Check out these May 2026 plein air painting events, highlighting groups all over the United States. Bonus: Catch this month’s deadlines so you don’t miss out on upcoming opportunities.
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May 2026 Painting Events
Arkansas
EUREKA SPRINGS PLEIN AIR FESTIVAL
Dates: May 5-9
Entry Deadline: May 1
Sponsoring Organization: Plein Air Painters of Eureka Springs
Venue: Museum of Eureka Springs Art, Eureka Springs, Arkansas
Format: Open
Jurors of Awards: Morgan Samuel Price, Jody Stephenson, Steve Beacham
Award Total: $5,500+
Contact: Charlene Brisson, [email protected], 760.637.1378
Website: www.eurekaspringspleinairfestival.com
Paint the magic of the Ozarks. Everywhere, a masterpiece waiting to be captured of Victorian architecture and stunning natural beauty. Featured guest, award-winning Florida plein air painter and international instructor Morgan Samuel Price. Registration includes 2x 3-hr demo/workshops (one with Morgan), 4x paint-outs, 1x quick draw, and nightly reception to sell your art. Over $5,500 in prizes. Five days of artistic inspiration and building like-minded friendships. All levels welcome. Less than 1 hour from Branson — warm up for the Plein Air Convention.
California
LOST SIERRA PLEIN AIR ART FESTIVAL
Dates: May 9-17
Contact: Mark V. Reynolds, [email protected]
Website: www.lostsierrapleinair.com
BENICIA PLEIN AIR GALLERY PAINT OUT
Dates: May 31-June 6
Contact: Jessica de Jesus, [email protected]
Website: www.beniciapleinair.com
Colorado
OPA 35th NATIONAL JURIED EXHIBITION
Dates: May 26-31
Opening Reception Date: May 29
Sponsoring Organization: Oil Painters of America
Venue: Steamboat Art Museum, Steamboat Springs, Colorado
Format: Juried
Juror of Awards: Mark Boedges
Award Total: Over $100,000
Contact: Liz Pusch, [email protected], 815.356.5987
Website: www.oilpaintersofamerica.com
Celebrate 35 years of excellence in representational oil painting at the Oil Painters of America’s 35th National Juried Exhibition & Convention in beautiful Steamboat Springs, Colorado. The National Exhibition will be on view at the Steamboat Art Museum from May 29 to August 29, showcasing more than 200 exceptional oil paintings by leading artists from across North America — all competing for the prestigious $25,000 Best in Show award. The convention, held May 26-31 at the Steamboat Grand Hotel, will feature inspiring painting demonstrations, engaging breakout sessions, a lively wet paint competition and sale, and more. Open to all. Registration required.
Georgia
PLEIN AIR, ART IN THE MOUNTAINS
Dates: May 14-17
Opening Reception Date: May 15
Sponsoring Organization: Gilmer Arts and Heritage Association
Venue: Gilmer Arts Gallery, Ellijay, Georgia
Format: Open
Juror of Awards: James Pratt
Award Total: $1,000
Contact: Pam Burns, [email protected]. 706.635.5605
Website: gilmerarts.com
Plein Air, Art in the Mountains uses the surrounding vistas of vineyards and orchards that make up our beautiful county at the southern end of the Appalachian Trail. There will be a two-day workshop on Wednesday and Thursday of that week (separate ticket), and on Thursday we offer a list of suggested vistas for a free day of painting around the county. Friday and Saturday artists choose from the prospectus of desired assignments. Friday night we host a meet-and-greet reception. Sunday morning is the quick draw competition, followed by a reception and auction to the public at our theater.
