Connecticut! One of the most beautiful states in the country. When it comes to adventures here, there are as many as you’ll find in some of the larger states across America. From rolling farmland to coastal hotspots, mountain regions to tiny towns, we’ve got it all. So if you’re looking for some kind of theme for exploring the Nutmeg State, then be sure to check out these awesome Connecticut road trip ideas. No matter what time of year you’re looking to visit, these are some of the best road trips you can possibly take.

Table of Contents

1-Day Road Trip In Connecticut

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  • Route: Silver Sands State Park > Nordic Fish > Greenwich Point Park
  • Distance: 35 miles
  • Trip Time: 1 hour
A long, leisurely weekend or week-long trip is great, but sometimes you just don't have the time. This one-day road trip in Connecticut offers a great deal of fun along a stunning sunrise-to-sunset itinerary. Get your cameras ready as you experience a sunrise and a sunset from two different Connecticut beaches, plus we’ve included a lovely spot to stop and grab a bite to eat. This road trip is easily doable year-round, and might just become a tradition for you and your family.

3-Day Weekend Road Trip In Connecticut

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  • Route: Ocean Beach Park > Harvey’s Beach > Hammonasset Beach State Park
  • Distance: 35 miles
  • Trip Time: 1 hour
Everyone loves taking extra time off, and if you love the beach, this 3-day weekend road trip is right up your alley. Short and sweet, this itinerary takes you to some of the Nutmeg State’s most spectacular beaches where you can swim, sun, or just sit and enjoy the water. Since the drive time between each destination is so short, you can rest assured you’ll be spending more time sitting in the sand than in your car.

Coastal Lighthouse Road Trip

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  • Route: Sheffield Island Lighthouse > New Haven Harbor Lighthouse > Avery Point Lighthouse > Stonington Lighthouse Museum
  • Distance: 110 miles
  • Trip Time: 3 hours
So many New England towns along the coast are known for historic lighthouses, and this road trip shines the spotlight on them. There's just something about a lighthouse, those beacons of bright that in many places have served as illuminated guideposts for seafaring vessels for decades. This coastal lighthouse road trip itinerary spans almost 120 miles and in about three hours’ time you will experience the best of the best of these stunning land structures.

Litchfield Hills Towns Road Trip

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  • Route: Woodbury > Washington > Litchfield > Kent > Salisbury
  • Distance: 65 miles
  • Trip Time: 1.5 hours
Peppered with beautiful rolling hills and charming hidden gems, the Litchfield Hills area is recognized as one of the most beautiful regions in Connecticut. This Litchfield Hills Towns Road Trip takes you to five charming small towns that will leave you clamoring for more.

Best Connecticut Road Trip For Spring

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  • Route: East Canaan > New Hartford > Kent > Warren > Shelton > Wallingford
  • Distance: 127 miles
  • Trip Time: 3.5 hours
With all of the flowers blooming and migratory birds fluttering about, spring is one of the best times of year to visit Connecticut. This short and sweet road trip may only clock in at 3.5 hours, but it’ll take you from the northwest corner of the state down to New Haven, exploring some of our favorite hidden gem vineyards along the way. In between visiting the local wineries in Connecticut stops off at Kent Falls State Park for a different type of cascade, the Kent Falls. Clocking in at 250 feet, it’s the tallest waterfall in Connecticut! As you take this wine and waterfall road trip through Connecticut, please remember to drink responsibly. Let’s be safe out there.

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Best Summer Road Trip In Connecticut

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  • Route: Stonington > East Lyme > Westbrook > Guilford > Branford > Fairfield > Greenwich
  • Distance: 122 miles
  • Trip Time: 3 hours
When the summer rolls around, thoughts often go straight to the beach---those sandy, wide open spaces, sun-packed spots that feed your mind, body, and soul. This summer road trip in Connecticut itinerary traverses through some beautiful coastal towns and cities with beaches that draw folks from all over the state. Feast on lobster rolls as you stop off for lunch, and don’t forget the sunscreen!

Best Connecticut Road Trip For Fall

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  • Route: Macedonia Brook State Park > Mohawk State Forest > Dennis Hill State Park > Peoples State Forest > Talcott Mountain State Park > Manchester > Shenipset State Forest > Pachaug State Forest > Sleeping Giant State Park > Mt Tom State Park
  • Distance: 280 miles
  • Trip Time: 7 hours
One of the most fun things to do every autumn for many people is to take in the beautiful fall foliage. And there's no denying that in Connecticut the colors are nothing short of magnificent. This makes a great excuse for a Connecticut road trip in the fall. Get ready to enjoy some of the best multi-hued views imaginable as you take a scenic ride through some of the best leaf-peeping spots in the state.

