Take This Road Trip Through Connecticut’s Most Charming Small Towns For An Amazing Experience
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Taylor Ellis
Author
The small towns of Connecticut are by far some of the most beautiful and charming small towns in the country. Especially if you know which ones to visit. This cross county road trip will take you through some of the best towns Connecticut has to offer, and guide you to the great eats and attractions they include!
Please note, Haight-Brown Vineyard is temporarily closed.
So get ready to catch a peek of every corner on this perfect weekend drive. To take advantage of all the towns have to offer, plan to make this a two day trip. But if you're just looking for sights, this is easily a one day drive.
The quaint town has a beautiful downtown area.
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It's also home to the Chester ferry, one of the last remaining ferries in Connecticut. Visit Cedar Lake for boating and swimming opportunities the whole family will enjoy.
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And if you get hungry, stop by the River Tavern for some truly unique dishes.
Host to the beloved village of Niantic, you won't want to miss this town!
You can do some great antiquing here, not to mention the incredible hiking at Oswegatchie Hills Nature Preserve. Visit Rocky Neck State Park as well if you're an outdoor explorer!
But don't forget to grab a meal at The Shack, a local diner with big flavors.
Where else can you see the scenery of rolling hills like this in Connecticut?
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Plan ahead and snag some tickets to a show at The Bradley Playhouse or enjoy a day of shopping through their collection of antiques, boutiques and family owned businesses.
The dining here is simply superb, so you'll have a hard time choosing, but 85 Main and Victoria Station Cafe are among the best!
If you're looking for a town with a slower pace, you will love it here! The Hicks-Stearns Family Museum is a colonial masterpiece filled with history.
Arts of Tolland/Facebook
Visit Arts of Tolland for a look at a quaint and community-inspired art museum.
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Grab a slice at Camille's Wood Fired Pizza for a meal to remember.
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The small farm town vibes and friendly faces will have you ready to move in.
You'll have a lot of laughs over at Matterhorn Mini Golf! And some sweet ice cream.
Dine at Flatbread Company for fresh and organic ingredients in a family-friendly environment!
Welcome to the antiquing capital of America!
Take a walk through the White Memorial Conservation Center for four thousand acres of pure nature immersion. Or visit Haight-Brown Vineyard for some cheese and wine.
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For a more full meal, stop by West Street Grill for a truly refreshing salad and some delicious entrees.
If this is towards the end of your trip, Collis P. Huntington State Park is a dreamland for sunset watching.
Warrup's Farm will let you pick your own produce, and it tastes way better than store bought!
The Spinning Wheel looks traditional on the outside, but the flavors are out of this world!
This is one of the best coastal towns in the state!
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Home of Hammonasset Beach State Park and RJ Julia Booksellers, this town could easily be the spotlight of the trip!
Enjoy a nice beach day here as you meander down Main Street before sitting down at Cafe Allegre for a high class mediterranean experience.
Love these small towns? Pay a visit to Mystic to see the best maritime village in the states!
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