Waterbury, Prospect, Naugatuck, Beacon Falls, Oxford, Seymour, Ansonia and Derby
Approximate Mileage: 65
Approximate Driving Time: Full Day Trip
Summary: Start in Waterbury I-84 east exit 22, left on S. Main St., go under I-84 overpass, left on Grand St.*; at jct. of Grand and Meadow St., right on Meadow St.; at the 3rd light right on West Main St., bear left around the Civil War Monument, keeping the Waterbury Green on right. At the end of Green take a right on North Main St at the next light, go straight on Bank St., at jct. of Bank and Grand St., left on Grand St., straight on Union St. straight on Hamilton Ave./Rte. 69 south to Prospect. At jct. of Rte. 69 and 68, take Rte. 68 west to Rte. 8 south to Exit 27/Maple St. to Naugatuck. Right off exit on Maple St., first right on Water St., to Naugatuck Historical Society. Take Cedar St. (straight out of Society) left on Church St. At end of Church St., left on Rubber Ave., left on Old Firehouse Rd. right on Maple St. to Rte. 8 south to Beacon Falls to exit 24; end of ramp right on Rte. 42 west to Oxford. At jct. Rte. 42 and 67 in Oxford, right on Rte. 67 north for .2 mile to Oxford Green, retrace steps passing jct. of Rte. 42 and 67 continue on Rte 67 south to Seymour. At jct. Rte. 313 and 67, take Rte. 67 east go under the Rte. 8 overpass, first right on Main St./ Rte. 115 south. At the jct. of Rte. 313 and 115, right on Rte. 313 west (Broad St.) cross Naugatuck River, at the light, continue straight onto West St. to The Seymour Historical Society and Green. Retrace your steps to Rte. 313 and 115 take Rte. 115 south through downtown Ansonia. At the jct. of Rte. 115 and 243, take a left on Rte. 243 east (Elm St.) to the red General David Humphreys House.* Retrace your steps continue on Rte. 115 south. At the jct. of Rte. 115, 8 and 34 in Derby, take a right on Rte. 34 west and drive through downtown Derby. Just past the Gilder Yale University Boathouse (left) take first right on E St. go up the hill, at the end of the road take a left on Hawthorne Ave. (Osborndale State Park - right on Chatfield St. follow for 1 mi.) follow for 2 mi. to the Osborne Homestead Museum and the Kellogg Environmental Center on left. Leaving the museum and center, take a right on Hawthorne Ave., at the first stop sign take a right on Lakeview Terrace, at the stop sign, bear right, at the next stop sign, take a right on Rte. 34 west. At jct. of Rte. 34 and 188, take a right on Rte. 188 north towards Quaker Farms and Southbury to I-84 east to Waterbury to exit 22 where this tour began.
To reach the Palace Theater, from South Main St. proceed straight after the first traffic light and turn right on Scovill St. to the parking garage on your left. In 1920, Thomas Lamb designed The Palace Theater in the Renaissance Revival style; note the eclectic mix of Greek, Roman, Arabic and Federal motifs on the buildings exterior and its ornate dome ceilings and grand lobby spaces inside. The Palace began as a movie and vaudeville house and changed venues with the times until it closed in 1987. Eighteen years later the newly restored theater has once again become the cultural heart of Waterbury.
Proceeding on Grand St. to explore more of the city's rich architectural history. Today many of its gracious colonial revival buildings house a variety of shops. At the first light, on your left, note the elegant Art Deco granite Post Office replete with Egyptian hieroglyphics.
Driving along Grand St. you will pass an imposing municipal complex designed by architect Cass Gilbert. Further along, on the left is the Colonial Revival style brick and limestone City Hall completed in 1915 and on the right is the Chase Building, designed in the Renaissance Revival style and now part of an expanded City Hall. Next is the library with a 1919 statue of Benjamin Franklin by noted American sculptor Paul Wayland Bartlett.
At the jct. of Grand St. and Meadow St., (3rd light) on the left is Library Park, designed by Frederic Law Olmsted, son of the famed Central Park designer. Along the parks lower wall there are 47 sandstone and granite grave markers, which is all that remains of the time when the park was the town 's burying ground from 1686-1890.
