What's happening in Clackamas County
One of the things I love most about this area is how much there is to do -- from summer concerts and county fairs to farmers markets and holiday parades. Here's what's coming up in our communities.
Upcoming events across the county.
Whether it's a rodeo in Canby, a music festival in Estacada, or Oktoberfest in Happy Valley, these are the events that bring our communities together. I'll keep this page updated as new events are announced.
Canby First Thursday Night Market
A monthly evening market on First Thursdays featuring local artisans, food vendors, live music, and a wonderful community atmosphere. Next up: October 1 and November 5.
Swan Island Dahlia Festival
The 100th anniversary of Swan Island Dahlias! Nearly 50 acres of dahlia fields and display gardens with over 375 varieties, live music on weekends, food carts, flower-arranging classes, and local vendors. Free admission and parking. A must-see for garden lovers and an incredible spot for photos.
Down the River Clean-Up
A free on-water community clean-up event on the Clackamas River. Bring your kayak, canoe, or raft and help keep our beautiful river clean. Gloves and bags provided. A great way to give back to the natural spaces that make Clackamas County so special.
Canby Dahlia Run
A scenic run through the famous dahlia fields at Swan Island Dahlias, with 5K and 10K distances. Runners wind through nearly 50 acres of blooming dahlias during the peak of the Dahlia Festival. A unique and beautiful way to experience Canby's floral treasure.
Willamette Autumn Wine Walk
A strolling wine event through the charming Historic Willamette Business District, featuring local wineries and cideries, live music, raffles, and shopping. Tickets include tastings at each stop, a commemorative wine glass, water, and snacks.
Willamette Chalk Walk Festival
Watch artists transform the pavement into colorful chalk masterpieces in the Historic Willamette district. A creative, family-friendly event paired with the Autumn Wine Walk later that day.
Boring Marathon, Half Marathon & 5K
An annual race through the scenic countryside of Boring, Oregon, with marathon, half marathon, 10K, and 5K distances. Part of the Boring Marathon weekend that also features a health and wellness expo. A fun challenge for runners of all levels (and yes, the swag is anything but boring!).
FOBtoberfest
A German-themed Oktoberfest celebration produced by FOB Taproom and the Clackamas County Fair & Event Center. Features authentic German cuisine, German import brews and local favorites, live music, and entertainment. A festive way to welcome the fall season with the whole community.
Molalla Heritage Apple Festival
Hosted by the Molalla Area Historical Society, this festival offers demonstrations of early settler skills, food, vendors, and history tours. A wonderful way to explore Molalla's rich pioneer heritage.
Milwaukie Repair Fair
Part of Milwaukie's Sustainability Fair -- bring your broken items (small appliances, clothing, electronics) and volunteers help repair them for free. A practical, community-building event that reduces waste and connects neighbors.
St. Josef's Grape Stomping Festival
A Canby tradition celebrating the grape harvest with live music, wine and food pairings, grape stomping competitions, vineyard tours, and local artisans. A wonderful way to welcome the fall season at one of Clackamas County's most beloved wineries.
Happy Valley Drive-In Movie Night
A free drive-in movie under the stars featuring the classic Back to the Future. Bring a blanket or a comfy camping chair and enjoy a fun, nostalgic evening with the whole family.
Estacada Oktoberfest
Estacada's annual Oktoberfest celebration fills downtown Broadway with live music, local food and drink, artisan vendors, and games. Features a costume contest, pumpkin painting, pie eating, polka music, and traditional fare. A festive fall day in one of Clackamas County's most scenic river towns.
Gladstone Harvest Festival
A free, family-friendly harvest festival at the Gladstone Community Center. A cozy way to celebrate the season with neighbors right before the Halloween festivities begin.
Gladstone's Goblin Gathering
A safe, family-friendly trick-or-treat celebration hosted by the City of Gladstone. Costumes encouraged, candy guaranteed, and that small-town Halloween charm the kids will remember.
Happy Valley Oktoberfest
Happy Valley's annual Oktoberfest fills the park with Wiener Dog Races, a Chicken Dance Contest, a Paulaner Stein Hoist Competition, live entertainment, food vendors, and a kids' community pumpkin patch. The kind of family fun that makes Happy Valley such a wonderful place to raise kids.
Oregon City Fall Fest
The second annual OC Fall Fest featuring live entertainment (including Reel2Real band), artisan vendor booths, community booths, food trucks, a petting zoo by Bring The Barn, character meet-and-greets, and pumpkin activities. A wonderful fall celebration for the whole family.
