1. Annisquam Harbor Lighthouse

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Gloucester, MA

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Annisquam Harbor Lighthouse

3.3 (3 reviews)

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Eastern Point Lighthouse - Gorgeous views of the water

Eastern Point Lighthouse

4.4(10 reviews)
1.5 mi

Beware: This is not a polished tourist destination. Only visit if you're looking for a bit of…read moreadventure. To get to the Eastern Point Lighthouse, you have to turn down a road marked as private. (Apparently it isn't, really?) Then, you pass some other unwelcoming signs. Then you finally get to a small gravel parking lot with a sign that says "All are welcome!" The lighthouse isn't operational or open for tours. It's surrounded by fencing that makes it look condemned. But, if you walk through some sand and rocks along the water and then do a small bit of rock climbing, you can get a good view of an iconic lighthouse. When I visited, it was freezing rain and very windy. When I climbed up on the rocks to take a picture, the winds up there were so strong I was worried they'd blow my phone out of my hand. Combined with the sense that I was almost trespassing, it was oddly thrilling. There's not enough going on to warrant a long trip, but if you're in the area, want a fun diversion, and are fine driving down narrow, possibly private roads to a small gravel parking lot before navigating sandy, rocky, seaweedy tidewaters to see something iconic, it's a worthwhile diversion.

If you're in Gloucester and looking for something non-beachy to do, I recommend checking out…read moreEastern Point Lighthouse and walking across the breakwater to Dog Bar Lighthouse. First, you have to turn onto a private street lined with ridiculously beautiful mansions that you will never be able to afford in your lifetime and possibly your children's, staffed by a security guard (tell him you're here to see the lighthouse). After you drive past the private beach and the yacht club, all bedecked with No Trespassing and Private Entry Only signs to make you feel as unwelcome and plebian as possible by the 1% of Gloucester, you'll see the parking turn-off for the lighthouse. There, we met a very kind lady from Mass Audubon who explained the various migrational birds roaming around the area. You can't actually see or tour the lighthouse because it's fenced around and, from a distance, looks a little worse for wear. But looping around the side across some rocks, you can hop onto the jetty and stroll around and take in the sights. Great spot for photographers. It was beating down with zero shade and we forgot to put on sunscreen before heading out so we did a quick out-and-back but otherwise, it'd be a neat area to sit. $10 fee per vehicle (cash or QR code). No fee if you walk in. Definitely wear close-toed shoes; sandals or flip-flops on slippery rocks are a recipe for disaster. Also, watch out for poison ivy along the path to the jetty.

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Eastern Point Lighthouse
Eastern Point Lighthouse - Sunset was magical

Sunset was magical

Eastern Point Lighthouse

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Hammond Castle Museum - What do you want a meaning for? 
 Life is a desire, not a meaning.
 --Charlie Chaplin

Hammond Castle Museum

4.1(132 reviews)
2.2 mi

Our first stop on a whirlwind road trip on the east coast as "leaf peepers", seekers and admirers…read moreof fall foliage. I really enjoy historic house tours, and why not a castle? John Hays Hammond, Jr, the inventor of radio control, lived here for the first 35 years while it was also a museum. He used part of it as the laboratory for working on his inventions. He hosted parties and collected antiquities and art from all over the world, and built the castle in three continuous sections that mirrored 11th century medieval, 13th century Gothic, and 15th century Renaissance style architecture. Lots of narrow hallways and spiral staircases, a covered courtyard, and even a hidden passageway (though you can't explore that). My favorite room was the library! Our tour guide, Joe, spoke very rapidly to pack in as much information as possible--Very knowledgeable and eager to answer questions. Cool little museum gift shop. Clean bathrooms. Onsite free parking if you purchase your tickets online ahead of time. You can decide to do the self-guided tour or have a tour guide. Highly recommend! Gorgeous view of the Atlantic Ocean!

