Litchfield's historic borough and the surrounding landscape feature rolling hills and picturesque estates, making it the quintessential New England town. Tourists visit Litchfield during the winter, spring, summer and fall seasons to enjoy the scenery, shop on West Street and to partake of a number of well-established restaurants in the area. Some tourist and travel officials say that Litchfield is the second most-visited town in the state, next to Mystic and its famous Seaport. Litchfield offers a number of waterways and lakes for public enjoyment, including Bantam River , the pond at Mount Tom State Park and Bantam Lake. The latter can be found in the town of Litchfield and the neighboring town of Morris. Both Mount Tom and Bantam Lake contain public and private beaches and feature boating, fishing and swimming. In the wintertime, ice fishing and sailing are popular sports, as well.

Many outdoor activities are enjoyed in a number of areas around town, including the 4,000-acre nature preserve of the White Memorial Foundation . But it is the historic and the natural features of the town that draws hundreds of visitors to Litchfield throughout the year. The Litchfield Historical Society boasts a museum of its own dedicated to the town's rich past. The town's center offers a bookstore, elegant clothiers, and award-winning restaurants. Considered the state's finest example of a typical late 18th-century New England village, the entire center of the village settled in 1720 is a National Historic Landmark. While Williamsburg had to be restored, Litchfield simply has been maintained by its residents as a living museum. Most of the old homes and buildings are occupied. Some are opened to the public on Open House Day one Saturday in July. The Litchfield Historic District is clustered around the long, wide green and along North and South streets (Route 63). The statuesque, gleaming white Congregational Church is said to be the most photographed in New England.Note that the bank and the jail share a common wall at North and West streets. Along North Street are Sheldon's Tavern, where George Washington slept (he visited the town five times), plus the birthplace of Harriet Beecher Stowe. South Street is a broad, half-mile-long avenue where two U.S. senators, six Congressmen, three governors and five state chief justices have lived. Here too is the Tapping Reeve House and Law School (1773), the first law school in the country. The house with its handsome furnishings and the tiny school with handwritten ledgers of students long gone are open in conjunction with the Litchfield Historical Society Museum at 7 South Street, which has four galleries of early American paintings, decorative arts, furniture and local history exhibits.

Just east of town are Haight Vineyard & Winery , the oldest farm winery in Connecticut, and Topsmead State Forest , a 511-acre preserve atop a knoll a mile east of Litchfield Center offering scenic views, picnic sites and trails as well as an English Tudor mansion that was once the summer home of the Chase brass family of Waterbury.

Litchfield's fortunes declined during the later years of the nineteenth century. The town did not have the ample water supply and rail transportation necessary to establish industry and the village became a sleepy backwater. Rediscovered as a resort community in the late nineteenth century, Litchfield became a popular spot for vacation, weekend and summer homes. The town embraced the Colonial Revival movement and by the early Century many of the homes began to sport the white paint and black shutters we see today. There are a wide variety of shops in Litchfield, including dozens of arts and antique shops. There are also clothing stores, bookstores, craft shops, flower shops, health clubs and much more. There are three museums, the Litchfield History Museum, the Tapping Reeve House and Law School and the White Memorial Conservation Centre Museum. Also, you can find many restaurants catering to every palate.

Litchfield children are educated at Litchfield Center School is for kindergarten through third grade; Litchfield Intermediate School serves fourth through sixth graders. Litchfield High School.The Forman School.