Canby Auto Swap Meet
An automotive swap meet and flea market at the Clackamas County Event Center. A treasure-hunter's paradise and a great way to browse parts, tools, and collectibles with the community.
WillametteFest
West Linn's fall community celebration in the historic Willamette neighborhood. Local food, music, and the kind of small-town warmth that makes this area so special.
Milwaukie First Friday in October
Milwaukie's beloved First Friday block party returns in October with live music, art displays, local vendors, food, and that unmistakable community feeling. Free to attend and fun for all ages.
Milwaukie Fall into Gardening
A free gardening workshop for the community, covering fall planting, garden preparation, and seasonal tips from local horticulture experts. A great way to prepare your garden for the cooler months.
Fall Fest in the Forest
Live music, a dog costume contest, and family activities in a beautiful forested setting. A cozy fall event that captures the spirit of West Linn's outdoor lifestyle.
Oregon City Repair Fair
Bring your broken items (small appliances, clothing, electronics, and more) to the Oregon City Library and volunteers will help repair them for free. A wonderful sustainability event that reduces waste and builds community connections.
Milwaukie Trunk or Treat
A free, family-friendly Halloween event with decorated trunks, candy, and candy alternative options. A safe and fun way for the little ones to show off their costumes and celebrate the season.
Estacada Creepy Crawl
Safe trick-or-treating for families in downtown Estacada, presented by the Estacada Area Chamber of Commerce. A fun and festive way for little ones to celebrate Halloween in our charming river town.
Oregon City Trick or Treat Main Street
A free, family-friendly Halloween event where Main Street businesses hand out candy to costumed visitors of all ages. Stroll through historic downtown Oregon City, show off your costumes, and enjoy a safe, spooky afternoon.
Canby's Spooktacular Village
A family-friendly Halloween celebration in downtown Canby with trick-or-treating at local businesses, costume contests, and festive fall activities. A safe, fun way to celebrate the spookiest day of the year with the whole family.
Happy Valley Halloween Market
The market goes spooky for Halloween with trick-or-treating for the kids, festive vendors, and plenty of fall produce. A fun way to make a full day of the season's last Saturday market.
Fir Point Farms Harvest Festival
A beloved fall tradition just south of Oregon City featuring a massive corn maze, pumpkin patch, hayrides, farm animals, cider mill, and a country store. Weekends bring live music and food vendors. A perfect family outing that captures the beauty of autumn in Clackamas County.
Happy Valley Harvest Market
Over 150 vendors with fall produce, artisan goods, and holiday shopping. A great way to kick off the holiday season and support local growers and makers.
Happy Valley Tree Lighting Ceremony
The annual tree lighting at City Hall, featuring horse-drawn carriage rides, Christmas carolers, hot cocoa and cookies, and a visit with Santa. A magical start to the holiday season for the whole family.
Happy Valley Procrastinators Holiday Market
A holiday-themed market perfect for last-minute gift shopping. Local artisans, food vendors, and festive cheer -- your one-stop shop for finding those perfect presents while supporting local businesses.
Halloween in Willamette
A family-friendly Halloween celebration in the charming Historic Willamette district. Trick-or-treating at local shops, festive fun, and the cozy small-town atmosphere that makes West Linn so special.
Willamette Brews and Spirits Stroll
A strolling fall event through the Historic Willamette District featuring craft brews, spirits, and cider at participating local stops. A relaxed way to support small shops while enjoying seasonal flavors.
Country Christmas Bazaar (53rd Annual)
One of the Pacific Northwest's largest holiday craft bazaars, now in its 53rd year. Hundreds of artisan booths packed with handcrafted gifts, home goods, and holiday decor -- a one-stop shop for supporting local makers.
Small Business Saturday
A day to shop locally in the Historic Willamette Business District, where independently owned shops, boutiques, and restaurants roll out special offers and that small-town welcome. A wonderful way to keep your holiday dollars in the community.
Canby Light Up the Night (25th Annual)
Canby's dazzling holiday tradition: a 6:00 PM lighted parade through downtown followed by a tree-lighting ceremony at Wait Park around 6:30 PM. Carolers, community warmth, and the official welcome of the season.
Estacada Tree Lighting
Estacada kicks off the holidays with carols, a visit from Santa, local vendors, and the lighting of the downtown tree at Harvest Market Square. A cozy, small-town celebration in our scenic river town.
