Connecticut offers an abundance of possibilities for freewheeling families. Wedged between New York’s Hudson Valley and the Quinebaug River, the state’s rolling orchards, forested mountains and brilliant foliage represent some of the East Coast’s loveliest scenery — barely an hour’s drive from New York and Boston. So, whether you’re looking for a series of long weekend breaks or some quality family time, mix and match the areas below or string it together for a fabulous 10-day tour.

The Quiet Corner

Start at the beginning, in Northeast Connecticut’s Quiet Corner, where Washington plotted revolution on Lebanon’s green, Prudence Crandall challenged racial hatred in Canterbury and patriot-spy Nathan Hale was nurtured. Hale was in the Continental army in 1776 when his father built the red Georgian homestead on the edge of the Nathan Hale State Forest. Colonial cooking demonstrations and lantern tours bring the era vividly to life.

Moving along National Scenic Byway 169, it’s hard to believe revolutionary hearts were set ablaze in this peaceful green valley lined with orchards and dairy farms. Stop off in Pomfret for ice-cream at We-Like-It or small-town friendliness at Vanilla Bean Cafe, then take the kids on a Quiet Corner safari to pet the local bison at Creamery Brook Bison Farm and get lost in the corn maze at Buttonwood Farm.

Around Mystic

Middle Wharf carry away sloop Regina M at Mystic Seaport. Image by Stephen Saks/Getty Images.

Wend your way south from Griswold to the sunny slopes of North Stonington and stop in at Jonathan Edwards Winery. Housed in a picture-perfect dairy barn on a hilltop overlooking the Atlantic, it’s a perfect spot for an afternoon picnic.

From here, the sea beckons in Mystic, where you can sign up for sailing summer camp or explore the 17-acre Mystic Seaport Museum. You can spend a whole day here ducking in and out of 60 historic buildings, four tall ships and over 500 smaller vessels. Interpreters bring Mystic’s maritime history to life explaining crafts like oystering, ship rescue and whaleboating.

Then, head down the coast to Groton’s US Naval Submarine Base, where big kids and small can board Nautilus, the world’s first nuclear-powered submarine. Feed budding submariners just across the water in New London at Captain Scott’s Lobster Dock.

From Groton to New Haven, Connecticut’s coastline is lined with vineyards, beaches and historic towns. Handsome Essex was established at the mouth of the Connecticut River (just four miles inland) in 1635 and preserves its Federal-era homes. Next to the Steamboat Dock is the Connecticut River Museum, where eagle-spotting cruises launch between December and March.

Historic locomotive steam train. Image by Stephen Saks/Getty Images.

The best way to experience the river is to take the Essex Steam Train to Deep River and then the riverboat up to East Haddam. East Haddam’s most famous resident, Sherlock Holmes actor William Gillette, built a turreted castle on the Seven Sisters Hills in 1919. Modelled on the medieval castles of Germany’s Rhineland, it certainly has that movie magic. Pick up deli treats at Simon’s Marketplace in Chester, and make a day of it with a picnic in the 125-acre state park adjoining the castle.

Back on the coast road again, head through genteel Madison to the marshy doorstep of Hammonasset Beach State Park, a 1100-acre oasis, with a two-mile pine-backed beach.

New Haven

Yale-Harkness Memorial Tower, New Haven. Image by Lou Jones/Getty Images.

White-steepled churches and neo-Gothic turrets characterize America’s third oldest university, Yale. Tour the campus with a student guide for fascinating tidbits on university life, although the guides refrain from mentioning the ‘tombs’ scattered about campus. No, these aren’t filled with corpses; they’re secret fraternity houses, whose member lists read like a ‘who’s who’ of high-powered politicos.

Talking of corpses, Grove Street Cemetery has an awesome collection of sarcophagi, obelisks and headstones marking the passing of illustrious New Havenites, including Noah Webster, the author of America’s first dictionary and telegraph inventor, Samuel Morse.

For more life-affirming culture, don’t miss Yale University Art Gallery, home to 185,000 objects, including artefacts from Asia, South America and Africa. Afterwards, head straight to Frank Pepe’s Pizzeria for New Haven’s signature dish, the white-clam pizza.

Lake Candlewood

With a surface area of 8.4 square miles Candlewood Lake is Connecticut’s largest, created in the 1920s with water from the Housatonic River. On the western shore, in New Fairfield, Squantz Pond State Park is a great place for leaf-peeping, while in Brookfield and Sherman acres of gnarled grapevines line the hillsides.

White Silo Farm Winery opens for blackberrying in September. Adults might also enjoy a taste of the farm’s speciality wines made from farm-grown fruit. And, you’ll no doubt want to stop off in Sherman at American Pie to fill-up on blueberry crumb and harvest fruit pie. For the ultimate bird’s-eye view of the foliage, consider a late afternoon hot-air-balloon ride with GONE Ballooning in Southbury.

The Litchfield Hills

Kent has previously been voted the spot in all of New England for fall foliage viewing. Hike to Caleb’s Peak in the Macedonia Brook State Park for fantastic views of the Housatonic Valley, then indulge in ice cream at Backcountry Outfitters. The 15-mile drive from Kent to West Cornwall along CT 7 is one of the most scenic in the whole state, passing the tumbling waterfall of Kent Falls State Park. And, in autumn, the nearby Connecticut Antique Machinery Association powers up its steam locomotives.

On rainy days, locals watch films at the Bantam Cinema, a converted barn on Lake Waramaug and, in summer, everyone heads north to catch vintage car races at the Lime Rock Race Track. But the highlight of summer is lazy days along the Housatonic River, where campers vie for scenic spots in Housatonic Meadows State Park and hikers amble along the longest, flattest stretch of the Appalachian Trail between Georgia and Maine. Spring kayakers pack up their boats as the white water turns placid, perfect for birders and fly fishing. Housatonic River Outfitterscan show early starters the ropes on half- and full-day fishing trips with gourmet picnics to boot.


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