About Paint Annapolis

Now in our 25th year, Paint Annapolis brings over 110 artists for a week of painting out on the streets of our beautiful historic city.

Paint Annapolis, hosted by MFA is a unique painting event that brings thousands of artists and art lovers to Annapolis the first week of June, and puts international professional visual artists from the US, Canada, and Europe in the streets of Annapolis and Anne Arundel County.

As the premier plein air painting event for this historic sailing town, Paint Annapolis is the backbone of Annapolis Arts Month – a month-long celebration of visual and performing arts.

There are daily painting events all over the city for you to enjoy, and the art created during the week of Paint Annapolis is on display for an additional two weeks with public receptions including the fun and delicious Muffins and Mimosas event.

A prestigious event, artists receive prizes over $19,000 over the course of the first week.

This city-wide celebration creates energy with street banners advertising the event throughout downtown Annapolis and up West Street.

Promotion of Paint Annapolis through our website, social media, and email reaches more than 20,000 artists and art lovers.

Reaching more than 20,000 artists and art lovers, Paint Annapolis is promoted through our website, social media, and email, as well as the celebrated local art magazine, UpStART, and other publications. Paint Annapolis is promoted throughout the Mid-Atlantic region by Visit Annapolis and Anne Arundel County (VAAAC) and is featured in the national Plein Air Magazine’s Ultimate Guide.

MFA relies on the generous support of our sponsors to pull of this artistic showcase. Please join us as we create connections that enrich life through art and become a sponsor. With sponsorship levels from $15,000 – $50, there is a place for everyone who believes in art and artists to support this event. Whatever level of sponsorship you choose, your gift helps make Paint Annapolis better each year.

If you are interested in sponsoring 2026, click the button below or contact our Executive Director, Patrice Drago at patrice@mdfedart.org

Sponsor Paint Annapolis

If you are interested in potentially hosting a Juried Artist, please fill out this form.

The 2026 Paint Annapolis Week of Events

May 31 to June 5 – Artists will be painting all over the city from morning to night – and throughout the night, too. Walk around downtown and catch the artists in action.

Artists have an opportunity to vie for the Nocturne award by creating paintings any night between dusk and dawn. On June 3, artists are encouraged to paint during West Street’s Dinner Under the Stars. Reserve your spot at your favorite restaurant to dine al fresco and watch many artists set up to begin painting their nocturnes from dusk to dawn. Watching artists paint is free and open to the public.

DAY BY DAY:

Sunday, May 31 – Dueling Brushes

Paint Annapolis kicks off with the Dueling Brushes painting and exhibition! Watch the artists create an original painting from a blank canvas in 2 hours downtown and throughout Eastport between 9 – 11 AM, and then take the water taxi or drive over to the vibrant Eastport peninsula to see and buy the pieces made that morning. Join us at 222 Severn Ave near Pier 3 in Eastport for an exhibition of the work from 11:30 AM – 2 PM. Awards announced at 1 PM. This event is free and open to the public.

Tuesday, June 2 – Paint the Bay Reception

Come see some of the Juried Artists’ first works featuring the lovely Chesapeake on display and for sale, and enjoy wine and hors d’oeuvres at the “Paint the Bay” reception sponsored by PNC. Join us at the Park Campus of the Annapolis Maritime Museum (7300 Edgewood Road) from 6 – 8 PM. Awards announced at 7 PM. Attending this event is free and open to the public.

Thursday, June 4 – Art on the Avenue

Art on the Avenue is an evening of art, music and celebration, where Maryland Avenue is closed to traffic. From 6 – 8 PM Juried and Public Artists exhibit a painting they have created that best showcases the architecture of Historic Annapolis, with awards given at 7 PM. Attending this event is free and open to the public.

Friday, June 5 – Collector’s Party and Juried Artist Awards Ceremony

This ticketed event at MFA Circle Gallery gives you a first introduction to the full body of works created by the Juried Artists throughout the week, and to witness the Awards Ceremony. At this event, you have an opportunity to be the first to add their work to your collection. Tickets for this event will be available for purchase on May 1. (Limited quantity)

Saturday, June 6 to Saturday, June 20 – Paint Annapolis Exhibition Officially Open

Exhibitions of work by both the Juried and Public Artists will be on display at Circle Gallery (18 State Circle) and the Pop-Up Gallery (13 School Street). Both galleries are open everyday 11 AM – 5 PM.

Saturday, June 6 – Opening Reception

The full and complete Paint Annapolis Exhibition officially opens with an Opening Reception from 5 to 7 PM, where you get to see all the public artists works as well as additional juried artists works.  Public, Teen and Young Artist awards are announced during this reception, including the awards selected by the Mayor of Annapolis. The Pop Up Gallery and Circle Gallery are open daily for two weeks following the reception to give the public an opportunity to see and purchase artwork created during this historic week. Attending this event is free and open to the public.

Sunday, June 7 – Muffins and Mimosas

The painting is done; awards are given and now it’s time to relax! Take a leisurely stroll through both galleries and enjoy the wonderful art made over the past week while sipping on a Mimosa and munching on a muffin from 11 AM – 1 PM. Attending this event is free and open to the public.

Sunday, June 13 – Annapolis Arts Day

Come celebrate the work and enjoy light refreshments at both galleries from 12 – 4 PM. Attending this event is free and open to the public.

Saturday, June 20 – Last Day, Closing Reception

Today is your last chance to see the incredible work created earlier this month. Circle Gallery and the Pop Up Gallery are both open until 5 PM and you are invited to join us at the Pop Up Gallery for one last party celebrating this incredible week of painting! Join us from 5 – 7 PM for your last chance to view the work created by all the talented Public and Student Artists. The Mayor’s Award will be announced at 6 PM. Attending this event is free and open to the public.

* Dates are subject to change *

Paint Annapolis 2025

Paint Annapolis has been the premier painting event for this sailing town, bringing the community together to share in the beauty of painting en plein air, or painting outdoors. Every year during the first full week of June, we look forward to an exciting week of painting these historic streets.

With a combination of artists juried into the competition and public and student artist participation, we had more than 115 artists competing this year. The artists produced 315 plein air paintings in a 5 day period from June 1 – June 5, 2025.

Artists, collectors, sponsors, and community members attended four different painting events and celebrated with the artists as MFA gave out over $19,000 in awards.

Click the links below to meet the 30 juried artists, see the beautiful art, and meet the jurors who selected the award-winning works last year.

Paint Annapolis is successful because of our sponsors. We are so grateful for the generosity of our sponsors and host families whose belief in the arts makes Paint Annapolis possible. Below is a list of all of our 2025 sponsors.