Gladstone Winter Market & Holiday Tree Lighting
A festive winter market with 45+ vendors during the day, followed by the annual holiday tree-lighting ceremony at 4:30 PM with free hot cocoa, carols from the Gladstone School Choir, and a visit with Santa.
Willamette Main Street Tree Lighting
The Historic Willamette district lights up for the holidays with a festive tree-lighting gathering along Willamette Falls Drive. Hot drinks, friends, and the small-town charm of this riverside neighborhood.
Estacada Christmas Lights Parade
A glowing holiday parade through Estacada with free hot cocoa and festive light displays along the route. A charming way to welcome the season in one of Clackamas County's most scenic river towns.
Winter in Willamette Holiday Market
A festive holiday market in the Historic Willamette district featuring local artisans, seasonal gifts, food vendors, and holiday cheer along the beautiful Willamette riverfront.
Farmers markets & weekly happenings.
Some of the best parts of living here aren't one-time events -- they're the weekly rhythms. Farmers markets where you run into neighbors, grab fresh produce, and enjoy a little live music. Here are a few favorites.
Oregon City Farmers Market
Fresh local produce, artisan goods, and community vibes every Saturday. The summer market runs through October 31; the harvest market picks up November 1, and the holiday market runs Saturdays through December 20 before switching to a winter schedule. Accepts SNAP/EBT with Double Up Food Bucks match.
Milwaukie Sunday Farmers Market
Over 75 vendors weekly with fresh produce, food, and live music. A Sunday morning staple for the whole community since 2008.
Milwaukie First Friday
Milwaukie's largest block party -- a celebration of art, music, food, and community. Live music, art displays, and local vendors fill downtown. Free to attend and fun for all ages.
Happy Valley Farmers Market
A weekly Saturday market running through the end of October with 130+ vendors featuring fresh local produce, artisan goods, and a welcoming community atmosphere. EBT accepted.
Sunnyside Farmers Market
A vibrant weekly market in Clackamas with fresh local produce, artisan foods, handmade crafts, and live music every Saturday.
Canby Farmers Market
Fresh local produce, baked goods, flowers, crafts, live music, and wine tasting every Saturday morning in downtown Canby. A great way to start your weekend.
Gladstone Community Market
A seasonal community market on the first and third Wednesdays of the month, hosted at High Rocks along the river. Local vendors, food, and a beautiful waterfront setting.
Wednesdays in Willamette Summer Street Market
A weekly evening street market in the historic Willamette district. Local vendors, food, and a relaxed midweek gathering spot along the river. This Wednesday (September 9) is the final market of the summer season.
Shady Dell Train Park Public Sundays
Free miniature railway rides every Sunday at this beloved Molalla train park. A wonderful family outing that runs through the fall.
Recently Happened
Events that have wrapped up recently. Many of these return annually -- check back for next year's dates.
Molalla Train Fest
MolallaThe 71-year Molalla tradition wrapped up Labor Day weekend with model train displays, live steam rides, food vendors, and family fun. Free miniature railway rides at Shady Dell continue on Sundays through October 25. Returns Labor Day 2027!
Happy Valley Concerts in the Valley
Happy ValleyHappy Valley's free summer concert series brought live music to the park every Thursday evening with food vendors, a splash pad, and playground. The season finale on August 27 closed out another great summer. Returns next year!
Canby's Big Night Out Street Dance
CanbyCanby's Big Weekend kicked off with live music from Radio Riots and Paradise of Samoa, plus local food and beverage vendors, bouncy houses, arcade truck, and free children's activities. A fun summer evening under the lights. Returns next August!
Cutsforth's Cruise-In
CanbyThe 31st Annual Cutsforth's Cruise-In brought classic cars, live music, food, and Canby Rotary Club's BBQ to Wait Park, with proceeds supporting local non-profits. Returns next summer!
Clackamas County Fair and Canby Rodeo
CanbyThe biggest event of the year in Canby wrapped up on August 22 with five days of PRCA rodeo performances, livestock exhibits, carnival rides, open class exhibits, and live music. Returns August 2027!
Celebrate Molalla
MolallaA free community festival filled downtown Molalla with live music, kids' crafts, food vendors, artisans, and over 100 community booths. Returns next summer!
JESSFEST
EstacadaA grassroots country music festival founded by Estacada's own Jessie Leigh wrapped up its four-day run with independent country artists, camping, games, and a Cowboy Church service. Keep an eye out for next year's dates!
Wilsonville Party in the Park
WilsonvilleA summer community celebration with live music, food vendors, and family-friendly activities. Returns next summer!
