Top 15 Attractions and Activities in Derby, CT

The city of Derby, located at the junction of the Housatonic and Naugatuck Rivers, once encompassed a large area that includes the present-day towns of Ansonia, Beacon Falls, Seymour, and Oxford.

Today, covering just 5.3 densely populated square miles, Derby is officially recognized as the smallest municipality in Connecticut.

During the 19th century, this area was a thriving center for the textile and metalworking sectors and was the birthplace of the first electric trolley system in New England.

Visitors can stroll along the riverbanks of Derby on the Derby Greenway, discover the legacy of a pioneering woman industrialist at Osbornedale State Park, and explore the rural Connecticut landscape through various cider mills, fruit farms, and wineries.

1. Derby Greenway

On this two-mile pathway along the Naugatuck and Housatonic Rivers, you can gain significant insights into Derby and its neighboring communities.

This trail is the most utilized multipurpose path in the state, tallying over 300,000 visits in 2017. The Derby Greenway was developed in phases from 2004 to 2013, and it is part of the broader Naugatuck River Greenway Trail System, which is set to extend for 44 miles from Derby upstream to Torrington.

While walking, you will traverse three cities, witness six bridges, and observe the dikes constructed following the catastrophic Flood of 1955 that overflowed both rivers and resulted in 87 fatalities.

The scenic highlight of the trail includes O’Sullivan’s Island, effectively a peninsula at the confluence, adorned with deciduous trees.

2. Osbornedale State Park

The Osborne family is notably referenced in the industry history of the Naugatuck Valley, having owned a range of textile and metalworking factories.

Frances Osborne (1876-1956) was particularly sharp in her endeavors, gradually acquiring the land that now constitutes Osbornedale State Park through various purchases.

Primarily situated in Derby and along the Housatonic River, Osbornedale State Park encompasses 417 acres that were once a fusion of dairy farms, now transformed into meadows and wooded areas across rolling hills.

The park features Pickett’s Pond for fishing, several marked trails, and a museum and environmental center, details of which are provided below.

3. Osborne Homestead

Frances Osborne is a captivating figure worth exploring further, particularly in connection with her residence inherited from her father.

This elegant Greek Revival structure, built in 1840, was acquired by Wilbur Osborne in 1867. Frances resided here with her second spouse, Waldo Kellogg, who renovated the building into the Colonial Revival style during the 1910s.

During guided tours, you will uncover details regarding Frances’ achievements as a businesswoman, admire her extensive ceramic collection, and learn about her commitment to conservation, which led her to gift the estate to Connecticut in the 1950s.

The gardens surrounding the Osborne Homestead are enchanting, featuring flowering trees, neatly trimmed shrubs, and a stunning rose garden.

4. Kellogg Environmental Center

Managed by the Connecticut Department of Energy & Environmental Protection, the Kellogg Environmental Center serves as a valuable resource for children, educators, and the general public.

Here, visitors can explore exhibits related to environmental and natural science, including informational panels, photographs, and many mounted birds. Throughout the year, the center organizes weekend programs, family workshops, and nature walks.

Activities typically include geological insights about the area, bird-watching excursions, trivia nights, and discussions on the nature and history of the Naugatuck Valley.

5. Birmingham Green Historic District

Located north of Derby’s central business district, the town green presents an elegant setting, bordered by streets that offer distant views across the Housatonic River.

Standing on Derby Green (also known as Birmingham Green), you are positioned in a carefully planned city developed in the 1830s by entrepreneurs Anson Phelps and Sheldon Smith.

They relocated three churches from the old city center at Derby Landing on the east bank of the Naugatuck River to surround the green.

At the northernmost point of the green stands the Civil War Memorial.

The northern, eastern, and western sections are home to three prominent churches: the Romanesque Revival United Methodist Church (1895), the neo-Gothic Episcopal Church (1843), and the Greek Revival Congregational Church (1845).

6. Sterling Opera House

Capturing attention in the southwest corner of Derby Green is a striking Italianate structure, established in 1889. The architect, H. Edwards Ficken, is renowned for his work on Carnegie Hall in New York.

The lower two levels housed Derby’s city hall and police station until the building’s closure in 1965, while the upper floor transformed into a performance venue that hosted notable personalities from the early 20th century, including Amelia Earhart, Harry Houdini, Lionel Barrymore, and Red Skelton.

As of 2019, the Sterling Opera House had remained unoccupied for more than 50 years; however, the exterior is well-maintained, and plans for its renovation have been proposed.

7. General David Humphreys House

The Revolutionary War officer and close friend of George Washington, David Humphreys (1752-1818), was born in this house located in Ansonia.

The property is currently managed as a museum by the Derby Historical Society; it was originally constructed as a residence for Derby’s minister in 1698. Rev. Daniel Humphreys moved in here in 1734 and married the widow Sarah Riggs Bowers in 1739. David Humphreys was their fourth son, subsequently serving as an aide-de-camp to General Washington and later becoming the first ambassador of the United States to a foreign nation (Spain and then Portugal). The house is accessible weekdays (10:30-14:30) and has been restored to reflect an appearance from the mid-18th century.

Numerous original features remain intact, including the hand-carved paneling throughout and a spacious fireplace in the rear chamber.

