Winding Way Bed and Breakfast & Art Gallery

39 Union Street, Rockland, Maine 04841
Innkeeper(s): Anne and Jon McMath, owners & innkeepers; Terry and Patti Lawry, Assistant Innkeepers
  • Introduction

    Winding Way Bed and Breakfast and Art Gallery is located in Rockland, Maine. It is a unique property as it combines a working art studio, art gallery and lodging. 

     The bed and breakfast offers two comfortable guestrooms, each with a private ensuite bathroom. Both rooms are located on the second floor of the 1855 Victorian home, with updated amenities.

    Winding Way Bed and Breakfast is located in the middle of Rockland, where restaurants, shopping, art galleries, museums, and the  ocean are all  just a  short  walk away . Anne and Jon, the proprietors of the inn, are very knowledgable about the local arts community and are also avid bicycle riders. They are happy to share information about what there is to do in the area and provide you with maps.

    A continental plus breakfast is served in the mornings, and local ice cream is available in the afternoon as the house was home to an ice cream parlor in the 1900's.

    Parking is available, and off-site parking can be arranged. The entire Winding Way Bed and Breakfast can be rented for more privacy or to accomodated a larger group with children.

  • Insider's Info

    Travelers are always looking formemorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Anne McMath for sharing her own secrets with!
    Why do most travelers stay at your inn?

    Our proximity to town, good value, interest in art, closeness to The Wyeth Center and The Farnsworth Museum, friendly people, small property (only 2 rooms,) but a family can rent the whole house and then children are accepted

    What are you best known for? 

    We are best known for being an in town B&B, having an art gallery on site, nice decor, and a delicious self serve breakfast of individual quiches, scones & yogurt parfaits.

    What makes your inn unique?

    It was an ice cream parlor in the 1900s.  We serve ice cream to the guests and tell them the history of the house, and about Mr. and Mrs. Thurlow, who owned it and for whom our rooms are named.

    What do you love most about your inn?

    I love the light that comes from all of the windows; I love the soft pastels and seaside decorations.

    If someone has never been to your city, what is the #1 reason to come visit?

    To be in a beautiful Maine coastal town where lobster and tourism are the basis for the economy. We have 21 art galleries

    What’s the best compliment you have ever received about the inn?

    "Great attention to detail in the decorating. Although it was only one night it felt like the honeymoon we never had."


    What’s the best kept secret about the area?

    It's many gourmet restaurants

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    Go to Port Clyde, which is at the end of one of our peninsulas. It is a beautiful Maine coastal village where you can see a lighthouse, eat at a general store, take a ferry to Monhegan Island, and if you have time, stay overnight. Visit their art galleries and eat pie and ice cream at a village shop.

    Is there anything within walking distance of your inn?

    Many things- Rockland Harbor, ferries to 2 beautiful islands, The Farnsworth Museum, The Wyeth Center, The Strand Theater, Many wonderful restaurants, wine bars coffee shops and a bike shop where you can rent a bike to explore the area

    What is your favorite restaurant/food in the area?

    There are so many. I guess I would have to say Archer's on the Pier because of the view of the lighthouse and ferries coming and going right out the window. The food there is moderately priced and good, and they have lobster.

    Any good area guides/websites that travelers could reference?

    The Penobscot Chamber of Commerce's magazine has a print and online version.

    How many rooms does your inn have?

    We have two rooms plus a sleeping couch, pack-n-play, and toddler bed.

    Do you accept pets?

    NO. Harbor Hounds in Rockland is excellent and they even have a swimming pool for dogs.


  • Breakfast

    A self serve breakfast is ready when you are and served in the sunny downstairs kitchen area. Breakfast can also be enjoyed in the privacy of your own room, as well as the sunporch or  the patio area, where you can enjoy cool Maine mornings and plan your day.

    Winding Way Breakfast  is available until 11:00am. A Keurig machine is also provided for fresh individual cups of tea or coffee. Bottled water, coffee, tea and cocoa are available throughout the day. Snacks and cold beverages are served in the afternoon.

    Offerings include:

    • scones
    • individual quiches sometimes with lobster !
    • breads
    • yogurt parfaits
    • cheeses
    • peanut butter
    • jams
    • butter
    • juices
    • fresh fruit
    • granola
    • cereals

    We are happy to accomodate guests with special diets or preferances, with advanced notice.

  • Check In

    Check in is between 2:30 PM and 4:30 PM.

    If you will be arriving outside of theses hours we will need to be notified so that someone wll be at the house to greet you. If you will be late please call us at 207- 593-7955 so we can make arrangements for you. Thank you.

    Checkout is 11 AM.