Middleboro's On Cranberry Pond Bed & Breakfast is in the heart of the cranberry capitol of the world. We are nestled between the waters of Cranberry Pond and picturesque New England cranberry bogs. Middleboro is a great destination. Middleboro is the home of Tom Thumb and a lot of history. Part of King Philips war was fought right here in town. Middleboro, Massachusetts is also known for Oliver Mill Park, named after Judge Oliver back in the 1700's. where the herring run and canoe races are launched. Native American artifacts can be seen at the Robins Museum. We are a quant little town yet still country 76 square miles and only a short distance to a major highway. Country fairs and antique shops. So, enjoy a peaceful nights sleep in the quiet of the country.