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5 Unforgettable Connecticut Scenic Drives To Experience

Compared to other states in New England, Connecticut is relatively small. However, what it lacks in size, it more than makes up for in breathtaking views, unique experiences, and some of the best New England scenic drives year-round.

You can experience some of the most beautiful scenic drives in Connecticut in the span of a few hours, though there are often many enticing places to stop along the way.

Whether you’re interested in ziplining, sampling fresh produce, golfing, fishing, or more, you’ll find all of these (and more) on the best scenic drives in Connecticut.

Connecticut Scenic Drives You Need to Try

Connecticut Scenic Drives: South Litchfield Hills (CT-272 N, US-44 W, and US-7 S)

  • Distance: 52.8 miles
  • Time needed: 1 hour 15 minutes direct to 1 full day

Litchfield Hills is one of the best scenic drives in Connecticut, and there is plenty to see and do along the way. You can choose to take many routes, but we like the drive from Litchfield to Kent the best.  You’ll take CT-272 N from Litchfield to Norfolk before reaching North Canaan. From there, take US-7 S until you conclude your drive in Kent.

USA Connecticut Scenic Drives - Lichfield Hills

There are plenty of stunning roadside views along these back roads in Connecticut, especially during the fall. Visit the Action Wildlife Foundation near Goshen, where you can experience a drive-thru safari to get up close and personal with over 350 exotic animals. Children will love the petting zoo, and the foundation also gives hayrides in the fall.

Next, browse the unique specialty shops in downtown Torrington or take in the breathtaking scenery at Stillwater Pond State Park. Then travel to Norfolk and climb Haystack Mountain to get to the tower, where you get an unforgettable view of Vermont’s Berkshires and the Green Mountains.

Pro Tip: If you’re not an experienced hiker, it will likely take you 30-45 minutes to walk the half-mile trail to the top of Haystack Mountain.

And lastly, be sure to stop at Bull’s Bridge on your way to Kent. This historic bridge crosses the Housatonic River and is a great place to pause for a photo opportunity.

USA Connecticut Scenic Drives - Bulls Bridge

When to Go: Enjoy this scenic Connecticut drive year-round, although some attractions may not be open during the winter months.

Connecticut Scenic Drives: Merritt Parkway (CT-15 S)

  • Distance: 41 miles
  • Time needed: 40 minutes direct to 1 full day

If you’re planning a Connecticut road trip to New York, enjoy the pastoral route by taking Merritt Parkway. Not only is this one of the most beautiful roads in the state, but it’s also one of the few roads to be listed on the National Register of Historic Places. Best of all, you don’t have to worry about semi-trucks, and it’s a less hectic alternative to I-95.

One of the most fascinating aspects of the Merritt Parkway is the 69 Art Moderne and Art Deco-style bridges motorists can enjoy along the way from Milford to Greenwich, CT. Perhaps this is why one historian described Merrit Parkway as “one of the most beautiful and best-engineered highways of the time.” No two bridges along the route are alike, and only three have been replaced in over 50 years.

USA Connecticut Scenic Drives - Merritt Parkway

Merrit Parkway provides easy access to several interesting stops along the way, such as Boothe Memorial Park and Museum near the northern end of the route in Stratford. This sprawling 32-acre property has lush rose and wedding gardens, a miniature lighthouse, a clock tower museum, and much more. 

You can also take exit 37 off Merrit Parkway to visit New Canaan Nature Center, where you can hike the trails, drink fresh apple cider, and explore the Discovery Center.

When to Go: Although you can take Merrit Parkway year-round, it is lovely during the warmer months when you can see the bridges more clearly.

Connecticut Scenic Drives: Connecticut River Loop (CT-9 S, CT-156 W, and CT-154 S)

  • Distance: 32 miles
  • Time needed: 50 minutes direct to 1 full day

This historic scenic drive takes you through some of the most beautiful places in Connecticut and around a portion of the Connecticut River. Begin your journey in the iconic New England town of Essex and travel to Lyme via CT-9 S and CT-156 W before concluding your drive back in Essex.

