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Central Oregon Weekend Planner, Sept 27th - Sept 29th 2019



Sept. 27th - Sept. 29th, 2019

Great Harvest Obstacle Challenge

SAT - Terrebonne - An obstacle course run to get your holiday season jump started!
Run, Jump, Climb to the Challenge!

This 3+ mile multi-obstacle sprint course will challenge participants in strength, agility and mental fitness. A great opportunity for individuals and teams! 7am - sign up here!

Bend Film Great Gatsby KickOff Party

FRI - The Great Gatsby-themed gala kicks off the 2019 BendFilm Festival! Enjoy vintage craft cocktails, wine, beer, inspiring hors d’oeuvres, prizes from Bend area businesses, a sneak peek at this year’s films, dancing, and a rip-roaring good time. You’ll get your exclusive first look at this year’s 2019 BendFilm Festival Guide and you’ll know why G5 plays host to the Annual BendFilm Festival Kick-Off Party! Dressing up is encouraged! 6pm, $25

Sisters Fresh Hop Festival

SAT - Come celebrate ten years of fresh hops and fresh beers at this toast friendly rite of autumn. There will be food trucks, a bouncy house, and music from The Brothers Reed and Tony Lompa. Like last year, the festival takes place at the Three Creeks Brewing production facility on Barclay Drive to provide a more brewery-like atmosphere. Kids and dogs are allowed at the event, but not inside of the beer tent. Bring your friends and family for a great time! Admission is free. Tasting glass and tokens $15.

McKay Creek Cowboy Gathering

SAT – Wine Down Ranch, 6500 McKay Creek Rd., Prineville -  Benefit for H.O.R.S.E.S. on the Ranch, an equine-assisted therapy & learning program. Event features local artists, leatherworkers, silversmiths and more! Free - 10am-9pm. Email for more info =

2019 Green Tour Of Homes

SAT – The 19th annual Green Homes Tour, presented by the Environmental Center, which highlights green buildings and the local hometown heroes who are choosing a brighter, greener, solar energy fueled future. This tour is a great opportunity to visit these properties and physically experience the possibilities, while hearing the stories of lessons learned along the pathway to sustainable building.

Live Music

FRI-SUN - Bend Roots Revival is a grass-roots event, with six stages for live music, art, education programs, workshops, and camps. The annual gathering of artists and fans is grand celebration Bend’s unique creativity and the end-of-summer party for locals in Bend! Proceeds from sales, sponsorships, and donations at this event support art and music education through Rise Up, Inc., an organization with a mission to ensure access to the basic human right of education.

SAT – The Tower Theatre hosts John McEuen and the String Wizards with bluegrass, country, and west coast country rock mixtures.

SUN – Sisters Saloon Open Mic Night, Open Mic at Sisters Saloon hosted by Bend musician, Victor Johnson. Covers and originals, all ages welcome. 190 E. Cascade Ave., Sisters

Bigfoot & Brews

SUNMcMenamins Old St. Francis School in Downtown Bend hosts world-renowned speakers, researchers and celebrities. “Finding Bigfoot” star Cliff Barackman and Monster X Radio hosts unravel hoaxes and stories

Mt. Bachelor

ONGOING – The Mt. Bachelor Bike Park offers 13 miles of downhill trails and different options for various skill levels.    

DD Ranch Pumpkin Patch

9/28 - 10/31 – Terrebonne - Fall fun is endless at the DD Ranch! There is no admission charge and parking is free. The Pumpkin Patch is huge – you are sure to find the perfect pumpkin. On weekends there are:
Pony Rides, Petting Zoo, Kids Corral, Hay Maze, DD Dirt Express Train, Hay Ride, Cowboy Arcade, and much, much more!


  • Abominable

  • Judy

  • 10 Minutes Gone

  • First Love

  • The Day Shall Come

  • The Pretenders

  • Sister Aimee

  • 10E

  • Nineteen Summers

  • The Gliksmans

  • Sea of Shadows

  • The Laundromat

  • Old Boyfriends

  • The Golden Glove

  • Prey

  • The Curse of Buckout Road

  • The Climbers

  • Doorbeen

Click here for movie times and theaters.







These are just a few ideas, whatever you choose to do we hope you enjoy yourself and spend time with your favorite people.

Have a great weekend!
Shane and Denise