15 Best Things to Do in New Milford (CT)

The prosperous town of New Milford rests on the northeastern shore of Lake Candlewood. Generations of wealthy New Yorkers have set up second homes in these parts.

One such estate belonged to the industrialist Frank Harden in the middle of the 20th century. This 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 enveloping countryside is quintessential New England to me, with some rugged slopes, and glorious colors in fall.

The downtown is in rude health too, for its locally-owned restaurants, boutiques and amenities. Elsewhere, 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. The town green is fronted by palatial Victorian homes, restaurants, civic buildings, and two grand churches.

One of the buildings that caught my attention is the home of the Village Center for the Arts. This is a Greek Revival-style church from 1830, later turned into a hardware and antiques store. The center is a non-profit community arts hub for New Milford.

New Milford Town Green continues to be a gathering place for seasonal events. For example, In the advent season there’s a line of Christmas trees down the middle of the green. These are illuminated with a special Lighting Ceremony at the end of November.

In August, I love the atmosphere on Saturday evenings, when there’s a weekly concert at the bandstand.

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 1,200 feet above sea level, 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.

I was most impressed with Lovers Leap Bridge, constructed by the Berlin Iron Bridge Company in 1895. Also be sure to check out the Yellow Cat Tea House, a vine-clad remnant from the Hurd estate. To the northwest 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. This organization collects, preserves and interprets 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 artifacts.

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 The Great Fire of 1902

I was also excited to learn more about New Milford lawyer and statesman, Roger Sherman (1721-1793). He was the only man to sign all of the United States’ founding documents

4. Harrybrooke Park

In the southwestern 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. Now, 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 with a waterfall. In the late-1950s Marilyn Monroe and Arthur Miller, who lived in neighboring Roxbury were regulars on the estate.

Recently, the property has been repopulated with peacocks, which were once abundant here.

5. Bank Street

For a town of just 28,000, New Milford has a thriving main commercial artery. Bank Street is replete with independent local businesses, all paired with arresting views of the West Connecticut hills to the east and west.

There’s a yoga studio, a toy shop, a bookshop, a jeweler, a salon/spa, an ice cream parlor, a cheese shop, and a health food store. Complementing them is 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 small plates, and healthy options at the River & Rail Cafe (No. 21).

Turn it into a true date night with a movie at the historic Bank Street Theater, dating back to 1902 and with a later Art Moderne facade. I adore downtown theaters like these, still showing first-run 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.

I don’t think it’s hard to see why many New York residents have second homes on Candlewood Lake. Along the 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. This can be found 12 miles away, around the lake’s west shore. Meanwhile New Milford’s little Dike Point Park requires a reservation 24 hours in advance.

7. TheatreWorks

You can take the pulse of West Connecticut’s cultural scene at this small but punchy producing theater.

The setting is a former Black Adventist Church building. This was raised in 1902, then 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. This is chock full of dramas, comedies, and musicals, with something for most tastes.

For my part, I caught an endearing performance of the Tony Award-winning 25th Annual Putnam County Spelling Bee and loved every minute.

8. Elephant’s Trunk Flea Market

For close to 50 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 every Sunday from April to December. The vendors change every week, and the experience has been different every time I’ve come.

In fact, the sellers come from all over the East Coast. On a typical Sunday there will be upwards of 500, all set up and ready to trade by 7:00 AM.

General admission to the market is nominal, but if you’re an avid deal-seeker you can pay more for early access. For instance, the Early Buyers’ pass will get you onto the field by 5:30 AM.

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 struck me about Bull’s Bridge was the length of the crossing, at more than 100 feet.

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 Memorial Day weekend to Labor Day.

Lynn Deming Park has a large parcel of sand pitching gently into the lake’s calm waters and fringed by woods.

Lifeguards are on duty through the season, generally between 11:00 AM and 6:00 PM. For additional amenities there are bathrooms, a pavilion and picnic tables in the woods behind.

It all sounds perfect to me, but the one drawback is only residents with a car pass can 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. You can check out the latter, marked with interpretive boards. To me it looks like a Medieval tower thanks to its Gothic arch.

12. Bridgewater Country Fair

The little town of Bridgewater, directly south of New Milford, has a wholesome and popular country fair in mid-August.

The event celebrated its 70th anniversary in 2022 and raises money for the Bridgewater Volunteer Fire Department. It’s 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. You’ll see new fire-fighting trucks and equipment, as well as beautiful vintage machinery.

Over the weekend there are tents for BBQ, fried dough, fried oreos (my kryptonite), tacos, beer, roast beef, roast chicken, ice cream, and fruit smoothies. There’s a lot going on each day, with carnival rides, tractor pulls, arts and crafts, and live music.

And of course, it wouldn’t be a country fair without a ton of competitions. These cover 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 front nine here is forgiving, and will get you into your groove. This was followed by a back nine that tested my 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 surprisingly low, and if you want to squeeze in nine holes before the sun goes down there are special twilight fees.

The Clubhouse restaurant serves a range of wraps, flatbreads, pizzas, burgers, and sandwiches. It also enjoys an elevated view of the 18th, and has refreshment carts out on the course.

14. Housatonic River Brewing

This craft brewery opened in New Milford in 2018, and has roots that go back much further. The founder has been in the brewing industry for decades, and brewed his first beer in the 1980s.

When I went to press, Housatonic River Brewing had a core of eight main beers. Among them is Willie Make It (Hazy IPA), and the refreshing Duffer (Lager). I fell in love with Sacred Grounds, a Coffee Porter in collaborations with Grounds Coffee Roasters.

There’s also an assortment of wines and hard seltzers, and a different food truck outside every night. Housatonic River Brewing is famed as a live music venue, with shows booked months in advance.

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. There’s a large swath of grass, a skate park, tot playground, basketball court, two baseball fields, tennis courts and a pavilion.

Just across Young’s Field Road you’ll find a kayak launch for a gentle paddle on the river,

On foot, if you feel like staying out for a bit longer, you can follow a section of the New Milford River Trail. This part of the greenway traces the Housatonic for five miles from Boardman Road to Gaylordsville.

When I wrote this list there were plans for a total 13 miles of trail, including a rail-trail section.