Set on beautiful Cuttyhunk Island, CIAR's Plein Air Painting Workshop (September 18 - 22, 2026) with renowned painter Marc Dalessio offers a unique opportunity to paint directly from Cuttyhunk's sweeping coastal landscape. Each day includes up to six hours of instruction, with demonstrations and guidance covering composition, value, color theory, painting mechanics, materials, and the historical and aesthetic foundations of landscape painting. The workshop is open to oil painters of all levels, from beginning to experienced, with much of the instruction offered one-on-one as Marc works with participants throughout the day. Participants explore Cuttyhunk on foot, painting the stunning vistas from observation and swimming on the island's pristine beaches.
Artists stay together at the historic Avalon Inn, sharing meals prepared by CIAR’s acclaimed Visiting Chef, Julie Carrion. Evenings offer time to relax and gather as a group, including a special tasting of freshly harvested Cuttyhunk oysters and an evening of live music under the stars, creating a rich balance of focused instruction, camaraderie, and the inspiration of island life.
CIAR also has an open application for the 2026 Fall Artists' Residency, which is geared toward professional visual artists working in all media: https://www.cuttyhunkislandresidency.com/fallresidency-2026
Residency Eligibility
Residency Experience Summary
Application Information
The Fall 2026 Plein Air Painting Workshop welcomes 12-14 participants and is open to oil painters of all levels, from beginners eager to learn plein air painting to more experienced artists looking to expand their practice.
Participants stay at the historic Avalon Inn. Costs vary depending on whether you choose a private or shared bedroom. If you are applying with friends and would like to room together, you are welcome to indicate this on your application.
- Single room (private bedroom): $3,300 – $3,700
- Double room (shared with one other): $2,500 – $2,800
- Triple room (shared with two others): $1,950
- Islander rate (Cuttyhunk residents who don’t need housing): $1,300
The workshop fee covers your entire experience on Cuttyhunk, including accommodation at the Avalon Inn (towels and linens included), daily painting workshops with Marc Dalessio, and three meals each day, lunch and dinner prepared by acclaimed Visiting Chef, Julie Carrion. It also includes to-go snacks for painting excursions, social hour hors d’oeuvres with a complimentary glass of wine each evening, a tasting of freshly harvested Cuttyhunk oysters, an evening of live music, and coffee and tea throughout the day.
Participants are responsible for their securing and paying for their own travel to and from Cuttyhunk, including ferry shuttle tickets and luggage ($50 each way + $5 per checked bag) from New Bedford, MA. An overnight stay in New Bedford may be necessary to catch the morning ferry.