39 Union Street, Rockland Maine
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Winding Way Bed and Breakfast and Art Gallery
39 Union Street
Rockland, ME 04841
207- 593-7955

Contact Us
Welcome! We hope that you will come visit us soon at Winding Way Bed and Breakfast and Art Gallery. We think we have unique accomodations on the coast of Maine, Our  B&B is also a working studio space and watercolor art gallery, located directly across from The Wyeth Center and around the corner from The Farnsworth Art Museum.  Parking is available right on the property which is an added benefit during the busy summer months.

Our two comfortable guest rooms are located on the second floor of this circa 1855 Victorian house. We have recently updated the house, adding ensuite bathrooms for comfort and privacy. If your family or group would like exclusive access to the rooms, sitting room, breakfast room and enclosed stone patio, it is possible to reserve the entire B&B. 

So many of our guests this past season have come to have dinner at Primo Restaurant and it has been their reason for coming to Rockland. Primo was voted among the 20 best restaurants by Gourmet Magazine.  We are .8 ml from Primo . We even had a set of guests who walked
 there ( in the rain) but if you don't have your car we can arrange a taxi for you.

​We want to thank all of our guests who stayed with us our first season. We enjoyed meeting all of you.
We had guests from 26 states and 6 countries. Remember we are open all year.
We hope to see you soon!

Anne and Jonathan McMath

The most delightful comfortble small guest house I have ever stayed in.

The Winding Way B & B in Rockland, Maine, is a real delight and my 4 nights were not only comfortable, but really pleasureble. The hostess is just that- she welcomes you as if to her own home. The 2 rooms are tastefully, generously, and creatively arranged to maximise the pleasure and welcome environment one always longs for when travelling. Breakfasts are more than generous: beautifully prepared,and presented in the lovely kitchen/dining room; daily made lemonade is left in a carafe,with cookies, for when you come on from a day exploring the local sights or soaking up the great American art on the galleries only minutes walk away. Not only that... The house is itself a watercolour gallery.  . Artist's  work decorate the walls throughout the whole B&B. A guest sitting room is a great place to relax, puruse the many local brochures,magazines art books, tourist information or to play games etc. If you are ever in Rockland,Winding Way is the place to stay  . (courtesy of Bed and ). 5 stars KP , England

“Around the corner from the Farnsworth”

Reviewed September 6, 2013 
A great location ... comfortable up-to-date rooms with thoughtful touches. Two bedroom upstairs each with a private bathroom and a common sitting room. High quality construction and decor ... And we loved the ice cream in the freezer and fresh baked cookies and blueberry scones in the afternoon! Breakfast was a serve yourself ... fresh strawberries, granola, real vanilla bean yogurt, quiche, multigrain bread for toasting with blueberry preserves, and orange juice, etc. Everything we could have wanted and more. And did I mention the art gallery downstairs? All-in-all it was one of the best memories of our trip to Maine. We loved the Winding Way and hope to stay there again!

Stayed September 2013, traveled as a couple"
 Our reservation system is realtime and up to date 
all of the time.
 Paintiing by one of our gallery artists
 For information on all of the exhibits at the Farnswoth Museum go to :


April 26, 2014 – December 31, 2014
The Wyeth Center
The art of the Wyeths – N.C., Andrew and Jamie – is a direct result of their familiarity with and fascination for life along midcoast Maine, reaching back to N.C.’s decision to bring his family to the area in 1920. The Wyeths’ interests have included the coast’s dramatic shoreline and islands, including Monhegan, the lives of fishermen and farmers, and the boats, houses, barns, lighthouses and other structures scattered throughout the midcoast. Their interest in these subjects is part of a long-standing tradition of work done by artists and artisans in Maine since the eighteenth century. In addition to works by the Wyeths, the exhibition will also include a selection of paintings by James G. Babbidge, George Bellows, Walter Dean, James Fitzgerald, Rockwell Kent, Fitz Henry Lane, William Edward Norton, William Pierce Stubbs, Frederick Waugh, and Andrew Winter; and a selection of ship models that include the Red Jacket clipper ship, the seven master schooner Thomas Lawson, and the only known ship model by John Haley Bellamy. Organized by Farnsworth Registrar Angela Waldron.
This exhibition is made possible through the generous support of: Anna Mae & George Twigg, III

The primary media sponsor of this exhibition is Maine Home + Design
 The Wyeth Center, our neighbor will open April 26th. Their opening show will be: 
As a long time fan of her father, Winding Way wants to let you know that Lisa Marie Presley will give one performance at The Strand Theater in Rockland on June 19th at 7:30 PM. The theater is a block away from us and we will be there :)
 To read more about the artist and/ or purchase tickets for this performance or others at The Strand go to
 Lisa Marie Presley at The Strand Theater June 17
 Due to a cancellation we have the Sarah Room available for 2 nights during the Lobster Festival July 29 and 30.