Escape to: Gloucester
By Joanne Scully and the Editors of Farewell Travels
Say the word “Cape” when referring to Massachusetts and inevitably, it is followed by the word “Cod.” But there’s another Cape many Bostonians and other New Englanders love to escape to: Cape Ann, which is on the northern edge of Massachusetts Bay.
At the center of it all is Gloucester, which was actually one of the first English settlements in what would become the Massachusetts Bay Colony. Today, it’s a lively seafaring community (and oldest fishing port on the East Coast) with several truly worthwhile attractions and restaurants and coastal scenery that inspired some of America’s great artists (including Winslow Homer and Edward Hopper).
Here’s what you need to know.
Beaches even the non-beach-goer loves. The Atlantic-whipped beaches of Cape Ann are ideal for beach lovers whether you're interested in plopping down to  soak up rays or taking long leisurely strolls (especially nice at low tide when you can wander along sand bars).
There are more than half a dozen beaches to take your pick of in Gloucester alone including Good Harbor Beach (a wide expanse of white sand) and Wingaersheek Beach, in the western part of Gloucester. The latter runs along the Annisquam River and Ipswich Bay and has mica in the sand which shimmers like someone stirred a handful of diamonds in it. Don’t miss out on visiting Singing Beach in nearby Manchester. The extremely fine sand squeaks with every step.
Prime kayaking waters. Magnolia Beach  on Raymond Street in Magnolia (a section of Gloucester) is a beautiful place to launch a kayak. You can paddle out to Kettle Island and go ashore, then carry on exploring quiet coves and beaches. For launching, there’s a public landing and several spots for cars. Best to go at high tide for a shorter walk with your kayak.
Don’t have kayaks? Essex River Basin Adventures in nearby Essex offers equipment, instruction and guided tours.
Ridiculously fresh seafood. Plan on having outstanding seafood here. We were really wowed by the swordfish (and the popovers) we had at Passports on Main. At Latitude 43, which overlooks Gloucester harbor, you practically order your dinner right off the boats pulling in.
Espresso and… Okay, this is not Sicily, but it sure tastes like it in Caffé Sicilia (40 Main Street), our number one choice for coffee, espresso and…homemade Italian cookies. Are the cookies worth the calories? Let’s just put it this way. What happens in Caffé Sicilia, stays in Caffé Sicilia.
Get out on the water! A must for any warm-weather visit to Gloucester is taking a cruise around the harbor. A highlight of our visit was listening to Gloucester native  Captain Tom Ellis and his son Heath fill us in on stories of the past on the 60-foot-long historic
Schooner Thomas E. Lannon. We especially loved how they pointed out views painted by Edward Hopper. Another option? Take a lobstering tour around Gloucester Harbor with
Cape Ann Harbor Tours.
Check out the Castle and 1920s “cottage.” Plan to spend an hour at Medieval-style Hammond Castle. Built by inventor, electrical engineer and collector Dr. John Hammond Jr. in the 1920s, it served as a home and repository for Hammond’s artifacts collected while abroad. Also take time to see Beauport on Eastern Point (across the bay from downtown Gloucester). The “summer cottage”- turned-museum was built by Henry Davis Sleeper, an interior decorator and antiquarian of the 1920s. The house was always filled with prominent guests as colorful as the jungle green apple bedroom, and the décor changes whimsically from room to room. Take the tour to find out why Sleeper emerged from the secret stairwell dressed in costume. One of the most precious views of Gloucester is from the Cottage’s Golden Step Dining Room, where the town resembles a little Venice.
For the love of art. Rocky Neck Art Colony is a huddle of artists’ studios on the water in East Gloucester. Mingle with illustrious artists past and present as you stroll through the narrow streets, popping into galleries along the small peninsula.
Shopping around. Gloucester is home to a variety of small one-of-a-kind shops and galleries. On Main Street, check out the Cape Ann Olive Oil Company, where you can sample different olive oils, and the The Bookstore of Gloucester, where you can purchase books and local artwork. On the  waterfront, be sure to pop in the Jeff Weaver Gallery. Weaver is in demand for his depictions of Gloucester and its environs in paintings and drawings. If your tastes lean more towards the vintage, drive over to nearby Essex where you can score some antiques that actually graced some of the grand homes you see perched on the ocean cliffs.
Overnight wonder. The Stacy House of Bass Rocks Ocean Inn, which was designed by George O. Stacy (a prominent local builder and hotelier in the late 1800s) was nicknamed “The Wedding Cake House” because it was a wedding gift to Mr. Stacy’s bride. The seaside “mansion” which was restored in 2007 (with much of the original woodwork preserved) is on the National Register of Historic Places and has three suites with Jacuzzi tubs and ocean views.
Photo Credits: The Cape Ann Chamber of Commerce provided these images.
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