Are you looking to explore some historical stone locales? This Connecticut Castle Road Trip is not just for looking at…you can actually step inside some of these stone wonders and see how they’ve transformed to fit modern times. An original structure with its original furnishings, a scenic mountain overlook, and a historical art museum are waiting for you on this trip, all behind incredible towering structures. You’re going to love making this drive! It is one of the best road trips in Connecticut.

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At 114 miles, this three-hour drive can be completed in one day, even with the locales that require hiking. So buckle up and get ready for a day of fun as you conquer the Connecticut Castle Road Trip. You can see the map for yourself by clicking here.
1. University of Connecticut School of Law
UConn School of Law/Facebook
Who knew UConn had a castle? Stop by the Law Library and feel like you're in a royal study as you enjoy the peaceful quiet and soaring ceilings.
Smaley/Wikimedia
With several castle structures surrounding the green, you'll feel transported to another era altogether. Not to mention the fact that you're paying a visit to one of the state's most beloved schools that also happens to be one of the most beautiful places in Connecticut.
2. Wadsworth Antheneum Museum of Art
Wadsworth Antheneum Museum of Art/Facebook
This historic castle is also the longest continually operating art museum in the United States. The building itself is as much a work of art as the treasures inside.
Sinewy polyp/Flickr
Inside you'll find regal decor mixed with modern installations, a perfect pairing of the past and present. A leisurely stroll through this castle is a must. If you're looking for things to do in Connecticut, this is a great place to visit.

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3. Gillette Castle
Ronhjones/Wikimedia
This is the perfect place to bring out that lunch you packed and enjoy a nice picnic. The quirky interior of this stone gem is nothing short of fascinating.
Jean K./Yelp
There's also an incredible view. If you want more information about this famous castle, click here. This is one of the most unique places in Connecticut.
4. Sleeping Giant Tower
Bob P.B./Flickr
A quick and easy one-and-a-half-mile hike will get you to this tower. Hiding inside of Sleeping Giant State Park, this mountain is famous for its appearance.
Bob P.B./Flickr
Climb to the top of the castle structure to find a spectacular observation deck with panoramic views. You'll be blown away in every season.
5. Heublein Tower
John Cudworth/Flickr
The last stop on this castle road trip, one of the best road trips in Connecticut, is the Heublein Tower. This 165-foot tower is a sight to behold, and gets more impressive the closer you get to it. It's definitely worth a visit during the fall.
Doug Kerr/Flickr
You'll love the scenery this mountaintop castle provides, as is this is one of the prettiest walks you'll ever take. For more information about this locale, check out the hike

Have you been to all the gems on this castle road trip route before? What are some other best road trips in Connecticut? Tell us about it in the comments.

For more cool excursion ideas, check out our list of Connecticut’s Most Unforgettable Road Trips by clicking here.

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More to Explore

Best Road Trips In Connecticut

Melissa | July 26, 2021

What are some of the best things to do in Connecticut?

Oftentimes, one of the best things to do is to take a day trip somewhere, and Connecticut has many options when it comes to day-trip destinations. You can head to East Haddam and explore this popular waterfront town. A visit to Avery’s Beverages in New Britain will allow you to create your own soda inside an old barn and you’ll be able to take some home with you! You can also head to the beach for the day and Connecticut has plenty of pristine sandy beaches. For more day trip ideas, read our Best Day Trips in Connecticut article.

What are some of the most unique things to do in Connecticut?

The Constitution State is filled with unique things to do and for that, we are very lucky! One thing you may enjoy is visiting the bizarre roadside attractions around the state. From the Otis Elevator Test Tower in Bristol to Paul Bunyan in Cheshire and Frog Rock Roadside Park in Eastford, there are plenty of unique things to see. You can find more on our list of the most bizarre roadside attractions in Connecticut. You may also want to stop by the ultra-unique PEZ Visitors Center in Orange to view thousands of PEZ dispensers from throughout the years and learn the history of the company.

What are some of the most beautiful places in Connecticut?

If you are searching for some of the most beautiful places in the state, head to our post 13 Unimaginably Beautiful Places In Connecticut That You Must See Before You Die for some ideas. The list includes Enders Falls in Granby, Walnut Beach in Milford, Thimble Islands in Branford, and many more!

 

 

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Featured Addresses
University of Connecticut School of Law, 55 Elizabeth St, Hartford, CT 06105, USA
Wadsworth Atheneum Museum of Art, 600 Main St, Hartford, CT 06103, USA
Gillette Castle State Park, 67 River Rd, East Haddam, CT 06423, USA
Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT 06518, USA
Heublein Tower, Simsbury, CT 06070, USA