Winchester is a small town in the southern Berkshires, hailed for its quality of life. This has much to do with the beautiful nature all around.
There are lakes, ponds, brooks, natural springs and wooded hills to discover, but Winchester’s Winsted section also has the feel of a small city.
This was one of the first mill towns to crop up in Connecticut, and that heritage endures at places like Whiting Mills, home to a little community of artists and a large-scale mural project.
Winsted has attractions that are at once nostalgic and fresh, like a duckpin bowling alley and a 1920s cinema combined with an eatery.
Let’s explore the best things to do in and around Winchester, Connecticut:
1. Town Green National Historic District
Winsted came together around a narrow strip of land, now East End Park, on the western bank of the Still River at the end of the 18th century.
The oldest buildings on the green’s margins are from around the 1810s.
The east side has large properties from this time, with big grassy intervals, while the southern end was developed later in the century, gaining a denser commercial appearance.
At the northern end is the solemn, stone-built Romanesque Revival Congregational Church dedicated in 1903. The most impressive residence is the Gideon Hall, Jr.
House at 49 Main Street, in the Greek Revival style and recognized by its Doric colonnade.
From the bottom of East End Park you can go west through Winchester’s 1.5-mile long commercial district, lined with turn-of-the-century architecture hosting antiques shops, a fine array of restaurants, a bowling alley and a bistro-cinema, which we’ll cover below.
2. American Museum of Tort Law
Developed by the renowned attorney and activist Ralph Nader, when this museum opened in 2015 it became the first law museum in the country.
The aim of the attraction is to educate visitors on two main matters: Trial by jury and the advantages of tort law.
For the uninitiated, this deals with wrongful injuries, from medical malpractice, environmental disasters, motor vehicle crashes, defective products and the like.
You’ll learn about precedent-setting cases, dipping into seven in detail (like the Liebeck v.
McDonalds hot coffee case) and see an exhibition of dangerous toys.
An 11-minute movie presentation recounts the evolution of trial by jury and tort law.
In 2019 the opening times were irregular, but you could arrange a guided tour of this award-winning museum ahead of time.
3. Bridge Street/Prospect Street Rail Trail
This short but worthwhile walk traces the Mad River through Winsted for about a third of a mile.
The trail is on the former railbed of the New York, New Haven and Hartford Railroad, raised on a narrow ledge over the water.
As you go you’ll see old signals leftover from the days of the railroad, but also enlightening are the informative plaques that have been installed by the path.
As well as recalling the railroad these go into detail on the flood of 1955, when the Mad River burst its banks leaving parts of Winsted three meters underwater.
4. Winchester Center
Go south out of Winsted on the winding Winchester Road, and in under ten minutes you’ll be at Winchester to see an archetypal New England village around a little green.
The first thing you’ll notice are clean lines of the Winchester Center Congregational Church, with Doric columns, and dedicated in June 1842. Sitting across Newfield Road is the 19th-century Winchester Center Old Academy, a cute single-story schoolhouse where the local historical association operates a museum with artifacts dating back to Winchester’s earliest days.
The museum opens in summer, and during special events like the Winchester Grange Annual Strawberry Festival in mid-June.
5. Solomon Rockwell House
The home of the Winchester Historical Society is a distinguished Greek Revival mansion, commissioned in 1813 by Solomon Rockwell, one of the town’s early industrialists who owned two iron forges in the town.
The house is a muddle of buildings, with a series of ells including an older property dating from the middle of the 18th century.
But what will steal your gaze is the main block’s stately Ionic portico.
The museum inside is open by appointment and its ten rooms hold compelling details about Winchester’s rich manufacturing heritage, as well as artifacts from the Civil War.
The 19th-century carriage barn chronicles many decades of workmanship in Winsted starting with scythes at the end of the 18th century.
6. Soldiers’ Monument and Memorial Park
This dignified ensemble was erected in open space at the end of Crown Street in 1889-90 to commemorate the people of Winchester who participated in the Civil War.
Capping the hill is the monument’s centerpiece, a three-level square Medieval-style tower composed of ashlar granite and topped with crenellations.
Projecting from one corner of this 13-meter structure is a kind of circular bartisan crowned by a bronze figure of a soldier with a flag in hand.
Down the steps by the park drive is a single-story pavilion in the same style.
The monument has just come through a long-term renovation, funded entirely by donations.
7. Gilson Cinema & Cafe
As the name tells you, at the Gilson Cinema & Cafe you can watch a first run movie and enjoy a full meal at the same time.
There’s a waiter service and a well-stocked bar, and your seat will have a small table in front, so you can tuck into anything from soups to salads, wraps, burgers, sandwiches and pasta dishes.
The theater building dates to 1926, and was given its new concept when the owners took over in the mid-80s.
Waiter service continues throughout the movie and checks are collected shortly before the movie ends.
