Best Winding Country Road to Plan a Road Trip Around

Route 44
A Country Drive into New England from Kerhonkson, NY to Hartford, CT

For a picture-perfect country drive, plan a road trip down Route 44 starting just outside of Kerhonkson, NY and driving through rural New York and Connecticut, ending in Hartford. If you’ve got time, continue on to Providence, Rhode Island, and through Massachusetts, ending in Plymouth. The entire route is 237 miles long.

Plan a Road Trip

This winding road is a favorite of road trippers for the beautiful Mid-Atlantic/New England scenery (really eye-popping in early to mid October when the leaves turn) and many charming towns that dot the route. You’ll pass through apple orchards and farms, cresting hills and diving deep into leafy valleys, before being confronted with sweeping views of the countryside.

Plan a Road Trip into New England – Stop #1
Lake Minnewaska, NY
Your start in the famous Hudson Valley is a great send-off due to the natural beauty of the Mid-Atlantic region (so gorgeous that the area inspired an entire school of painting). Start just outside of Kerhonkson, NY on 44 and drive to Lake Minnewaska, which is right off of Rt. 44. The beautiful forest, dramatic cliffs, and the crystal-clear lake are all worth seeing and were originally part of the famed Mohonk Mountain House property. I went on my favorite hike of all time here - between the beautiful scenery, encounter with a bear, a swim in crystal clear water, a picnic on a beach, and stuffing myself silly with wild blueberries, I still can't pick which part was my favorite!

Plan a Road Trip into New England – Stop #2
Poughkeepsie, NY
Next, stop in Poughkeepsie, NY – a great town situated directly on the banks of the Hudson River. With the famous Culinary Institute of America next door, make sure to try one of the restaurants here – there’s lots of great ones to choose from. There’s also wonderful tax-free (!) shopping, local museums, art galleries, and it doesn’t hurt that it’s a fun town to explore (especially the Main Mall Row on Main Street).

Plan a Road Trip into New England – Stop #3
Lakeville and Salisbury, CT
Also be sure to stop in either Lakeville or Salisbury, CT; both are small quaint New England towns located next door to each other. My cousin and her husband have a house there and it’s easy to see why they chose to live in the area – it’s extremely picturesque.

Plan a Road Trip into New England – Stop #4
Hartford, CT
If you plan a road trip for just the weekend on this route, your last stop will be Hartford. Be sure to see Mark Twain’s house in Hartford – it’s a definite must-do with the museum’s wonderful tours that highlight Mr. Twain’s great sense of humor and the fascinating story of the author’s life.

Continuing on to Rhode Island? You’ll have to ride through more urban areas but you’ll also be passing some great state parks, lakes, and towns before getting to Providence. Rt. 44 goes right through the heart of Providence, and if you plan a trip that includes this city, be sure to visit historic Federal Hill – one of the highlights of this town.

After that you’ll be in Massachusetts and at a certain point you’ll have to make a choice of whether you want to continue on 44 to Plymouth (44 turns into a highway and all the prettiness goes bye-bye) or head out to the Cape. When I plan a road trip in this area, I always choose the Cape as it’s so beautiful and there are so many great seaside towns and lots of fantastic seafood (especially clams).

This is a quintessential Mid-Atlantic/New England road trip route year-round, but particularly as a leaf-peeping trip in the fall to view this rolling eastern countryside at its best. Charm central!

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