9 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.

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.

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!

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.

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.

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.

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.

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.