A statue of Michael McGivney, a city native and the founder of the Knights of Columbus frames the center of the intersection and the Waterbury Republican American Newspaper with its distinctive Clock Tower rising 240 feet over the city is across the street.
Beginning in 1909 this building served as the Union Station of the New York, New Haven and Hartford Railroad Company. It was modeled after the Torre Del Mangia in Sienna Italy and designed by McKim, Mead and White at a cost of $322,000. The President of the Railroad, C.W. Mellon traveled in Italy, the story goes, noticed the tower, and decided to put it on the next depot he built.
Take a right on Meadow St., at the jct. of Meadow St. and West Main St. (2nd light) take a right on West Main St., bear left around the Civil War Monument, one of the few memorials to represent the theme of a united nation emerging from a tragic war represented by Lady Victory holding out an olive branch.
On your left is the Mattatuck Museum with its striking contemporary design by Cesar Pelli, (parking in lots on Park Place or along the Green). The museum 's displays depict the story of northern slavery and the industrial history of the Naugatuck Valley when clocks, brass buttons and rubber goods were household goods worldwide.
On the second floor, two galleries are devoted to 18th c. through 20th c. Connecticut Art and one has changing exhibits. The third floor has a remarkable display of 10,000 buttons, all manufactured in Waterbury.
Continue on West Main St. past the Odd Fellows Building, circa 1895 that uses sandstone, brick and terra cotta creating a look reminiscent of villas on the canals of Venice and the imposing Immaculate Conception Church built in 1928.
Moving along, the Elton at number thirty was once a grand hotel whose design was inspired by classical France. It was here on the balcony that John F. Kennedy made his last campaign speech in 1960.
At the end of Green take a right on North Main St. The elegant Bronze Horse Fountain that served as a drinking trough for horses was erected in 1888 as a simple memorial to Caroline Welton, a lover of animals. The statue depicts Knight, Caroline's favorite horse.
At the next light go straight on Bank St. the impressive Howland Hughes Store on the right complete with Greek columns, whimsical roof brackets and gothic arches is oldest continuously operating department store in the state. Today, it houses the Connecticut Store, an extensive gallery of imaginative and tasteful Connecticut products.
Shoppers may learn a bit of Connecticut history while finding unique gifts. For example, few may be aware that the Waterbury Button Company has been supplying buttons for U.S. military uniforms since the War of 1812. Today they make buttons for most of the services, for marching bands and state police departments nationwide, as well for companies from Donna Karan and Polo to J.C. Penney.
Handsome gift sets of blazer buttons sold here include buttons designed for professions such as doctor and lawyer, and for hobbies like sailing or tennis. History buffs should relish replicas of the buttons made for the officers and crew of the ship Titanic. This is also the only company licensed to create buttons featuring the state seal for all 50 states.
Another standby, the Wiffle Ball, is another Connecticut product, born over 50 years ago in Shelton, and still a family-run business. Balls, bats, flying saucers, official caps and signature ties are among the offerings in their Waterbury outpost.
At the jct. of Bank and Grand St., take a left on Grand St., continue straight on Union St. (1.5 miles) to Timexpo: The Timex Museum on the left easily identified by the 40 ft. high Easter Island Moai Statue. Located in renovated brass mill Timexpo's exhibits trace the history of Waterbury Clock from the 1850's to the company it became in 1969, the Timex Corporation. The museum's. Coincidences or Connections Gallery is a tribute to the theories of Thor Heyerdahl about ocean travel by ancient civilizations. Leaving Timexpo, retrace your steps out of the parking lot, at the light take a left on Union St. and continue past Brass Mill Center Mall, continue straight on Hamilton Ave./Rte. 69 south to Prospect.
Enter Prospect, on Rte. 69 south, passing the Hotchkiss House Museum where the Hotchkiss Family lived from 1820-1978. The second floor of the house operated as a private academy from 1820-1840, after the school closed, the house evolved with the times and today tours by appointment offer a glimpse of family life in a rural Connecticut town. The Shed behind the house displays the work of local artists on Saturdays from 10-4 March through December.