Estacada Concerts in the Park
EstacadaThe final concert of the season on August 20 featured NW Playboys (Country) at beautiful Wade Creek Park. Returns next summer with a new lineup!
West Linn Music in the Park
West LinnThe summer concert series wrapped up August 20 with tribute bands Petty Fever (Tom Petty), Wild Boys (Duran Duran), and more. Returns next summer!
West Linn Movies in the Park
West LinnThe final movie of the summer series was screened at dusk at Willamette Park. Bring a blanket and enjoy the show next summer!
Oregon City Concerts in the Park
Oregon CityFree live music every Thursday evening filled the summer air with food trucks, local vendors, sponsor booths, and a Kid's Zone. The summer series wrapped up August 13 with Rockit Radio. Returns next summer!
Oregon City Porchfest
Oregon CityA free, community music festival with over 85 artists performing on 50 porches across the historic McLoughlin neighborhood. Walked and biked between porches to enjoy singers, guitarists, and youth performers. Returns next summer!
Oregon City Festival of the Arts (10th Annual)
Oregon CityA decade of celebrating local art! Over 50 art booths, live music, hands-on activities, and food drew crowds to the End of the Oregon Trail grounds. Returns next year.
Boring & Dull Day
BoringBoring's annual celebration of its sister-city relationship with Dull, Scotland, featured a classic car show, vendors, and the kind of small-town charm that makes Boring anything but. Returns next year!
Milwaukie Porchfest
MilwaukieMilwaukie's beloved neighborhood music festival ran its 7th year with live performances on porches, driveways, and public spaces throughout the city. Walked, biked, and danced between stages. Returns next summer!
Pickathon
Happy ValleyOne of the Pacific Northwest's most celebrated indie music festivals wrapped up its milestone year at Pendarvis Farm. 55+ artists across multiple stages. A nationally recognized gem right in our backyard.
Gladstone Community Festival
GladstoneGladstone's signature summer celebration brought together the whole community with a grand parade, classic car show, food trucks, live entertainment, Kids Village, pickleball tournament, and movies in the park. Next year's dates will be announced soon!
Harefest
CanbyThe mother of all tribute band festivals -- three days, two stages, 24 tribute bands. Keep an eye out for next year's dates.
Oregon Renaissance Faire
CanbyA medieval-themed festival with jousting, artisan vendors, live entertainment, and period costumes. Held every weekend in June. Returns next year!
Molalla Buckeroo
MolallaA beloved Fourth of July tradition -- five nights of professional rodeo action, kiddie parade, Rascal Rodeo, and all the small-town patriotism you can handle. Returns every year.
Canby Independence Day Celebration
CanbyDowntown Canby came alive with a street fair, live music, food vendors, kids' activities, a car show, and a community parade. A classic Fourth of July celebration.
Happy Valley 4th of July Family Festival
Happy ValleyA full day of community fun -- morning hike, parade, live music, carnival games, inflatable attractions, food vendors, a beer garden, and fireworks to cap it all off.
West Linn Old Time Fair
West LinnCarnival rides, a timber show, classic car and boat show, the beloved Old Time Parade on Saturday morning, live music, and food booths all weekend. The 71st annual returns July 2027!
Milwaukie Fest
MilwaukieA community celebration featuring games, movies in the park, live arts, food, and activities along Main Street. A signature Milwaukie summer event that returns every July.
Stringbender Festival
Oregon CityOregon City's premier bluegrass and roots music festival wrapped up its three-day run at Red Mud Ranch. Camping and music on the creek. A hidden gem -- keep an eye out for next year's dates!
First City Celebration (15th Annual)
Oregon CityOregon City's signature summer street festival filled Main Street with live music, eclectic vendors, family activities, food, and drinks. A celebration of Oregon City's history as the first city in Oregon.
Estacada Arts at the Creek
EstacadaThe 4th Annual Arts at the Creek filled Wade Creek Park with all-day live music, art vendors, free interactive art activities, face painting, food vendors, and dancing. Returns next summer!
Happy Valley National Night Out
Happy ValleyA nationwide community-building event brought neighbors, law enforcement, and first responders together with live music and family fun. Held in partnership with Happy Valley First Responders. Returns next year!
Event details are based on publicly available information as of September 7, 2026. Dates, times, and locations may change -- I recommend checking each event's official website for the latest details. Want me to add an event? Let me know!
New to the area? Let's find your place.
These events are just one piece of what makes Clackamas County special. If you're thinking about making a move, I'd love to help you find the community that fits your life.
Let's Talk About Your Move