The 5 Best Road Trip Destinations in Connecticut

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  • River Valley
  • Litchfield Hills
  • Mystic Country
  • Fairfield
  • Greater New Haven
  • Roadside Assistance
Ready for beautiful foliage, literary history, and an adventure you’ll never forget? Connecticut is a state with hidden treasures just waiting to be discovered, and these road trips will take you on all of them.
From water parks and famous authors’ houses in River Valley to outdoor experiences in Fairfield to a haunted hotel in Mystic Country, we have you covered with some of the best road trip destinations in the Constitution State!
Before we begin, though, remember that the number one priority of any drive is safety—and nothing kills the fun quicker than a flat tire or a stalled-out engine. With Jerry’s roadside assistance program, you’ll be covered for emergency assistance, towing, lockouts, and even Uber credits. Jerry’s got you covered so that all you have to do is focus on your trip and the road!
And with that, let’s begin!

1. River Valley

Why you should go
There’s nothing better than a summer adventure, and this part of Connecticut proves it. River Valley, located in central Connecticut, is home to everything from the Mark Twain House and Museum to Brownstone Adventure Sports Park to the Connecticut River Museum. River Valley has everything you want to do this summer, and more.
What to do
If you’re looking for somewhere jam-packed with exciting new activities and good times, River Valley is the place to be! Have an adventure at Brownstone Adventure Sports Park—get out on the water, jump from a cliff, or even go rock-climbing! The possibilities are endless, and so is the fun, but it doesn’t stop there.
For a quieter time, check out the historical Mark Twain House and Museum to learn more about one of the world’s most famous authors, or head to the Connecticut River Museum to learn more about the historic importance of Connecticut’s waterways.
Three people taking photos of the red brick exterior of the Mark Twain House and Museum in River Valley, Connecticut
Mark Twain House and Museum

2. Litchfield Hills

Why you should go
If you want to keep up the summer fun, with a touch of sophistication and plenty of beautiful views, Litchfield Hills is the place to be. Here, you’ll find delicious dining and celebrations of artistry, like the Brookfield Craft Center. But, you’ll also find fun for everyone at places like Quassy Amusement and Waterpark.
What to do
Check out Brookfield Craft Center, which shows off beautiful works of art and is home to fully functioning art studios!
If you’re looking for a more rambunctious adventure, head over to Quassy Amusement and Waterpark, which has everything from water slides and rides to classic arcade games to Lake Quassapaug, where you can have some fun on the water or just relax on the beach.
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A red covered bridge stands out against the snow in Kent Falls State Park in Litchfield Hills, with bare trees in the background
Litchfield Hills, Connecticut

3. Mystic Country

Why you should go
Even the name sounds magical—and that’s only the beginning! Mystic Country is home to some of the most beautiful hiking trails and nature centers in the state, as well as a historic waterfront district and a dinosaur park! One trip to Mystic Country, and you’ll feel like you’re truly getting a breath of fresh air.
What to do
Get out into nature on the beautiful hiking paths! If you’re here with the whole family, The Dinosaur Place—a nature park filled with life-size dinosaur statues—is sure to be a must-see.
If you’re a little older, though (and interested in some of the state’s history coming to life…or undeath), try staying the night at Captain Grant’s Inn in Preston. Visitors have reported sightings of a colonial woman and her child, as well as Revolutionary-era soldiers.
White houses settled along the water in Mystic River Country. The sky is completely gray.
Mystic River Country, Connecticut

4. Fairfield

Why you should go
In Fairfield County, you’ll have both city delights and country fun at your fingertips! With the shops and restaurants of Greenwich and New Canaan and picking your own fruit at Silverman’s Farm, you’ll be in for a wonderful time.
What to do
If you’re looking for upscale dining and shopping, head into one of the nearby cities, like Stamford or New Canaan.
There’s also plenty to do in the country. Pick your own fruit at Silverman’s Farm, ride horses at Mead Farm, and learn more about the natural wonders of Connecticut at Webb Mountain Discovery Zone.
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Trees wrapped in lights illuminate the night-time streets in downtown Stamford, Fairfield County
Stamford, Connecticut

5. Greater New Haven

Why you should go
If you’re looking for a more fast-paced vacation, Greater New Haven is the perfect destination. It’s home to the Connecticut Audubon Society Coastal Center and the Shore Line Trolley Museum, but Greater New Haven also has plenty of lively restaurants, theaters, and more!
What to do
Check out the art scene! Greater New Haven is home to the Yale Art Museum, the Yale Center for British Art, and the Art Capsule. There’s no better place to see art from around the world—old and new.
If you’re looking for something a little more lively, though, head over to Firehouse 12 for delicious food paired with live performances and a state-of-the-art recording studio!
For something out of the ordinary, check out the Shore Line Trolley Museum (with a working trolley!) and the Connecticut Audubon Society Coastal Center, where you can see all kinds of New England avian life.
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A manicured lawn and Gothic building of the prestigious Yale University in New Haven, Connecticut
Yale University, New Haven, Connecticut

Drive safely with Jerry

Now that you know all about the hidden gems of Connecticut, it’s time to get out on the road! But, before you do, you want to make sure you’re protected for any eventuality—after all, a water park isn’t much fun if you lose your car keys on the waterslide!
Luckily, with Jerry’s [roadside assistance program], you’ll be able to relax knowing that you’re covered for lockouts, towing, Uber credits, and more! (And the best part? It only costs $6.99 to insure one vehicle!) This way, you can hit up all the local attractions and haunts worry-free, and have the time of your life in one of the most vibrant little states in the U.S.
Jerry blew my mind, honestly. From start to finish, using the app took me 10 minutes and I ended up with $100 of savings a month. Best of all, customer service answered all my questions about rental car reimbursement and roadside assistance.” ––Savanna R.
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