Massachusetts has a lot to offer and there are plenty of reasons to venture a bit farther than your town line. When you get the itch to explore this great state, just pick one of the amazing road trips below and hit the pavement. There is nothing like cruising the open-road, windows down, music up, and enjoying a trip to some worthy attractions. Whether you’re taking a weekend trek or just an afternoon drive, check out the best road trips in Massachusetts you can take.
- The Massachusetts Ice Cream Trail
Yelp/Charlotte A. Got a sweet tooth? Us too, which is why we love this epic ice cream road trip through Massachusetts. It will take you across the state to some of the best ice cream shops around. Places like White Farms Ice Cream in Ipswich, Mt. Tom’s Homemade Ice Cream in Easthampton, and Peaceful Meadows in Middleboro will all charm you with their decadent cones. More info and directions here
- Atlantic White Cedar Swamp, Wellfleet
Instagram/Mirandahull13 You’ve never seen a place like this before. Deep in the Cape Cod National Forest, the Atlantic White Cedar Swamp is a magical spot filled with towering trees, colorful foliage, and a raised boardwalk that will take you through groves of white cedars and swampland.
- Horseneck Beach State Reservation, Westport
Flickr/Phillip Capper This spot is probably one of the most beautiful coastal parks in New England. Horseneck Beach State Reservation is the only place in the state where you can camp right on the dunes, and it offers spectacular ocean views. If you don’t want to make this road trip an overnight affair, just stop by for an afternoon of hiking, swimming, and exploration. (Route 88, Westport Point, Westport)
- Hidden Beaches Road Trip
Flickr/MOTT This road trip will take you to the coolest hidden beaches in the state. It starts from the northern tip of coastal Massachusetts and runs all the way down the South Shore and up through the arm of Cape Cod. You’ll hit gorgeous spots in Gloucester, Marshfield, and Wellfleet, plus plenty of others. Don’t forget to pack enough sunblock!Click here for more information and directions.
- Gunn Brook Falls, Sunderland
Flickr/MOTT Live out west and in the mood for a quick road trip? Check out Gunn Brook Falls in Sunderland, where a 0.2-mile hike will deliver you to a gorgeous waterfall that offers 35 feet of sparkling cascades. You can pack a picnic and enjoy the view, or keep exploring the rest of the forest landscape.
- The Massachusetts Castle Road Trip
Hammond Castle It might surprise you to learn that Massachusetts is home to a number of incredible, fairy-tale-style castles. This road trip will take you from east to west on an incredible castle-hunting adventure. You’ll see amazing places like Herreshoff Castle in Marblehead, Hammond Castle in Gloucester, and Searles Castle in Great Barrington. More info and directions here
- Metacomet-Monadnock Trail
Flickr/James Does your idea of a road trip involve less pedal to the metal and more actual legwork? Then the Metacomet-Monadnock Trail may be the weekend trip you’ve been looking for. Spanning an exhilarating 148 miles of stunning landscape, this trail will take you through Hamden, Hampshire, Franklin, and Worcester counties. It will leave you feeling accomplished and in awe of Massachusetts’ natural beauty.
- Rockport
Flickr/Jayne This quiet fishing village is one of Massachusetts’ unsung summer destination heroes. Will charm in spades and waterfront views that will take your breath away, Rockport is a peaceful town that makes for a great place to spend a day or weekend. Stop by the Pewter Shop to pick up a handmade gift and head down to the harbor to snap a photo of the iconic red shack Motif No. 1.
- Massachusetts Abandoned Places Road Trip
SUBSTREET/Dan Turner If you like your history with a side of creepiness, this is the road trip you’ve been longing for. Our abandoned spots road trip will take you to some of the most significant and interesting abandoned places in the state, such as Belchertown State School for the Feeble-Minded and the ghost town of Dogtown. Please note that some of these places forbid trespassing and visitors should keep to a safe and legal distance. More info and directions here
- The Ultimate Massachusetts Waterfall Road Trip
Flickr/Rob Weir Who doesn’t love discovering an amazing waterfall in their own backyard? Massachusetts is actually littered with stunning cascades and this road trip will take you to the best of the lot. You’ll be able to explore waterfalls like Bear’s Den Falls in New Salem, Bash Bish Falls on Mount Washington, and even dine beside a waterfall in Hatfield. More info and directions here
So, what do you think about the best road trips in Massachusetts? Have you taken any of these before? Share with us your experiences in the comments section! Looking for more great Massachusetts trip inspiration? Take a look at these 10 small-town festivals that you’ve never heard of but are worth checking out.
