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Top Connecticut Road Trips Destinations- Best Vacation Itinerary

Connecticut’s proximity to urban cities like New York puts it under the radar of many road trippers looking to explore the East Coast of the US. Everyone else has included the attractive coast areas with beautiful lighthouses in their itineraries. That’s a good thing, but there’s more to quirky attractions than just that. We’ve explored the greater part of Connecticut and come up with some of the best destinations that will make your road trip a lifetime memory.  So have a look at our unique sampling of Connecticut road trips destinations.

Check out these unusual Connecticut attractions that you wouldn’t want to miss out on during your escapade! If you want to look at some affordable things to do in Connecticut, you can check out our dedicated sampling also.

Want to establish a quick connection with Connecticut? Check out the slides below for a summary of top Connecticut road trips destinations:

01. The State Capitol – One of the Most Attractive Connecticut Road trips

Hartford seems to be lackluster, but there are a couple of things that will make your trip here worthwhile. If you haven’t been to Connecticut’s capital before, you might want to start your road trip in Hartford with the State Capitol. 

With a shiny golden dome to its top, this marble gothic edifice stands as one of the city’s most attractive spots, drawing people’s attention from various parts of the state and the country. Its exterior is magnificent, adorned with sculptures, stained glass, medallions, and ornamental reliefs. 

As you tour around the building, you’ll also come across an 18-foot gorgeous statue that at some time topped the Capitol’s dome. There are also plenty of other attractions here relating to the history of the Civil War, including Nathan Hale’s statue, regiments of the Connecticut battle flag, and a Liberty Bell replica. 

Be sure to book your tour guide reservations in advance for a lovely tour inside the State Capitol building. 

02. Merritt Parkway – National Scenic Byway

Connecticut Road trips - National Scenic Byway

Connecticut is one of the states that are known for its heavy traffic. However, Connecticut’s Route 15 is an exception to that – commercial traffic is restricted here and commuters are in plenty as compared to the big interstates such as I-84 and I-91. 

Merritt Parkway is the section of Route 15 that is between Greenwich and Milford. Connecticut has got fewer routes as pleasant as Merritt Parkway, which is why it was selected as a National Scenic Byway as well as listed on the National Register of Historic Places. 

This route is usually covered with lots of trees especially during autumn while the coastal section presents beautiful scenery worth a road trip. On this route, you can proceed southwards to New York or take the route north beyond Stratford, then go via New Haven and Hartford. 

03. Cushing Brain Collection in New Haven – Part of Yale University

This rare collection is part of the prestigious Yale University and houses a wide variety of preserved brains that were found to have tumors among other conditions. The Cushing Collection was donated to Yale University after the demise of Harvey Cushing in 1939. 

The Cushing Center has got a lot to see and discover, so be prepared to explore as much as you can. Apart from the specimen displays, you can immerse yourself in watching the videos, read books, and see some of the most prized manuscripts and books by Dr. Cushing. 

Be sure to reserve your tours to Cushing Center in advance before your road trip. 

04. Saw Mill City Road – One of the Best Connecticut Road trips with Spooky Attractions

Spooky Connecticut - Connecticut road trips

If you’re after a different kind of thrill, you might want to pay this route a visit. Located in Shelton, Saw Mill City Road is among the spookiest roads in Connecticut. The single-track lane maps a route running through the woodlands near Shelton town, and holds some scary myths. 

One of the stories is that people from a legend in Connecticut, known as “Melon Heads” are at times spotted on this route. This is a certain group of people said to lead a simple lifestyle and have some deformities on their heads. They are said to have secluded themselves from the rest of society. 

Whether it’s a known fact or just a myth, this road is certainly ghostlier, especially if cruising it in night. 

05. Litchfield Hills – Farmland & Rural Charm

This is the northeastern region of Connecticut that lies between the Massachusetts and New York borders. It’s prominent for its farmlands, rivers, lakes, and rural charm. This is the place to visit to get away from the hassles of city life and rejuvenate the body. 

You can explore the northwestern section of Connecticut by cruising through Route 22 running between New Milford and Litchfield towns. Make a stop at any smaller towns you come across this route, then immerse yourself into Bantam Lake that rests between the neighboring Morris and Litchfield. 

06. Holy Land USA, Waterbury – Christians Attractions & Performances

Holy Land - Connecticut road trips

This was once a theme park very popular in the region and attracted over forty thousand people annually, but now it’s been abandoned. Among the attractions in this place included a replica of numerous sites in the Holy Land together with a series of Christian attractions and performances. 

