukie featuring illuminated art installations, storefront window displays, and twinkling lights along Historic Main Street. The winter 2026-27 season dates are announced in the fall; check the Downtown Milwaukie events page for the schedule. A beautiful evening stroll that brings the community together.

Portland (15 min drive)

An annual literary festival produced by Literary Arts. The main festival day on Saturday, November 7 features author readings, panel discussions, book signings, and a book fair with independent publishers, preceded by the free Friday Night Book Market on November 6 and events all week. A wonderful event for book lovers, just 15 minutes from Milwaukie.

Millennium Plaza Park, Lake Oswego (10 min drive)

A pet-friendly fall market and community festival at Millennium Plaza Park in Lake Oswego, featuring local vendors, makers, fresh produce, and food booths alongside canine companions. A fun, dog-friendly way to spend a fall Sunday just 10 minutes from Milwaukie.

Reynolds High School, Troutdale (25 min drive)

A vibrant celebration of Hmong culture and the new year at Reynolds High School in Troutdale, about 25 minutes from Milwaukie. Traditional music and dance performances, authentic food, and vendor booths make it a colorful, family-friendly outing.

Yonder Lucky Find Vintage, Milwaukie

A fun night of Golden Girls trivia hosted by Yonder Lucky Find Vintage in Milwaukie. Test your knowledge of the classic sitcom with friends, with prizes for the winning team and a cozy vintage-shop atmosphere. A lighthearted local social event close to home.

Millennium Plaza Park, Lake Oswego (10 min drive)

Lake Oswego's annual tree lighting celebration at Millennium Plaza Park features a holiday marketplace, live music, Santa visits, hot cocoa, and the ceremonial lighting of the tree around 5:30 PM. A festive way to start the holiday season just 10 minutes from Milwaukie.

Downtown Oregon City (15 min drive)

The Downtown Oregon City Association lights the holiday tree in historic Oregon City with music, Santa, and community festivities. A festive way to start the holiday season just 15 minutes from Milwaukie.

Samaritan Odd Fellows Lodge #2, 10282 SE Main St, Milwaukie

A creepy-Christmas twist on bingo hosted by Torchsong Entertainment at the Samaritan Odd Fellows Lodge in Milwaukie. A sassy Krampus calls the numbers, Christmas-villain singers perform hilarious parody songs, and holiday-themed prizes, trivia, and sing-alongs round out the night. An offbeat, adults-friendly seasonal outing right in town.

Clackamas County Fairgrounds, Canby (15 min drive)

A spectacular winter festival at the Clackamas County Fairgrounds with 200,000+ holiday lights, an indoor holiday market, artisan vendors, food and drink, live entertainment, and visits with Santa. A sprawling winter wonderland just 15 minutes from Milwaukie.

The Grotto, NE Portland (20 min drive)

A candlelit walk through the gardens and plazas of The Grotto, with choral performances from 200-plus choirs, an outdoor nativity, and a warm holiday atmosphere. Runs nightly November 27 through December 30 (closed Christmas Day), 5:00 – 9:30 PM. About 20 minutes from Milwaukie.

Keller Auditorium, Portland (15 min drive)

Oregon Ballet Theatre's beloved production of George Balanchine's The Nutcracker returns to Keller Auditorium for the holiday season. A festive family tradition featuring Tchaikovsky's timeless score, dazzling costumes, and stunning choreography, just 15 minutes from Milwaukie.

Oregon Convention Center, Portland (20 min drive)

Portland's largest indie craft fair at the Oregon Convention Center, featuring 200-plus local makers selling handmade gifts, art, and goods. DJ sets, DIY workshops, and a festive atmosphere make it a one-stop holiday shopping destination about 20 minutes from Milwaukie.

SE Portland (25 min drive)

Portland's historic Peacock Lane neighborhood transforms into a twinkling holiday light display each winter, historically running December 15 through 31 with a mix of pedestrian-only and drive-through nights. A beloved, free seasonal tradition about 25 minutes from Milwaukie.

Portland International Raceway (25 min drive)

A three-mile drive-through light display at Portland International Raceway, traditionally opening the weekend after Thanksgiving and running through New Year's Eve. Millions of lights, themed tunnels, and holiday scenes from the comfort of your car. About 25 minutes from Milwaukie.

Portland Expo Center (25 min drive)

A regional Christmas craft, food, and gift show at the Portland Expo Center featuring hundreds of vendors with handmade gifts, holiday decor, specialty foods, and seasonal treats. A one-stop start to holiday shopping about 25 minutes from Milwaukie.

Portland metro (20 min drive)

A festive Portland holiday tradition over Thanksgiving weekend, bringing decorated trees, live entertainment, and seasonal family fun to the metro area. A cheerful way to start the holiday season about 20 minutes from Milwaukie.

Pioneer Courthouse Square, Portland (15 min drive)

Portland's official holiday kickoff the day after Thanksgiving, when the 75-foot tree at Pioneer Courthouse Square lights up with a community sing-along. A festive downtown tradition just 15 minutes from Milwaukie.

