Leave City Hall and proceed on U.S. Rte. 1 south. At 8.3 miles on the left is the Big Chicken Barn Antiques and Used Books. At mile 12.7 the road passes the northern end of Toddy Pond and at mile 16.5 crosses the Orland River. At mile 17.0 turn left onto Rte. 175 and pass through the village of Orland; then turn south along the shore of Penobscot Bay. At mile 24.8 Rte. 175 turns left, but continue straight onto Rte. 166. Turn right onto Rte. 166A at mile 26.6 then right again onto Rte. 166 at mile 30.3. This route ends at Castine’s town dock at mile 32. Walk around the village to see the many old buildings and to savor the town’s varied history. Castine is the home of the Maine Maritime Academy and its training ship the State of Maine. When you leave Castine stay on Rte. 166 to mile 36.1, then turn right onto Rte. 199 toward Penobscot. At mile 39.5 go straight onto Rte. 175 south through the village of Penobscot at mile 41.3. Stay on Rte. 175 to Brooksville, crossing the reversing falls on the Bagaduce River (mile 56.9)

   At mile 47.2 turn right to West Brooksville on Rte. 176. Several fishing harbors, including Smith Cove, Orcutt Harbor, and Buck’s Harbor, are on this road. At mile 57.0 is the junction with Rte. 175. Go straight to the junction with Rte. 15 at mile 57.6. Turn left toward the town of Blue Hill. At mile 64.4 Rte. 172 joins Rte. 15. Blue Hill is at mile 65.1. Follow Rte. 172 to the village of Surry on the shore of Patten Bay at mile 72.1. Continue on Rte. 172 to Ellsworth at mile 78.4.