Sights of Cape Ann, Post 26-27
- Jimmy Lee
- Jul 5
- 4 min read
Updated: 4 days ago
This week our luggage remained in one location while we explored Cape Ann by day. Here is a recap of places and sights we saw in and around the Massachusetts towns of Gloucester, Essex, and Rockport, as well as a sail on Massachusetts Bay.
Friday, June 26 – Wednesday, July 1, 2026
(Posted by Jimmy, written by Sondra)
Cape Ann Weather & Transportation
Refreshing weather greeted our arrival in Cape Ann. Most of the days were sunny and pleasant with highs in the 70’s while the lows hovered around 60, a nice contrast to the upper 90’s of Guatemala.
During our week onboard Quest II with the Whitlocks we ventured out and about with the aid of the Cape Ann Transportation Authority (CATA) bus network. It is a robust system connecting the various commercial areas of the towns on Cape Ann with well scheduled routes, air conditioning and best of all, free to ride. Most of the drivers were very helpful to locals and tourists alike. Some of the schedule and route data in Google maps was not 100% accurate, so cross checking with the CATA website is recommended. Buses do not operate on Sunday, but Uber drivers were readily available when we needed a ride.
Around the Cape
Outside of Gloucester we visited the shipyard of the Essex Historical Society and Shipbuilding Museum, which was a pleasant little gem. Wooden ships have been constructed here since 1668 and now also has a hands-on museum.
Historical Essex Shipyard
In the other direction we visited the quaint town of Rockport with many shops and art galleries. Just outside of town is Halibut Point State Park. The state park, free to pedestrians and cyclists, was granite quarry from 1840 until 1929. It is a very pretty site with a self-guided tour that provides information about how the quarry operated.
Halibut Point State Park
Just outside of Gloucester we hiked along on the Dogtown Trails near the Babson Reservoir. In the late 1700’s there was a prosperous community of about 500 people. Now only some foundations remain. Roger Babson, the founder of Babson College, purchased most of the Dogtown area and donated it to the City of Gloucester. During the Great Depression he hired unemployed stonecutters to carve inspirational words or phrases on boulders in the Dogtown area.
Sailing Massachusetts Bay
We took advantage of a great weather day to take Quest II out 17 miles offshore to the Stellwagen Bank. On their northbound trek to Gloucester, Cam and Denise had seen whales and thought we could head there to try to find some whales. Just as we finished our lunch, Denice spotted whale activity in the distance and we all jumped into action to bring the boat about. Afterwards we just kept pointing in the direction of the occasional large splashes and spouts seen in the distance. However, over time the splashing vanished, and we never got close to any whales. Once near the end of the bank, we turned around and enjoyed a great downwind sail in 15-20 knots of wind on a boat that could handle a lot more wind. All in all, it was a lovely day on the water! Jimmy and I really enjoyed the opportunity to do a bit of sailing while our boat is taking a summer break.
Gloucester
Gloucester is a historic fishing village that still has a strong fishing industry alongside a few tall ships. One evening while the local tall ships were coming back from their tours or maintenance runs, a visiting tall ship, Windjammer Angelique came into the harbor, sailing right past our bow. We suspect she is on her way south to attend some of the Independence Day celebrations taking place along the eastern seaboard.
Angelique and the local tall ships in Gloucester Harbor
Across the harbor from downtown Gloucester is the North Shore Arts Association which has been in operation since 1922. Entrance to view the gallery was free and well worth the visit. Further down from the gallery is, Rocky Neck, which claims to be America's Oldest Working Art Colony. It is a nice area to wander with several galleries available to peruse.
During the one hot day of our visit, we walked over to State Fort Park and spent the afternoon at Half Moon Beach. Sitting in the shade with our backs along the boulders and the occasional dip in 65-degree water, made for downright pleasant conditions.
Along the Gloucester Boardwalk
The first half of our visit here the town was celebrating St. Peter's Fiesta where the main attraction was the Greasy Pole contest. One afternoon we took our dinghy over to the site of the competition to see what it was all about. There, the beach spectators and anchored boats surrounded a wooden platform located off of the beach that had a 40-ft long telephone phone cantilevering off of it, covered in a questionable greasy material. Contestants took turns attempting to cross the pole and grab the flag perched on the far end.
This video shows one failing competitor followed by the victor crossing the pole.
Click to watch video which starts at 1:17:28
We found Gloucester to be a great location to spend a week with friends and could easily spend more time here. However, it is time to switch gears to begin the next phase of our trip: hiking in New Hampshire and Maine.
Post 26-27
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