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13 Labor Day Weekend Events in the Portland Area 2018

  |  Happenings, Local Happenings, Neighborhood Insight, Portland

Labor Day is almost upon us! While this means school is starting up and summer is unofficially over, there is so much fun yet to be had. In fact, some of the most beautiful days in the Pacific Northwest are still on the horizon.

Savor the final days of summer at one of the many events in the Portland area on Labor Day weekend, from flower festivals to half marathons, and wine tasting to outdoor movies.


Annual Dahlia Festival | Canby, OR

August 25–27 + September 1–3

Annual Dahlia Festival Canby, OR

The Annual Dahlia Festival is taking over Swan Island Dahlias in Canby for two weekends of flowers, food, music, and lots of fun. View over 400 floral arrangements of colorful dahlias, plus over 15,000 cut dahlia blooms on display in three indoor display rooms. The festival will feature live music, floral arrangement demonstrations, food vendors, refreshments, entertainment, and much more. Visit this free festival on the weekend before Labor Day weekend or Labor Day weekend!


Cambia Portland Classic | Portland, OR

August 30–September 2m

Many Portlanders are well-accustomed to the Cambia Portland Classic, a women’s professional golf tournament on the LGPA Tour. Founded in 1972, this annual event is the oldest continuous event on the tour! Each year, proceeds from the tournament are donated to local children’s charities, totalling over $15 million in donations since the event’s inception. Be a part of the excitement by purchasing tickets for the Cambia Portland Classic, ranging from general admission to VIP options.


Concerts + Movies in the Park | Portland, OR

August 31–September 2

Concert and Movies in the Park Portland, OR

Photo Courtesy of Portland Parks & Recreation and Ben Brink

Finish off the 12th season of Portland’s free Movies in the Park series with some of the last showings at parks throughout the Portland area. Grab a lawn chair, blanket, snacks, and head to one of these local parks for free live music followed by a movie screening!

Friday, August 31: Luuwit View Park

Music: Portland Kora Project (West African harp meets soul and jazz)

Movie: Inside Out

Saturday, September 1: Montavilla Park

Music: The Alphabeticians (Family-friendly rock ‘n’ roll)

Movie: Paddington 2

Sunday, September 2: Overlook Park

Music: Soul Vibrator (Power-funk and yacht rock)

Movie: Wonder Woman


Oregon Symphony at the Zoo | Portland, OR

September 1

Oregon Symphony at the Zoo

Photo Courtesy of Leah Nash via The Oregon Symphony

The Oregon Symphony is launching their 2018/19 season at the Oregon Zoo! This two-hour program will feature classical favorites, including Gershwin’s An American in Paris, Bizet’s Carmen Suite, and Tchaikovsky’s 1812 Overture. Enjoy the sweet sounds of the symphony amidst the gorgeous natural setting of the zoo, surrounded by wildlife. Doors open at 5 p.m., the concert begins at 7 p.m., and tickets range from $35–95. Concert tickets also include zoo admission on the day of the show!


Oregon Wine Country Half Marathon | Carlton, OR

September 1–2

This isn’t your average half marathon experience! Travel to the tiny town of Carlton just west of Portland for the Oregon Wine Country Half Marathon. Hosted in Yamhill County in the heart of the Willamette Valley, race participants rave about the small-town charm, sunrise views, scenic course, great wines, and the exciting post-race wine and music festival. This is the perfect Labor Day weekend “run-cation”, featuring a day filled with activity, from the half marathon to the Wine and Music Festival presented by Ken Wright Cellars. Register for the Oregon Wine Country Half Marathon to be a part of this thrilling race in the heart of Oregon’s Wine Country!


Art in the Pearl | Portland, OR

September 1–3

Art in the Pearl Portland, OR

Photo Courtesy of Kamala Dolphin-Kingsley via Art in the Pearl 

Every year, Art in the Pearl sets up shop in the Pearl District’s North Park blocks on Labor Day weekend. This vibrant arts event has been named one of the top 10 arts and crafts fairs in the country! Visit with over 100 artists showing and selling a range of beautiful work, including wooden furniture, paintings, photography, glass, clay, metal, jewelry, and much more. The festival fills the Northwest Portland Park blocks with an abundance of art, theater, music, and hands-on activities for all ages. Art in the Pearl is completely free and requires no tickets for entry.


