Paint Annapolis covers downtown Annapolis with more than 10,000 brushstrokes in just one week. Not like any other art event, this one turns the city into an open-air gallery with a live and breathing canvas.
In 2025, Paint Annapolis will have a lot of new and exciting features, such as bigger painting areas on the water, the chance to paint at night under the historic lamplight, and a record number of selected artists from all over the country. For most people, art events mean indoor exhibitions. Paint Annapolis, on the other hand, brings artists into the streets, parks, and harbors of Maryland’s capital to paint live, or “en plein air.”
This lively plein air art festival has been celebrating the place where history, culture, and talent meet for more than twenty years. But 2025 looks like it will be even more exciting: more community interaction, new public classes, and easier entry for new artists. This guide tells you everything you need to know about Paint Annapolis, from important dates and events to artist groups and guest tips, whether you are a curious traveler, an art buyer, or a person who lives in the area.
Let us look at the stories, colours, and brushwork that make this one of the most-anticipated art events on the East Coast.
What Is Paint Annapolis?
Paint Annapolis is more than just an event; it is a custom that shows how a city beats through its art. The Maryland Federation of the Art (MFA) started this event in 2002 with the goal of getting artists out of their workshops and onto the streets to paint Annapolis’s historic beauty in real time.
The idea comes from the movement of plein air painting, in which artists paint outside to catch the scenery and mood of the place they are in. Paint Annapolis has become a big culture event over the years, with hundreds of people from all over the country coming to see the artists and browse the art. These artists, both new and experienced, set up their easels all over Annapolis painting scenes—from the busy harbour to the quiet parts of Church Circle.
The event is more than just seeing things, though. People can talk to painters, ask them questions, and watch their work in progress in real time. This encourages creative dialogue between artists and the public. For many people in the area, it is a chance to see places they know through the eyes of an artist. This is a new way for tourists to experience Annapolis’s rich history, colour, and personality.
It has a big effect on the neighbourhood art community. Paint Annapolis celebrates local artists, makes the city more known as an arts centre, and makes art more accessible through public events, shows, and learning opportunities.
There is a lot of history, culture, and imagination at Paint Annapolis, which is right in the middle of Maryland’s capital city.
Key Dates and Schedule for Paint Annapolis 2025
Between June 1 and June 8, Paint Annapolis 2025 will turn Annapolis’s historic streets and waterfronts into a lively outdoor art exhibition. The artworks will be on display until June 21.
Here are the events of the week:
May 31 – June 1: Artist Check-In
The artists who are going to the event will check in and get their supplies ready, which will set the stage for a week of creative exploring.
Sunday, June 1: Dueling Brushes (Quick Draw)
Beginning at 9:00 AM and going until 11:00 AM, “Dueling Brushes” is a lively quick draw event that sets off the fair. In central Annapolis, artists have two hours to start from scratch and make a painting. After the awards are given out at 1:00 PM, the finished works will be displayed at Susan B. Campbell Park from 11:30 AM to 2:00 PM.
Tuesday, June 3: Paint the Bay Reception
This is the “Paint the Bay” event. It will take place at Bay Ridge Marina, 80 East Lake Drive, from 6 PM to 8 PM. At this event, chosen artists’ views of the Chesapeake Bay will be shown. Wine, oysters, and other light starters will be available. There will be an awards ceremony at 7:00 PM.
Wednesday, June 4: Dusk to Dawn Nocturne Painting
During the “Dusk to Dawn” nocturne painting session, artists will capture the beauty of the city at night. Artists can paint at any time, but the best time for them to do it is during Dinner Under the Stars on Inner West Street on June 4 from 5 PM to 10 PM.
Thursday, June 5: Art on the Avenue
“Art on the Avenue” is an event in which artists exhibit their work along the city’s streets so that people can enjoy it and connect with it.
Friday, June 6: Juried Artists’ Awards Ceremony and Collector’s Reception
At the awards event and collector’s gathering, you can celebrate the artists’ work. This event recognises great works and gives fans a chance to buy one-of-a-kind art pieces.
Saturday, June 7: Opening Reception
The official opening gathering for Paint Annapolis 2025 takes place at 86 Maryland Avenue. People can get their first look at the carefully chosen artworks at this event.
Sunday, June 8: Muffins and Mimosas
End the week with “Muffins and Mimosas,” a casual event where people can look at the exhibition and enjoy light refreshments.
June 1 – June 21: Exhibition of Works
The festival’s art will be on display at the Paint Annapolis Pop-Up Gallery until June 21, giving people plenty of time to look at them and buy them.
Where Does Paint Annapolis Take Place?
