Cape Ann Lighthouse Tour

The only thing better than a boat tour is two boat tours! In early August, not long after my trip around Portsmouth Harbor, I saw six beautiful lighthouse and reviewed the history of Essex County, MA on a two-and-a-half hour ride given by the family-run company Harbor Tours Inc. of Cape Anne. This tour had everything: fishing vessels, draw bridges, islands, and a boat named King Eider after a large sea duck. Tickets are $45 for adults, $42 for Seniors, $20 for children, and $0 for children 2 and under. While this is on the upper end of my spending, the trip was well worth the price.

A small sailing boat with two masts passes by in the harbor. On the island behind the sailboat, a small white lighthouse with a black top peaks out from behind trees A vast expanse of harbor with a rambling 19th century lighthouse in the distance. A white lighthouse with a red roof and many attached buildings standing on a rocky shore.

Ten Pound Island Light Island in Gloucester, MA was not named for its weight or for an amount of money but for the sheep pounds or pens kept on the island. In 1817, local people believed they saw an unidentified ocean creature swimming near the island. The first lighthouse was built by 1821, although to keep ships same and not to keep away ocean creatures. Winslow Homer stayed at this lighthouse in 1880. The next year in 1881, the lighthouse tour was replaced by the one we see today. This lighthouse has been on the National Register of Historic Places since 1988.

A pair of thin brown stone lighthouses on a long, thin island across the harbor. A green buoy floating in a harbor. The stern of the boat takes up the bottom right. A harbor island with a small white lighthouse and a lighthouse keeper house.

Eastern Point Lighthouse in Gloucester, MA was built in 1832. Its most famous resident was landscape painter Winslow Homer, who created nostalgic scenes of life before the Civil War. (I had learned a lot about him during a presentation back in 2023.) Today, the United States Coast Guard controls the lighthouse, which has been automated since 1985. The lighthouse has been on the National Register of Historic Places since 1987 and stands next to Eastern Point Wildlife Sanctuary aggressively managed by Mass Audubon.

A white lighthouse with a black top has a small shed with a red roof attached to the left. The building stands on the rocky shore beside the harbor. A pile of rocks beside the harbor Italian Villa Style House Near the Water

Fifty-acre Thacher Island in Rockport, MA sports twin lighthouse, the only surviving twins in the United States. Officially known as Cape Ann Light Station, these were originally built in 1789, as people believed two lighthouse would be easy to see, helping sailors determine their place in the water and improving the safety of their travel. Because of their place on Cape Ann, they were once called “Ann’s Eyes”. The island has a tragic history, as it was named for the Thacher family. In 1635, Anthony Thacher sailed his boat, the Watch and Wait on a trip with his wife Elizabeth, four children, and eight cousins. The boat tragically wrecked on the island, with only Anthony and Elizabeth surviving. Massachusetts General Court gave the island to Anthony as compensation, and it was originally called “Thatcher’s Woe”. The island has been on the National Register of Historic Places since 1971.

House Shaped Like a Boat A grey Colonial Revival style building with a long wraparound porch on stilts over the water. Green metal girders underneath an arch bridge spanning the water.

Straitsmouth Island Light Station in Rockport, MA stands on 30-acre Straitsmouth Island, once known for wrecking ships. English explorer John Smith first encountered Straitsmouth while traveling through the area in 1614. The currently lighthouse was built in 1896, the third lighthouse on the island. Sharing the island is the recently restored lighthouse keeper’s house built in 1878. Today, the lighthouse is on the National Register of Historic Places, while the island is managed by Thacher & Straitsmouth Islands Association.

A green metal arch bridge spanning a narrowing river. A short concrete drawbridge with one section opening up to let boats through. A big house with a tree growing through the porch

Annisquam Harbor Lighthouse in Annisquam, Gloucester, MA takes its name from the Annisquam River, which now connects Gloucester Harbor to Ipswich Bay thanks to Blynman Canal. The canal was built almost as soon as Europeans colonized the area, with its earliest form dating to the 1640s. Two drawbridges span the canal. One has a single lifting section and allows trains to pass over. The other is Blynman Canal Drawbridge, which has two lifting sections and spans the canal as part of Western Avenue. It lists to let boats through and then closes to cars and bicycles pass, which it does about 9,500 times to year according to MassDOT. This bridge is currently be repaired during the off-season. As for the lighthouse, it was built in 1897 as the third lighthouse on the site and has been on the National Register of Historic Places since 1987.

A short drawbridge with two sections drawing open. A long wooden horizontal pole attached to a platform in the middle of the harbor. A rectangular metal building with the words Cape Pond Ice The Coolest Guys around on the side.

Other sights included interesting bridges, houses, and a dangerous pole. Annisquam River Bridge, also known as the A. Piatt Andrew Bridge named after a U.S. Congressman and architecture expert who happens to make frequent appearances on this blog. Along the route, the tour guide pointed out a house that looked like an Italian villa, a house shaped like a boat, and a house with a tree growing through the middle of its porch. These were just as interesting as the two museums along the route: Historic New England’s Beauport Sleeper-McCann House and Hammond Castle, both of which I had visited on previous trips to the area. The pole for St. Peter’s Fiesta, an Italian-American festival that takes place on June 29 and is sponsored by Good Harbor Group. While the ceremony includes serious elements like a worship service, blessing the boats, and carrying a shrine to St. Peter through the streets, it also includes a silly element. Men try to run across the Greasy Pole to capture a flag but usually end up falling in the water.