Top 15 Attractions in Winchester, CT: Discover the Best Activities

Winchester is a charming town situated in the southern Berkshires, celebrated for its excellent quality of life largely due to the stunning natural surroundings.

The area is rich with lakes, ponds, brooks, natural springs, and tree-covered hills to explore, while the Winsted section of Winchester offers the ambiance of a small city.

As one of the initial mill towns developed in Connecticut, its heritage persists at locations such as Whiting Mills, which houses a vibrant community of artists and a notable mural project.

Winsted features attractions that blend nostalgia with modernity, such as a duckpin bowling alley and a vintage 1920s cinema paired with a dining establishment.

Let us delve into the most compelling activities available in and around Winchester, Connecticut:

1. Town Green National Historic District

Winsted developed around a narrow strip of land, currently East End Park, beside the western bank of the Still River at the close of the 18th century.

The oldest structures on the green’s periphery date back to the 1810s.

The eastern side features expansive properties from this era, characterized by large grassy spaces, while the southern end underwent later development in the century, adopting a more commercial facade.

At the northern terminus stands the solemn, stone-crafted Romanesque Revival Congregational Church, established in 1903. The most notable residence is the Gideon Hall, Jr.

House at 49 Main Street, exemplifying the Greek Revival architectural style, recognized for its striking Doric colonnade.

From the base of East End Park, visitors can stroll westward along Winchester’s 1.5-mile commercial corridor, adorned with turn-of-the-century architecture, hosting antique shops, a diverse selection of restaurants, a bowling alley, and a bistro-cinema, which will be discussed further below.

2. American Museum of Tort Law

Founded by the esteemed attorney and advocate Ralph Nader, this museum debuted in 2015 and stands as the first law-themed museum in the nation.

The primary mission of this institution is to enlighten visitors regarding two critical concepts: Trial by jury and the merits of tort law.

Tort law deals with wrongful injuries, encompassing areas such as medical malpractice, environmental disasters, vehicular accidents, defective products, among others.

Exhibits detail significant precedent-setting cases, focusing intensively on seven (including the Liebeck v. McDonald’s hot coffee case) along with a display featuring hazardous toys.

Additionally, an informative 11-minute film chronicles the development of trial by jury and tort law.

In 2019, visiting hours were irregular; however, it was possible to arrange guided tours of this award-winning museum in advance.

3. Bridge Street/Prospect Street Rail Trail

This short but rewarding walk follows the Mad River through Winsted for approximately one-third of a mile.

The pathway is situated on the former railbed of the New York, New Haven and Hartford Railroad, elevated on a narrow ledge above the water.

Along the route, remnants of old signals from the railway days are present, while informative plaques installed along the path provide valuable insights.

These plaques recount the history of the railway and detail the flood of 1955, during which the Mad River overflowed, submerging parts of Winsted by three meters.

4. Winchester Center

Traveling south from Winsted along the meandering Winchester Road, you will arrive in under ten minutes at Winchester, where a quintessential New England village encircles a quaint green.

The first landmark you’ll notice is the elegant facade of the Winchester Center Congregational Church, featuring Doric columns and inaugurated in June 1842. Directly across Newfield Road lies the charming, 19th-century Winchester Center Old Academy, a single-story schoolhouse where the local historical society administers a museum showcasing artifacts from Winchester’s foundational years.

The museum operates during the summer months and during special events such as the Winchester Grange Annual Strawberry Festival held in mid-June.

5. Solomon Rockwell House

The residence of the Winchester Historical Society is an elegant Greek Revival mansion, commissioned in 1813 by Solomon Rockwell, an early industrialist in the town who operated two iron forges.

The house comprises a complex of structures, featuring a series of ell connections and an older section dating to the mid-18th century.

However, the most striking feature is the main building’s refined Ionic portico.

Inside, the museum is accessible by appointment, showcasing ten rooms filled with intriguing insights into Winchester’s industrial legacy, alongside artifacts from the Civil War.

The 19th-century carriage barn chronicles several decades of craftsmanship in Winsted, beginning with the production of scythes at the end of the 18th century.

6. Soldiers’ Monument and Memorial Park

This solemn monument was established in a public area at the end of Crown Street between 1889 and 1890 to honor Winchester residents who served in the Civil War.

Dominating the site is the structure’s centerpiece, a three-tiered square Medieval-style tower composed of ashlar granite and embellished with crenellation.

Protruding from one corner of this 13-meter edifice is a circular bartizan crowned with a bronze representation of a soldier holding a flag.

By the park drive, there is a single-story pavilion designed in the same architectural style.

The monument recently underwent extensive renovation, entirely funded through community donations.

7. Gilson Cinema & Cafe

As indicated by its name, at the Gilson Cinema & Cafe, patrons can enjoy contemporary films while indulging in a full dining experience.

The establishment provides table service and a well-stocked bar, with tables positioned in front of each seat, enabling attendees to enjoy a menu that includes soups, salads, wraps, burgers, sandwiches, and pasta options.

The cinema building originated in 1926 and underwent a transformation in the mid-80s under new ownership.

