The Perfect Long Weekend In Connecticut

September 14, 2013 8:00 AM

(credit: Thinkstock)

The advantage of our small state is that in a short span of time, it is possible to cover its major attractions. A long weekend is the perfect opportunity to plan a leisurely itinerary and enjoy its fall beauty.

Hartford to Litchfield

Head out from the capital Hartford, on a 35-mile, under one-hour drive to the town of Litchfield, center of Litchfield county. This is a renowned fall resort not only for Nutmeggers, but also for the nearby Big Apple state. Leave I-84W for CT-4W at exit 39. Follow that until it becomes CT-118, and brings you into Litchfield via CT-6, among rolling hills and serene beauty. Indulge in a picnic at Topsmead State Forest, once the summer cottage estate of Edith Morton Chase. Stroll on the marked trails through the estate gardens and visit the cottage. Later browse the antiques shops, art galleries, historic homes and gardens around the region.

Litchfield Inn
432 Bantam Road
Litchfield, CT 06759
(860) 567-4503

Litchfield to Kent

After breakfast, embark on a leisurely drive of just over 20 miles to Kent. Take Route 202 and travel west for about seven miles to the intersection with Route 341. Turn right onto Route 341 and travel to the intersection with Route 7 in Kent. Turn north onto Route 7. The park is 4.5 miles further on. Kent Falls, in the northeastern corner of the town, are a series of waterfalls in Falls Brook, originating in Warren. Flowing west, it plunges approximately 70 feet in a dramatic outpouring, descending in several cascades to the valley floor before joining the Housatonic River. The water has carved the limestone bed of the stream into fascinating shapes and depressions. The Native Americans called this area “Scatacook” and there is ample evidence of ancient settlements and camps. A major highlight of the park is the re-constructed covered bridge built in 1974 by a park employee, Edmund Palmer. The cascades are the fullest in spring after the winter thaws. But they are dramatic at any time of the year. Fall foliage season is a perfect time to visit, adding brilliance to the special atmosphere. This exceptional scenic spot has been featured in travel magazines and television advertisements.

The Inn at Kent Falls
107 Kent Cornwall Road
Kent, CT 06757
(860) 927-3197

Related: Top Day Trips For Under $100 In The Connecticut Area

Kent to Greenwich

A drive of a little over an hour and approximately 60 miles south meanders over US-7, Routes 55 and 22. Then follow along I-684 and I-287-E, bringing you from the bucolic beauty of the Litchfield Hills to the swanky grandeur of Greenwich in Fairfield county, the home of the rich and powerful. Bordering New York state, Fairfield opens the door to New England with interesting museums, majestic mansions and more. Coastal Fairfield is the gateway to the region. Beautiful architecture, working marinas and eclectic restaurants are tucked in among beaches and upscale shops. Visit Greenwich Avenue – the Rodeo Drive of the Northeast. Famous museums include the Barnum Museum in Bridgeport, the Bruce Museum in Greenwich and the Lockwood-Mathews Mansion in Norwalk. Children will be entertained at the Maritime Aquarium in Norwalk, Stamford Museum and Nature Center in Stamford and the Beardsley Zoo in Bridgeport. Explore the iconic historic lighthouse and nature preserve on Sheffield Island, Norwalk. Have a gourmet seafood dinner on the marina and take an evening harbor cruise of the coast.

Delamar Greenwich Harbor
500 Steamboat Road,
Greenwich, CT 06830
(203) 661-9800

Greenwich to Essex

Set off this morning along I-95N, CT-9N and CT-154 for one of the true gems of the Connecticut shoreline. A beautiful drive of 80 miles and 1.5 hours brings you to Essex Village. Nestled into a forested indentation of the Connecticut River, Essex is the archetypal New England riverside town of historic buildings and tree-shaded streets. The three villages of Essex, Centerbrook and Ivoryton combine to create an experience that is unique. Each features exquisite examples of Colonial and Federal architecture, antique shops, boutiques, inns, restaurants and marinas. The Connecticut River Museum, Essex Steam Train & Riverboat, the Griswold Inn and Ivoryton Playhouse are prime examples of bygone historical landmarks, reflecting a culture steeped in history. Walk up Main Street from the dock and duck into neighboring alleys and offshoots to enjoy the splendors of this highlight of your four-day trip. Then indulge in a seafood fest at the Griswold Inn, and stay the night at this iconic oldest continuously operating tavern in the USA built in 1776. Or make your way home either via the highway or scenic byways and secondary roads that allow more absorption of the atmosphere and ambiance of rural Connecticut.

The Griswold Inn
36 Main St.
Essex, CT 06426
(860) 767-1776

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Bina Joseph, a resident of Glastonbury, CT is a freelance writer covering all things travel-related in Connecticut.
A passionate veteran of the travel industry, Bina has visited more than 40 countries, giving her a unique, global perspective. Her work can be found at

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