Located near Bar Harbor across Frenchman Bay, the Grindstone Neck peninsula is 1/2 mile wide by 1 1/2 miles long, jutting into Winter Harbor. In 1889 the Gouldsboro Land Improvement Company bought 300 acres of farmland to build a residential summer colony. They hired Nathan Franklin Barrett to design the subdivision, which Barrett described as a combination of artificial and picturesque styles. He proposed 198 cottage lots of at least one acre and arranged them on roughly parallel roads, with a primary road (Grindstone Avenue) running the length of the peninsula’s spine through woodlands to dramatic ocean views at the tip. The end of the peninsula was ultimately improved with a massive cut-granite bench and a granite staircase leading to the rocky shore.
Within the first year nearly 30 cottages, many Shingle style, were built or under construction. Like the overall subdivision, cottage landscapes were a mix of formal and naturalistic styles, with linear paths, driveways, and stone walls set among ledge outcroppings and informal shrub beds.
The early 1890s saw the construction of an oceanfront clubhouse and casino with an observatory and 165-foot-long piazza, the three-story Grindstone Inn, the Shingle-style Episcopal Church, and the Grindstone Neck Golf Course designed by Alex Findlay. The inn burned in 1956, but the clubhouse, church and golf course remain. The summer colony never reached its full potential, with resident John Moore owning most of the vacant lots by 1895, but what was completed is largely intact today.