23 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).

One of the few museums in the country devoted entirely to clocks and watches, this 1801 house has more than 5,500 timepieces on display. Though the majority of them are American timepieces dating 1800–1940, the museum does have clocks dating to 1680 and watches dating as far back as 1595. Many of the clocks are kept running and chiming, making the museum a prime place to be when the big hand strikes "12." The gift shop is worth a stop to browse the clock-themed items including jewelry and ornaments made from clock gears and chocolate alarm clocks and gear-shaped chocolates.

Early Kent residents Jacob and Isaac Bull first built a bridge on this site in 1760, where it was later crossed—as local legend has it—by George Washington. The current covered bridge was built in 1842, and is one of just a handful of covered bridges left in the state still open to traffic. It has been reinforced over the years, and 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.

One of the largest collections of antique carousel pieces in the country is housed here. Full-size pieces in the Coney Island, Country Fair, and Philadelphia styles are on display, as are miniature carousels. The museum is also home to an arts gallery, which hosts changing exhibitions, and the Museum of Fire History, which displays photos, antique equipment, and memorabilia. The museum maintains the Bushnell Park Carousel in Hartford (closed January and February).

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 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.

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. New England witch and cemetery tours are available in October, and the museum itself celebrated its 100th anniversary in June of 2025.

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.

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.

The site of a former dairy, the brewery now produces some of the more compelling beers in the state, from IPAs made with their farm-grown hops, to lagers, smooth wheat ales, and farmhouse ales with an eye-opening array of flavors found in wildly collected yeasts. Few places in the country offer a closer connection between the farm, nature, and the beverage in your hand. An on-site tasting room allows for samples and drinks at the farm, with bottles, cans, and growlers to-go. There's no food, so bring your own snacks for the visit.

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.

Within a bowl-shaped valley in the northwest corner of Connecticut lays a winding ribbon of American road racing history. Tied for the second oldest sports car track in the country, Lime Rock Park has welcomed fans and enthusiasts every year since 1957. But don't come expecting grandstands or bleachers, as there are just rolling grass viewing areas both inside the track and out. There are food concessions, but guests bring chairs and coolers to witness roaring action from IMSA, NASCAR, Trans-Am, and more, plus a yearly Labor Day historic festival featuring racing machines ranging from the Formula 1 cars of the 1920s to the lightning-quick and thunder-loud sports cars of the modern era. Depending on the series, race fans are welcome to stroll the paddock infield where drivers like Mario Andretti, Derek Bell, Tom Kristensen, and local heroes Dan Gurney and Paul Newman have hit the track. 

In this well-regarded museum, seven neatly organized galleries highlight family life and work during the 50 years following the American Revolution. A centerpiece is a collection of belongings—including a uniform and personal memorabilia—that belonged to local resident Benjamin Tallmadge, who was a member of the Culper Ring (America's first spies) in the Revolutionary War. 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.

Families have been enjoying the rides here for more than a century. There are kiddie rides, family rides that mom and dad even enjoy, and thrill rides—more than two-dozen rides altogether—plus Splash Away Bay Water Park. The custom-designed Wooden Warrior roller coaster is rated one of the top 25 in the world. An added bonus: there are discounts for military families.

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 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.