Happy Holidays

Joy to the Bend: Happy Holidays & Happening in Bend

We heart the holiday season in Central Oregon.

From hot chocolate dates around fire pits and early morning runs at Mt. Bachelor to ice skating at The Pavilion and SantaLand in the Old Mill District, Bend and the surrounding areas embrace the winter months with a zeal rarely seen outside of the North Pole.

Come join us along the Deschutes River for some of our favorite holiday cheer!

Visits with Santa in Bend, Oregon

While there’s no SantaLand in 2020, families will still be able to see Santa in-person Dec. 4-5, Dec. 11-12, and Dec. 18-19. 

As part of the new Santa experience this year, two special red North Pole mailboxes will be placed in the Old Mill District – one near Ben & Jerry’s Ice Cream and the other by Jimmy John’s – from Nov. 27 to Dec. 19. Children are encouraged to drop off their letters to Santa at any time, complete with a return address, as all letters will receive a response.

With a little help from his friends in Bend, Santa will be driven through the Old Mill District in the back of a pickup truck to pick up the letters during the following dates, Dec. 4-5, Dec. 11-12, and Dec. 18-19 at 1 p.m. each day.

These letter runs will allow Santa to wave and interact with everyone in the Old Mill District, but in a way that respects the current health and safety guidelines.

The public is encouraged to come down and cheer on Santa on Fridays and Saturdays before Christmas as he collects his holiday letters. We do ask that spectators maintain proper distance between one another and Santa and his special helpers.

Tree of Joy

This season give a gift to a child or family in need through the Tree of Joy in SantaLand.

A partnership between the Salvation Army, the Rotary Club of Greater Bend and the Old Mill District, the Tree of Joy ensures that every child in Central Oregon experiences the joy of Christmas.

This year, the traditional in-person Tree of Joy with tags is on hold, but we are still asking for your support. If you would like to participate by purchasing a gift for a child, visit the Rotary Club of Greater Bend website for children’s names and gift ideas!

Delivery of unwrapped gifts are due back to The Salvation Army in Bend at 515 NE Dekalb near Bend High School by December 16. The Salvation Army is receiving gifts Monday through Friday, from 9 a.m. to 4 p.m.

Thank you for your continued support of those in need in Central Oregon.


Due to the current pandemic, caroling has been canceled for 2020. Come experience the glorious sounds of local choir groups next holiday season in the Old Mill District. Throughout December 2021, we’ll feature various choral groups along the river and throughout our shops and restaurants.