2021 Best of Entertainment in Bend, Oregon

Oregon has reached its vaccination goals, ended all COVID 19-related restrictions, and fully opened again – which means everyone in Bend is excited to finally get out again and spend some time with each other at our favorite events. If you’re new to living in Bend, you may be wondering just what events to look forward to. Let’s look at Bend’s best entertainment options for the rest of the year!

Les Schwab Amphitheater Concerts

If you’re wondering what to do in Bend now that there are no crowd restrictions, Les Schwab has put together an incredible late summer/autumn lineup this year, and you should be able to find something you or your family will enjoy. Death Cab for Cutie, Dave Matthews Band, Modest Mouse, Jimmy Eat World, Flogging Molly…there’s a lot to choose from in 2021! Act quickly to find tickets at reasonable prices!

First Fridays

The First Friday Art Walks are back every month until cold weather arrives, and it’s a better way than ever to spend your Friday evening. Downtown Bend opens and spills out into the streets with exhibits, discounts, and free drinks. For those wondering what to do in Bend, it’s a great way to get acquainted with many downtown businesses and people – you’ll be planning additional outings in no time.

Music on the Water/Munch N’ Music

These are two summer music series ideal for more laidback outdoor activities in Bend. One focuses on the beautiful views at Elk Lake Resort, while the other encourages you to enjoy local snacks at Drake Park.

Family Fun Float

If you are looking for things to do in Central Oregon with the family, we highly recommend preparing for the July 14th Family Fun Float at the Sunriver Marina, which offers two to six-person rafts for a fun river floating experience.

Deschutes County Fair & Rodeo

For more traditional fun, the County Fair & Rodeo starts on July 28th and packs the Redmond Expo Center with events, carnival games, food, exhibits and animals, concerts, and of course the rodeo itself.

Bend Beer Chase 2021

This September 25 event is for the more athletic – and beer lovers, of course! It’s a relay race with six-person teams that covers around 55 miles from Bend to Redmon and back. Even if relay running isn’t your style, you can happily cheer on friends or help runners find each other to form teams! There are also a variety of smaller races (often beer related as well), being planned across the city for those interested in a less strenuous option.

Theater in the Park 2021

Theater in the Park continues August 20 with a Dark Park production of Into the Woods. We especially recommend getting VIP tickets if possible, as they include catering from the delicious local Peruvian fusion restaurant Hola!.

Bend Oktoberfest

Oktoberfest is back in style starting on September 18th, bringing back the classics like stein holds, beer bongs, dancing, traditional music, the wiener dog race, and – of course – lots and lots of beer. A wide variety of local food and products will also be available, with plenty of highlights on traditional German foods plus much more, so there’s sure to be something for everyone here.

Bend Fall Festival

Those moving to Bend should always mark the date for our seasonal festivals. While Summerfest just passed us by in early July, the Bend Fall Festival is coming up the weekend of October 1st, where downtown is blocked off and filled with incredible food, music, art, and products from around the Northwest. Don’t miss it!

BendFilm Festival 2021

The 10-day BendFilm Festival starts on October 7th and is an excellent way to catch up on the latest indie and upcoming films, meet your favorite directors and actors, make connections for a future in the industry, and much more. If you’re a movie buff, you’ll want to start making plans ASAP.