Litchfield Hills is Connecticut’s best-kept secret — rolling farmland, covered bridges, vineyards, and fall foliage that rivals Vermont without the crowds. Kent Falls is worth the drive alone, and the small towns feel like time capsules of old New England.
Litchfield Hills
Plan a Trip to Litchfield Hills →Scroll
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Region
connecticut
Best Time
May, Jun, Sep +1 more
Daily Budget
$50–$350 USD
Getting There
Drive from Hartford (45 min) or NYC (2 hours). Best explored by car — no public transit.
Before You Go: Travel Insurance
Unexpected injuries on mountain trails or winter roads can lead to costly medical bills. We recommend SafetyWing for every trip — it's affordable, covers medical and evacuation, and you can sign up even after you've left home.
"We've thankfully never had to file a claim, but having it is peace of mind every time we board that plane." — Scott
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