This NEW tour introduces a mix of the areas oldest and newest establishments while showcasing the culinary creativity that is alive and well in Boothbay Harbor! Join our friendly, local tour guides and be introduced to six locally-owned businesses to explore and taste their delectable, native-to-Maine foods. Enjoy a lively walk to restaurants, gourmet shops, and a beautiful, historic inn overlooking the harbor while you taste your way through town! You’ll learn about the history of Boothba...

This guided walk will show you a side of Boothbay Harbor's waterfront you've never seen! You'll learn the ins and outs of lobstering, see the sites of shipbuilding, hear of early fisheries, lighthouses, rum running and even pirates. What industries used to line the shore? Were there sea serpents? Was there any Naval activity in the area? Tour the shore with Maine's largest walking tour company to hear all of the above and more, including shanties, as you walk in the footsteps of early Boothba...

Portland Head Light is Maine's oldest lighthouse and one of New England's most photographic locations. Tour the museum located inside the Keepers Quarters, to learn the history of the light, then enjoy a truly rare opportunity to climb the spiraling staircase of the 20-foot tower to take in the breathtaking views from the inside of the lantern. Space is very limited advanced reservations required. The climb to the top of the tower is strenuous and may not be appropriate for those with health ...

Join The Lady in the Red Cloak for a lantern lit walking tour of Boothbay Harbor. Discover the back streets and hidden stories of the village, its mysteries and haunts. Learn some history of the area, see the "most haunted building in Maine," hear many ghostly tales, including that of private Mr. Duffy and the welcoming ship captain, all while you experience a one-of-a-kind evening in this quaint harbor town. The moderate walk, suitable for all ages, lasts approximately 90 minutes and is by r...

Join artist Jennifer Linskey for a day of plein air painting and drawing at Castle Tucker. Beautiful vistas of the Sheepscot River, historic Wiscasset village, and our nineteenth-century house and grounds offer an ideal setting for landscape painters of all levels. Jennifer will discuss composition and color mixing. Beginners welcome. Bring your own materials, lunch, and a hat. Enjoy the day and gather for an afternoon critique with the instructor. Weather permitting (please call). $20 Histor...