Paint the Town - April 20-23, 2023

Chestertown RiverArts Paint the Town, April 20-23, 2023 

"Paint the Town" is very popular with plein air artists from all over the mid-Atlantic region because of the natural beauty of our area, with its many waterways, scenic farms, historic buildings and wonderful gardens This is a great opportunity for artists to get out of their studios and paint outdoors while enjoying Maryland's beautiful Eastern Shore. It is also a great weekend to network with peers and catch the attention of the town's local residents, visitors, art enthusiasts and collectors.

"Paint the Town" is a 4-day event and artists have the opportunity to lose themselves while exploring the beautiful countryside and capturing it in their paintings. After 3 days of painting, artists gather back together on Saturday afternoon to frame & hang their finished work in RiverArts' gallery in preparation for the "Wet Paint Show & Sale. Once the show is up, the participating artists vote for "Best in Show" and "Best Body of Work". The ribbons will be placed just before the show opens to the public.

At 5:30 p.m. artists and their guests, RiverArts members and other gallery visitors are welcome back into the gallery for the "Wet Paint Show & Sale" reception. At 6:00 p.m., there will be a brief awards ceremony followed by a reception where everyone has the opportunity to mingle and shop. Collectors are cautioned not to hesitate to make their selections because sales tend to be brisk and paintings sell quickly during the Saturday evening reception. However, if more time is needed, the Show & Sale will reopen on Sunday morning and the paintings that are still available may be purchased until 3:00 p.m. This gives visitors another chance to view the show and add an amazing piece of local art to their collections.

Artists with busy schedules who are unable participate in all 4 days of our "Paint the Town" event may still sign up to participate in our one day "Quick Draw" competition on Sunday, May 1st. Artists should plan to arrive Sunday morning between 8:00-9:00 a.m. and after checking in, artists will have 2 hours to explore the downtown Chestertown area and complete a Quick Draw painting. Artists are asked to return at 11:00 a.m. to set up their paintings on easels for viewing and judging by an outside judge. While the judge is making their selections, the public will also be invited to vote for the “People’s Choice Award.” At noon, the "Quick Draw" Awards will be presented for the 1st, 2nd, and 3rd places and the People's choice award announced. After the awards presentations, Quick Draw artists are invited to display and sell their "Quick Draw" paintings at the gallery until 3:00 p.m. This allows you the opportunity to meet and greet potential buyers and collectors. It also give you one more chance to chat with fellow artists before heading home. Cash prizes will be awarded at the Wet Paint Show & Sale as well as the Quick Draw!

This year, we've extended the exhibit an additional week, to give artists additional time to display and sell their work. Participation in the extended exhibit is not mandatory but encouraged.


  • PAINT THE TOWN DATES: April 20-23, 2022
  • "WET PAINT SHOW & SALE": Saturday, April 22, 2022; 6:00-8:00 p.m.
  • "QUICK DRAW": Sunday, April 23, 2022
  • PICK UP of ART: (extended exhibit): Sunday, April 29, 1:00-3:00 p.m. or Monday, April 30, 10:00 a.m. -12:00 p.m.
  • REGISTRATION DEADLINE: Sunday, April 15 - Paint the Town registrations will open the 1st week of February. Watch our newsletters for the announcement. Click the link to the right to join our mailing list and stay informed about all RiverArts' events, exhibits, programs and classes.

RiverArts' "Paint the Town" registration (all 4 days including "Quick Draw"): RiverArts Members: $50 Paint the Town, Non-Members: $65

Paint the Town "Quick Draw" 1 day registration (Sunday only): RiverArts Members: $15, Non-Members $20

If you have questions or need help with your registration, please contact RiverArts: info@chestertownriverarts.org or call W: 410-778-6300. 

Registration Info

REGISTRATION DEADLINE: Sunday, April 24 - Paint the Town registration will open the 1st week of February. Watch our newsletters for the announcement.

Click the below to join our mailing list and stay informed about all RiverArts' events, exhibits, programs and classes.