Portland Fall Festivals 2020

Faerieworlds - North Plains, OR - Aug 21 to Aug 23, 2020
Enter the realm of the faerie at this annual music and arts festival. Located at Horning’s Hideout west of Portland.

Lake Oswego Collector Car and Boat Show - Lake Oswego, OR - Aug 23 to Aug 23, 2020
Admission is free and all proceeds benefit Oswego Heritage House and Museum, the City’s home of local history preservation, community events, and educational programs! What started out as a handful of collector cars on display at Millennium Plaza in 2000 has grown to become one of the Region’s best known shows with free admission and shuttles for everyone. Don’t miss the Summer’s most unique gathering of Collector Cars and Classic Boats on display at all three Lake Oswego venues, including George Rogers Park, Sundeleaf Plaza and Foothills Park.

Pork-landia BBQ - Canby, OR - Sep 7 to Sep 7, 2020
Come celebrate the last Sunday of summer with BBQ ribs and music on the patio at St Josef’s Winery.

Rose City Comic Con - Portland, OR - Sep 11 to Sep 13, 2020
Portland’s premier pop culture event at the Oregon Convention Center.

Portland Dragon Boat Festival - Portland, OR - Sep 12 to Sep 13, 2020
A DragonSports USA organized dragon boat race held annually in September. Enjoy live entertainment, food vendors and a beer garden, plus beautiful views of the Willamette River while watching a 500m dragon boat race.

Oregon Fall Wine Country Half Marathon - Canby, OR - Sep 12 to Sep 12, 2020
Run a sanctioned 13.1 miler through the vineyards at St Josef’s and down the quiet surrounding country roads.

Oregon Independent Film Festival - Portland, OR - Sep 15 to Sep 30, 2020
Screens 75+ films from 10+ countries over two weeks at multiple venues including The Clinton Street Theater in Portland and the Bijou and Metro cinemas in Eugene.

Oktoberfest and Brewfest at Kennedy School - Portland, OR - Sep 19 to Sep 19, 2020
More than a dozen German-style craft beers, plus burgers, brats, and warm pretsels to nosh on while enjoying live music fron noon to 9pm.

Cornish Apple Festival - Cornish, ME - Sep 26 to Sep 26, 2020
This free festival is held in historic Cornish Village on the last Saturday in September. Event includes apple pie contest, live entertainment, arts & crafts, 5K race and other activities. It is a fundraising event for the Cornish Association of Businesses.

Flock and Fiber Festival - Canby, OR - Sep 26 to Sep 27, 2020
Demonstrations, workshops, livestock shows and kids’ activities. Since 1997.

Hood River Hops Fest - Hood River, OR - Sep 26 to Sep 26, 2020
Since 2003, Hood River County, surrounded by world renowned hop growing regions, has hosted brewers each September who share their fresh-hop beer creations. More than 50 breweries offering more than 60 fresh-hop beers, plus a variety of food vendors, live music, and a collectible mug, are yours to enjoy for a beer garden ticket price of $15 (21+, presale rate – under 21 free but only allowed until 5pm). A portion of proceeds are given back to the community’s non-profit organizations.

St Josef Grapestomping Festival - Canby, OR - Sep 26 to Sep 27, 2020
Grapestomping in 1200 gallon oak barrels, dancing, 400 lbs of sausages and sauerkraut, drinks, and more. Admission is $10 per person and includes souvenir glass, and you may even get picked to stomp the grapes with a partner!

Freeport Fall Festival - Freeport, ME - Oct 2 to Oct 4, 2020
A three day festival showcasing New England artists and craft makers on the L.L.Bean campus and downtown Freeport, plus live music, Chodwah Challenge, food, and more!

The Wedge - Portland, OR - Oct 3 to Oct 3, 2020
Taste and buy hundreds of cheeses (plus other specialty foods and beverages) from 75+ artisanal producers. Don’t forget your cooler!

Fryeburg Fair - Fryeburg, ME - Oct 4 to Oct 11, 2020
Livestock exhibition, parade, competitions like the Fireman’s Muster and the Skillet Throw, midway rides and carnival games. Admission is $12 a day.

FashioNXT - Portland, OR - Oct 7 to Oct 10, 2020
Portland’s Fashion Week, called #1 in the US after New York Fashion Week! Incubators and accelerator to help the next generation of fashion talents, plus services for fashion and technology.

Hood River Valley Harvest Fest - Hood River, OR - Oct 9 to Oct 11, 2020
More than 120 vendors will be present offering local food, produce, arts & crafts; wine, cider, and beer tastings. Kids area with bouncy houses, face painting and more make this event fun for the whole family. Adult tickets are $6 a day. Discounts for seniors and military. Kids under 12 are free. A portion of the proceeds are donated to non-profit organizations in the community.

Portland Film Festival - Portland, OR - Oct 12 to Oct 18, 2020
MovieMaker Magazine called it one of the coolest film festivals in the world. This festival brings a week of film premieres, networking, workshops, guest speakers, Q&A’s and more to Portland.

York Harvestfest & Kidfest - York Beach, ME - Oct 17 to Oct 17, 2020
Annual event for 30+ years on the weekend after Columbus Day. Held from 9 AM to 4 PM. Live performances, food, kids games, juried craftors, HarvestFest, and horse-drawn wagon rides at Short Sands Beach. Public parking at York’s Wild Animal Kingdom.

OgunquitFest - Ogunquit, ME - Oct 23 to Oct 25, 2020
Pumpkin decorating, scarecrow contest, costume parade, classic car show, craft show, wagon rides and more.

Northwest Food & Wine Festival - Portland, OR - Nov 7 to Nov 7, 2020
Enjoy over 600 wines and spirits, and 50 restaurants at this half-day wine and gourmet food celebration. VIP includes an extra hour plus Winemaker’s Talk and reserve tastings, Belgian Trio sampling by Stella Artois, keepsake, and overall advance preview of all wineries and distilleries. Since 2005. 21+ event.

Portland Book Festival - Portland, OR - Nov 7 to Nov 7, 2020
Formerly called Wordstock, this annual book festival returns again, and is held at the Portland Art Museum and nearby venues. Enjoyed by about 10,000 people each year, this festival offers over 100 authors in various onstage events, pop-up readings, and writing workshops, plus a book fair, local food trucks and more!

Holiday Food and Gift Festival - Portland, OR - Nov 13 to Nov 15, 2020
A series of holiday festivals comes to Portland once more! Thousands of attendees complete their holiday shopping early, with hundreds of exhibitors offering one of a kind gifts including arts and crafts, decor, clothing, gourmet food and more!

Wild Arts Festival - Portland, OR - Nov 21 to Nov 22, 2020
Celebrate nature in arts and books at this event, benefitting the Audubon Society of Portland. Fun for the whole family awaits with children’s activities from noon to 2pm Sunday.