Yelp/Charlotte A.
Got a sweet tooth? Us too, which is why we love this epic ice cream road trip through Massachusetts. It will take you across the state to some of the best ice cream shops around. Places like White Farms Ice Cream in Ipswich, Mt. Tom’s Homemade Ice Cream in Easthampton, and Peaceful Meadows in Middleboro will all charm you with their decadent cones. More info and directions here
Instagram/Mirandahull13
You’ve never seen a place like this before. Deep in the Cape Cod National Forest, the Atlantic White Cedar Swamp is a magical spot filled with towering trees, colorful foliage, and a raised boardwalk that will take you through groves of white cedars and swampland.
Flickr/Phillip Capper
This spot is probably one of the most beautiful coastal parks in New England. Horseneck Beach State Reservation is the only place in the state where you can camp right on the dunes, and it offers spectacular ocean views. If you don’t want to make this road trip an overnight affair, just stop by for an afternoon of hiking, swimming, and exploration. (Route 88, Westport Point, Westport)
Flickr/MOTT
This road trip will take you to the coolest hidden beaches in the state. It starts from the northern tip of coastal Massachusetts and runs all the way down the South Shore and up through the arm of Cape Cod. You’ll hit gorgeous spots in Gloucester, Marshfield, and Wellfleet, plus plenty of others. Don’t forget to pack enough sunblock!Click here for more information and directions.
Live out west and in the mood for a quick road trip? Check out Gunn Brook Falls in Sunderland, where a 0.2-mile hike will deliver you to a gorgeous waterfall that offers 35 feet of sparkling cascades. You can pack a picnic and enjoy the view, or keep exploring the rest of the forest landscape.
Hammond Castle
It might surprise you to learn that Massachusetts is home to a number of incredible, fairy-tale-style castles. This road trip will take you from east to west on an incredible castle-hunting adventure. You’ll see amazing places like Herreshoff Castle in Marblehead, Hammond Castle in Gloucester, and Searles Castle in Great Barrington. More info and directions here
Flickr/James
Does your idea of a road trip involve less pedal to the metal and more actual legwork? Then the Metacomet-Monadnock Trail may be the weekend trip you’ve been looking for. Spanning an exhilarating 148 miles of stunning landscape, this trail will take you through Hamden, Hampshire, Franklin, and Worcester counties. It will leave you feeling accomplished and in awe of Massachusetts’ natural beauty.
Flickr/Jayne
This quiet fishing village is one of Massachusetts’ unsung summer destination heroes. Will charm in spades and waterfront views that will take your breath away, Rockport is a peaceful town that makes for a great place to spend a day or weekend. Stop by the Pewter Shop to pick up a handmade gift and head down to the harbor to snap a photo of the iconic red shack Motif No. 1.
