Maine State Route 166
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| Maintained by MaineDOT | |||||||
| Length: | 14.9 mi (24.0 km) | ||||||
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| South end: | Main Street/Battle Avenue in Castine | ||||||
| North end: |
   US 1 / SR 3 / SR 15 in Orland
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| Counties: | Hancock | ||||||
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| Location: | Castine |
| Length: | 4.1 mi (6.6 km) |
| Existed: | 1947–present |
State Route 166 (SR 166) is part of Maine's system of numbered state highways, located in the southern coastal part of the state adjacent to the mouth of the Penobscot River. It runs just under fifteen miles (24 km) between the town of Castine and Orland at U.S. Route 1 (US 1) and SR 3/SR 15.
The southern terminus of SR 166 is located at the intersection of Battle Avenue and Main Street in Castine, near the Maine Maritime Academy main campus. Battle Avenue carries the initial stretch before turning northward as Castine Road as the route exits the downtown area. SR 166A splits off just to the northeast towards the Bagaduce River to the east. SR 166 turns to the northwest at this point to run closer to the Penobscot River along The Shore Road. This portion of the road heads north through the settlement of West Castine passing some small houses along the way. Continuing north, intersecting the northern end of the SR 166A half-loop at Morse Cove. Now in the town of Penobscot and following Castine Road again, SR 166 parallels the river even closer and reaches the terminus of SR 175 at the settlement of West Penobscot.
North of SR 175, the road ends paralleling the Penobscot River but begins following the route of the Orland River at South Orland within the town of Orland. Past here, SR 166 heads into a less populated stretch of land, mostly in wooded areas. As the road comes closer to the center of the town, the number of houses lining the road increases. SR 166 curves to the west at Old Country Road and crosses the Orland River on a small bridge. Now in the business district of the town, SR 166 passes small markets, boating shops, and a post office a peninsula known as Leaches Point. After passing a few more houses, Castine Road and SR 166 ends at a stop-controlled intersection with Arcadia Highway (carrying US 1, SR 3, and SR 15).
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