Illinois
15th PRAIRIE PLEIN AIR COMPETITION AND SHOW
Dates: April 24-May 8
Contact: Roxane Benvenuti, [email protected]
Website: www.prairiecenter.org
Maryland
PAINT ANNAPOLIS 2026
Dates: May 31-June 7
Opening Reception Date: May 31
Sponsoring Organization: Maryland Federation of Art
Venue: Circle Gallery, Annapolis, Maryland
Format: Combination
Jurors of Awards: Selection: Gavin Glakas, Awards: Jill Basham
Award Total: $19,000
Contact: Laura Carty, [email protected], 410.268.4566
Website: mdfedart.com/paintannapolis
For 25 years, Paint Annapolis has been the premier plein air painting event for this sailing town, bringing the community together to share in the beauty of painting outdoors at the waterfront and along the Chesapeake Bay area. Paint Annapolis will kick off with the Quick Draw and have new events almost daily. Work will be on display and for sale from May 31-June 20. Paint Annapolis has something for everyone — from artist to art lover to collector. We are so excited to see you for a week of painting in our historic streets!
Missouri
13TH ANNUAL PLEIN AIR CONVENTION & EXPO
Dates: May 14-18
Sponsoring Organization: PleinAir Magazine
Venue: The Ozarks Event, Branson, Missouri
Contact: PleinAir Magazine, 561.655.8778 or 800.610.5771
Website: www.pleinairconvention.com
The Plein Air Convention & Expo is the world’s largest gathering of outdoor artists. With 80+ instructors, it’s built to inspire and sharpen your skills. Enjoy big-screen indoor demos in watercolor, pastel, acrylic, gouache, and oil, plus daily group painting with on-site instructor feedback. Explore the giant Expo Hall for supplies and frames at deep, convention-only discounts, and see the public art show of faculty and attendee work, and much more.
AUGUSTA PLEIN AIR ART FESTIVAL
Dates: April 23-May 2
Sponsoring Organization: Greater Augusta Chamber of Commerce
Venue: Harmonie Verein, Augusta, Missouri
Format: Open
Award Total: $15,000
Contact: Ann Struckhoff, [email protected], 314.435.3599
Website: augustapleinair.com
The Augusta Plein Air Art Festival provides artists with the opportunity for market growth, skill enhancement, artistic recognition, and to experience Missouri Wine Country with other artists. This 10-day event has 15 paint-outs, three theme paints, workshops, and a final sale and festival. Final judging awards Best of Show, Artists’ Choice, People’s Choice, and 1st, 2nd, 3rd, and Honorable Mention in four categories. Art gallery open daily to display and sell artwork. All levels welcome.
4th ANNUAL HISTORIC WEST BOTTOMS PLEIN AIRÂ
Dates: May 15-17
Contact: Alex Hamil, HWBA2026 Director, [email protected]
Website: bcawfoundation.org
New Mexico
THE MOTHER ROAD PAINT OUT
Dates: May 15-October 3
Show Dates: September 4-October 3
Sponsoring Organization: Plein Air Painters New Mexico
Website: www.papnm.org
This is a non-juried plein air event open to artist members of Plein Air Painters of New Mexico (PAPNM) and the Amarillo Art Institute (AAI). Artists may paint plein air anywhere along the historic route 66 in Texas, New Mexico and/or Arizona during the Paint Out period.
North Carolina
NORTH CAROLINA PLEIN AIR ART FESTIVAL
Dates: May 11-17
Opening Reception Date: May 11
Sponsoring Organization: North Carolina Plein Air Art Festival
Venue: New Bern Farmers Market, New Bern, North Carolina
Format: Combination
Jurors of Awards: Selection Juror: Aimee Erickson
Awards Juror: Russell Jewell
Award Total: $16K+ 12K
Contact: Kippy Hammond, [email protected], 858.205.5979
Website: www.ncpleinair.org
Now in its 6th year, North Carolina Plein Air Art Festival will feature 38 nationally acclaimed plein air artists in Eastern Carolina, rich in maritime and historic sites. Eighteen returning award-winning artists will be joined by 20 more by jury and welcomed by local hosts for the event. Exhibition/Sales Gallery with fresh paintings daily in New Bern and paint-outs in Oriental and Beaufort make a spectacular week of 20 free demos, gallery talks, workshops, youth activities, and a Quick Paint. $16K in prizes & awards; $4,000 Best of Show.
