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Scenic Road Trips and Tours in Connecticut

Explore the Back Roads and Main Streets of New England

There’s nothing like a road trip through the scenic backroads and charming seaside villages of New England. Connecticut features some of the best scenic routes in the country, winding through picture-perfect fall foliage in between quintessential New England communities with town greens and church steeples peeking through the trees. Along the way, you’ll drive by classic farmhouses, covered bridges, and historic sites that date back to Colonial and Revolutionary times. Stop in at quaint antique shops to pick up something to bring home, then find a neighborhood restaurant to taste classic New England cuisine including fresh seafood, farm-fresh apples, and New-Haven style pizza.

A drive through the famous fall foliage should be near the top of the list for anyone visiting Connecticut. The roads are bursting with colorful leaves that you can take in from the passenger seat and from behind the wheel. You’ll encounter a breathtaking mix of yellows, reds, purples, and oranges that you can only find in New England during the crisp autumn season.

Discover New England’s Maritime Trail which makes its start in Connecticut. Drive along the stunning shores of Connecticut for views of beautiful beaches and thriving coastal wetlands. Keep an eye out for seabirds and wildlife frolicking along the shore. Tracing a course north along the Long Island Sound, the Connecticut seashore is dotted with quaint seaside towns like Old Saybrook, Mystic, and Groton. From Bethel and Danbury, you can head south to the start your tour of coastal Connecticut in Norwalk and work your way up to Mystic Seaport where you and your family can experience the fascinating history of maritime New England.

In Fairfield County, you can drive to New York for a taste of the city life or head into the Northwest Connecticut to see an idyllic side of the state. Explore Litchfield Hills to discover rural scenery and pristine parks that border the famous Berkshires. Soak in views of rolling hills and serene landscapes that offer a glimpse back to a simpler time in New England. Merrit Parkway is a National Scenic Byway that starts at the border of New York and moves up through Greenwich along the Gold Coast towards West Haven. This drive takes you across Art Deco bridges and through some of the most beautiful towns in Connecticut. In the Northeast Corner not far from Mansfield, head onto State Route 169 to see this National Heritage Corridor that takes you along picturesque rivers and lush woodlands.

Drive through the Connecticut River Valley to visit the state capital of Hartford where you can tour the Old State House and visit iconic art museums. Then head to the higher education hub of New Haven, home to the world-famous Yale University. Drive along the historic campus and experience the youthful energy of this Ivy League city.

Connecticut is a wonderful place to take a road trip through New England. Get behind the wheel to discover this incredible state from the parks to the seashore. You never know what you’ll find around the bend!

Drive New Haven to Mystic, CT

Start in New Haven, CT

See: Hard to believe that bustling New Haven, with its innovative arts vibe, Yale University liveliness, and red-hot culinary scene was founded by Puritans in 1638. A shady green heart beats at the center of it all: historic New Haven Green is a 16-acre oasis that’s been there since the city’s start, not far from the Old Campus’s dizzying turrets and towers.

The green is edged by Chapel Street, a main thoroughfare where everything happens, including free entry to the outstanding Yale University Art Gallery – from early African art to late Picasso and beyond. Across the street, the Yale Center for British Art has the largest collection outside Great Britain – the building alone is a masterwork. Yale Repertory Theatre is a short walk (Meryl Streep’s early stomping grounds), with area shops in abundance.

Weigh in on New Haven’s notorious pizza wars: Frank Pepe’s Pizzeria, Sally’s Apizza, or Modern Apizza? If you can’t decide, Miya’s Sushi elevates culinary innovation, with whimsical items like an invasive species menu.

Drive: New Haven to Old Saybrook, CT Along Long Island Sound

Pick up US-1 N (34 miles; 1 hr)

Like gleaming pearls strung near water, these five pretty Connecticut towns edge Long Island Sound along Route 1. Heading west to east, Branford boasts a banquet of restaurants, including Le Petit Café, with an award-winning four-course French bistro menu. Japanese, Indian, Italian, and American options dot the downtown, too. Further east, Guilford’s famous town green is surrounded by shops, with painter Brendan Loughlin’s sunflowers splashed on random doorways, lending a dash of Van Gogh color.

In Madison, there’s stellar beach reading to be had at R.J. Julia Booksellers – a three-minute drive from two miles of sandy heaven at Hammonasset Beach State Park. Bucolic Clinton offers full spectrum shopping: a trove of treasures at the Antique Center on Main Street or 70 outlet stores minutes away at Clinton Crossing Premium Outlets.

Finally, breathe the sea breezes in Old Saybrook, where you can shop the downtown that Kate Hepburn made famous, and cycle along the water out to sun-dappled Fenwick – an idyllic area where the screen legend lived for happy decades.

Drive: Old Saybrook to Mystic, CT

US-1 N (29 miles; 50 min)

It’s one thing to read about cramped ships quarters – it’s another to climb below deck and feel it in an 1841 whaling ship like the Charles W. Morgan, the oldest commercial vessel still in the water. The refurbished ship returns to Old Mystic Seaport – a glorious “living history museum” – in August 2014, after her 38th voyage (this time as a teaching vessel), but meanwhile the 19th-century seafaring village offers up plenty of diversions, with 60 antique buildings and a working shipyard. Complete the high-seas picture with a visit to the beluga whales at the terrific Mystic Aquarium.

For a slice of movie history, check out Mystic Pizza, in Mystic proper. This cozy joint celebrates the film that was Julia Roberts’s big break, and the movie plays on an endless loop in the background, flavoring every bite.