15 Best Things to Do in Derby (CT)

The city of Derby, at the confluence of the Housatonic and Naugatuck Rivers, once covered a vast area comprising the now separate towns of Ansonia, Beacon Falls, Seymour and Oxford.

Nowadays at just 5.3 densely populated square miles, Derby is officially the smallest city in Connecticut.

In the 19th century this was a manufacturing hotbed for the textile and metalworking industries, home to the first electric trolley system in New England.

You can walk along the dikes by Derby’s rivers on the Derby Greenway, learn about a pioneering woman industrialist at Osbornedale State Park and break out into the Connecticut countryside at cider mills, fruit farms and wineries.

1. Derby Greenway

You can learn a surprising amount about Derby and its neighboring cities on this two-mile trail by the Naugatuck and Housatonic Rivers.

This is officially the most trafficked multipurpose trail in the state, with more than 300,000 trips recorded in 2017. The Derby Greenway was laid down in stages from 2004 to 2013 and belongs to the Naugatuck River Greenway Trail System, which will eventually run for 44 miles from Derby upriver to Torrington.

On your walk you’ll pass through three cities, see six bridges and the extent of the dikes built after the devastating Flood of 1955, bursting the banks of both rivers and claiming 87 lives.

One of the prettiest parts of the walk is O’Sullivan’s Island, which actually a peninsula at the confluence, covered with deciduous trees.

2. Osbornedale State Park

One name that recurs in the history of industry in the Naugatuck Valley is Osborne, as the family owned a catalogue of textile and metalworking factories.

Frances Osborne (1876-1956) was especially astute, and pieced together the land for Osbornedale State Park with a series of purchases.

Mostly in Derby and on the Housatonic River, Osbornedale State Park is 417 acres of what was once a patchwork of dairy farms, now meadows and woods on rolling hills.

There’s a pond for fishing (Pickett’s Pond), several blazed trails and a museum and environmental center, which we’ll cover below.

3. Osborne Homestead

Frances Osborne is a fascinating character and merits a little more investigation, at the house she inherited from her father.

This refined Greek Revival building is from 1840 was purchased by Wilbur Osborne in 1867. Frances lived here with her second husband Waldo Kellogg, who remodeled the building in the Colonial Revival style in the 1910s.

On guided tours you’ll learn about Frances’ success as a businesswoman, see her rich ceramic collections and find out more about a passion for conservation that led to her deeding the estate to Connecticut in the 1950s.

The gardens around the Osborne Homestead are very pretty, with flowering trees, neatly clipped shrubs and an exquisite rose garden.

4. Kellogg Environmental Center

Belonging to the Connecticut Department of Energy & Environmental Protection, the Kellogg Environmental Center is a resource for school-age children, educators and also the general public.

Here you can browse exhibits relating to the environment and nature (information panels, photos and lot of mounted birds). In every season the center schedules weekend programs, family workshops and nature walks.

Typically you can get to know the geology of the region, take a bird walk, take part in trivia nights and attend talks on the nature and history of the Naugatuck Valley.

5. Birmingham Green Historic District

North of Derby’s central business district is a rather stately town green, flanked by roads that give you a distant view across the Housatonic River.

Standing on Derby Green (aka Birmingham Green) you’ll be in the middle of a planned city, developed from the 1830s by the entrepreneurs Anson Phelps and Sheldon Smith.

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

At the highest point of the green, towards the north is the Civil War Memorial.

Meanwhile much of the north, east and west frontages is taken up by three imposing 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

Holding your attention in the south-west corner of Derby Green is a beautiful Italianate building, dating to 1889. The Sterling Opera House’s architect H. Edwards Ficken is most famous for working on New York’s Carnegie Hall.

The two lower levels housed Derby’s city hall and police station until the building closed in 1965, while not long after it opened the upper floor became a performing arts venue, hosting some of the biggest personalities of the first half of the 20th century, like Amelia Earhart, Harry Houdini, Lionel Barrymore and Red Skelton.

As of 2019 the Sterling Opera House had been abandoned for more than 50 years, but the exterior is well-preserved and plans have been drawn up for a future renovation.

7. General David Humphreys House

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

The property, managed as a museum by the Derby Historical Society, was constructed for Derby’s minister in 1698. Rev.

Daniel Humphreys took up residence in 1734, marrying the widow Sarah Riggs Bowers in 1739. David Humphreys was their fourth son, and he became an aide-de-camp for General Washington and later the United States’ first ambassador to a foreign country (Spain and then Portugal). The house is open on weekdays (10:30-14:30) and has been returned to a mid-18th-century appearance.

Lots of original detail remains, in the hand-carved paneling throughout and the expansive fireplace in the rear chamber.

8. BAD SONS Beer Company

The name of this craft brewery in Derby is a tribute to the Lower Naugatuck Valley, as an acronym using the first letters of Beacon Falls, Ansonia, Derby, Seymour, Oxford, Naugatuck and Shelton.

