Paint the Town Details & 2020 Registration

11th Annual Paint the Town-April 23-26, 2020

We regret that this event has been cancelled due to the Coronavirus

Paint the Town registration includes: 

Three days of painting
Artists’ dinner Friday night
Informal lunch Saturday afternoon
Wet Paint Reception & Sale Saturday evening
Quick Draw competition Sunday morning.

Registration Deadline: April 8th

Registration Fees:

Members $50
Non-Members $65
Quick Draw Only $15

Cancellation Policy:
Refund of registration fees less 10% administrative fee for cancellation before April 8, 2020. We cannot issue refunds for registrations cancelled after April 8th.


Wednesday April 22:

4:00 -7:00 p.m. Early Registration at RiverArts

Thursday April 23:

8:00-10:30 a.m. Registration, coffee and snacks at RiverArts Gallery, then artists paint on location in town or throughout the surrounding areas.

Friday April 24:

8:00-10:30 a.m. Coffee and snacks at RiverArts Gallery before you head out to paint at the location of your choice in town or the surrounding area
6:00 p.m. Wine social hour at RiverArts followed by complimentary buffet dinner for registered artists at 6:30pm

Saturday April 25:

8:00-10:30 a.m. Coffee and snacks at RiverArts. We encourage you to paint in downtown Chestertown to heighten excitement about the Wet Paint Sale
1:00 p.m. Gallery open for framing and hanging of Wet Paint Sale paintings. Snacks provided for artists during setup
3:00 p.m. Deadline for Plein Air works to be framed & hung in gallery
3:15 – 4:00 p.m. Artists vote for Artist’s Choice awards (Best in Show and Best Body of Work)
5:15 p.m. Placement of ribbons
5:30-8:00 p.m. Reception and sale open to general public
6:00 p.m. Announcement of winners and introduction of winning artists to the public

Sunday April 26: Quick Draw:

8:00-9:00 a.m. Gallery open for stamping of blank canvases. Coffee and snacks available
9:00-11:00 a.m. Artists paint in & around downtown Chestertown
11:00-11:30 a.m. Artists assemble with easels in Fountain Park for judging. Work may be framed or unframed
11:30-Noon: Judging
Noon: Announcement of winners and awards
Noon-3:00 p.m. Quick Draw paintings taken to RiverArts Gallery for display and sale
3:00-4:00 p.m. Pick up unsold work at RiverArts Gallery

Guidelines for Artists

  • Artist display locations in the gallery for the Wet Paint Sale are chosen by lottery (each space is 36″ W x 72″ H).
  • Painting size limit: Paintings can be no wider than 32 inches framed and must fit within the assigned space.
  • Please make sure your panels, canvases, papers, mats, glass and backing boards have all been pre-sized to fit, frames pre-wired and everything is set for quick, easy framing.
  • Wrapped canvases must be properly wired for hanging.

Please fill out the form below to register for our the full Plein Air event or the Sunday Quick Draw event. Clicking the submit button will take you to a payment page. Registrations are final after payment is received. Space is limited, first come, first served.

Please call 410-778-6300 or email with any questions. We look forward to seeing you in April!