Artists painting historic Annapolis waterfront scenes during the Paint Annapolis Festival

Paint Annapolis Festival 2026

June 06, 2026•1 min read

🎨 Paint Annapolis Festival 2026
📅 May 31 – June 20, 2026
📍 Downtown Annapolis & Various Locations Throughout the City
💲 Many events are free and open to the public

Paint Annapolis is one of Annapolis' most beloved annual arts events, bringing more than 100 professional artists from around the United States, Canada, and Europe to paint the city's historic streets, waterfront views, and charming neighborhoods. Visitors can watch artists create paintings in real time throughout downtown Annapolis and Anne Arundel County.

Highlights

🖌️ May 31
Dueling Brushes Kickoff Event
Watch artists create original paintings from blank canvases between 9:00 AM and 11:00 AM, followed by an exhibition and artwork sales in Eastport.

🌊 June 2
Paint the Bay Reception
Featuring Chesapeake Bay inspired artwork, awards, wine, and hors d'oeuvres.

🎨 June 4
Art on the Avenue
Maryland Avenue transforms into a celebration of art, music, and local culture with artists displaying works inspired by Historic Annapolis.

🏆 June 5
Collectors Party & Awards Ceremony
An exclusive opportunity to view and purchase artwork before the public exhibition opens.

🖼️ June 6 – June 20
Paint Annapolis Exhibition
Artwork created during the festival is displayed at Circle Gallery and the Pop Up Gallery in downtown Annapolis.

🥂 June 7
Muffins & Mimosas
Enjoy a relaxing morning viewing artwork while enjoying complimentary refreshments.

See Full Sched Here : https://mdfedart.com/paintannapolis/?utm_source

Why Locals Love It

Paint Annapolis is more than an art festival. It turns the entire city into an outdoor studio where visitors can stroll through downtown, watch artists at work, explore local shops and restaurants, and experience the beauty of Annapolis through the eyes of talented painters. It has become a signature event during Anne Arundel Arts Month and attracts thousands of visitors each year.

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Heather Taylor, GRI

I’m Heather Taylor, a Realtor® with RE/MAX One in Annapolis, Maryland, proudly serving buyers and sellers throughout Anne Arundel and Prince George’s Counties — including Annapolis, Crofton, Gambrills, Odenton, Davidsonville, Crownsville, Severn, Severna Park, Glen Burnie, Pasadena, Bowie, and beyond. Real estate is one of my greatest passions, and I dedicate the time, energy, and focus needed to ensure my clients always feel supported. My goal is to make every transaction as smooth and stress-free as possible while helping you achieve your real estate dreams. My clients know me for my calm, responsive guidance, deep local knowledge, and the personalized care I bring to every step of the process. Whether you’re relocating, downsizing, or making room to grow, I provide strategic, high-touch support tailored to your unique goals — never a one-size-fits-all approach. Relocation Downsizing with ease and confidence Upsizing and move-up strategies for growing families

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