The bustling town of New Milford is located on the northeastern shore of Candlewood Lake, where generations of wealthy New Yorkers have built second homes.
One of the estates, which belonged to industrialist Frank Harden in the mid-20th century, has since become elegant Harrybrook Park, with its own museum in Harden’s first-floor home built in 1941. Like any self-respecting New England town, New Milford has quaint greenery and stately Victorian architecture.
The city centre is also healthy, with locally owned restaurants, boutiques and amenities, while the shores of Candlewood Lake are lined with golf courses, marinas and beaches.
1. New Milford Township Green
This long stretch of lawn and trees runs along the east side of New Milford city centre and is preceded by palatial Victorian homes, restaurants, civic buildings and two magnificent churches.
The New Milford Township Green remains a gathering place for seasonal events.
The biggest of these is Country Market Day at the end of June, with over two hundred stalls made up of vendors and community organisations over two days for food, old-fashioned games, arts and crafts, live music and lots of kids things to do.
In the coming season, there is a row of Christmas trees in the middle of the green space, which have a special lighting ceremony at the end of November
2. Lover’s Jump State Park
At the turn of the 18th century, according to tradition, Princess Lilinonah, daughter of the Potatuck Indian chief Waramaug, and her lover jumped to their deaths from the rock from which the park was named.
Lovers Leap is 365 meters high, and if you’re in high spirits, it’s a great vantage point overlooking the Housatonic River Gorge.
About a third of the park’s 160 acres was donated by the Heard family in 1972. Complementing the natural beauty, Lover’s Leap State Park has many interesting historical sites, such as the stunning Lover’s Leap Bridge built by Berlin in 1895, Iron Bridge Company and Yellow Cat Tea House, the vine remnants of Heard Manor.
On the northwest side of the park, you can see the ruins of a mill by the water.
3. New Milford Historical Society and Museum
At the northern end of Greentown is a complex managed by the New Milford Historical Society, which collects, preserves and interprets objects and documents related to the New Milford area.
The main gallery is attached to Knapp House (1815), a commercial store from 1796 and the first bank in New Milford in 1822. The museum’s permanent exhibits cover a range of topics, all expertly researched and accompanied by a wealth of artifacts.
These are Black Lives Matter in the history of New Milford, the former colonial peoples of New Milford, tobacco growing in New Milford, the creation of Candlewood Lake, and business and commerce in New Milford in the 20th century, to name a few .
You can also investigate New Milford lawyer and statesman Roger Sherman (1721-1783), the only one who signed all the founding documents of the United States.
4. Harrybrook Park
Harrybrook Park is located at the southwest corner of Lovers Leap State Park on an estate donated to the town by New York industrialist Frank Harden and his wife Elizabeth.
The couple spent their weekends and holidays here from 1941 to 1965, and their former home is preserved as a home museum filled with period furniture, decor and art.
Outside there are manicured gardens, two gazebos, picnic areas and a picturesque riverside walk.
Marilyn Monroe and Arthur Miller, who lived in neighbouring Roxbury, are known to have visited the Harden family in the late 1950s.
In 2019, Harrybrook Park welcomed its first pair of peacocks (named Liz and Frank) in over three decades.
5. Bank Street
For a town of just 28,000 people, New Milford has a bustling main shopping street filled with independent local businesses and stunning views of the western Connecticut hills through a canyon of east and west buildings.
There is a yoga studio, a toy store, a bookstore, a jewelry store, a salon/spa, a health food store, and restaurants here and along Rail Street and Main Street.
Lucia (51 Bank Street) serves modern Italian cuisine, Zaragoza (31) offers snacks, and River & Rail Cafe (21) offers fast food and healthy options.
Turn it into a real date with a movie at the elegant Bank Street Theatre, which dates back to 1920 and shows new Hollywood films.
6. Candlewood Lake
A big contributor to New Milford’s appeal is its proximity to Candlewood Lake.
This narrow body of water has meandering, wooded banks and was formed in the 1920s by a hydroelectric dam just south of the confluence of the Housatonic and Rocky rivers.
It’s not hard to see why many New Yorkers own a second home on Lake Candlewood, with beaches, golf courses, marinas and plenty of other recreational amenities along the idyllic 60 miles of shoreline.
New Milford has a public beach, Lynn Deming Park (residents only) and a waterside golf course.
You can also rent a kayak or jet ski from Gerard’s Marina a little further south.
For a beach that’s open to all, there’s Squantz Pond State Park, 12 miles west of the lake, and Little Dike Point Park in New Milford, which requires 24-hour advance reservations.
Take the pulse of Western Connecticut’s cultural scene at this small but well-structured production theater.
The setting is a former Black Adventist church building built in 1902 and repurposed for performing arts by the New Milford Center for the Creative Arts in the 1970s.
The owner has been known as TheaterWorks since 1992 and has a season from early March to the end of December.
Some of the picks for the 2019 season are Ronald Harwood’s Quartet, David Mamet’s Prosecution Witness and Race.
