About Gary's Olde Towne Tavern
The area was settled in 1790. Farming was limited by the soil, which consisted of gravely loam, its surface strewn with glacial erratic boulder, leaving us with lots of rocks. The uplands, however, provided good grazing for livestock, and hay become the principal crop.
Names for Naples, Italy, the town was incorporated on March 4, 1834, from parts of Otisfield, Harrison, Raymond, and Bridgton. Between 1845 and 1856, it annexed more land from Sebago, Otisfield and Bridgton. The Songo Lock, park of the chain of locks stretched to the coast, was completed two years before the town incorporation and linked Long Lake, Brandy Pond and Sebago lake with the Portland Harbor allowing passage of boats from Harrison to Portland through the Cumberland and Oxford canal in Standish. A canning factory and cooperage were established at Naples village. The community also produced carriages, men’s clothing, boots, and shoes.
The beautiful scenery of the lakes, however, would make tourism the dominant industry. Visitors in the 19th century included Henry Wadsworth Longfellow and Nathaniel Hawthorne. To accommodate his passengers, Charles L. Goodridge of Sebago Lake, Songo River & Bay of Naples Steamship Company built a hostelry on a knoll at the southern end of Long Lake. On July 26, 1899, the Bay of Naples Inn opened with 80 bedrooms. The Bay of Naples Inn, which faced Mount Washington and the east side of the White Mountains, was a popular resort during the early 20th century. Automobile tourist began arriving after designation of Theodore Roosevelt International Highway in 1919 (now Route 302).
According to the Naples Historical Society, this was not the first time the tavern had occupy the site at 678 Roosevelt Trail. In the late 1700’s it was the site of an Inn and Tavern which served travelers on the stage coach run between Portland and Bridgton. Though the tavern burned down in the early 1820’s, it was quickly rebuilt only to burn again in 1876. The present building was built around 1880 and over the decades has been used as both family residence and previous dining establishments such as The Epicurean Inn and Bray’s Brewpub & Eatery.