At the jct. of Rte. 69 and Rte. 68, take a left on Rte. 68 east to the Prospect Green. Take a right on Center Street to tour the Green with its fieldstone Meeting Place, a classic Congregational Church, the Center School House circa 1867 and the 1907 Soldiers Monument. Retrace your steps to the jct. of Rte. 68 and Rte. 69, take Rte. 68 west to Rte. 8 south to Exit 27/Maple Street.
Naugatuck is known for the accomplishments of its residents including J.H. Whittemore who changed the look of the community with 11 architectural commissions to McKim, Mead and White; Charles Goodyear who received a patent for the vulcanization of rubber in 1843; and Peter Halajian who opened a candy store that evolved into Peter Paul Mounds. Today, the factory on Rte. 63 south is the only place in the world where Mounds and Almond Joys are made.
At the end of the exit take a right on Maple St. crossing the Naugatuck River. Take your first right on Water St., the Naugatuck Historical Society Museum is on the right located in the former 1910 Train Station built of stucco and brown sandstone in the Spanish Colonial revival style. The museum 's collections illustrate the industrial, educational, and family life of the town.
To explore some of the most beautiful architecture in the region, go straight out of the Train Station's parking lot onto Cedar St.; at the stop sign take a left on Church St. On the left is a Post Office circa 1917 built in the Spanish Colonial Revival Style and to the right is St. Frances Church, circa 1890 designed in the Gothic Revival style. A little further along, on the left, is the 1894 Neo-Classical Revival styled Library constructed by McKim, Mead and White of pink granite and crowned with a continuous frieze incised with names of famous authors. Fluted ionic columns and bronze lamp stands flank the recessed entrance of the Library that has an elaborate domed rotunda and a gold and red mosaic tiled floor. Across the street is the 1902 Congregational Church with its distinctive tower and elaborate entrance designed in Baroque Neo Classical Revival style by McKim, Mead and White.
Next on the right, is the Green laid out by McKim, Mead and White in 1931. The Green has a classically balanced axial plan with the lawn and the paved walkways radiating from the 1885 Civil War Monument and the 1895 Memorial Fountain.
At the light, you will see the 1896 Hopson Block made of red and gold brick in the Renaissance Revival style on the left and St. Michael's
Church made of red brick in the high Victorian style on the right.
At the end of Church St., take a left on Rubber Ave., a left on Old Firehouse Rd. a right on Maple St. and continue on Rte. 8 south.
The drive along Rte. 8 south from Naugatuck to Beacon Falls is bordered by undulating hills that follow the serpentine course of the Naugatuck River making it a scenic drive any time of year. Take Exit 24 to Beacon Falls at the end of the ramp take a right on Rte. 42 west. Beacon Falls was once a thriving company town with busy textile and rubber factory complexes; today it is a somnolent riverside town. Driving along Rte. 42 west you will pass Beacon Mill Village, on the National Register, which was the headquarters for the Home Woolen Company in 1863, and more recently, for the Beacon Falls Rubber Shoe Company until 1930 when it became part of the Uniroyal complex. Today, it has been converted to housing. The Mill complex remains a testament to this town 's industrial heritage that included the invention of the friction match in 1843.
Leaving Beacon Falls, cross the Naugatuck River on Hearne W. Beaver Jr. Memorial Bridge, named and dedicated as the first Memorial in Connecticut to a soldier killed in the Vietnam War. Along Rte. 42 west to Oxford you will pass a one room schoolhouse, built in 1779, a walk in entrance to Naugatuck State Forest and several historic homes that pre-date the American Revolution.
At the jct. of Rte. 42 and Rte. 67 in Oxford take a right on Rte. 67 north follow for .2 mile passing St Peter's Episcopal Church built in 1834 in the Gothic style. Take a right on Academy Rd. to visit the "Upper" Green and the classic federal styled Oxford Congregational Church built in 1795.
