some lesser-visited but culturally and historically rich towns that still capture Connecticut’s charm:

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1. Litchfield (Northwest CT)

• A classic New England town green with 18th–19th century houses.

• Important Revolutionary War history (site of a colonial military academy).

• Tapping Reeve House & Law School – the first law school in America.

• Surrounded by rolling hills, great for combining history + scenic drives.

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2. Cornwall & Cornwall Bridge

• Famous for the West Cornwall Covered Bridge (1841) – one of New England’s most photographed bridges.

• Quiet, rural, but rich in early colonial and industrial mill history.

• Artists’ haven with a very “untouched” New England vibe.

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3. Old Saybrook

• One of the oldest towns in CT (1635), founded at the mouth of the Connecticut River.

• Katharine Hepburn Cultural Arts Center celebrates the town’s most famous resident.

• Lovely shoreline, historic inns, and a slower pace compared to Mystic.

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4. Stonington Borough (next to Mystic but often overlooked)

• Tiny, picturesque seaside village with colonial homes right on the water.

• Rich maritime and whaling history.

• Old Lighthouse Museum offers sweeping coastal views.

• Great alternative if you’ve already “done” Mystic.

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5. Lebanon

• During the Revolution, it was called the “Heartbeat of the Revolution in CT.”

• Lebanon Green is one of the longest town greens in New England.

• Key leaders of the Revolution (like Governor Jonathan Trumbull) planned the war effort here.

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6. Windsor

• CT’s oldest English settlement (1633).

• The Windsor Historical Society preserves colonial homes and stories.

• Strong ties to Native American and Puritan history.

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7. Ridgefield

• Charming town with Revolutionary War history — site of the Battle of Ridgefield (1777).

• Scenic Main Street lined with historic homes, churches, and shops.

• Ridgefield Playhouse and Aldrich Contemporary Art Museum add a cultural touch.

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8. Kent

• Small, artsy town with rich industrial past (iron furnaces, mills).

• Home to Kent Falls State Park (historic covered bridge, old mills).

• Lots of art galleries and antique shops.

 Option 1: Northwest Hills Cultural & Historic Loop (2–3 days)

Day 1 – Litchfield

• Walk the historic town green.

• Visit the Tapping Reeve House & Law School (America’s first law school).

• Stay overnight at the Litchfield Inn or a local B&B.

Day 2 – Cornwall & Kent

• Drive through scenic backroads to Cornwall and walk the West Cornwall Covered Bridge.

• Continue to Kent:

  • Visit Kent Falls State Park (waterfalls + historic mills).

  • Explore art galleries and antique shops.

• Stay in Kent or return to Litchfield for the night.

Day 3 – Ridgefield

• Head south to Ridgefield, site of the Battle of Ridgefield (1777).

• Stroll the historic Main Street, visit the Keeler Tavern Museum (once fired upon by the British).

• Option: visit the Aldrich Contemporary Art Museum for a cultural twist before heading back.

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