Labor Day Vineyard Wine Tasting | Wilsonville, OR

September 1–3

Labor Day Vineyard Wine Tasting Terra Vina Wines

Photo Courtesy of Terra Vina Wines

Relax in the idyllic vineyard setting at Terra Vina Wines, a winery estate nestled in the heart of the Willamette Valley in Wilsonville. Their Labor Day Vineyard Wine Tasting event will feature tours of the vineyard, heavy with grapes approaching harvest. Bring a picnic, sample wines, and enjoy the gorgeous view at this enriching winery event just outside of Portland. Terra Vina will be open on Saturday, Sunday and Monday from 12–6 p.m.


Tour de Lab | Portland, OR

September 2

Tour de Lab Portland, OR

Photo Courtesy of Rohith Gunawardena via Tour de Lab

Embark on a multi-pub bicycle tour adventure with Tour de Lab, featuring a 45-mile Big Dog route and an 18-mile Puppy route. The tour features a hearty breakfast, a hot dog buffet lunch, free beer and a pint glass, and lots of fun throughout. The after party will have bikes, dogs, hot dogs, music and beers — what more could you ask for? The Tour de Lab is hosted by Events by Axiom and benefits DoveLewis, a local non-profit emergency animal hospital offering advanced veterinary care 24 hours a day, 365 days a year.


Oregon Bunny Palooza | Portland, OR

September 2

Oregon Bunny Palooza

Calling all bunny lovers! The Oregon Bunny Palooza is a festival celebrating domestic pet rabbits and the people who love them. This fun-filled day is filled with activities, education, vendors, a silent auction, and more rabbit-filled fun! You can adopt or foster a bunny, ask bunny-related questions, pick up supplies and toys, and much more. This event benefits Rabbit Advocates, a local non-profit rabbit rescue serving Oregon residents of Multnomah, Clackamas, Washington, and Columbia counties, and Washington residents of Clark County.


Labor Day Sunday BBQ and Show on the Patio | Canby, OR

September 2

Labor Day Sunday BBQ and Show on the Patio St. Josef's Winery

Photo Courtesy of St. Josef’s Winery

Head to St. Josef’s Winery in Canby for BBQ ribs and live music on the patio. Enjoy the day by the vineyards, sample wines, play a game of cornhole, or picnic in the tiered rose garden at the pond. No reservations are needed and there is no cover charge for this family-friendly event! Food is available from 12:30–4 p.m., music will play from 1:30–4:30 p.m., and the tasting room is open from 12–5 p.m.


Timberline Labor Day Mountain Music Festival | Government Camp, OR

September 3

Timberline Labor Day Mountain Music Festival

Don’t miss this annual tradition at Timberline Lodge on Mount Hood, located about 60 miles due east of Portland. The Timberline Labor Day Mountain Music Festival features a full day of live roots music in the historic outdoor amphitheater, food and drinks, and much more. The lodge has teamed up with Boyd’s Coffee Company and the Mt. Hood Brewing Company to create this exciting free event filled with endless music.


Dropbox Derby | Portland, OR

September 3

Dropbox Derby Portland, OR

Photo Courtesy of Jess Pierson via Lovett Deconstruction, Inc.

The 2nd Annual Dropbox Derby is the perfect event for DIY fanatics, design junkies, or fans of Portland’s quirky, innovative, and unique talent. The design-build challenge features 20 teams of builders, artists, and designers competing to create a unique work out of salvaged materials according to a chosen theme. This unique event at the Eastbank Esplanade Festival Lots is free to attend and will feature food, drinks, and live music!


Roy Webster Cross-Channel Swim | Hood River, OR

September 3

Each Labor Day at dawn, a large group of swimmers jumps into the Columbia River and swims a 1.1-mile stretch across to Hood River. The Roy Webster Cross-Channel Swim is the Columbia River’s biggest and oldest official swim event, attracting hundreds of brave participants from around the world. While registration for this year’s event is full, you can witness this exciting swimming event on Monday, September 3!


Happy Labor Day!

What annual events are on your calendar this year? Let us know in the comments below!

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About the Author

Courtney Itami

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