An impressionistic painting of a boat docked on a river with city buildings and clock tower in the background, reflecting in the water.

Paint out Party & art Sales

“Riverboat Twilight at the Port”

Lyudmila Tomova Clark

2025 Grand Prize

Info for Artists
What is a Paint Out?
Meet the Artists

2026 Friday paint out Party & Art Sale

Celebrate art and Dubuque! Enjoy conversations with artists.

Food, drinks, and live music!

DATE/LOCATION

Friday, 25 September 2026
6:00-9:00PM
Steeple Square | 101 E. 15th St., Dubuque, IA

Purchase Tickets!

2026 Saturday Art Sale

The party and sale continue! New art continues to be hung on Saturday

Food Vendors
Live Music

DATE/LOCATION

Saturday, 26 September 2026
9:00AM-4:00PM
Steeple Square | 101 E. 15th St., Dubuque, IA

Free Admission

NEW LARGE ART SALE!

Purchase larger works at Bluff Strokes Art Center. Thirty 2026 Paint Out Artists will exhibit work. These will be created prior to the Paint Out week and might be studio paintings or styles other than plein air. The only requirement for the artists is that the works are larger than those at the Paint Out sales on Friday and Saturday. We want to highlight the range of our artists’ work.

Become familiar with artists’ styles and come back to see their new plein air work on Friday night and Saturday.

Date/location

Wednesday, 23 September 2026
Noon-8:00PM
Bluff Strokes Art Center | 1201 Locust St., Dubuque, IA

Free Admission

Sale of Prior Works

Purchase artists’ works completed prior to our 2026 paint out. Become familiar with artists’ styles and come back to see their new work on Friday night and Saturday.

Quick Paint and Nocturne Paintings will be hung for viewing (not for sale).

Date/location

Thursday, 24 September 2026
5:00-7:00PM
Steeple Square | 101 E. 15th St., Dubuque, IA

Free Admission

People browsing artwork at Steeple Square gallery in Dubuque, IA with stained glass windows and high vaulted ceilings during the Bluff Strokes annual Paint Out.

VENUE

We are so fortunate to partner again with Steeple Square. The Steeple Square Community Event Center offers a unique setting for our event. In fact, it’s a work of art itself. Enjoy the beautifully renovated space while you enjoy friends, meet the artists, and shop for original art.

Thursday, Friday, and Saturday events take place at Steeple Square.

Wednesday’s large art sale happens at Bluff Strokes Art Center.

Thank you, 2026 Sponsors!

Email to become a sponsor

PAST WINNERS

2025‍ ‍2024‍ ‍2023‍ ‍2022‍ ‍

2019‍ ‍2018

A woman painting on a canvas set up outdoors on a city sidewalk with cars driving by in the background.
A man wearing a cowboy hat, sunglasses, a vest, and jeans standing outside a brick building, looking at a display of small items on a wooden table. There are signs on the wall, including one with rules about skateboarding, bicycle riding, rollerbladi
A photographer in a red hoodie and black pants standing outside in an empty parking lot, capturing the large red brick church with two tall steeples topped with crosses during the day.
A man wearing a straw hat and navy jacket standing in front of a tall cornfield, working on a wooden easel with a canvas or paper during the Bluff Strokes annual plein air Paint Out.
A man in a straw hat and striped shirt painting on a canvas set on an easel outdoors near the Mississippi River, surrounded by trees and greenery during the Bluff Strokes annual plein air Paint Out.
A woman wearing a wide-brimmed hat and checkered shirt painting a landscape scene on an easel, with a bridge and the Mississippi River in the background.
A person with gray hair wearing a blue jacket and brown shorts is standing outdoors, painting on an easel in a park-like setting with green grass, trees, and a stone bridge in the background under a clear sky.
People browsing artwork at Steeple Square in Dubuque, Iowa, a church turned art gallery with high, arched ceilings and stained glass windows during the Bluff Strokes annual plein air Paint Out patron party.
A man with gray hair wearing a black leather jacket stands in front of framed paintings at an art gallery. The paintings depict rural scenes, including a red vehicle, a group of people in a field, and a landscape with horses.
Two women viewing paintings at an art gallery, one pointing at a painting, with additional artworks displayed around them.
A female artist paints on a canvas at an indoor theater with an orchestra performing on stage below.
View of an ornate theater balcony with two men working with lights and equipment.
A young girl with long blonde hair smiling and holding a framed photograph of a bridge and cityscape at night that she purchased at the annual Bluff Strokes plein air Paint Out art sale.
Art exhibit with various landscape paintings and portraits displayed on a wall at an indoor gallery with spotlights and church-like architecture.
People viewing art at the annual Bluff Strokes plein air Paint Out at Steeple Square in Dubuque, Iowa, with framed paintings on the walls and booths in the background.
A man and woman at an art gallery, looking at framed artworks on the wall; the man is pointing at one piece while holding a drink, the woman is holding a drink.
Group of people at a social event or conference in a well-lit room with large windows, some holding papers and engaging in conversation.