Backyard Road Trips

Exploring the Litchfield Hills of Connecticut: Scenic Drives & Local Flavors

The Litchfield Hills of Connecticut are seriously a hidden gem- with gorgeous natural beauty and an incredible food scene. It’s the perfect place to escape the hustle and bustle of everyday life and soak up picturesque views and local flavors. Let’s start exploring the Litchfield Hills!

Scenic Drives

Get ready to hit the road and enjoy some winding routes that give you breathtaking views of rolling hills, thick forests, and peaceful lakes.

  • Route 7:
  • Follow this route along the Housatonic River. You’ll go through the cutest little towns and spot a covered bridge or two. The best part? The stretch from New Milford up to the Massachusetts line!
  • Route 44:
  • Climb over those hills and valleys, take in the panoramic views, and definitely pull over at the scenic overlooks.
  • Litchfield Loop:
  • Even though it was planned for motorcycle riders, this is the perfect first taste of the region for any type of wheels—cars, bikes, whatever! It’s kind of a circular route that takes you right through the heart of everything, showing off the natural beauty and historic charm. You’ll pass through tiny towns like Norfolk and Washington, but also bigger ones like Litchfield and Torrington.
Rand’s View in Salisbury is not far off Route 44.

Local Flavors

Time to eat! You can seriously treat yourself to the region’s amazing food, from places that are strictly farm-to-table to charming little cafes and markets.

The Smithy Market in New Preston.
  • Farms and Farmstands:
  • Track down fresh produce, fantastic artisanal cheeses, and homemade jams right at the roadside stands. Averill Farm is the spot for apple picking when it’s in season—plus, their apple cider donuts and other goodies are a must-have.
  • Restaurants
  • You’ll be savoring dishes made with super fresh, locally sourced ingredients that celebrate the area’s farming history. Make sure you try amazing restaurants like Community Table in New Preston. Or try a quick bite at the Smithy Market in New Preston or Marty’s Cafe in Washington.
  • Breweries and Wineries
  • Grab a sample of the craft beers and wines being made right here in the Litchfield Hills—they all have such unique flavor profiles. Do not miss Hopkins Vineyard in Warren and Kent Falls Brewing Company in Kent.
Kent Falls Brewing Company

Places You Have to See

Check out the most charming towns and natural wonders that make the Litchfield Hills so special.

Kent Falls in late autumn
  • Kent Falls State Park:
  • Hike up to the top of the falls for absolutely stunning views of the cascading water, or just take in the sight from the bottom.
  • White Memorial Conservation Center:
  • Explore miles and miles of trails and get a look at the region’s diverse wildlife and ecology. Visit the small museum on the property.
  • Litchfield Town Center:
  • Go browse the antique shops and art galleries, and grab a bite at the delicious eateries in this historic town center.

Enjoy the quiet and the undeniable charm while exploring the Litchfield Hills! It’s a perfect mix of great drives and delicious food.

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