The prosperous town of New Milford rests on the north-eastern shore of Lake Candlewood, where generations of wealthy New Yorkers have set up second homes.
One such estate belonged to the industrialist Frank Harden in the middle of the 20th century and has since become the genteel Harrybrooke Park, with its own museum in the one-floor home Harden built in 1941. Like any self-respecting New England town, New Milford has a quaint green and a helping of stately Victorian architecture.
The downtown is in rude health too, for its locally-owned restaurants, boutiques and amenities, while the shores of Candlewood Lake are lined with golf courses, marinas and beaches.
1. New Milford Town Green
This long finger of lawns and trees runs down the east side of downtown New Milford, and is fronted by palatial Victorian homes, restaurants, civic buildings and two grand churches.
New Milford Town Green continues to be a gathering place for seasonal events.
The biggest of these is Village Fair Days at the end of June, when for two days the way is flanked by more than two hundred booths by vendors and community organisations, for food, old-time games, arts and crafts, live music and lots of things for children to do.
In the advent season there’s a line of Christmas trees down the middle of the green, and these are illuminated with a special Lighting Ceremony at the end of November
2. Lovers Leap State Park
At the turn of the 18th century, according to tradition the Pootatuck Indian Chief Waramaug’s daughter, Princess Lillinonah, and her lover jumped to their deaths from the rock that gives this park its name.
Lovers Leap is 365 metres high and if you’ve got the energy is a great vantage point over the Housatonic River gorge.
The park is in 160 acres, about a third of which was donated by the Hurd family in 1972. To go with its natural beauty Lovers Leap State Park has lots of interesting scraps of history, like the stunning Lovers Leap Bridge, constructed by the Berlin Iron Bridge Company in 1895, and the Yellow Cat Tea House, a vine-clad remnant from the Hurd estate.
To the north-west side of the park you can make out the ruins of mills by the water.
3. New Milford Historical Society and Museum
At the north end of the Town Green there’s a complex of buildings in the care of the New Milford Historical Society, collecting, preserving and interpreting objects and documents relating to the New Milford area.
The main gallery is attached to the Knapp House (1815), a mercantile store from 1796 and the first bank in New Milford, from 1822. The museum’s permanent exhibits cover a range of topics, all expertly researched and accompanied by lots of artefacts.
To name a few, these are, Black Life in the History of New Milford, New Milford’s Pre-Colonial Peoples, Tobacco Farming in New Milford, the Creation of Candlewood Lake and Business and Commerce in New Milford in the 20th century.
You can also investigate New Milford lawyer and statesman, Roger Sherman (1721-1783), the only man to sign all of the United States’ founding documents.
4. Harrybrooke Park
In the south-western nook of Lovers Leap State Park, Harrybrooke Park is on an estate donated to the town by the 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 kept as a house museum, enriched with period furniture, decoration and art.
Out in the grounds are manicured gardens, two pavilions, picnic areas and a picturesque river walk.
In the late-1950s Marilyn Monroe and Arthur Miller, who lived in neighbouring Roxbury are known to have paid the Hardens a visit.
In 2019 the Harrybrooke Park welcomed its first pair of peacocks (named Liz and Frank) in more than three decades.
5. Bank Street
For a town of just 28,000 New Milford has a thriving main shopping street, replete with independent local businesses and with arresting views of the West Connecticut hills through the canyon of buildings to the east and west.
There’s a yoga studio, a toy shop, a bookshop, a jeweller, a salon/spa, a health food store and a slew of restaurants both here and along Railroad Street and Main Street.
Lucia (51 Bank St) serves modern Italian cuisine, while you’ll find tapas at Zaragoza (No. 31) and quick bites and healthy options at the River & Rail Cafe (No. 21).
Turn it into a true date with a movie at the elegant Bank Street Theater, which goes back to 1920 and shows new Hollywood releases.
6. Candlewood Lake
Something that contributes a lot to New Milford’s appeal is its proximity to Candlewood Lake.
This narrow body of water has sinuous, densely 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 York residents have second homes on Candlewood Lake, and along its 60 miles of idyllic shoreline are beaches, golf courses, marinas and a wealth of other leisure amenities.
New Milford has a public beach, Lynn Deming Park (restricted to residents), and a golf course by the water.
You can also rent a kayak or motorboat from Gerard’s Marina, a little way south.
For a beach open to all, there’s Squantz Pond State Park, 12 miles around to the lake’s west shore, while New Milford’s little Dike Point Park requires a reservation 24 hours in advance.
You can take the pulse of West Connecticut’s cultural scene at this small but perfectly formed producing theatre.
The setting is a former Black Adventist Church building, raised in 1902 and repurposed for performing arts by The Creative Arts Center of New Milford in the 1970s.
Since 1992 the owners have been known as TheatreWorks, with a season from the start of March to the end of December.
Some of the picks from the 2019 season were Ronald Harwood’s Quartet, Witness for the Prosecution and Race by David Mamet.
