Gloucester, Essex, Manchester-by-the-Sea, and Rockport make up Cape Ann, where the topography resembles Maine more than Cape Cod.
Wendy Hodgson’s old house was once owned by an American Impressionist who was inspired by the rocky coast, sand beaches, tidal estuaries, farm fields, and old settlements in this historic part of New England. From the luminist Fitz Henry Lane to Edward Hopper and Emile Gruppe, artists have flocked to the region—and still do. Visit galleries and art museums like the Marblehead Arts Association, located in the 18th-century King Hooper Mansion, or the Cape Ann Museum. For a more hands-on approach, take a plein-air painting class at the Rocky Neck Art Colony.
In towns up and down the coast, the sea is a central character. A few ways to experience coastal life: Stroll around the working Gloucester harbor, climb aboard a replica cargo ship at the Salem Maritime site, or go whale watching on an excursion from Gloucester or Newburyport.
If a beach day gets rained out, head for a house tour. Many of the house museums date to the 18th century. But then there’s Castle Hill in Ipswich, a 59-room Stuart-style mansion designed for the Crane family (of plumbing fame) by David Adler in 1924, with grounds by the Olmsted Brothers and a spectacular site near Crane Beach. Beauport in Gloucester, built by groundbreaking interior decorator Henry Davis Sleeper between 1907 and 1934, is a unique place that helped propel the 20th-century Colonial Revival. Be sure to see the Samuel McIntire Historic District in Salem for spectacular Federals. That city’s Peabody Essex Museum owns 24 historic structures and gardens you can visit, too.
What to Eat
North Shore towns now have great cuisine year-round, but in the summer you’ll want to try an “in the rough” place: steamed lobster or fried clams—and a bib.
Where to Stay
This is not the land of cookie-cutter hotels and chain restaurants. In Salem, the Hawthorne is a boutique hotel with 89 guest accommodations, great Colonial Revival ambiance, and two on-site restaurants. Rockport’s Emerson Inn by the Sea, a "baby grand" historic hotel, is truly a throwback to more genteel times. All North Shore towns have excellent bed-and-breakfast inns.