1. Discovering Massachusetts’ North Shore
The North Shore of Massachusetts may have a lower profile than other parts of New England; however, that is the charm of this coastal gem.
2. Exploring Gloucester
My journey began in Gloucester, America’s oldest seaport, about an hour’s drive north of Boston. In 1606, French explorer Samuel de Champlain arrived at Gloucester Harbor, referring to it as “le beau port.” Consequently, English colonists followed, and by the early 19th century, the fishing and shipbuilding industries thrived.
The Cape Ann Museum (capeannmuseum.org) documents this maritime history and houses a remarkable collection by Luminist painters such as Winslow Homer and Edward Hopper, who captured the unique effects of light on coastal landscapes through their artistry.
3. An Ideal Stay
One of the best views in Gloucester is from the recently renovated rooftop bar and pool at the 94-room Beauport Hotel (beauporthotel.com; doubles from $199). After checking in, I explored the town and enjoyed lunch at Seaport Grille (seaportgrillegloucester.com; entrées $16–$36), where I indulged in a flavorful tequila-and-lemonade cocktail, a tangy lobster roll, and crispy onion rings with pronounced hop flavor.
4. Nautical Adventures
That afternoon, I strolled Wingaersheek Beach before embarking on the 64-foot schooner Thomas E. Lannon (schooner.org; 90-minute trips from $33). We sailed past Hammond Castle—constructed between 1926 and 1929 by inventor John Hays Hammond Jr. in a medieval style—and Eastern Point Lighthouse, which has guided ships through Gloucester Harbor for over a century.
5. A Day in Ipswich
Saturday’s journey took me to Ipswich and the historic Castle Hill on the Crane Estate (thetrustees.org), a 2,100-acre seaside property featuring gardens and a stunning mansion overlooking Ipswich Bay. You can walk trails leading to Steep Hill and Crane Beaches, both protected habitats for the piping plover. I refueled at Great Marsh Brewing Co. (thegreatmarsh.com; entrées $15–$28) with a delicious shrimp po’boy and hand-cut fries.
6. Overnight in Rockport
I stayed at the Emerson Inn (theemersoninn.com; doubles from $269), which was built in 1871 on a bluff in Rockport overlooking Sandy Bay. The recently restored inn had a warm, snug ambiance, reminiscent of visiting a wealthy, eccentric relative with its elegant decor and freshly baked cookies. A thunderstorm rolled in overnight, creating a soothing soundtrack of rain against the windows as I drifted to sleep.
7. Rockport to Salem
On Sunday, I explored Rockport’s downtown, still waking up at 10 a.m. I enjoyed a strawberry pastry from Helmut’s Strudel (69 Bearskin Neck; 978-546-2824) while wandering through the rain-washed streets surrounded by charmingly painted houses. My final destination was Salem, often misperceived due to its historical witch trials in 1692, but today it’s vibrant and culturally rich.
A highlight was the Peabody Essex Museum (pem.org), which houses an impressive collection of Asian art, including a 200-year-old Chinese merchant’s house that has been painstakingly reconstructed on the property.
8. A Whimsical Farewell
I decided to wait out another storm at Pentagram (pentagramsalem.com), reputedly the best witchcraft shop in Salem. In a cozy booth, co-owner Leanne Marrama interpreted tarot cards, relating them to personal experiences, including a recent family loss.
Once the storm passed, I joined my husband at the ferry wharf for a boat ride to Bakers Island, where visitors can explore the picturesque lighthouse and tranquil walking trails. In a fading sunset, we feasted on a delightful picnic while the sounds of the sea surrounded us, making for a serene ending to our North Shore adventure.