Since its closure in 1984, this attraction is decaying gradually. Even though most of the structures are still standing, the site is being reclaimed by nature slowly. And that makes it a bizarre but interesting place to visit. 

07. Gillette Castle State Park – 24 Room Medieval Stone Mansion

Situated in East Haddam, this newly refurbished park offers lots of attractions including a mansion, gem-filled geological formation, and hiking trails. 

The irresistible feature in Gillette Castle is the mansion, designed by the famous actor William Hooker Gillette who played Sherlock Holmes and is Thomas Hooker’s descendant. The mansion consists of 24 rooms and is built with a resemblance to a medieval stone fortress. 

Another attraction making this road trip worthwhile is the geological formations; diopside, tourmaline, and garnets. Most of us probably know them from jewelry stores, while some can recall them from 5th grade’s study of rocks. Here, you are going to see them perfectly with crystal formations in an uncommon black tourmaline found in some of the hike trails in the park. 

Gillette Castle State Park also has campgrounds and picnic areas along the river where you can spend some quality time with your buddies or family. 

08. New England Trail – Hikes, Campsites & More!

New England Trail - Connecticut road trips

This is perhaps one of the longest trails in the state, spanning the length from the Connecticut coastline to Massachusetts. Along this route, you’ll come across various hiking trails to suit all levels of skill, and campsites along most of these trails. 

New England Trail has got rotating art projects as well as learning programs to suit families’ delight. This makes it a perfect destination if looking for a place to experience a lovely summer escapade. 

09. Connecticut State Route 169 National Scenic Byway 

Starting from the southeastern section of the state in Norwich, running all the way to the north in Woodstock, State Route 169 National Scenic Byway houses most of the things Connecticut is famous for – bucolic farmland, pleasant small towns, and a lot of lively foliage during fall. 

A lot has changed about this place over the years, but the charm and tradition of the people are still part of the communities residing in the area. This is your opportunity to explore some of the historical attractions on this road. Pay a visit to Pomfret’s magnificent churches with a history dating back to the 1800s. You can also head to the Roseland Cottage Bowen House Museum located in Woodstock to find out what the life of prosperous families of the mid-19th century used to be. 

Alternatively, you can drive without any destination in mind just to explore the towns on this route to admire their unique architecture and neatly maintained parks. 

10. The Frog Bridge, Willimantic – 500 Feet Long

The Frog Bridge, Willimantic - Best Connecticut Attractions

Built in 2000 and 500 feet long, this is just a bridge running across a river in the US, but with a single feature that makes it a worthwhile destination for memorable Connecticut road trips. Each of the four corners of the bridge has enormous green frog sculptures resting on plinths carved with an appearance resembling thread spools. 

This design traces its origin back to the 18th century during the shower of frogs that freaked residents to fire weapons at the frogs. A state of unrest among the residents had climaxed in June 1754 following past attacks on towns during the French and Indian War. In the middle of the night in Windham Center, the town’s residents were awakened by commotions and screams but couldn’t determine the source. They responded by firing, which turned out that the commotion was caused by frogs. This eventually gave birth to the town’s symbol. 

This bridge stands out as one of the attraction sites in the state due to this history of the origin of the bridge. 

11. West Rock Ridge State Park – 627 Feet Above Sea Level

West Rock Ridge State Park - Best of Connecticut

Rising to about 627 feet above the sea level, the West Rock Ridge presents a magnificent view of the Long Island Sound and New Haven Harbor for a length of about 200 square miles. Being the twin to the East Rock, the West Rock is a gigantic Basalt cliff that gives Westville a distinctive appeal. 

This stunning spot is situated in New Haven and offers lots of amazing fun-filled activities such as boating, fishing, biking, horseback riding, and hiking. 

West Rock Ridge State Park rests on a 1,700-acre land that extends north into Bethany and Hamden. The park has 23-mile-long trails for dog walking and hiking in Blue-Blazed Regicides Trail. The Red and White Trails are best suited for mountain biking and horseback riding. 

Wrapping Up Connecticut Road Trips Destinations

Connecticut State is certainly a haven where families can escape to when they need to get their minds off the hassles of the busy life of the city. Each of the destinations listed here is a surefire way to satisfy those cravings for a fun-filled summer adventure. If you’re not into the activities, don’t worry, as Connecticut has plenty of less strenuous fun activities and places to visit, such as zoos, aquariums, museums, casinos, and historical sites.

Hope our sampling of Connecticut road trips destinations helps you plan an amazing vacation. To have the experience of a lifetime, book your vacation rentals at Rental Trader. If you need any more information, fill our web form or give us a call, we’ll be happy to help you.

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