One of Maine's oldest settlements, York, which is about 45 mi/75 km southwest of Portland, was called Agamenticus when it was established in 1624. Visitors can learn about the town's past at the Old Gaol Museum and at many historic buildings: the Elizabeth Perkins House, the Emerson-Wilcox House, Jefferd's Tavern and the First Parish Church. York Harbor has been a fashionable resort for more than a century: Boston Brahmins and other wealthy New Englanders built grand summer mansions along the shore (similar to those in Newport, Rhode Island). It's still popular, especially as a shoving-off point for yachts and sportfishing boats (http://www.oldyork.org/index.html).
Take a walk along the cliffs from Harbor Beach and be sure to see the views of the Isles of Shoals and the Boon Island Light. For those interested in hiking, the nearby 250-acre/100-hectare Vaughan Woods State Memorial has a network of foot trails. A short drive on Highway 1A will take you to Long Sands Beach. A local road at the north end of the beach takes you to Cape Neddick, popular with photographers and artists because of its white cast-iron lighthouse built in 1879. A tour of York Village can be combined with a visit to Kittery.
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