Castles have always reminded me of fairy tales. But Hammond Castle is a fairy tale with a…read moredistinctly Gothic twist. There was something about the story of its lonely owner and the maze of dark little passageways, hidden entrances, and unexpected exits between rooms that gave me chills. It felt less like I was walking through a castle and more like I had stepped into a fortress where it is eternally Halloween.... Why - because this castle has the unique story of being built from ruins of so many European structures, real structures. Roman pillars from Italian ruins, medieval doorways from French monasteries sometimes even entire rooms dismantled stone by stone and shipped. This inventor (known for the remote control and 400 odd patents), was no doubt super rich, who dreamed and created one of a kind castle to live in. He delighted in calling him the preserver of heritage, some called it plunder and also claimed it was cursed having been built on ruins. No wonder, there are innumerable 'stories' of haunting associated with this castle. There are plenty amazing locations for pictures. The architecture is captivating, it is a popular location for weddings given the dramatic backdrop. Costing anywhere between $6000 to $10K just for the space. I was cautious to walk with my tour group when inside the castle, it was not just to listen to the many interesting scraps of information but also to ensure am surrounded by people......lol Hammond Castle is perched directly on a rocky cliff overlooking the Atlantic Ocean, so its pretty scenic in soo many ways. Its beautiful, its strange, it has loads of mini stories from past and present, something very different. Was I able to pique your interest yet .... ?!

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Hammond Castle Museum - Hammond Castle

Hammond Castle

Hammond Castle Museum - The afternoon knows what the morning never suspected.
     --Robert Frost

The afternoon knows what the morning never suspected. --Robert Frost

Hammond Castle Museum - Hammond Castle

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Hammond Castle

Rockport Town of

Rockport Town of

4.2(17 reviews)
4.4 mi

AN ABSOLUTELY MUST DO! 4 & 1/2 STARS. A beautiful quaint little New England village with…read moreSpectacular Water Views. You won't find chain restaurants, mall stores, nor the same old coffee shops here. In Rockport there are art galleries, & T Shirt Shops, boutiques, & local restaurants - a little something for everyone. Be sure to walk down the end of Bearskin Neck to see the beautiful coastline shoreline & boats in the water. IT LOOKS LIKE A PICTURE POSTCARD. Bring your sneakers, you'll do some walking here throughout the town. Two of the best places to get a little treat are Tucks Home Made Chocolates & Helmut's Strudel Shop. It used to be, you had to have mega bucks & be really rich to have the Good Life, not anymore. The Game has changed. You've been Upgraded. Now You Can Live Like a King on a Limited Budget!

In the summer Rockport is mobbed with tourists. Filled with art galleries, touristy shops and…read morerestaurants it makes a pleasant day out. Late Spring/early summer or late summer/early Autumn are less busy times. Parking is on street, and pay at the kiosk. Put your receipt on the dash where it can be seen. Parking is also available in the surrounding neighborhoods for no fee. Just plan to walk a ways to get into town. Rockport has become so popular lately, there is simply not enough parking to support the tourist trade. Pro-tip: when parking in the surrounding neighborhood, either 'pin' your vehicle location to your phone map, or remember which intersection you parked near. We found one woman wandering around looking for a particular street. We know an artist who has a studio here and stopped in to see his work. We also stopped in to other galleries during our stay. We considered staying to walk around and get a bite to eat, but decided in the end to just get back on the road. We visited the Paper House nearby.

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Rockport Town of
Rockport Town of
Rockport Town of

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Straitsmouth Island Lighthouse - I don't think I'm suppose to be here

Straitsmouth Island Lighthouse

4.0(2 reviews)
4.7 mi

Pretty cool little place. Had a very nice clear day to enjoy the short hike. I will definitely…read morebring the family to check this place out

A lighthouse for the…read more birds The area around Cape Ann is a treacherous place indeed and a whole lot of ships have been lost over the centuries. So it is natural that a whole bunch of lighthouse would be built here. The very first light on the small 2 acre Straithmouth Island was back in 1835 but was a poorly constructed pile of junk. It was rebuilt in 1851 but the fierce storms and wild winters soon took a toil on that one too. So in 1896 the present 37 foot light was built and a small 6th order Fresnel lens added. Over the decades all lighthouses were automated and many, like this one, declared redundant and were closed. The little island ended up as private property until 1967 when the island and lighthouse was donated to the Audubon Society. It is now a bird and wildlife sanctuary and is off limits to humans. The light and the few remaining buildings got hammered and damaged in the Oct. 1991 "perfect storm" but the little lighthouse preserved and survived. It can now be seen closely by kayak or from certain points in Rockport and the twin lights of Thatcher island can be seen from certainly angles. Not a tall light and not an exceptionally old light. But it is a tough little guy that managed to survive everything that natural and man could throw at it.

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Straitsmouth Island Lighthouse - A very rocky beach

A very rocky beach

Straitsmouth Island Lighthouse - A barren little island

A barren little island

Straitsmouth Island Lighthouse - But a nice area to kayak

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But a nice area to kayak

Annisquam Harbor Lighthouse - landmarks - Updated November 2026

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