If you’re in town in June, take note of the 2019 launch of the 10 Minute Games Festival, which has a calendar of readings, receptions and shows to help young talent thrive.
8. Elephant Trunk Flea Market
For over four decades, bargain hunters, upcyclists, food lovers, collectors, treasure hunters and entrepreneurs of all kinds have flocked to New Milford’s huge outdoor market.
The Elephant Trunk Flea Market trades every Sunday from April to December, and no two weekends are alike.
Suppliers come from all over the East Coast and on a typical Sunday there will be over 500 suppliers all set up and ready to trade by 07:00. Normal admission to the market is $2, but if you’re an avid deal seeker, you can purchase an Early Buyers pass to enter the venue by 05:45, while super loyal shoppers can get Superearly Buyers tickets in the cover of darkness Go down to 04:45!
9. Bull Covered Bridge
Crossing the Hosatonic River just outside the New Milford border is one of only three surviving covered bridges in Connecticut.
The site has had a crossing since 1760, built by Jacob and Isaac Bull.
The oldest timber on the current lattice truss bridge dates back to 1842, with additional bracing added over the past 180 years or so.
What impresses you about Bull’s Bridge is that the crossing is over 30 meters long.
As with all covered bridges, the shelter above protects it by isolating the wooden bridge floor from the elements.
Bull’s Bridge has been listed on the National Register of Historic Places since 1972 and is passed west by the world-famous Appalachian Trail.
10. Lynn Deming Park
New Milford has its own public beach at Candlewood Lake, open from Memorial Day to Labor Day.
Lynn Deming Park has a large expanse of sand gently plunged into the calm waters of the lake, surrounded by woods.
There are lifeguards throughout the season, generally between 11:00 and 18:00, as well as bathrooms, gazebos and picnic tables in the woods behind.
This all sounds perfect, but the biggest downside is that only residents with a car pass can use the park.
If you are visiting family in New Milford, you will need a vehicle to enter.
11. Mine Reserves
In this natural and historical reserve next door to Roxbury, you’ll stumble upon the ghostly remains of a 19th-century iron mine and furnace.
Half of the hills here are in New Milford, and the reserve is on the eastern slope, the Roxbury side.
Shafts have been dug in the mountains from the first days of European settlement, but the main large-scale operation was established in 1865 by the Shepaug Spathic Steel Company to mine iron carbonate ore.
The mine and the furnace were in operation until 1905, and you can take a look at the latter, marked with an interpretive panel that looks like a medieval tower due to its gothic arches.
12. Bridgewater Country Fair
The wealthy town of Bridgewater, just south of New Milford, hosts a healthy and popular country fair in mid-August.
The event will celebrate its 70th anniversary in 2022 and raise funds for the Bridgewater Volunteer Fire Department, Connecticut’s last self-sustaining fire department.
The three-day celebration kicks off Friday night with a parade of volunteer fire brigades from Connecticut and New York state, showcasing new fire trucks and equipment, as well as beautiful vintage machinery.
On weekends there are BBQ tents, fried dough, tacos, beer, roast beef, roast chicken, ice cream and fruit smoothies, accompanied by rides, tractors, crafts and live music.
Of course, it wouldn’t be a country fair without competitions for everything from eating pies to canning, fruit, vegetables, flowers, baking, livestock and even eggs.
13. Candlewood Valley Country Club
New Milford has a well-regarded public golf course in rolling countryside beside Candlewood Lake.
A forgiving front nine will get you in top shape, and then a back nine that will test your accuracy tremendously.
You’ll do better than most if you keep your score intact through the doglegs, narrow fairways and multiple obstacles on the 13th, 14th, 15th and 16th holes.
It costs $42 on weekdays and $50 on weekends (walking), but if you want to squeeze in nine holes before the sun sets, you’ll need to pay a special twilight fee.
The Clubhouse restaurant serves burritos, flatbreads, pizzas, burgers and sandwiches with elevated views of the 18th court and refreshment carts outside the court.
14. Nightmare brewing
You can sip local drinks at this relaxed craft brewery, dump pints and flights from Thursday through Sunday, and cheer on the growlers.
When we put this list together in August 2019, there were five beers to choose from, including Hostile Hitchhiker, a Hops Pale Ale, Ominous Basket, a Blonde Ale, and three IPAs.
There’s always a guest tap, and as of this writing, it’s a cider from Spoke + Spy Ciderworks in Middletown.
The bar offers snacks, and if you want something more hearty, you can bring your own or order from the Cobblestones American Grille.
15. Young’s Field
Nestled on the Housatonic River in the center of town, Young’s Field is a great place to get some fresh air, with a large lawn, a skate park, children’s playground, basketball courts, two baseball fields, tennis courts and a gazebo.
There is a kayak ramp just across from Young’s Field Road, and if you want to stay outside a bit longer, you can take the New Milford River Trail, a paved greenway that runs along Housatonic from Boardman Road to Gaylordsville 5 miles.
Where to Stay: Best Hotels in New Milford, CT (CT)
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