8. Whiting Mills
This beautiful old mill complex was developed to make hosiery at the turn of the 20th century and has been on the National Register of Historic Places since 1985. In the early 20th century the mill manufactured hosiery and underwear for men, and as fashions changed, wool garments became the main product.
In 1965, the Winchester Spinning Company, as it was then known, decamped to more modern facilities in South Carolina.
In 2004 one of the buildings was taken over by a sophisticated community of artists, craftspeople, health practitioners and little manufacturing companies.
There are painters, potters, photographers, a candle-maker and many more.
In a typical week you could visit for a yoga class or painting workshop, but Whiting Mills is best visited during semi-annual open days, when you can poke around the building, watch artists at work and get into all sorts of interesting conversations.
9. American Mural Project
At the same site in Winsted is what is claimed to be the world’s largest collaborative art project.
The ongoing American Mural Project, a tribute to the American worker, will measure more than 35 meters long, almost 15 meters high and more than three meters deep.
Led by artist Ellen Griesedieck, the project has so far been worked on by more than 15,000 children and adults, and another 30,000 from all 50 states will create pieces of the mural before it’s finished.
When we wrote this article in autumn 2019 the second mill building was due to open to the public as a visitor center following a renovation.
10. Sue Grossman Still River Greenway
Running between Winchester and Torrington is a light, three-mile trail on another stretch of the New York New Haven and Hartford Railroad’s Naugatuck Division.
Setting off from the Winchester trailhead, the asphalt path carves through wetland, and you’ll hear the murmur of the Still River from behind the undergrowth.
In spring and summer you should see plenty of rabbits as well as deer or two darting through the trees.
Occasionally you’ll have to cross quiet, local roads, and these are well-marked.
There are planned extensions to lengthen the trail into downtown Winsted and Torrington.
11. Highland Lake
Sweeping out from the south-west side of Winsted is a beautiful 440-acre lake, bounded by wooded hills and looking like a quintessential New England vacation escape.
The lake is natural, being fed by underground springs, as well as streams like Sucker Brook to the west and Taylor Brook to the south.
There are year-round and seasonal residences all along its shores, many with their own little docks.
But the good news if you’re not staying at Highland Lake is you can use the state boat launch at 297 West Lake Street for a trailered motorboat.
The town also maintains not one but two small beaches on the shore.
12. Platt Hill State Park Scenic Reserve
You can stride out into a piece of the Berkshires at nature reserve above the west shore of Highland Lake.
The park was drawn up in the 1950s using funds donated by the noted Connecticut antiquarian and conservationist George Dudley Seymour.
The trails on Platt Hill are unmarked, but the main loop is clear and undemanding.
You can revel in the wildflowers in summer, and pack a lunch to spend a bit more time admiring the Northwest Connecticut landscape.
13. Norbrook Farm Brewery
Connecticut is awash with craft breweries but Norbrook Farm Brewery in Colebrook is a true homespun operation that the community has taken to its heart.
There are vistas of the Berkshires at the taproom, which has a lovely copper bar.
Something else to love is that although there will be up to 14 beers on tap, Norbrook Farm has perfected a selection of six signature beers.
Among them is an American IPA, a Saison, a Kölsch, a Porter and Beckley Furnace, an American-style Brown Ale brewed with pale malt and an array of specialty malts for toasted notes.
Farm Day IPA is also worth noting, being brewed with rotating hops and malt, so may be different depending on the time of year.
To sample a few there are tasters in a range of sizes and the brewery posts the tap list on line.
Also check online for details of live music, while Wednesday is darts night, as there’s a new Winmau board in a space above the taproom.
14. Burr Pond State Park
Travel down the east shore of Highland Lake and you’ll get to a state park around a manmade body of water for swimming, fishing and other fun in the water.
Burr Pond isn’t just pretty to look at, as it has a tale to tell, at the site of the world’s first commercially viable condensed milk factory, established by its inventor Gail Borden in 1861. The building was felled by fire in 1877 but the foundations are still visible and marked by an information plaque.
Walkers can join the 2.25-mile loop around the pond, and walk for two miles in state-managed greenery through Paugnut State Forest to Sunnybrook State Park via the John Muir Trail.
15. Laurel Duckpin Bowling Lanes
If you’ve never tried duckpin bowling, it’s a whole other ballgame to tenpin bowling and there’s an alley for it on Main Street in Winsted.
Duckpin balls come without finger holes and are a little larger than a softball.
As for the pins, these are also shorter and lighter than ten-pins, but have the same spacing, so getting a strike is a real achievement.
For that reason you’ll be given three rolls per frame.
Laurel Duckpin Lanes also exudes a kind of mid-century appeal, and comes with paper scoring and manual resets.
Bumpers are available for youngsters and there are also three old-school pinball machines to try out.