Table service continues throughout the film screening, with checks collected just prior to the conclusion of the presentation.

8. Whiting Mills

This historic mill complex, developed for hosiery production at the beginning of the 20th century, has been listed on the National Register of Historic Places since 1985. In the early 20th century, the mill was dedicated to the manufacturing of hosiery and undergarments for men; as fashion trends evolved, wool garments became the primary product.

In 1965, the Winchester Spinning Company, as it was then named, relocated to modern facilities in South Carolina.

In 2004, one of the buildings was repurposed by an artistic community that includes artists, craftspeople, health practitioners, and small manufacturing enterprises.

Among the residents are painters, potters, photographers, and a candle maker, among others.

A typical week might include events like yoga classes or painting workshops, but Whiting Mills is best experienced during semi-annual open days when visitors can explore the building, observe artists at work, and engage in fascinating discussions.

9. American Mural Project

Located at the same site in Winsted is the claim to being the world’s largest collaborative art project.

The ongoing American Mural Project, a homage to the American worker, is set to measure over 35 meters in length, nearly 15 meters in height, and more than three meters in depth.

Led by artist Ellen Griesedieck, the project has already involved more than 15,000 individuals, both children and adults, with plans for another 30,000 participants from all 50 states to contribute to the mural before its completion.

As of the time of writing in autumn 2019, the second mill building was anticipated to open as a visitor center following renovation.

10. Sue Grossman Still River Greenway

Linking Winchester and Torrington is a pleasant three-mile trail located on a segment of the former New York, New Haven, and Hartford Railroad’s Naugatuck Division.

Commencing from the Winchester trailhead, the paved path winds through wetland areas, where the soothing sounds of the Still River can be heard from the surrounding vegetation.

During spring and summer, you may encounter plenty of rabbits and possibly a deer or two navigating through the trees.

Occasionally, the path crosses quiet local roads, which are well-signposted.

Future extensions are planned to lengthen the trail into the downtown areas of both Winsted and Torrington.

11. Highland Lake

Expanding from the southwest quadrant of Winsted is a picturesque 440-acre lake, bordered by wooded hills, creating an ideal New England getaway.

The lake is a natural creation, nourished by underground springs as well as streams such as Sucker Brook to the west and Taylor Brook to the south.

Year-round and seasonal homes line its shores, many equipped with private docks.

Fortunately, if you are not staying at Highland Lake, the state boat launch located at 297 West Lake Street is available for trailered motorboats.

The town also maintains two small beaches along the coastline.

12. Platt Hill State Park Scenic Reserve

Visitors can explore a piece of the Berkshires at this nature reserve located above the west shore of Highland Lake.

Founded in the 1950s with contributions from the eminent Connecticut antiquarian and conservationist George Dudley Seymour, the park offers designated trails, although they are unmarked; the main loop is discernible and relatively gentle.

During summer, visitors can delight in colorful wildflowers, and it is advisable to bring a picnic to enjoy while soaking in the beauty of the Northwest Connecticut landscape.

13. Norbrook Farm Brewery

Connecticut is replete with craft breweries, yet Norbrook Farm Brewery in Colebrook stands out as a genuine community-focused venture.

Guests can enjoy panoramic views of the Berkshires from the taproom, which features a charming copper bar.

Notably, although there may be up to 14 beers on tap, Norbrook Farm has excelled in producing a selection of six signature brews.

These include an American IPA, a Saison, a Kölsch, a Porter, and Beckley Furnace, an American-style Brown Ale crafted with pale malt complemented by various specialty malts for a toasted flavor profile.

Farm Day IPA also deserves mention, brewed with rotating hops and malts, thus varying by season.

Visitors can opt for tasting flights offered in various sizes, and the brewery publishes its tap list online.

Additionally, check for information regarding live music events, while Wednesday features darts night, facilitated by a new Winmau board located above the taproom.

14. Burr Pond State Park

Proceeding along the eastern shore of Highland Lake, one will find a state park surrounding a manmade reservoir ideal for swimming, fishing, and various recreational activities.

Burr Pond is not only visually appealing; it holds historical significance as the location of the world’s first commercially viable condensed milk factory, established by inventor Gail Borden in 1861. The original structure succumbed to fire in 1877, but the foundations remain visible, marked by an informational plaque.

Visitors can enjoy a 2.25-mile loop trail encircling the pond and embark on a two-mile walk through state-managed woodlands from Paugnut State Forest to Sunnybrook State Park via the John Muir Trail.

15. Laurel Duckpin Bowling Lanes

If you have yet to experience duckpin bowling, it offers a distinct alternative to traditional tenpin bowling, and a dedicated alley is located on Main Street in Winsted.

Duckpin bowling utilizes balls without finger holes, slightly larger than a softball.

Moreover, the pins in duckpin bowling are shorter and lighter than their tenpin counterparts, yet spaced similarly, making strikes a notable achievement.

Consequently, players are afforded three rolls per frame to account for this challenge.

Laurel Duckpin Lanes also embraces an appealing mid-century aesthetic, offering paper scoring systems and manual resets.

Bumpers are available for younger participants, and there are also three classic pinball machines to enjoy.