Boston's North Shore: Rockport

A Relaxing Weekend on Boston’s North Shore

Massachusetts offers a never-ending array of vacation settings, from the wooded beauty of the Berkshires to the beaches of Cape Cod, or the cultural and activity center of Boston. Boston’s North Shore is generally defined as the mainly coastal towns directly above Boston.

While there are many other interesting towns on Boston’s North Shore, we’ll focus on four towns that we toured on a recent weekend. For the traveling poker player, Boston’s North Shore can work as a base to play at the Brook Casino and Tavern in Seabrook NH and Chasers in Salem NH. If Encore Boston Harbor in Everett ever opens their poker room again (which is in doubt) that would be an option as well.

A Visit to Boston’s North Shore


Rockport is a small community (under 7,000 residents) that sits at the tip of Cape Ann. While small, Rockport fits a lot of retail, antique, art, and dining venues into their very quaint downtown area. As we were there offseason, many places were not open, but we still were able to find enough interesting shops to fill our morning. In terms of dining, good seafood options abound. The area around Rockport offers many walking and bike trail options. Overall, a nice relaxing area for a variety of activities.

Boston's North Shore: Rockport


To the west of Rockport is the much larger and well-known town of Gloucester. The town was established as a vibrant fishing community, and made famous by the Gorton seafood business. Gloucester received international attention several years ago because of the Andrea Gail tragedy that was detailed in the book and film The Perfect Storm. The town’s most iconic image, the Fisherman’s Memorial (see below) is found along an extensive oceanside path with beach below. Beaches of varying sizes, ease of access, and texture (rocky vs. sandy) abound. Leave plenty of time for a leisurely beach walk. You will find they produce a sense of calm and peace.

Gloucester is spread out, so you’ll want to plan your meals and activities before you go. Beyond the Memorial, you’ll want to spend some time visiting the shops on Main Street. Gloucester also offers abundant whale watching. There are several different companies who run whale watching trips in season. If you are interested in whale watching, we suggest you do an Internet search and check to see if there are any deals. This is not a cheap activity.

The Gloucester Fisherman
The Gloucester Fisherman


Salem has gone all-in on their historic witch trials. Located south of Rockport and Gloucester, Salem’s downtown feels like the main street of a Wiccan theme park. Every shop offers occult-lite products or some wordplay on witchcraft in their name. Nevertheless, the town is attractive, with cobblestone streets, pretty parks, and numerous historic buildings.


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The Salem Witch Museum mounts a very kitschy 45-minute show on the history of the witch trials that is fairly entertaining and informative. At the other end of the spectrum, Salem also houses the Peabody Essex Museum, a beautifully designed and well-conceived museum with an eclectic span of exhibits. The PEM is part art museum and part natural history space. If you are a museum fan, the PEM should be a key stop on your Boston’s North Shore visit. The House of the Seven Gables (made famous by the Hawthorne story) also stands in Salem, and is well worth a visit.

Dining options are plentiful in Salem. The town is replete with delis,  ice cream parlors, and restaurants ranging from casual to upscale.

Salem Witch Museum
Salem Witch Museum


You really have to work to visit Marblehead. The town is out on its own peninsula and you have to wind your way from Route 128 about 15-20 minutes through Salem to get there. If you make the trip, you will find a scenic colonial town with narrow streets and historic houses that will take you back a couple of centuries. As with the towns above, one of the main attractions of Marblehead is to walk around the downtown shopping and snacking.

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Outside of downtown, there is a historic lighthouse at Chandler Hovey Park. The park provides a look at the unusual and interesting iron lighthouse structure and offers a nice view across the channel at downtown Marblehead. Also be sure to visit Fort Sewall and Old Burial Hill. Old Burial hill offers many historic gravestones for those who are fans of grave rubbings and old inscriptions.

Boston's North Shore: Marblehead

Marblehead also boasts several excellent restaurants. In a previous trip we ate at Five Corners, which was excellent but temporarily closed on our most recent visit. On this visit we ate seafood from Maddie’s Sail Loft one evening which was very good.  Also, be sure to visit Shubie’s Market which offers an array of prepared food, cheese, desserts, and wine. We consider it one of Boston North Shore’s best high-end markets.

On this visit, we stayed for two nights at the historic Harbor Light Inn. There we found to one of the prettiest rooms we have encountered in years. Due to COVID restrictions, the Harbor Light encourages visitors to order food in. We did so and were set up in a private fireplace parlor to eat our meal on china with cloth napkins and drank a great bottle of wine from the Inn.

Our private dining room


Boston’s North Shore is a great area to experience New England’s coastal beauty, shop, and eat some excellent meals. he North Shore is also central to Boston if you’re looking for a more metropolitan experience, or coastal New Hampshire for poker and sandy beaches. If you’re in New England, Boston’s North Shore is not a bad choice to experience an enjoyable, eclectic weekend.

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