Best Winter Road Trip In Connecticut

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  • Route: Farmington > Plantsville > Southbury > Westport > Stamford
  • Distance: 94 miles
  • Trip Time: 2.5 hours
While winter may not scream, “Let’s take a road trip!” you’d be surprised at how stunning the state is when everything is cloaked in fresh snow. This winter road trip itinerary fully embraces the season and is chock full of traditional (e.g. ice skating and skiing) and unique and perhaps little well-known (e.g. maple sugaring or bald eagle watching) activities that are sure to delight and inspire.

Family-Friendly Connecticut Road Trip

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  • Route: Stepping Stones Museum for Children > Uncle Buck's Fish Bowl and Grill > Connecticut's Beardsley Zoo > The Dinosaur Place > Bushnell Park > White Memorial Conservation Center .
  • Distance: 153 miles
  • Trip Time: 3 hours
Chock full of interesting museums, beautiful parks, exciting attractions, interactive animal adventures, and more, this family-friendly Connecticut road trip offers so much for kids and adults alike. From Norwalk to Litchfield, this is one family-friendly road trip that the entire family can enjoy.

Road Trip to Connecticut Landmarks & Natural Wonders

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  • Route: Sleeping Giant State Park > Bluff Point State Park > CT-169 > West Cornwall > Kent Falls State Park > Sleeping Giant State Park
  • Distance: 248 miles
  • Trip Time: 5.5 hours
Any road trip through Connecticut simply must include some of the state’s stunning landmarks and natural wonders. If you are an outdoor lover, get ready...this trip will blow your mind as it meanders through some of the most scenic places in the state! From waterfalls to dense forests, this road trip shows off Connecticut’s natural beauty like no other.

Road Trip to Best Small Towns in Connecticut

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  • Route: Chester > East Lyme > Putnam > Tolland > Canton > Litchfield > Redding > Madison
  • Distance: 266 miles
  • Trip Time: 5.5 hours
If you ever want to really experience what it’s like to live in any particular state, then you have to check out the state’s small towns. Small towns are the heartbeat of each state, and Connecticut’s small towns are simply amazing. You’ll discover and enjoy several charming towns on this adventure which traverses several of the state’s most picturesque counties. Each one of these towns would make for a memorable getaway, too.

So what did you think about these awesome Connecticut road trip ideas? Did they make you want to create your own Connecticut road trip map? Have you been to any of these places listed? We’d love to read all about your experiences in the comments section below.

For road trip planning and packing tips, check out OnlyInYourState’s Ultimate Road Trip Packing List. Whether you’re leaving for a single day or a week-long road trip, you can’t forget the snacks: here are 50 on-the-go snack ideas perfect for traveling.

If you haven’t gotten enough of a Connecticut fix yet, check out these top ten places to visit in the state:

 

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More to Explore

Adventures in Connecticut

Lysa Allman-Baldwin | March 30, 2023

What are the most popular landmarks to visit in Connecticut?

  • The Mark Twain House in Hartford is where this famous write lived for nearly 20 years.
  • The Charles W. Morgan in Mystic is the only surviving wooden whaling ship from the 19th-century American merchant fleet and the world's oldest surviving merchant vessel.
  • Fort Griswold in Groton played an important role during the contentious American Revolutionary War.

Read on to learn more about some of the most popular landmarks to visit in Connecticut.

What are the most popular state parks to visit in Connecticut?

  • Hammonasset Beach State Park in Madison is popular for its beautiful beach and miles of trails.
  • Harkness Memorial State Park in Waterford draws folks for its views of the Long Island Sound and 8th century English gardens.
  • Silver Sands State Park in Milford is popular for its beach views and walking and biking trails.

Read on to learn more about some of the most popular state parks to visit in Connecticut.

What are the major highways in Connecticut?

  • Route 169 has been officially named a National Scenic Byway and several sections along the way are officially designated as historic districts.
  • S. Route 1 runs parallel to Interstate 95 and is one of the most popular scenic drives in Connecticut.
  • Route 7, which is also referred to as the Ethan Allen Highway, travels through many of Connecticut’s major cities including Canaan, Norwalk, and others.

Read on to learn more about some of the major highways in Connecticut.

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