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Cape Ann, Massachusetts - Gloucester, Rockport, 
Essex & Manchester-by-the-Sea

 Lighthouse on Cape AnnŐs Annisquam River.

 Lighthouse on Cape Ann's Annisquam River.

Cape Ann is Massachusetts' "other" cape, less famous and much smaller than Cape Cod, but no less interesting. This promontory of land just 30 miles northeast of Boston includes the city of Gloucester and the towns of Rockport, Essex and Manchester-by-the-Sea. This cape's close proximity to Boston offers some interesting vacation possibilities, as many visitors find lodging here and take day trips into Boston using the train. Conversely, if you're lodging in Boston, a side trip to Cape Ann is a must. Whatever your choice, Cape Ann is a great vacation or getaway spot.

Cape Ann was the second stopping point of the Pilgrims. A splinter group from Plymouth seeking good fishing grounds landed here in 1623, and dubbed it "Cape Anne" after Queen Anne of England. What they found here quickly changed the course of American history. Gloucester is a sheltered, deep-water port, a safe place to keep a vessel even in harsh winter storms. It's also located within a day's sail of George's Bank, one of the richest fishing grounds. Fishermen were heard to say that the water was so thick with fish you could simply reach down and scoop them out with your hand. With these natural advantages, Gloucester soon became America's premier fishing port. Fishing activity has recently been slowed by over-fishing and government regulation, but Gloucester remains an active port where fishermen and lobstermen go out to sea daily.

GloucesterŐs Good Harbor Beach.

Gloucester's Good Harbor Beach.


While in Gloucester, you can walk the Maritime Trail. This newly created historic/scenic walking trail ties together the many historic points in Gloucester. There are actually 4 trails and you can walk one or more of them as you wish. All of this is explained in a trail map that you can get from the Gloucester Department of Community Development (978-283-9781). You can also pick one up at the Gloucester Visitors Welcoming Center at Stage Fort Park (Route 127, just west of the "Fisherman" Statue on the Boulevard), as well as at many hotels in in the area.

Gloucester and Rockport also have a number of beautiful beaches. Even in mid season the beaches are generally not overly crowded, but the parking lots are. So on hot days, especially during the weekends, make it a point to arrive early. Parking fees for non-resident cars range from $10-$15.

Gloucester bills itself as the whale watch capital of the world, and with good reason. It's the closest port to the whale feeding grounds, and there are four companies here, taking 100,000 people a year to see the great whales. In addition to whale watching, Gloucester offers deep sea fishing excursions and boat tours of every variety.

Rockport's Famous Motif #1.

Motif #1 — Rockport, MA


This quaint village at the tip of Cape Ann has a lot going for it. Highlights include scenic beauty, seacoast and beaches, art galleries (many of international recognition), restaurants, shopping, scenic walks, and peace and quiet.

Rockport's downtown village is comprised of Main Street, Dock Square, Bearskin Neck, and South Street. There are many dozens of shops, art galleries and restaurants. In fact, just walking around is one of the most popular activities in Rockport.

If you're interested in purchasing a piece of artwork, then Rockport is one of the best places visit. There's a long-running tradition of art in Rockport, and there are a number of established galleries, where you can find the kind of artwork to enjoy for a lifetime.

Rockport also offers a number of fine restaurants and small cafes, some on the waterfront and others just a block or two away. Rockport is unusual in that it's a "dry" town. This means that alcoholic beverages aren't served in restaurants and there are no liquor stores here. Restaurants generally allow you to bring your own wine or other beverages, but may charge for set-ups (glasses, corkscrew, etc.). You should ask about this when making reservations. There are several liquor stores in nearby Gloucester.


Antique shop in Essex on Cape Ann.

Antique shop in Essex on Cape Ann.

Essex is a beautiful small town, famous for clams and shipbuilding. In recent times Essex has become known for the large number of antique shops along Route 133 and adjacent roads. It's also a dining mecca, with more restaurants for a town of its size than anywhere we've seen. You won t get lost here, because there are only three major roads, Route 133, Route 22 and Southern Avenue.

During the great age of sail, when huge fishing and trading ships went to sea, they sailed from Gloucester and other ports, but many were built here in the tiny town of Essex. The heritage of building these great vessels can be seen in the impressive Essex Shipbuilding Museum.

The Essex River is the outstanding physical feature of Essex, and river tours are available through Essex River Cruises. It's a narrated scenic trip of a beautiful river with wildlife and other interesting features, and it's definitely a worthwhile trip.


Manchester is a beautiful New England town with a quaint downtown area, picturesque harbor and a wonderful beach. Singing Beach is one of the nicest beaches anywhere, so named because the sand makes a squeaking sound as you walk across it. However, the parking lot near the beach is for residents only. There's a parking lot downtown, from which you can walk the half mile or so to the beach, which many people do. The commuter rail also stops in town, and has become a popular way for Boston-area residents to reach the beach easily.

In the downtown area, the harbor is adjacent to a nice park with swings and a softball field. Concerts and events are also held there during the summer. There are just a few restaurants, but definitely worth the trip for lunch or dinner. Manchester's quiet beauty, and easy access to Salem, Boston, and the rest of Cape Ann are just a few reasons you'll enjoy staying here.

Route 127 is a scenic road that runs the length of Manchester-by-the-Sea. Toward Gloucester, you can follow it completely around the rest of Cape Ann and circle back into Manchester-by-th-Sea. Toward the west, it takes you through beautiful parts of Beverly, where you can cut over to Salem on Route 22 and 1A.

The "by-the-Sea" extension of Manchester is actually part of the town's name. Several years ago a movement started up by a group of residents who felt that every mention of Manchester was associated with the much larger New Hampshire city of the same name. So the group promoted a campaign to change the name of the town to Manchester-by-the-Sea. And it was approved by a close margin in a town meeting vote.

To quickly find attractions, restaurants and shops on Cape Ann, use the Find Attractions search engine. To quickly locate lodgings, use the Find Lodging search engine.

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