15 Best things to do in Winchester (CT)

Winchester is a small town in South Berkshire known for its quality of life. This has a lot to do with the beautiful nature around.

There are lakes, ponds, creeks, natural springs and wooded hills to discover, but Winchester’s Winstead district also has a small city feel.

This was one of Connecticut’s first mill towns, and that legacy lives on in places like Whiting Mills, which has a small community of artists and a large mural project.

Winstead attractions are both nostalgic and fresh, like the Duck Bowling alley and a 1920s movie theater combined with restaurants.

Let’s explore the best things to do in and around Winchester, CT:

1. Small Town Green National Historic District


At the end of the 18th century, Winstead gathered on a narrow strip of land on the west bank of the Steele River in what is now East End Park.

The oldest buildings on the edge of the green space were built around the 1810s.

The east side has large tracts of land from this time onwards with large grassy areas, while the southern end was developed later in the century with a more dense commercial appearance.

At the north end is the stately stone Romanesque Revival Congregational Church, built in 1903. The most impressive residence is Gideon Hall, Jr.

House at 49 Main Street in Greek Revival style and famous for its Doric colonnade.

From the bottom of East End Park you can head west through Winchester’s 1.5 mile long business district lined with turn-of-the-century buildings, with antique shops, a range of fine restaurants, bowling alleys and a bistro cinema, we will Introduced below.

2. American Tort Museum

American Tort Law Museum

Developed by prominent lawyer and activist Ralph Nader, the museum became the country’s first law museum when it opened in 2015.

The attraction is designed to educate visitors about two main issues: jury trials and the advantages of tort law.

For the uninitiated, this involves undue injuries caused by medical malpractice, environmental disasters, motor vehicle collisions, defective products, etc.

You’ll learn about precedent-setting cases, learn more about seven cases (such as Liebeck v. McDonald’s Hot Coffee), and view a dangerous toy exhibit.

An 11-minute movie presentation about jury trials and the evolution of tort law.

Opening hours for 2019 are variable, but you can schedule a guided tour of this award-winning museum in advance.

3. Bridge Street/Prospect Street Rail Trail

This short but worthwhile walk crosses Winstead’s Crazy River about a third of a mile.

Located on the former tracks of the New York, New Haven and Hartford Railroad, the trail is built on a narrow ledge above the water.

Along the way, you’ll see old signals from the railroad era, but also instructive are the roadside-installed information boards.

In addition to recalling the railway, these also detail the 1955 flood, when the Crazy River burst its banks and parts of Winstead were 3 meters underwater.

4. Winchester Centre

Winchester Centre

Head south from Winsted, follow the winding Winchester Road and in less than 10 minutes you’ll be in Winchester with a typical A New England village surrounded by a small green space.

The first thing you’ll notice is the clean lines of Winchester Central Congregational Church, with Doric columns and commissioned in June 1842. Across Newfield Road is the 19th-century Winchester Centre Old College, a lovely single-storey schoolhouse where the local historical society runs a museum with artifacts dating back to the early days of Winchester.

The museum is open during the summer and during special events such as Winchester Grange’s annual Strawberry Festival in mid-June.

5. Solomon Rockwell House

Solomon Rockwell House

Home to the Winchester Historical Society is a famous Greek Revival mansion, commissioned in 1813 by Solomon Rockwell, one of the town’s early industrialists, who owned two houses in the town. A blacksmith shop.

The house is a jumble of buildings with a series of Els, including an old property dating back to the mid-18th century.

But what really catches your eye is the stately Ion porch on the main block.

The museum inside is open by appointment, and its ten rooms feature striking details about Winchester’s rich manufacturing heritage, as well as artifacts from the Civil War.

The 19th-century carriage barn documents Winstead’s decades of craftsmanship, starting with the sickle in the late 18th century.

6. Soldiers Monument and Memorial Park

soldier monument

This stately ensemble was erected in the vacant lot at the end of Crown Street in 1889-90 to honour the people of Winchester who fought in the Civil War.

The summit is the heart of the monument, a three-story square medieval-style tower made of ashlar granite with a sawtooth top.

Protruding from one corner of the 13-meter-tall building is a circular bar with a bronze statue of a soldier holding a flag.

Under the steps of the park drive is a single-story pavilion in the same style.

The monument has just undergone a long-term renovation and is fully funded by donations.

7. Gilson Cinema and Cafe

Gilson Cinema and Cafe

As the name suggests, at Gilson Cinema & Cafe, you can watch a premiere movie while enjoying a full meal.

With waiter service and a fully stocked bar, there’s a small table in front of your seat, so you can indulge in anything from soups to salads, wraps, burgers, sandwiches and pasta.

The theatre building dates back to 1926 and was given a new concept when the owners took over in the mid 80’s.

Waiter service continues throughout the movie, with checks being collected shortly before the movie ends.

