Monhegan Tours


Monhegan Walking Tours

Imagine yourself on an island twelve miles out to sea, disconnected from your daily routine and surrounded by natural beauty. Our tours follow the footsteps of great artists like George Bellows, Rockwell Kent, and Edward Hopper, walking the same trails they hiked while carrying their canvases out to the cliffs. Together, we will explore sites that inspired many of the great masterworks of the 20th century.

Since 2010, Monhegan Island Walking Tours has made Monhegan Island's art history, natural history, and cultural history accessible with a wonderful and memorable experience. Our tours opens up Monhegan's rich art heritage and dynamic contemporary community through informative guided hikes and tours of artist studios and buildings on the National Register of Historic Places. Tours are custom-tailored to the specific interests and needs of the customer and can be focused on specific artists or locations on the island.

Running from May through October, groups of 10-15 people are guided on a series of hikes that explore the island's shipwreck, cliffs, forest, art history, and culture. Tour guide Leith MacDonald uses his experience hiking and painting on the island to match hikes safely with the physical ability of the group. Participants are invited to spend the night at the Trailing Yew, a long-time home of Monhegan's summer artist colony, in order to enjoy the true island experience but day trips are also possible.

Past tour groups have included museum staff and docents, accomplished artists, photography students, and Monhegan art enthusiasts.  Examples include:

·         Cape Cod Museum of Art

·         Farnsworth Art Museum

·         Island Institute

·         Maine Media Workshops

·         Monhegan Wellness

·         Plattsburgh State Art Museum

·         Portland Museum of Art

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" was the highlight of my two months in Maine"

"...Leith MacDonald was an ideal guide, enabling us to feel a connection with the island and the island community that we as outsiders couldn't have accomplished alone in such a short time."

Emily Schiffer

2010 Arnold Newman Prize winner

Founder, My Viewpoint Youth Photography Initiative

"Somewhat conversant with the impressive history of artists' visitations to Monhegan, I visited the Island on my own in 2007 and thoroughly enjoyed the varied landscape and picturesque quality of the village. I did not, however, get a broader or deeper understanding of the Island's history and artistic legacy until I joined a tour group in 2012 led by Monhegan expert Leith MacDonald. Leith knows the art history and current art scene on Monhegan extraordinarily well and shares that information in an open manner that suits both experts and novices. We took casual walks in the most important locales, viewed famous artists' studios and homes, visited galleries, and enjoyed a wonderful lunch. I highly recommend Leith's tour for those interested in an unique island in the Northeast that was an important incubator for American art."

Roger Dell

Director of Education, Farnsworth Art Museum

Former Lecturer, Harvard Graduate School of Education and Harvard Extension School


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