Paint Annapolis is memorable for its surroundings as well as its art. Imagine artists with their easels and brushes walking along the streets while ships go by in the background and church bells ring softly in the distance. That is Annapolis.
In historic downtown Annapolis, the Maryland Federation of Art (MFA) at 18 State Circle hosts the event. But the actual brilliance occurs everywhere—City Dock, Church Circle, Main Street, and even alleyways become outdoor studios.
Susan B. Campbell Park hosts several activities, such the “Dueling Brushes” Quick Draw, with spectacular Chesapeake Bay panoramas. Artists paint during “Dusk to Dawn” on Inner West Street during Dinner Under the Stars and in lovely neighbourhoods and waterfront marinas like Bay Ridge.
Paint Annapolis is warm and accepting. Families with strollers, tourists with restricted mobility, and senior art enthusiasts who prefer short walks between events adore the city’s small layout. Most events are ADA-accessible, and the downtown circulator service is convenient.
Parking: plan ahead. Use Gotts Court or Knighton garages since downtown spaces fill rapidly. Walking, biking, or riding the water taxi adds appeal.
Participating Artists: Meet the Talented Painters and Creatives
Paint Annapolis is not only about the gorgeous streets or attractive waterfront. But it is about the extraordinary talent that returns year after year, brush in hand and creativity burning bright.
Any Juried Artist Division’s painter must compete for selection. The Maryland Federation of Art (MFA) releases a Call for Entry in early spring, encouraging plein air festival artists from around the nation and beyond to apply. A group of experienced jurors then evaluates contributions for creativity, skill, and the ability to represent outdoor life in a new and true manner.
The result? A group of thirty to forty selected artists, each with their own style. Like a Maryland artist may exhibit watercolour seascapes beside New York impressionist brushwork.
Stewart White, famed for his celestial architectural sceneries, and Crystal Moll, whose vivid cityscapes convert commonplace streets into masterpieces, have performed at the event in previous years. Others depict urban life in quirky, abstract ways or with great realism that resembles photography.
Paint Annapolis encourages Public, Young, and Teen Artists of all ages and expertise levels to paint the town. Local artists may apply to choose events in these open categories without juried commitment.
Thinking of applying for 2026? Watch it on https://mdfedart.com/paintannapolis/ around January for application details. Annapolis has room for your plein air canvas, whether you are a beginner or an experienced exhibitor.
How to Attend Paint Annapolis: Tickets, Entry Fees, and Registration
How to experience Paint Annapolis? The festival has tickets for every art fanatic, which is excellent.
Many outdoor festivals, such Dueling Brushes and Art on the Avenue, are free for the public to enjoy. Walking around, watching artists paint, and seeing pop-up exhibits are free.
For closer access, the Official Paint Annapolis Exhibition and Collector’s Party need tickets. You may get a single-day or full-week tickets to all receptions, award ceremonies, and seminars. VIPs get early exhibition entry and artist meet-and-greets.
Festival workshops fill up quickly, so pre-registration is suggested. Professional artists lead these hands-on courses, making them ideal for beginners and advanced plein air painters.
Early birds and groups get savings, so sign up when tickets go on sale in late spring. Paint Annapolis welcomes art lovers and first-timers alike, so join the creative celebration!
Visitor Guide: How to Make the Most of Paint Annapolis
Are you going to Paint Annapolis for the very first time? You are going to love this! This lively event is more than just seeing artists at work; it is a full-on cultural experience in the middle of one of America’s most charming old towns.
Start Early to Catch the Action
Get up early to see artists in downtown Annapolis putting up their easels. Especially near City Dock and Susan B. Campbell Park, the best time to see artists catch the city’s beauty is in the morning light. Do not miss the quick-draw events where artists have to draw in record time. They are exciting to watch!
Explore Historic Annapolis and Local Flavors
During the middle of the day, take a walk through the city’s old streets and check out art places like the Maryland Federation of Art or ArtFarm Annapolis. Enjoy lunch at one of Annapolis’s popular seaside restaurants, like Lighthouse Seafood & Grill or Iron Rooster.
Join Workshops and Art Talks
There may be classes or artist talks in the afternoon. Check the event calendar. You can learn a lot about plein air painting and the local art scene at these sessions, even if you are not a painter yourself. Look out for niche classes like the Tree of Life Pour and Paint Workshop or themed sip and paint Annapolis nights.
Family-Friendly Fun
Paint Annapolis is fun for people of all kinds. Watch out for family zones and things that you can do together. Nearby parks and waterways with nice views make it easy to have a meal or take a break with the kids.
End Your Day with a Magical Sunset
As the sun goes down, go to City Dock to see artists paint the harbor at sunset. It is a beautiful sight. At the end of your stay, there may be an evening gathering or a fun event like Muffins and Mimosas.