BAD SONS’ taproom is in a striking brick industrial building, with lots of outdoor space.

There are regular visits from food trucks on weekends (think wings, Caribbean food, BBW and crepes), and on Thursdays and Fridays you can order takeout from Dew Drop Inn and Roseland Pizza respectively.

The brewery specialises in hoppy IPAS, which make up half of the 12 beers on tap in September 2019. These were accompanied by sours, a red ale, a stout and a lager.

There are board games inside, and a big fire pit outside for when the sun goes down.

9. Shelton Riverview Park

You can cross the Housatonic River to Shelton to look back at Derby from the west bank and see the 19th-century Derby-Shelton Dam, constructed to fill the Shelton Canal.

In the 17th century this park was the setting of a fort, constructed by the Pootatuck Indians who lived on the banks of the Housatonic, to prevent European colonists from progressing up the river.

There’s a playground for wee ones, a pair of ballfields, basketball courts and the white-blazed Bluff Walk, tracing the cliff top and offering occasional views between the trees.

At the east end of the park you can check out the preserved Shelton Canal locks, dating to 1867.

10. Beardsley’s Cider Mill & Orchard

Fall in Connecticut of course brings marvellous foliage, but is also apple season, and orchards like this one in Shelton grow an almost overwhelming number of varieties.

At Beardsley’s Cider Mill & Orchard there’s a pick-your-own season, roughly from mid-September to mid-October.

In chronological order, you can pick Gala, Macoun, Honeycrisp, Red Delicious, Braeburn, Granny Smith and Rome, and many more.

The farm store stays open until Christmas Eve, stocking the other produce grown here, including peaches, as well as local raw honey, apple cider, hard cider, scones, fruit breads and their famous cider apple donuts.

11. Indian Well State Park

On the west bank of the impounded Housatonic River is a 150-acre state park, with lofty mixed woodland, a beach, boat launch and the picturesque brook and waterfall that lends the park its name.

Indian Well is a horsetail waterfall, 4.6 meters high and with a splash pool at its foot enclosed by high mossy rocks.

After seeing the falls you could while away a warm sunny day at the beach and picnicking in the shaded grove close to the water.

Threading through the park is the Blue-Blazed Paugussett Trail, and keen anglers cast off for the plentiful small and largemouth bass, yellow perch, carp, sunfish, yellow perch and white catfish.

12. Frank P. Witek Memorial Park

At former reservoirs in the eastern part of Derby is a 144-acre park named in tribute to a local Medal of Honor recipient.

You might be interested to know that this was one of the earliest areas in Derby to be settled by Europeans.

Later, as the Borough of Derby swelled, brooks were dammed here to create reservoirs for steady water supply in the 1860s.

You can pay a visit to amble by the two ponds, and in the 2000s the town opened a pair of soccer fields at the park.

13. Jones Family Farms

In its 6th generation, the Jones Family has been working this land in Shelton for more than 150 years.

In summer you can call in to pick your own blueberries and strawberries. In autumn the pumpkins are ready, and Pumpkinseed Hill Farm becomes a family day out with hayrides, farmyard animals, a corn maze, autumn squash, apples and fall flowers.

Another string in the farm’s bow is the Jones Winery, begun in 2004 and growing grapes that do well in the Connecticut climate, like Chardonnay, Pinot Gris, Riesling, Vidal Blanc, Muscat Ottonel and Cabernet Franc.

These go into single varietal wines or blends to suit every palate.

A tasting of six wines includes a complimentary Jones Winery glass, and you can order a selection of CT and New England cheeses as accompaniment.

Finally, the Harvest Kitchen is a farm-to-table cooking studio for cooking and pairing classes, as well as farm education programs.

14. The Tradition Golf Club at Oak Lane

This daily fee golf course is within a few short miles, and was landscaped by the course architect Geoffrey Cornish.

The Tradition Golf Club has been reworked in the last few years, but the challenging yet engaging layout remains, rewarding accuracy and a polished short game.

The big hazards are the soaring trees, sneakily placed bunkers and surprising water holes.

The fairways hold no nasty surprises, although you will have to take on a couple of doglegs.

A nice touch is the club’s driving range with grass tees, open April to October ($13 for 70-75 balls).

15. Savino Vineyards

Go past Schreiber Park in Ansonia and you’ll arrive at a family-owned vineyard in eight hilly acres, cultivating premium vitis vinifera and American hybrid grapes.

Among the whites at Savino Vineyards are Vidal Blanc and Seyval Blanc, while the reds include Cabernet Franc, Merlot, Frontenac an St. Croix.

These are carefully blended to produce unique wines at a winery around a 100-year-old barn.

Visitors are welcomed for tastings on Saturday and Sunday afternoons from the first weekend of May to the weekend before thanksgiving.

The price for a tasting is an affordable $10 (including a souvenir glass), and you can order antipasti accompanied by olive oil imported from the owner’s Italian olive grove.