Pennsylvania
18th ANNUAL WAYNE ART CENTER PLEIN AIR FESTIVAL
Dates: May 3-9
Opening Reception Date: May 9
Sponsoring Organization: Wayne Art Center Plein Air Festival
Venue: Wayne Art Center, Wayne, Pennsylvania
Format: Juried
Juror of Awards: Mark Boedges
Award Total: $25,000+
Contact: Nancy Campbell, [email protected], 610.688.3553
Website: www.waynepleinair.org
The Wayne Art Center Plein Air Festival is one of the longest-running and most popular outdoor painting events in the country. Founded in 2008, Wayne Plein Air has welcomed over 500 artists to paint the splendor of the Philadelphia area and is one of the most eagerly anticipated cultural events in the region.
Texas
PLEIN AIR SOUTHWEST
Dates: May 3-9
Opening Reception Date: May 8
Sponsoring Organization: Outdoor Painters Society
Venue: Ashton Villa Estate, Galveston, Texas
Format: Juried
Juror of Awards: Bill Davidson
Award Total: $25,000
Contact: Tina Bohlman, [email protected], 972.741.6154
Website: www.outdoorpainterssociety.com
Plein Air Southwest is hosted by Galveston Historical Foundation. Artists compete for $22,000+ in cash and merchandise. The event takes place during the annual Historic Home Tour attracting thousands of visitors to the city. Artists will have the opportunity to interpret this historic island city as only a plein air painter can.
Virginia
PAINT GREAT FALLS
Dates: May 16-23
Opening Reception Date: May 23
Entry Deadline: May 1
Sponsoring Organization and Venue: The Arts of Great Falls, Great Falls, Virginia
Format: Open
Award Total: $2,500
Contact: Meralee Fredenburgh, [email protected], 703.232.1575
Website: www.artsofgreatfalls.org/events/paint-great-falls-2026
Compete for prizes, connect with fellow artists, and showcase your work at our final exhibition and awards reception. This weeklong celebrated community event offers an inspiring opportunity to paint the scenic landscapes of Great Falls.
Wisconsin
PLEIN AIR: A PAINT CEDARBURG EVENT
Dates: May 30-June 6
Opening Reception Date: June 5
Entry Deadline: May 30
Sponsoring Organization: Cedarburg Artists Guild
Venue: Cedarburg Cultural Center, Cedarburg, Wisconsin
Format: Open
Award Total: $8,500
Contact: Kerri Knapp, [email protected], 262.993.9517
Website: www.cedarburgartistsguild.com/paint-cedarburg
Celebrating 25 years, Plein Air: A Paint Cedarburg Event is Wisconsin’s largest gathering of outdoor painters. Over six days, artists capture the beauty of Ozaukee County’s quaint towns, charming farmlands, and scenic Lake Michigan shoreline. The week kicks off with Fresh from Cedarburg, a one-day painting event and public sale in historic downtown Cedarburg, and concludes with awards and an exhibition at the Cedarburg Cultural Center.
May Deadlines for Artists
- May 1: Eureka Springs Plein Air Festival (Eureka Springs, Arkansas)
- May 1: Plein Air Altitude (Winter Park, Colorado)
- May 1: Plein Air Grand Marais (Grand Marais, Minnesota)
- May 1: Paint Great Falls (Great Falls, Virginia)
- May 15: Plein Air Plus (Long Beach Island, New Jersey)
- May 30: Plein Air: A Paint Cedarburg Event (Cedarburg, Wisconsin)
- May 31: Paint Under the Big Sky (Big Sky, Montana)
- Next monthly deadline coming soon: The Salon Art Prize (formerly PleinAir Salon)
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Content prepared for the web by Cherie Dawn Haas, Editor of Plein Air Today