Both Essex and Lyme have many boutiques and antique shops filled with treasures waiting to be discovered, and there are also many stately historic buildings to see along the way. Take in both art and architecture at the Florence Griswold Museum in Old Lyme and enjoy a sweet treat at the Old Lyme Ice Cream Shoppe and Cafe.

The Connecticut River Loop also winds its way through several state parks, including Ferry Landing State Park. This tiny seaside area is perfect for a photo opportunity or two, and there is also a walking trail along the shoreline.

USA Connecticut Scenic Drives - Gillette Castle

Another popular stop along the Loop is Gillette Castle State Park. This 124-acre estate features a medieval-style castle designed by the late actor William Hooker Gillette. If you take a tour of the castle’s interior, you’ll be surprised!

Pro Tip: If you have children, stop by Ray of Light Farm in East Haddam. They can feed the goats and lambs without needing to make a reservation!

When to Go: You can travel the Connecticut River Loop year-round.

Connecticut Scenic Drives: Connecticut State Route 169 (State Highway 169)

  • Distance: 32 miles
  • Time needed: 1 hour direct to 1 full day

Explore the back roads in Connecticut with a drive along State Route 169. This one-hour drive is filled with lush green trees, peaceful winding roads, and many photo opportunities of rolling hills, quaint towns, and historic sites along the way.

Begin your drive on this two-lane country road at the Massachusetts border and conclude at Lisbon.

Make your first stop in Woodstock to visit Roseland Cottage, an eye-catching historic home that now operates as a museum. This Gothic Revival summer home is a sight to behold, and it even has an indoor bowling alley and a spectacular garden on the grounds. Before leaving Woodstock, be sure to savor a piece of gourmet pizza at Sweet Evalina’s Stand, voted Best Hidden Gem by Connecticut Magazine.

USA Connecticut Scenic Drives - Roseland Cottage

If antiquing is more your thing, stop at Scranton’s Shops in South Woodstock to find your next hidden treasure. Continue on to Lapsley Orchards in Pomfret, where you can enjoy fresh seasonal produce and fun activities through the fall.

Finally, stop to hike in Mashamoquet Brook State Park, an area rich in both history and beauty. Catch a glimpse of the fabled Wolf Den and marvel at Table Rock and Indian Chair, a few of the park’s natural rock formations.

When to Go: You can make this scenic drive in CT at any time of year, but the fall foliage is particularly breathtaking in autumn.

Connecticut Scenic Drives: Connecticut Coast Scenic Drive (I-95 S)

  • Distance: 108 miles
  • Time needed: 1 hour 55 minutes direct to 2 days

Your time in Connecticut wouldn’t be complete without taking the Connecticut Coast Scenic Drive from Stonington to Greenwich. You’ll wind your way down the coast, stopping at quaint seaside villages along the way and breathing in the brisk sea air. You’ll drive through all types of terrain, and there are many picture-perfect views you won’t want to miss.

Take some time to explore Stonington before embarking on your journey down coastal Connecticut. There are many exciting shops and restaurants, but the Stonington Lighthouse Museum is a true treasure. Climb the lighthouse tower and take in a breathtaking view of Long Island Sound, Rhode Island, and New York.

Pro Tip: If you’d like to visit the lighthouse, make sure you do so before October 15th

USA Boston Day Trips - Mystic Connecticut

Spend a few hours (or the day) in Mystic, where you can visit the Mystic Aquarium, explore the Mystic Seaport Museum, snap pictures of the Mystic Drawbridge, and enjoy some outdoor fun at TreeTrails Adventures. Finally, sit down to a delicious meal at any one of Mystic’s fine restaurants.

There are many sandy beaches and seaside escapes along this Connecticut road trip, so don’t be afraid to stop and bury your toes in the sand. The Maritime Aquarium at Norwalk is also a fascinating attraction, and there are several special exhibits open to the public over the summer months.

Norwalk is also home to the Stepping Stones Museum for Children, which is full of interactive exhibits for kids of all ages.

When to Go: Although the Connecticut Coast is beautiful in winter, we recommend driving between spring and fall to take full advantage of the many seasonal attractions.

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