20 Best Sights in The Litchfield Hills, Connecticut

In the same spot since 1976, this outdoor flea market has grown from a dozen or so vendors to more than 500 on a typical Sunday, along with food trucks offering everything from a snack to full meals. You'll never know what usual and unusual treasures you'll find spread out on the field, as every Sunday brings out a different collection of vendors selling all manner of antiques, collectibles, housewares, and merchandise, along with, simply, "things." Serious buyers arrive by 5:30 am and pay $20 admission for the privilege; other "early birds" prepay $10 online to enter at 7 am; the rest of us are happy to browse from 8 am to 2 pm and pay just $3.

This 4,000-acre nature preserve houses top-notch natural-history exhibits. You'll find 30 bird-watching platforms, two self-guided nature trails, several boardwalks, boating facilities, and 40 miles of hiking, cross-country skiing, and horseback-riding trails. The Nature Museum has displays depicting the natural diversity found throughout the preserve, dioramas, live animals, a beehive, a digital microscope, and other unique exhibits of interest to kids of all ages (especially the scavenger hunt).

Built in 1842, Bulls Bridge is one of a handful of covered bridges in the state still open to traffic; it was added to the National Register of Historic Places in 1972. If you feel like a hike, there is an easy trail that leads to waterfalls and a small gorge.

Visitors are welcome to watch potters as they work, producing a variety of items that are fired in an on-site, 35-foot-long, wood-fired tube kiln. A selection of items—including seconds—are available for purchase in the workshop. A larger store, located farther north in West Cornwall (415 Sharon-Goshen Turnpike), offers the wood-fired pots along with complementary items made by local glassmakers, woodworkers, and metalsmiths.

Dr. Frederick Shepard Dennis, the former owner of these 240 acres and a noted New York surgeon, lavishly entertained his guests—among them President William Howard Taft and several Connecticut governors—in the stone pavilion at the summit of the estate. From its 1,627-foot height, you have a panoramic view of Haystack Mountain and parts of New Hampshire to the north and, on a clear day, New Haven Harbor about 60 miles south. Picnic on the park's grounds or hike one of its many trails. Autumn foliage here is spectacular!

Hardware-store buffs and vintage-tool aficionados will feel right at home at this museum. Artist and author Eric Sloane (1905–1985) was fascinated by Early American woodworking tools, and his collection showcases examples of American craftsmanship from the 17th to 19th centuries. The museum contains a re-creation of Sloane's last studio and also encompasses the ruins of a 19th-century iron furnace. Sloane's illustrated books and prints, which celebrate vanishing aspects of Americana, are available for sale here.

A founding member of the Connecticut Wine Trail, the state's oldest winery opened its doors in 1975. You can stop in for tastings with or without a snack—or bring your own picnic. Enjoy live music as you sip on Saturday evenings.

One of the most spectacular views in the state can be seen from the 34-foot high stone tower atop Haystack Mountain (1,716 feet). You can see the Berkshires in Connecticut and Massachusetts, as well as peaks in New York and the Green Mountains of Vermont. A winding road will get you halfway there; then hike the rugged, half-mile trail to the top.

This 35-acre vineyard overlooking Lake Waramaug produces more than 14 varieties of wine—from sparkling to dessert. A weathered red barn houses a gift shop and a tasting room, where knowledgeable staff explain the various wines and wine-making techniques. A wine bar in the Hayloft, with views of the lake, serves a fine cheese and pâté board. There's also a picnic area.

The park is marked by its tall pine trees near the Housatonic River and has terrific riverside campsites (seasonal). Fly-fishers consider this 2-mile stretch of the river among the best places in New England to test their skills catching trout and bass (license required).

This is a family-friendly park: no alcohol allowed.

Heading north from Kent toward Cornwall, you'll pass the entrance to 295-acre Kent Falls State Park, where you can walk across a covered bridge, hike a short way to one of the prettiest waterfalls in the state, and picnic in the green meadows at the base of the falls.

The 95-acre parkland surrounding idyllic Lake Waramaug, one of Connecticut's largest and most picturesque natural lakes, is a great place for swimming, boating, fishing, and picnicking. The park has 76 campsites in wooded and open settings (with bathrooms and showers available) that are available from Memorial Day through Labor Day; canoes and kayaks can be rented on-site in summer, too.

In this well-regarded museum, seven neatly organized galleries highlight family life and work during the 50 years following the American Revolution. The extensive reference library has information about the town's historic buildings, including the Sheldon Tavern where George Washington slept on several occasions and the Litchfield Female Academy where, in the late 1700s, Sarah Pierce taught girls not only sewing and deportment but also mathematics and history.

Early-season trout fishing (license required) is superb at 2,300-acre Macedonia Brook State Park, where you can also hike and cross-country ski. The Blue Trail crosses several peaks, and you can see as far as the Catskills and Taconics in neighboring New York State. The expansive mountain views are amazing year-round; the leaves are magnificent in the fall.

With 11 miles of hiking trails, this 1,147-acre property—a mixture of forests, meadows, wetlands, ponds, and streams—provides myriad hiking opportunities. The visitor center shares its space with small hawks, an owl, and other animals in the live-animal display in the Natural History Exhibit Room; in the Children's Adventure Center, kids learn about the importance of water quality and watersheds, crawl through a tunnel to a beaver lodge, and look for various fish and other sea life in the large aquarium.

In 1774, Judge Tapping Reeve enrolled his first student, Aaron Burr, in what became the first law school in the country. (Before Judge Reeve opened his school, students studied the law as apprentices, not in formal classes.) This school is dedicated to Reeve's achievement and to the notable students who passed through its halls, including three U.S. Supreme Court justices. There are multimedia exhibits, an excellent introductory film, and restored facilities.

This property in the center of town includes the large, antiques-filled, gambrel-roof Georgian Colonial home of Dr. Samuel Seabury—who, in 1783, was elected the first Episcopal bishop in the United States. The house, built in 1740, and its outstanding furniture collection comprise one of the earliest and most authentic house museums in the region. The garden was designed in the 1920s by renowned British horticulturist Gertrude Jekyll. Though small, it's a classic, old-fashioned, English-style garden and the only one of the three Jekyll-designed gardens in the United States that are still in existence.

The exhibits in this small but excellent and thoughtfully arranged collection detail the history and continuing presence of 10,000 years of Native American life in New England, specifically in "Quinnetukut." Highlights include 15 acres of nature trails, a simulated archaeological site, and an authentically constructed 16th-century Algonkian Village with wigwams, a longhouse, a rock shelter, and more. A gift shop presents the work of some of the country's best Native American artists.

A romantic reminder of the past, this single-lane bridge over the Housatonic River is on Route 128, just east of U.S. 7, in West Cornwall. The 172-feet-long and 15-feet-wide lattice truss bridge was built in 1841 and still carries vehicular traffic. The design incorporates strut techniques that were later copied by bridge builders around the country.