If you’re in town in June, make a note of the 10-minute Play Festival, launched in 2019, while there’s a calendar of readings, receptions and programmes to help young talent flourish.
8. Elephant’s Trunk Flea Market
For more than forty years now, bargain-hunters, upcyclers, food-lovers, collectors, treasure hunters and entrepreneurs of all descriptions have descended upon New Milford for this enormous outdoor market.
The Elephant’s Trunk Flea Market trades ever Sunday from April to December, and no two weekends are alike.
Vendors come from all over the East Coast, and on a typical Sunday there will be upwards of 500 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 buy an Early Buyers’ pass to get onto the field by 05:45, while ultra-committed shoppers can get hold of Super-early Buyers’ tickets for entry under cover of darkness 04:45!
9. Bull’s Covered Bridge
Crossing the Housatonic River just outside New Milford’s boundaries is one of only three surviving covered bridges in Connecticut.
There has been a crossing at this site since 1760, constructed by a Jacob and Isaac Bull.
The oldest timbers from the current lattice truss bridge date to 1842, with additional supports added over the last 180 or so years.
What may strike you about Bull’s Bridge is the length of the crossing, at more than 30 metres.
As with all covered bridges, the shelter above preserves the wooden bridge floor by keeping it out of the elements.
Bull’s Bridge has been on the National Register of Historic Places since 1972 and is passed to the west by the world-famous Appalachian Trail.
10. Lynn Deming Park
New Milford has its own public beach on Candlewood Lake, open from Memorial Day to Labor Day.
Lynn Deming Park has a large tract of sand pitching gently into the lake’s calm waters and fringed by woods.
There are lifeguards all through the season, generally between 11:00 and 18:00, as well as a bathrooms, a pavilion and picnic tables in the woods behind.
It all sounds perfect, but the big drawback is that only residents with a car pass are able to use the park.
If you’re visiting family in New Milford you’ll all need to ride in one car to gain access.
11. Mine Hill Preserve
At this natural and historical conservation area just next door in Roxbury you’ll stumble upon the ghostly vestiges of an iron mine and furnace works from the 19th century.
The hill here is half in New Milford, while the preserve is on the eastern slope which is the Roxbury side.
Shafts had been dug into the hill from the first days of European settlement, but the main large-scale operation was set up by the Shepaug Spathic Iron and Steel Company in 1865 to mine carbonated iron ore.
The mine and furnace functioned up to 1905, and you can check out the latter, marked with interpretive boards and looking like a Medieval tower thanks to its Gothic arch.
12. Bridgewater Country Fair
The well-heeled little town of Bridgewater, directly south of New Milford, has a wholesome and popular country fair in mid-August.
The event will celebrate its 70th anniversary in 2022 and raises money for the Bridgewater Volunteer Fire Department, the last self-sustaining fire department in Connecticut.
The three-day celebration opens on the Friday night with a parade by Volunteer Fire Companies from around Connecticut and New York, showing off new fire-fighting trucks and equipment, as well as beautiful vintage machinery.
Over the weekend there are tents for BBQ, fried dough, tacos, beer, roast beef, roast chicken, ice cream and fruit smoothies, accompanied by amusement rides, tractor pulls, arts and crafts and live music.
And of course, it wouldn’t be a country fair without competitions for everything from pie-eating to canning, fruit, vegetables, flowers, baking, livestock and even eggs.
13. Candlewood Valley Country Club
New Milford has a highly-regarded public golf course out in the rolling countryside beside Candlewood Lake.
The forgiving front nine will get you into your groove, followed by a back nine that will test your accuracy in a big way.
If you come through the doglegs, narrow fairways and multiple hazards of the 13th, 14th, 15th and 16th holes with your score intact you’ll be doing better than most.
Rates are $42 on weekdays and $50 on weekends (walking), but if you want to squeeze in nine holes before the sun goes down there are special twilight fees.
The Clubhouse restaurant, serving wraps, flatbreads, pizzas, burgers and sandwiches, enjoys an elevated view of the 18th and refreshment carts out on the course.
14. Bad Dream Brewing
You can drink local at this relaxed craft brewery, pouring pints and flights, and filling growlers from Thursday to Sunday.
When we put this list together in August 2019 there were five beers on tap, including Hostile Hitchhiker, a hoppy pale ale, Ominous Basket, a blonde ale, and three IPAs.
There’s always a guest tap too, and at the time of writing this was a cider by Middletown’s Spoke + Spy Ciderworks.
Snacks are available at the bar, and if you’re up for something more substantial you can bring your own food or order in from Cobblestones American Grille.
15. Young’s Field
Sitting against the Housatonic River in the middle of town, Young’s Field is a convenient place to get some fresh air, with a large swathe of grass, a skate park, tot playground, basketball court, two baseball fields, tennis courts and a pavilion.
Just across Young’s Field Road there’s a kayak ramp, and if you feel like staying out for a bit longer, you’ll be right on the New Milford River Trail, a paved greenway tracing the Housatonic for five miles from Boardman Road to Gaylordsville.