Willamette & Columbia rivers (Milwaukie Bay Park is a great viewing spot)

Decorated boats light up the Willamette and Columbia rivers on selected nights from December 3 through 20, 2026. The Willamette Fleet is scheduled to pass Milwaukie Bay Park on Tuesday, December 8, Friday, December 11, and Tuesday, December 15 (arriving around 8:00 PM). Enjoy the show close to home with hot cocoa in hand.

100 SE Alder St, Portland (15 min drive)

A festive indoor night market in southeast Portland celebrating food, music, drinks, and local makers. A lively way to shop and snack local with friends through the holiday season, about 15 minutes from Milwaukie.

Pioneer Courthouse Square, Portland (15 min drive)

Heated tents, winter beers and ciders, and festive lights around the 75-foot holiday tree at Pioneer Courthouse Square. A cozy December tradition about 15 minutes from Milwaukie.

Portland metro area

A Nordic-inspired holiday market in the Portland metro featuring Scandinavian crafts, traditional foods, and seasonal gifts for the holidays. A cozy way to start the holiday season not far from Milwaukie.

Nordic Northwest, 8800 SW Oleson Rd, Portland (20 min drive)

A 40-plus-year Nordic holiday market tradition at Nordic Northwest in southwest Portland, offering Scandinavian crafts, traditional foods, folk music, and seasonal gifts. A cozy, old-world way to shop for the holidays about 20 minutes from Milwaukie.

Historic Willamette district, West Linn (10 min drive)

Shop local in the Historic Willamette district on Small Business Saturday, with shops and cafes around Knapps Alley welcoming holiday shoppers with specials and a festive small-town atmosphere. A cozy way to start holiday gift buying just 10 minutes from Milwaukie.

Mt. Angel, OR (about 40 min drive)

A German-style holiday market in the Bavaria-themed town of Mt. Angel, southeast of Milwaukie. Festive vendor stalls, regional foods, and holiday spirit make it a charming seasonal outing.

Historic Willamette district, West Linn (10 min drive)

A festive holiday market in the Historic Willamette district of West Linn, with local shops, makers, and vendors, plus a seasonal scavenger hunt through the neighborhood. A cozy small-town shopping outing just across the river from Milwaukie.

Pioneer Courthouse Square, Portland (15 min drive)

Portland's beloved annual holiday caroling competition at Pioneer Courthouse Square, where costumed teams perform for charity in a lively, joyful downtown tradition. A festive outing about 15 minutes from Milwaukie.

Portland (15 min drive)

Tuba and euphonium players of all ages gather in Portland to perform familiar holiday carols in a spirited annual TubaChristmas tradition. A charming, musical way to celebrate the season about 15 minutes from Milwaukie.

15909 SE Lark Ave, Milwaukie (right in the neighborhood)

A spectacular free holiday light display right in the 97267 neighborhood: 50,000-plus animated lights synced to music at a private home on SE Lark Avenue. Visitors can request songs by QR code and enjoy the show from the sidewalk or car. A magical, close-to-home holiday tradition.

Oregon Zoo, Washington Park, Portland (20 min drive)

An adults-only evening at the Oregon Zoo where guests 21 and older sip local craft beer and cider while strolling the first weekend of ZooLights. Live music, food carts, and the zoo's animals make it a festive date-night outing about 20 minutes from Milwaukie.

Oregon Rail Heritage Center, SE Portland (20 min drive)

A vintage steam train decked out for the holidays at the Oregon Rail Heritage Center in southeast Portland, with Santa aboard, holiday lights, and family-friendly rides. A charming seasonal outing about 20 minutes from Milwaukie.

Near Oregon City (15 min drive)

A family farm near Oregon City transforms into a Christmas wonderland with a 1,000-foot decorated walking trail, festive lights, and holiday scenes. A close-to-home way to enjoy the season just 15 minutes from Milwaukie.

Historic Willamette district, West Linn (10 min drive)

West Linn Parks and Recreation's annual Light Up the Night holiday parade steps off through the Historic Willamette district, followed by the Main Street Holiday Tree Lighting at 5:00 PM. Festive floats, music, and community groups make it a cheerful, family-friendly tradition just across the Willamette from Milwaukie.

Historic Willamette district, West Linn (10 min drive)

A festive walking tour of the Historic Willamette district in West Linn, with local breweries, distilleries, and tasting rooms pouring seasonal selections along the route. A fun, social evening just 10 minutes from Milwaukie.

West Linn Lutheran Church, West Linn (10 min drive)

A festive holiday craft bazaar at West Linn Lutheran Church featuring local makers, handmade gifts, and seasonal treats. A cozy way to kick off holiday shopping just across the Willamette from Milwaukie.

Portland metro (20 min drive)

A festive Foot Traffic race day in the Portland metro with half-marathon, 15K, 10K, and 5K distances, holiday costumes encouraged, and a lively finish-line celebration. A great way to stay active through the holiday season close to home.

NE Portland (20 min drive)

A traditional German Christmas market in northeast Portland with glühwein, holiday crafts, folk dancers, and a visit from St. Nikolaus. A cozy, old-world way to celebrate the season about 20 minutes from Milwaukie.

Lakeridge High School Auditorium, Lake Oswego (10 min drive)

A free holiday concert by the Lake Oswego Millennium Concert Band at Lakeridge High School, featuring festive seasonal music for the whole family. A warm, low-key way to enjoy the season just 10 minutes from Milwaukie.