To the left of the church is the Abel Wheeler House built in 1786 where the Terry James Historic Art Gallery is located. The Gallery features art from American History with a focus on American Military History. Retrace your steps passing the jct. of Rte. 67 and 42, and continue on Rte. 67 south to Seymour.
At the jct. of Rte. 313 and 67, take Rte. 67 east go under the Rte. 8 overpass, take your first right on Main St./ Rte. 115 south. To explore the Seymour Antiques District located on Bank St., park along Main Street.
Seymour, once part of Derby, has a unique place in Connecticut 's industrial history. It was here that David Humphreys, a friend of Washington 's and Jefferson 's and our nation's first Foreign Ambassador appointed to Portugal then Spain created a model-manufacturing village. In 1802, Humphreys shipped the first 100 Merino sheep from Spain to the U. S. He purchased 200 acres of land near a natural waterfall of the Naugatuck River and built a state of the art wool factory. The town quickly attained a national reputation for producing unparalleled woolen cloth. The rich and famous as well as Presidents Thomas Jefferson and James Madison used the cloth manufactured in Humphreysville, named in honor of David Humphreys. By 1850, the town was thriving with a variety of industries and many wanted to separate from Derby. The Governor granted the petition for separation in 1850 and the town was renamed Seymour in honor of the Governor.
Continue on Main St. to the jct. of Rte. 313 and 115. To visit the historic district of Seymour take a right on Rte. 313 west (Broad St.) cross the Naugatuck River, look to the right to see the dramatic falls that powered industry in Humphreysville. At the light, passing Broad Street Park on the right and the 1916 Congregational Church on the left, continue straight across onto West St.. Along the way pass the Trinity Cemetery that has burials dating to the 1700's. The Seymour Historical Society is located at the top of the hill, on the left, in the former home of Katharine Matthies. The Society has changing monthly exhibits of local memorabilia and displays of local artifacts relating to town history. Just beyond, at the 4 corners or doctors corners are four lovely colonial homes, some pre-dating the Revolutionary War, that were the residences of doctors for 100 years. To the right is the Trinity Episcopal Church built in 1797. Retrace your steps back to the jct. of Rte. 313 and Rte. 115 and continue on Rte. 115 south to Ansonia.
Entering Ansonia on Rte. 115 south you will pass the historic Farrel Corporation. Established in 1847 they still maintain and repair heavy equipment such as sugarcane mills for Hawaii and the Caribbean that they manufactured for 150 years. Upper Main St. (Rte. 115) of Ansonia still maintains much character, as most of the buildings are well over 100 years old. As you drive down lower Main St. you will note newer architecture that is the result of the devastating flood of 1955.
To visit General David Humphreys House, at the jct. of Rte. 115 and 243, take a left on Rte. 243 east (Elm St.), the red house is on your right across the street from a small cemetery. Located in Ansonia's Historic District, the Humphreys House 1698 c. is the birthplace of David Humphreys, Revolutionary War officer, author, first ambassador appointed by Washington to a foreign nation and successful woolen manufacturer. The house has been restored to its mid 18th c. appearance, incorporating elements of Lower Naugatuck Valley history from the pre-colonial, through the federal period. The Old Episcopal graveyard is across the street and was where the first Episcopal Church was built in 1746. The Church was moved and attached to the Humphreys House and used as a summer kitchen. The Church stood where Reverend Richard Mansfield, who served for 72 years, is buried.
To reach the Ansonia Nature Center continue past the Humphrey House,continue past the Humphrey House, bear right onto Platt's Hill Rd. at the triangle a block away, the road turns into Prindle Ave. at the stop sign at the top of the hill continue straight, take a right on Ford St. across from Emmett O'Brien Regional Tech. School, a left on Benz St., a right on Milan St; at the fork bear left on Deerfield Rd.; the Center is at the end of the road. A fine Interpretive Center surrounded by butterfly, wildflower and fern gardens along with several trails that wind their way through a variety of habitats can be enjoyed here. Retrace your steps to the jct., of Rte. 243 and 115.
