Fall Festive Events Around Central Oregon

Sunset Migration: Selected Paintings and Collages by Katie Dunbar

A visual conversation about movement, plastics and color, this exhibition by local artist Katie Dunbar runs through Wednesday, Sept. 30 at Deschutes Brewery, and features select paintings and collages in the brewery’s downstairs dining room. The Sunset Migration series portrays intimate and global situations of environmental and social concerns of Dunbar, who is also a successful graphic and mural artist. Check out Dunbar’s work for free from 11am-9:30pm at Deschutes Brewery & Public House, 1044 NW Bond St.

Fall Equinox & Cacao Ceremony

Friday, Sept. 25, 5-6pm It’s said that drinking pure chocolate cacao supports mood and well-being. Test the theory at a Fall Equinox Cacao & Sound Bath, a restorative evening that begins with a grounding cacao ceremony from Belize, and then flows into guided reflection and intention setting. The night caps off with a deeply restorative hypnotic meditation, light drumming and deep rest. Cost is $75 for the event, which is on Friday, Sept. 25 from 5-6pm at Juniper Preserve, 65600 Pronghorn Club Dr. in Bend.

OAC First Friday Open Studios & Gallery Show

Tour artist studios, explore the Open Arts Center’s current community exhibition and enjoy an evening of creativity, conversation and inspiration. OAC has 22 artist studios and collaborative spaces for use by its members, and there are also special events and classes for teenage artists. The OAC aims to provide a community-driven space for teens and adults to foster creativity, intergenerational learning and belonging. OAC also is launching its inaugural music series in October with intimate live performances, artist stories and live Q&A sessions. The free First Friday Open Studios & Gallery Show runs from 5-7pm on Friday, Oct. 2 at OAC, 992 NE 2nd St. in Bend, and again on Friday, Nov. 6.

Harvest Chef’s Pairing Experience

Foodies and oenophiles will delight in the Harvest Chef’s Pairing Experience, set for Wednesday, Sept. 30. Participants will indulge in a curated five-wine flight paired with four chef-created dishes in a communal experience so they can mingle and connect with other attendees while savoring each tasting. Cost is $95 for the experience at Willamette Valley Vineyards, 916 NW Wall St. in Bend, which has other seasonal pairing events coming up, including the Fall Chef’s Pairings Experience on Wednesday, Oct. 28 and the (Halloween) Candy and Wine Pairing Experience on Saturday, Oct. 31.

Young Entrepreneur’s Fall Market

The Young Entrepreneur’s Society of Central Oregon believes communities should invest in kids and their ideas and is showcasing that spirit at the 2026 Young Entrepreneur’s Fall Market. There’ll be unique goodies, handmade treasures and creative finds from more than 30 young Central Oregon makers. Attendees are helping kids build confidence, learn real world skills and discover the power of entrepreneurship. The market runs from 11am-2pm on Saturday, Oct. 3 at the Deschutes County Library in Redmond, 827 SW Deschutes Ave.

Dry Canyon Arts Speakeasy Fundraiser

Step back into the Roaring Twenties for a night of jazz, hidden doors and local creativity at the Dry Canyon Arts Association’s first fundraising event, “It’s a Roaring Good Time Speakeasy.” The 1920s-themed evening promises vintage glamour, live entertainment, cocktails by Gompers, a buffet and a costume contest. Attendees have to use a secret password to find the event’s hidden door, and there’ll be an art raffle featuring pieces by DCAA artists. The event is slated for Saturday, Oct. 3 at a secret downtown-Bend location, and is limited to 80 guests. Tickets are $100. All proceeds benefit DCAA programs.

Art in the West Closing Party 2026

Celebrate the closing of the 2026 Art in the West exhibition on Friday, Oct. 2, perusing approximately 130 original paintings, sculptures, photographs and mixed-media pieces that highlight the landscapes, wildlife and history of the high desert, which stretches from the eastern slope of the Cascades and Sierras to the Wyoming Basin and Colorado Plateau. Mingle with artists, watch live demonstrations and enjoy food and libations. The Art in the West exhibition is an annual juried fine-art exhibition and online silent auction. The doors open at 6pm, and the event is free and open to the public at High Desert Museum, 59800 S. Highway 97 in Bend.

The 20-Dollar Art Show

Bend’s biggest little art show returns Oct. 10-27. High Desert Museum is partnering with Bright Place Gallery to host the legendary 20-Dollar Art Show exhibition, which features the walls of the museum blanketed with 9,000 original, miniature masterpieces by more than 180 local and emerging artists. It’s a vibrant celebration of regional creativity, and opens on Saturday, Oct. 10 at High Desert Museum, 59800 S. Highway 97 in Bend. The exhibition is free with museum admission and runs through Tuesday, Oct. 27. For those looking to purchase the exhibited artwork, the opportunity arises at the 20-Dollar Art Show Extravaganza, which is on Friday, Oct. 23 from 5:30-8:30pm. The Extravaganza is an after-hours event that kicks off the art sale, which continues through Oct. 24-25 from 9am-Noon. Tickets must be purchased for the Extravaganza and are $5 for adults (16 and younger are free). Cost includes music, food and drinks, and there’ll be a no-host bar. Artists keep 100% of the profits from the sale of their works.

This article appears in the Source September 24, 2026.