8. Whiting Mills

Whiting Mills

This beautiful old mill was developed at the turn of the 20th century to make socks and has been listed on the National Register of Historic Places since 1985. At the beginning of the 20th century, the factory produced socks and underwear for men, and as fashion changed, wool clothing became the main product.

In 1965, the then-known Winchester Spinning Company relocated to a more modern facility in South Carolina.

In 2004, one of the buildings was taken over by a complex community of artists, artisans, health practitioners and small manufacturing companies.

There are painters, potters, photographers, candle makers and more.

During a typical week, you can visit a yoga class or a painting studio, but it’s best to visit Whiting Mills during its semi-annual open house, where you can wander around the building, watch the artists at work, and have all kinds of fun conversations.

9. The American Mural Project

American Mural Project

At the same location in Winstead, it is claimed to be the largest collaborative art project in the world.

The ongoing American mural project in honor of the American worker will be over 35 meters long, nearly 15 meters high and more than 3 meters deep.

Led by artist Ellen Griesedieck, the project has so far involved more than 15,000 children and adults, and an additional 30,000 people from all 50 states will create the murals before completion.

As we write this in the fall of 2019, the second mill building will be open to the public as a visitor center after a renovation.

10. Scottish Man Steel River Greenway

Scottsman Steele River Greenway

Running between Winchester and Torrington is a brisk three-mile trail on another section of the Naugatuck branch of the New Haven and Hartford Railroad in New York.

From the start of the Winchester Trail, the asphalt trail cuts through the wetlands and you’ll hear the murmur of the River Steele coming from behind the bushes.

During spring and summer, you should see plenty of rabbits and a deer or two flying around the trees.

Sometimes you have to cross quiet local roads, which are clearly marked.

There are planned extensions to extend trails into downtown Winstead and Torrington.

11. Highland Lakes

highland lake

Looking out from the southwest side of Winstead is a beautiful 440-acre lake surrounded by wooded hills that looks like a quintessential New England resort.

The lake is natural and is fed by underground springs and streams such as Sucker Brook in the west and Taylor Brook in the south.

There are year-round and seasonal dwellings along the shore, many with their own small marinas.

But if you don’t live in Highland Lakes, the good news is that you can use the state boat launch pad at 297 Westlake Street to ride a trailer motorboat.

The town also keeps two small beaches on the coast instead of one.

12. Mount Pratt State Park Scenic Preserve

Mount Pratt State Park Scenic Preserve

You can take a long walk into the Berkshires of the West Shore Nature Reserve of Highland Lakes.

The park was built in the 1950s using funds donated by renowned Connecticut antiquarian and conservationist George Dudley Seymour.

The trails on Mount Pratt are unmarked, but the main loop is clear and undemanding.

You can revel in wildflowers in the summer, then pack a lunch and spend more time admiring the Northwest Connecticut landscape.

13. Nobrook Farm Brewery

Nobrook Farm Brewery

Connecticut is full of craft breweries, but Norbrook Farm Brewery in Colebrook is a truly homegrown business that the community has taken to heart.

The bar has a view of the Berkshire family, where there is a lovely copper bar.

It’s worth mentioning that while there will be up to 14 beers to choose from, Norbrook Farm has rounded out the selection of six signature beers.

These include American IPA, Saison, Kölsch, Porter and Beckley Furnace, American Brown beers brewed with pale malts and a range of special malts.

It’s also worth noting that the Farm Day IPA is brewed with swirling hops and malt, so may vary depending on the time of year.

To taste some, there are tasters of all sizes, and the brewery has posted a list of taps online.

Live music details can also be viewed online, and Wednesday is dart night as there is a new Winmau board in the space above the bar.

14. Burr Pond State Park

Burr Pond State Park

Drive along the eastern shore of Highland Lake and you’ll arrive at a state park surrounding a man-made body of water where you can swim, fish and have other fun.

Not only does Burr Pond look beautiful because it has a story to tell, it’s home to the world’s first commercially viable condensed milk factory, established in 1861 by its inventor, Gail Borden. The building was destroyed by fire in 1877, but the foundations are still visible and marked with information boards.

Walkers can join the 2.25-mile loop around the pond and walk two miles in state-managed green space, through Paugnut State Forest, and on the John Muir Trail to Sunnybrook State Park.

15. Laurel Duckpin Bowling Lane


If you’ve never tried duck bowling, it’s nothing like bowling, and there’s an alley to play on Main Street in Winstead.

Duckpin balls have no finger holes and are a bit larger than softballs.

As for the pins, they’re also shorter and lighter than ten pins, but the spacing is the same, so getting a strike is a real achievement.

For this reason, you will get three rolls per frame.

Laurel Duckpin Lanes also exudes a mid-century charm, complete with paper grading and manual reset.

Bumpers are available for youngsters, and there are three vintage pinball machines to try out.

Where to Stay: Best Hotels in Winchester, CT (CT)
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