Take a left on Rte. 115 south passing the old Derby Town Green. To reach the Derby Greenway at the jct. of Rte. 115 and 243 take a right on Division St., the parking lot is on your left at the first light. Retrace your steps and continue on Rte. 115 south.
At the jct. of Rte. 115, 8 and 34 in Derby, take a right on Rte. 34 west passing the jct. for Rte. 8. Follow Rte. 34 west through Derby, located at the he confluence of the Housatonic and Naugatuck Rivers. For some time parts of the present day city of Derby were also known as Smithville and then Birmingham agriculture, foreign maritime trade, and manufacturing made the city prosperous. To explore the Green, take a right on Elizabeth St.and follow to the top of the hill. The Derby Green is notable for 3 churches, made of brick wood and stone, a Civil War Monument built by Derby and Seymour and the former Sterling Opera House, where the Military Order of the Purple Hearts held its first convention. The Opera House is now part of the Save America's Treasures program. Retrace your steps and continue on Rte. 34 west. Driving along the Housatonic River you will pass a series of well-preserved canals and the Ousatonic Dam built in 1870 that powered industry that once thrived.
Just past the Gilder Yale University Boathouse on your left, take your first right on E St. go up the hill, at the end of the road take a left on Hawthorne Ave., the Carnegie-funded Derby Neck Library started by local industrialist Wilbur Fisk Osborne is on the right. To reach Osborndale State Park, take a right on Chatfield St. follow for one mile to the entrance of the park. Retrace your steps back to the jct. of Chatfield St. at the triangle, and Hawthorne Ave., take a right on Hawthorne Ave., follow for 1 mile to the Osborne Homestead Museum and the Kellogg Environmental Center.
The house built in the mid-1800's, was enlarged and remodeled in the Colonial Revival style in the 1920's. Today the interior displays the original contents of the estate and celebrates the life of Frances Osborne Kellogg, an accomplished businesswoman and conservationist. The grounds are landscaped with formal flower gardens, ornamental shrubs, and flowering trees. Next to the House, the Center is a natural science and environmental educational facility operated by the Bureau of Parks and Recreation.
Leaving the museum and center, take a right on Hawthorne Ave., at the first stop sign take a right on Lakeview Terrace, at the stop sign, bear right, at the next stop sign, take a right on Rte. 34 west. Following the Housatonic River, you will be pass Pink Cove, a popular fishing spot and Indian Wells State Park located across the river. At the jct. of Rte. 34 and 188, take a right on Rte. 188 North towards Quaker Farms, a scenic and historic section of Oxford. (A second option is to continue on Rte. 34 west crossing the Stephenson Dam and continuing on Rte. 34 through Monroe and Newtown to the jct. of Rte. 34 and I-84, take I-84 east to Waterbury to exit 22 where this tour began.)
At the jct. of Rte. 188 and Rte. 334, continue on Rte. 188 north toward Southbury passing the Keith Mitchell Forest Reserve of 1000 acres of mature trees. Along the way, pass pre-revolutionary homes and the classic Episcopal Church. Entering Southbury, you will pass Southford Falls State Park. Starting in the mid.-1800's the waterfall on Eight Mile Brook provided power for a series of paper mills at this tranquil park. The most successful mill operation was the Diamond Match Company that used old paper and rags to make paperboard for matchbooks and boxes. This early recycling venture operated at Southford Falls until it was destroyed by fire in 1923. Today, one of the features of the park is the traditional covered bridge built by Ed Palmer and artist and author Eric Sloane based on 18th century arch design plans of bridge builder Theodore Burr. This historic park has a pond stocked with trout, picnicking, hiking on loop trails, and a tower lookout with inspiring views of the surrounding parkland.
At the jct. of Rte. 188 and Rte. 67, take a left onto Rte. 188 north and Rte. 67 north at the split of Rte. 67 and Rte. 188, take a right and continue on Rte. 188 north. Following this tree lined road you will pass the Oxford Airport. At the jct. of Rte. 188 and I-84, take a right on I-84 east to Waterbury exit 22 where this tour began.