8. BAD SONS Beer Company

The name of this craft brewery in Derby pays homage to the Lower Naugatuck Valley, serving as an acronym derived from the initial letters of Beacon Falls, Ansonia, Derby, Seymour, Oxford, Naugatuck, and Shelton.

BAD SONS’ taproom is located in an impressive brick industrial edifice, featuring ample outdoor space.

On weekends, food trucks frequently visit, offering a variety of cuisines including wings, Caribbean dishes, BBQ, and crepes. Additionally, on Thursdays and Fridays, takeout options are available from Dew Drop Inn and Roseland Pizza, respectively.

The brewery focuses on hoppy IPAs, which constituted half of the 12 beers available in September 2019, alongside sours, a red ale, a stout, and a lager.

The interior includes board games, and outside, a sizable fire pit is provided for when evening falls.

9. Shelton Riverview Park

Crossing the Housatonic River into Shelton provides an opportunity to gaze back at Derby from the west bank, where you can view the historic 19th-century Derby-Shelton Dam, constructed to supply water to the Shelton Canal.

This park served as a fort in the 17th century, established by the Pootatuck Indians who inhabited the banks of the Housatonic, intended to impede the advance of European settlers up the river.

Facilities within the park include a playground for younger children, two ballfields, basketball courts, and the white-blazed Bluff Walk, which follows the cliff edge and features occasional vistas through the trees.

At the eastern end of the park, you can explore the preserved Shelton Canal locks, dating back to 1867.

10. Beardsley’s Cider Mill & Orchard

Autumn in Connecticut not only brings stunning foliage but also celebrates apple season, with orchards such as this one in Shelton cultivating an impressive diversity of apple varieties.

At Beardsley’s Cider Mill & Orchard, the pick-your-own season generally occurs from mid-September to mid-October.

In chronological order, you can select from Gala, Macoun, Honeycrisp, Red Delicious, Braeburn, Granny Smith, Rome, among many others.

The farm store remains open until Christmas Eve, offering locally produced goods, including peaches, raw honey, apple cider, hard cider, scones, fruit breads, and the renowned cider apple donuts.

11. Indian Well State Park

Located on the western shore of the impounded Housatonic River, this 150-acre state park features towering mixed forests, a beach, a boat launch, and the scenic brook and waterfall that give the park its name.

Indian Well is a horsetail waterfall, standing 4.6 meters tall with a splash pool at its feet, surrounded by high, moss-covered rocks.

After viewing the falls, you may want to spend a pleasant day at the beach and enjoy a picnic in the shaded area adjacent to the water.

The park includes the Blue-Blazed Paugussett Trail, and aspiring anglers can attempt to catch abundant small and largemouth bass, yellow perch, carp, sunfish, yellow perch, and white catfish.

12. Frank P. Witek Memorial Park

Located in the eastern section of Derby, this 144-acre park was established in honor of a local Medal of Honor recipient.

Interestingly, this was one of the earliest regions in Derby to be inhabited by Europeans.

Subsequent to the borough’s expansion, brooks were dammed here in the 1860s to create reservoirs for a consistent water supply.

Visitors to the park can enjoy leisurely walks around the two ponds, and in the 2000s, the town developed two soccer fields within the area.

13. Jones Family Farms

Now in its sixth generation, the Jones Family has been cultivating this land in Shelton for more than 150 years.

During summer, visitors can pick their own blueberries and strawberries. In the autumn, pumpkins are harvested, and Pumpkinseed Hill Farm transforms into a family destination offering hayrides, farmyard animals, a corn maze, autumn squash, apples, and seasonal flowers.

Additionally, the farm operates Jones Winery, established in 2004, producing grapes that thrive in Connecticut’s climate, such as Chardonnay, Pinot Gris, Riesling, Vidal Blanc, Muscat Ottonel, and Cabernet Franc.

These grapes are blended to create distinctive wines in a winery housed within a barn that is around 100 years old.

Wine tastings include six varieties with a complimentary glass and pairing with local CT and New England cheeses.

Furthermore, the Harvest Kitchen serves as a farm-to-table cooking studio offering cooking and pairing classes, alongside educational programs about farming practices.

14. The Tradition Golf Club at Oak Lane

This daily-fee golf course is located just a few miles away and was designed by course architect Geoffrey Cornish.

The Tradition Golf Club has undergone renovations in recent years, yet the challenging and engaging design continues to encourage accuracy and skillful short game play.

Notable hazards include towering trees, cleverly positioned bunkers, and unexpected water features.

The fairways are relatively straightforward, though some dogleg challenges must be navigated.

A welcome addition is the driving range equipped with grass tees, open from April to October (costing $13 for 70-75 balls).

15. Savino Vineyards

Proceeding past Schreiber Park in Ansonia leads you to a family-run vineyard extending over eight hilly acres, dedicated to the cultivation of premium vitis vinifera and American hybrid grapes.

Among the white varieties at Savino Vineyards are Vidal Blanc and Seyval Blanc, while the red choices include Cabernet Franc, Merlot, Frontenac, and St. Croix.

These grape varieties are meticulously blended to create distinctive wines at a winery located in a historic barn that is nearly 100 years old.

Visitors are invited for tastings on Saturday and Sunday afternoons, starting from the first weekend of May until the weekend prior to Thanksgiving.

The tasting fee is an economical $10 (including a commemorative glass), and antipasti may be ordered alongside imported olive oil from the owner’s Italian olive grove.