This Connecticut shoreline drive will take you through some of the most beautiful and iconic New England towns, along a beautiful waterfront Leaving New Haven, travel south via Route 337 to Lighthouse Point Park. Take jog along Route 142 into Branford and then out from the center of town along Route 146 toward the peninsula and views of the Thimble Islands. Plan a ferry trip around the islands during the ferry tour season.
Continue on route 146 into the picturesque Guildford Town Green. Take route 146 back to Route 1 for a drive through the pretty town of Madison. Leaving Madison Center, Route 1 will take you to Route 450 to Hammonasset Beach State Park and the adjacent Hammonasset Nature Area Preserve.
Return to Route 1, heading eastward for more beautiful views of shoreline and marsh meadows. Go through Westbrook Center and enter Old Saybrook, home of The Katharine Hepburn Cultural Arts Center and Saybrook Point Resort & Marina.
Eastward bound, cross the Connecticut River and enter Old Lyme. Plan a visit to the Florence Griswold Museum, home of American Impressionism and many gorgeous gardens in season. Moving eastward from Old Lyme, the shore road is Route 156, which will take you through Rocky Neck State Park and into picturesque Niantic.
Leaving Niantic, Route 156 joins Route 1, which joins I-95 to cross the Thames River, which passes between New London and Groton. Ahead you will reach Mystic, home Mystic Seaport, Mystic Aquarium, and Olde Mistick Village, a quaint shopping village immediately off the highway.
From Mystic, take Route 1 for a beautiful shore drive into Stonington and Stonington Borough, also a place to find good dining and shopping, including many, many small antique shops.

Barns are the largest tool on the farm. Many are still in use; some are artifacts of a more-rural times in America. Most are catnips to photographers and painters and people simply interested in different ways of living. From 2006 to 2010 The Barns Project catalogued, described, and mapped Connecticut’s barns and distinctive, open-sided tobacco sheds (a crop that arrived in the region in the mid-1800s). The Barn Trail has seven routes throughout the state with sites that are open to the public, including working farms with farm stands, orchards, and wineries. Download the brochure and plan a scenic drive into rural America. More history of Connecticut barns. 203-562-6312. [photo courtesy Historic Barns of Connecticut survey by Preservation Connecticut]

Connecticut State Route 169 is a peaceful road through quiet villages, scenic woodlands, and quaint farmsteads amid rivers and rolling hills of the Quinebaug and Shetucket Rivers Valley National Heritage Corridor. Travelers pass photo-worthy small towns and Colonial structures and farms. Beautiful foliage greets you around every bend in September and October. Stop for a visit at Mashamoquet Brook State Park in the town of Pomfret. Byway map

This tour begins in Goshen (Rtes. 63 and 4), noted for its rolling hills and farming heritage. In Goshen center, notice the 1833 Congregational Church and the Victorian Old Town Hall.
To visit Miranda Vineyard, take Route 4 west from the center of town. To visit Sunset Meadow Vineyards, overlooking the Western Connecticut Highlands, take Route 63 south.
Use Route 4 west to pass Tyler Lake and head into the storybook village of West Cornwall. The town has a covered bridge and guided fly fishing trips nearby on the Housatonic River.
Continue on Route 7 north on a scenic road through Housatonic State Forest. At routes 7 and 126, take Route 7 north toward Falls Village. Main Street buildings include Greek Revival, Italianate, Second Empire and Queen Anne architecture.
At routes 44 and 7, take Route 44 west to Canaan and then on to Salisbury. Excellent fishing and a boat launch are at Twin Lakes. From Lakeville, take Route 41 south, one of the prettiest roads in the state, to Sharon.
Get onto Route 4 east and pass Mohawk Mountain ski area and Mohawk State Forest. Continue on Route 4 east to Goshen.