SUBSTREET/Dan Turner
If you like your history with a side of creepiness, this is the road trip you’ve been longing for. Our abandoned spots road trip will take you to some of the most significant and interesting abandoned places in the state, such as Belchertown State School for the Feeble-Minded and the ghost town of Dogtown. Please note that some of these places forbid trespassing and visitors should keep to a safe and legal distance. More info and directions here
Flickr/Rob Weir
Who doesn’t love discovering an amazing waterfall in their own backyard? Massachusetts is actually littered with stunning cascades and this road trip will take you to the best of the lot. You’ll be able to explore waterfalls like Bear’s Den Falls in New Salem, Bash Bish Falls on Mount Washington, and even dine beside a waterfall in Hatfield. More info and directions here
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Address: Massachusetts, USA
The OIYS Visitor Center
Best Road Trips In Massachusetts June 21, 2021 Marisa Roman What are the most well-known attractions in Massachusetts? While the road trips mentioned above will take you to some pretty phenomenal places, you might want to also learn about those must-visit attractions In Massachusetts. You know the ones we mean - the ones that truly represent what this state is all about. Fill up your calendar year with some of the most well-known attractions this state has to offer. Whether you’re looking to find the most jaw-dropping attractions in MA or the most incredible natural attractions, you’ll surely be busy all year long. What are the best road trips through Massachusetts? Out of all of the things to do in Massachusetts, especially for residents, taking a road trip often showcases the best there is to offer in one fell swoop. We’ve mentioned a few of the more popular road trips above, but still, Massachusetts has a lot more to see. For example, this road trip will take you to the most picturesque small towns in MA. Meanwhile, this road trip will take you to a handful of hidden beaches, many of which you might not have even known to exist! Also, if you want a more collective list of road trips in Massachusetts, click here. Each of these road trips has been created by us to highlight some of the best this state has to offer. What are the best day trips in Massachusetts? Day trips in Massachusetts can be a great way to enjoy pockets of beauty, nature, restaurants, and more. If you have nothing but time on your hands for the entire day, we recommend hitting the open road to check out a few of these MA attractions. Stop at Four Elements Salon in Westport for a Himalayan salt cave experience. Or spend the day exploring North Adams, Massachusetts, one of the coolest towns in the east!
The OIYS Visitor Center
Best Road Trips In Massachusetts
June 21, 2021
Marisa Roman
What are the most well-known attractions in Massachusetts? While the road trips mentioned above will take you to some pretty phenomenal places, you might want to also learn about those must-visit attractions In Massachusetts. You know the ones we mean - the ones that truly represent what this state is all about. Fill up your calendar year with some of the most well-known attractions this state has to offer. Whether you’re looking to find the most jaw-dropping attractions in MA or the most incredible natural attractions, you’ll surely be busy all year long. What are the best road trips through Massachusetts? Out of all of the things to do in Massachusetts, especially for residents, taking a road trip often showcases the best there is to offer in one fell swoop. We’ve mentioned a few of the more popular road trips above, but still, Massachusetts has a lot more to see. For example, this road trip will take you to the most picturesque small towns in MA. Meanwhile, this road trip will take you to a handful of hidden beaches, many of which you might not have even known to exist! Also, if you want a more collective list of road trips in Massachusetts, click here. Each of these road trips has been created by us to highlight some of the best this state has to offer. What are the best day trips in Massachusetts? Day trips in Massachusetts can be a great way to enjoy pockets of beauty, nature, restaurants, and more. If you have nothing but time on your hands for the entire day, we recommend hitting the open road to check out a few of these MA attractions. Stop at Four Elements Salon in Westport for a Himalayan salt cave experience. Or spend the day exploring North Adams, Massachusetts, one of the coolest towns in the east!
The OIYS Visitor Center
The OIYS Visitor Center
While the road trips mentioned above will take you to some pretty phenomenal places, you might want to also learn about those must-visit attractions In Massachusetts. You know the ones we mean - the ones that truly represent what this state is all about. Fill up your calendar year with some of the most well-known attractions this state has to offer. Whether you’re looking to find the most jaw-dropping attractions in MA or the most incredible natural attractions, you’ll surely be busy all year long.
What are the best road trips through Massachusetts?
Out of all of the things to do in Massachusetts, especially for residents, taking a road trip often showcases the best there is to offer in one fell swoop. We’ve mentioned a few of the more popular road trips above, but still, Massachusetts has a lot more to see. For example, this road trip will take you to the most picturesque small towns in MA. Meanwhile, this road trip will take you to a handful of hidden beaches, many of which you might not have even known to exist! Also, if you want a more collective list of road trips in Massachusetts, click here. Each of these road trips has been created by us to highlight some of the best this state has to offer.
What are the best day trips in Massachusetts?
Day trips in Massachusetts can be a great way to enjoy pockets of beauty, nature, restaurants, and more. If you have nothing but time on your hands for the entire day, we recommend hitting the open road to check out a few of these MA attractions. Stop at Four Elements Salon in Westport for a Himalayan salt cave experience. Or spend the day exploring North Adams, Massachusetts, one of the coolest towns in the east!
