The 5 Best Road Trip Destinations in Connecticut

These Connecticut road trips will take you through dreamy Mystic Country, around classy Fairfield, over the wild fun of Litchfield Hills, and more!
Written by Ben Guess
Reviewed by Carrie Adkins
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 to River Valley

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 in River Valley

Mark Twain House and Museum
  • Brownstone Adventure Sports Park
    : 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.
  • Mark Twain House and Museum
    : 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.
  • Connecticut River Museum
    : Not feeling literary? Head to the Connecticut River Museum to learn more about the historic importance of Connecticut’s waterways.

2. Litchfield Hills

Why you should go to Litchfield Hills

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 in Litchfield Hills

Litchfield Hills, Connecticut
  • Brookfield Craft Center
    : Check out Brookfield Craft Center, which shows off beautiful works of art and is home to fully functioning art studios!
  • Quassy Amusement Park
    : 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.

3. Mystic Country

Why you should go to Mystic Country

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 in Mystic Country

Mystic River Country, Connecticut
  • Take a hike
    : Get out into nature on the beautiful hiking paths!
  • The Dinosaur Place
    : 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.
  • Visit a haunted inn
    : 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.

4. Fairfield

Why you should go to Fairfield

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 in Fairfield

Stamford, Connecticut

5. Greater New Haven

Why you should go to New Haven

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 in Greater New Haven

Yale University, New Haven, Connecticut
  • 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.
  • Firehouse 12
    : 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!
  • Check out transportation museums: 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.

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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