Connecticut Cities and Regions

Connecticut may be the gateway to New England, but Fairfield is often considered part of the New York metro area, as many commuters call its affluent, boutique-lined towns (like Greenwich) and cities (like Stamford and Bridgeport) home. With 30 miles of coastline, upscale towns, and rolling countryside, Fairfield’s highlights include a mix of seaside marinas, elegant accommodations, cosmopolitan dining, New England charm, and local interest museums – both Bridgeport’s Barnum Museum and Norwalk’s Maritime Museum and Aquarium are popular attractions.

Home to Yale University for nearly 300 years, New Haven is a vibrant, eclectic, cultural mecca. Here, you’ll find international cuisine, top notch museums and performing arts centers, and shopping for everyone from bargain hunters to boutique belles. Although New Haven has a bad rap for crime, as long as you exercise common sense and avoid deserted areas outside of downtown (especially after dark), you should be fine. Nature lovers will want to venture outside of the city to some of Greater New Haven’s outdoors-y attractions – visiting the state’s longest saltwater beach at Hammonasset State Park, birdwatching at the Audubon Coastal Center in Milford, and taking a boating tour of the Thimble Islands off Branford.

Amidst the rolling hills of quiet, outdoorsy northwestern Connecticut, you’ll find quaint towns with steepled churches, village greens, and friendly inns. Hiking and cycling trails abound, as do opportunities for fishing, canoeing, and lake-swimming. Visit in the fall to catch harvest-time agricultural fairs and fiery fall foliage. Hit up Woodbury for prime antiquing, Bristol for the world’s best wooden roller coaster, and Thomaston for a 20-mile scenic ride on a vintage steam engine.

Hartford, Connecticut’s historic capital, sits on the banks of the Connecticut River. Literature buffs and historians will love exploring Mark Twain’s home and the Harriet Beecher Stowe Center, both located in the city. On your way out of the city, make time to visit these Connecticut River Valley favorites: East Haddam (34 miles outside of Hartford) to romp around in the expansive Gillette Castle and Estate, built by renowned actor and playwright William Gillette, and in Essex (37 miles outside of Hartford), the archetypal New England river town.

Connecticut’s southeastern pocket is one of contrast: Larger than life casino glitz and glamour in Mashantucket and Uncasville offset calm, coastal towns like New London and Mystic, both of which are famous their whaling and shipbuilding heritage. The latter, still home to many a fisherman, boasts a sail-filled harbor, a first class aquarium, and a glimpse into the seafaring life of its 19th century inhabitants at the Mystic Seaport Museum.

Aptly named for its abundance of rural and semi-rural towns (like Brooklyn, Pomfret, and Woodstock), Connecticut’s northeastern corner invites the automotive explorer to venture onto its timeless country roads to discover acres of greenery, rustic farmhouses, charming B&Bs, grazing livestock, pick-your-own orchards, and a vibrant antiques trade (CT 169 is one of the area’s most scenic byways).