Last Updated: January 17, 2022

Hidden Gems In Massachusetts

Massachusetts in New England is one of the most visited states in all of the United States and for good reason. Known as the “bay state” is home to a stunning coastline full of bays such as Massachusetts Bay and the well-known summer beach towns of Cape Cod Bay. It also has a deep history of culture and heritage which includes Harvard University and the Salem Witch Trials.

But if you want to get off the beaten path in Massachusetts it’s best to look beyond the main attractions and start searching out the hidden gems in this state, which is what we’re here to help with.

Join us as we look at the best-hidden gems in Massachusetts so you get to explore the best Massachusetts has to offer on your next visit.

Dungeon Rock, Lynn

Dungeon Rock, Lynn

The first of the best-hidden gems in Massachusetts we are going to look at is Dungeon Rock and the story behind it is a pretty awesome one.

Dungeon Rock aka Pirate’s Dungeon is a series of caves in the Lynn Woods Reservation area that was once used by a pirate in the 1600s named Thomas Veale. It’s said he lived in the cave with all of his loot but was then killed by an earthquake that covered his riches permanently.

The ins 1852 a man called Hiram Marble lived on the land and it’s said he met the pirate’s ghost who showed him where the treasure was. After a long time excavating the area with his son, they found nothing but the legend lives on.

It’s a pretty cool spot to visit and as you walk through the iron door and into the cave system it feels a bit spooky – be sure to bring a torch and some waterproofs.

Art of Jack Kevorkian, Watertown

If you’re looking for a hidden gem in Massachusetts that is a little “off the wall” shall we say then look no further than the Art of Jack Kevorkian in the Armenian Library and Museum of America in Watertown.

Jack Kevorkian, often referred to as Dr. Death, was a pathologist who assisted with over 130 suicides in his lifetime until he was arrested in 1999 for second-degree murder having taken the matter into his own hands.

He went on to die in 2011 after which his collection of art was left and is now showcased in the Armenian Library and Museum of America. The theme is death and the art is very gory, so this art show is likely to be a little shock to the system but still worth a visit.

Not all his pieces are always on display but there are 4 permanent ones so no matter when you visit, you’ll be able to see some of his art.

Becket Land Trust Historic Quarry and Forest, Becket

Becket Land Trust Historic Quarry and Forest, Becket

One of the must-visit hidden gems of Massachusetts, especially if you like to hike and have kids, is the Becket Land Trust Historic Quarry and Forest.

It was once the Hudson-Chester quarry when it was commercially mined but was abandoned in the 1890s along with all the mining tools and machinery. Nature quickly took the abandoned quarry back for its own and kind of created a museum wrapped in natural beauty.

When a mining company tried to start working in the quarry again in 1999 the local community quickly bought it and put it in a trust protecting what had become a stunning forest that was important to the local residents.

Today, it’s a beautiful spot and it’s wonderful to explore all the hiking trails, swim in the lake, get some fresh air, and jump off the quarry cliffs into the water.

Franklin Park’s Overlook Shelter Ruins, Boston

Another gem in Massachusetts that is often missed by tourists and even locals is the ruins of Fraklin Park in Boston. Now, you might be asking how a park could be so famous and it’s due to the fact that it was designed by Frederick Law Olmsted who is thought to be the top landscape architect ever.

Olmsted designed Central Park in Manhattan as well as countless others in the Massachusetts area but Franklin Park was thought to be one of his best and was often referred to as his “Emerald Necklace”.

The ruins of Franklin Park as some of the first structures he ever designed and included an archway, stone steps, fountains, and more.

Today the park is overgrown and unmaintained which has given rise to the stunning ruins. Make sure to visit it if you’re in the Boston area and it’s a great spot for a picnic in the summer too.

Block Island, Rhode Island

Block Island, Rhode Island

While technically in the state of Rhode Island, this gem is so close to Massachusetts and Martha’s Vineyard that we kind of had to include it.

Block Island is a stunning little island that is off the beaten path and is the perfect place to spend some time in the summer. It’s known for its outstanding natural beauty, diver flora and fauna, and cute coastal fishing villages that run the shoreline.

If you love the outdoors then you’ll have everything to explore on this island as it’s loaded with hiking trails, is a center for water sports such as kayaking and SUP-ing, the beaches are to die for, and waters around it are some of the best on the East Coast for fishing.

Cranberry Bog

Cranberry Bogs are another hidden gem of Massachusetts and while the name isn’t very inviting, don’t let it put you off making a visit. There isn’t just one Cranberry bog in Massachusetts, they are actually all over the state and they are quite a thing to see.

Imagine a bog, yes a bog of sludgy mud and shallow water, and now imagine it covered in a deep red cranberry-colored plant on the surface that makes the entire thing glow red when it’s in full bloom. Some of the most stunning views you might see in Massachusetts will be of a cranberry bog surrounded by trees and meadows.

Now, you shouldn’t need to travel very far in Massachusetts to find a cranberry bog, just ask a local where the closest one is or look it up online and then plan a day out of hiking and picnicking around it, you won’t regret it.

Hammond Castle Museum – Gloucester Massachusetts

Hammond Castle Museum – Gloucester Massachusetts

If there is one gem of Massachusetts that is set to blow your socks off it’s the Hammond Castle Museum in Gloucester. Hammond Castle is a huge Renaissance medieval-style castle that was built by the late John Hays Hammond Jr. as a wedding gift to his wife and it’s stunningly beautiful.

When you visit the Museum you can take yourself on a self-guided tour around the old castle and see the old war room, library, servant’s quarters, the great hall, a secret passageway, and the Natalie Hays Hammond exhibit room.

It’s not just the building that is worth looking at as you’ll also find a host of Hammond’s Roman, Medieval, and Renaissance artifacts from his collection as well as an eight-story pipe organ with 8,200 pipes with a stained-glass window. Plus, the secret passageway is super cool.

Echo Bridge, Newton

A really fun gem of Massachusetts to see and a great one for the kids is Echo Bridge. Echo Bridge was built back in the late 1800s and was the second-longest bridge of its type to ever be built at the time.

It’s a stunning bridge with a central archway that crossed the Charles River in Newton and it’s loads of fun to visit because it’s a whispering gallery. The arch of the bridge is perfectly designed to carry sound and when visiting the bridge you can test it out.

If you take the stairs down under the bridge you’ll find a platform that is designed for the public to play with the acoustics. It’s lots of fun to say your name and hear it whispered back to you across the water and loads of fun for kids too.

Dogtown & Babson Boulder Trail, Gloucestershire

If you love to hike and are looking for a trail that is a little different from the usual ones then the Dogtown & Babson Boulder Trail in Gloucester is one to try out.

The area of Dogtown was once home to a community of farmers and was established in the 1600s but later abandoned during a war in 1812 who left their dogs behind, hence its name Dogtown.

It was then during the Great Depression that Roger Babson decided to create a hiking trail that featured 30 gigantic boulders, known as the Babson Word Rocks, which each has a thoughtful etching on it.

Today, it’s a lovely trail to hike with very easy trails, and every now and then you’ll stumble upon a boulder with quotes like “Use Your Head” and “Never Try, Never Win” popping up as you go.

Ponyhenge, Lincoln

Ponyhenge is quite a weird and wonderful thing to see in Lincoln, Massachusetts and it’s unique the world over.

Ponyhenge is pretty much the pony and old rocking horse version of Stonehenge in the UK and no one knows who started it. One day in 2010, a lobby horse was put on a field and since then more and more old ponies and rocking horses have been showing up to it. The owners of the field don’t see to mind and have let the weird going’s on continue.

Another strange thing about Ponyhenger is that the horses all seem to change place overnight. They can be found lying on the ground, standing in a circle, and even lined up like they are about to be in a race.

A visit to Ponyhenge is very much worth it just because it’s so unique and odd to see a bunch of old toy ponies and rocking horses sitting in a field.

Bash Bish Falls

Bash Bish Falls

Another gem in Massachusetts, Bash Bish Falls is a must-see when you visit this great state. You’ll find it tucked away in the southwest corner of Massachusetts in Mount Washington State Park right on the border with New York’s Taconic State Park.

It’s a little off the beaten path but the hike to this series of cascading waterfalls is absolutely beautiful. The falls are made up of a number of different waterfalls that drop a huge 200 feet in total and are the highest waterfall in Massachusetts.

The last waterfall in the series drops 80 feet over boulders into a clam plunge pool below where it splits into two streams in a creek. From the top of the waterfall, you’ll have incredible views into the Taconic State Park of New York.

Skinny House, Boston

If you’re wandering around the streets of Boston you kind of have to go and take a look at Skinny House. It’s called Skinny House because it’s one of the narrowest buildings on a street of already very narrow apartments.

It’s said that the house, also referred to as the Spite House, was built out of spite to annoy his brother who lived just behind it. By building the Spite House all the sunlight was blocked out from his brother’s house.

At just 30 feet deep and 10 feet wide, this house really is tiny and you can find it on Hull Street in Boston.

Forest Hills Cemetery, Boston

Forest Hills Cemetery, Boston

Another place worth checking out while you’re in Boston is the Forest Hills Cemetery which you’ll find in the south of Boston near Jamaica Plain at the end of the MBTA train line.

While this is a cemetery it’s also a lovely park which helps make it a little less morbid to walk around and it’s huge too spanning some 275 acres. As you walk around the cemetery you’ll find lovely old sculptures which are both playful in style and quite beautiful and a lot of famous people were also laid to rest in there too.

The graves of E.E. Cummings, Anne Sexton, and Eugene O’Neill are just some of the famous people who were buried there.

About the Author Roger Timbrook

Roger is a little obsessed with travel. He has been to over 40 countries, broken 3 suitcases and owned over 10 backpacks in 12 months. What he doesn't know about travel, ain't worth knowing!

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