15 Best Things to Do in New Fairfield (CT)

The small town of New Fairfield is on the west shore of Candlewood Lake, the largest inland body of water in Connecticut.

While the lake is a famed second home for affluent New Yorkers, most of the plush houses by the shore in New Fairfield are lived in year round.

This is all in contrast to the days when New Fairfield was a buzzing summer destination.

Still, the best place to swim and relax around Candlewood Lake is partly in this town, at Squantz Pond State Park.

New Fairfield is on the north fringe of the city of Danbury, which puts a lot of shopping, culture and entertainment within a short car ride.

1. Candlewood Lake

One of the things that makes New Fairfield a desirable place to live is the big, painterly body of water to the east.

Candlewood Lake is the largest in the state at 11 miles long and two miles across at its widest point.

Much of Connecticut’s most expensive real estate is on its shores, and with that in mind it’s startling to think that there was no lake at all before the 1920s.

It was created by a hydroelectric below the Rocky River’s confluence with the Housatonic, calling on a workforce of almost 1,400 men for the construction.

Unsurprising, given its upmarket character, Candlewood Lake has lots of private beaches and marinas, but out-of-town and out-of-state visitors can idle by the water at Squantz Pond State Park and New Fairfield Town Beach for a fee.

For water activities, try Lakeside Watersports in Danbury, offering motorized thrills like waterskiing and wakeboarding.

2. Squantz Pond State Park

Maybe the best truly public space on the shores of Candlewood Lake is right in New Fairfield at Squantz Pond.

The name comes from Chief Squantz, the 18th-century Schaghticoke chief whose tribe held sway over what is modern day New Fairfield and Sherman.

He refused to sell this land, which was eventually acquired after his death.

What is now the state park was farmland until 1926, with high slopes under a mantel of hardwood forest, stooping to a cool, blue pond with a beach.

That beach is long and broad, and has a roped swimming area, bathrooms, a boat launch, picnic areas and lifeguards on duty most days during the summer break.

On the shore you follow trails west into the Pootatuck State Forest.

3. Pootatuck State Forest

Directly west of Squantz Pond is 1,200 acres of steep wooded terrain at the Pootatuck State Forest, which is more suited to activities like hiking, mountain biking and cross-country skiing in winter.

You can access this landscape via the same trails as Squantz Pond State Park, and there’s a tangle of blazed routes to choose from.

The most travelled path lifts you to a scenic rocky overlook above Squantz Pond on the Blue Trail, for a clear sight of the pond, but also Candlewood Lake off in the distance.

4. Green Chimneys Farm & Wildlife Center

More than 200 farm animals and injured wild species have a permanent home at this center just over the state line at Putnam Lake.

Green Chimneys is a multifaceted non-profit organization, mainly serving children and young people who have struggled in traditional learning environments with animal-assisted therapy at its heart.

On weekends the center opens to the public, and you can come by to look around the teaching barn, horse barn and outdoor paddocks between 10:00 and 15:00. Groups of six or more will have to sign up for a tour, and this takes in pigs, camels, llamas, horses, donkeys, cows, goats and many more animals, and also features pony rides and hayrides for wee ones.

Alternatively the Farm & Wildlife Tour will introduce you to non-domestic animals like owls, snakes, falcons and a condor, eagle and tortoise.

5. Danbury

Seconds to the south is a city often ranked as one of the most liveable in the United States.

From the late 18th century to the early 20th century Danbury was the country’s hat-making capital, manufacturing five million hats per year by 1887. Even now Danbury is affectionately dubbed “Hat City”. You can learn more about this aspect of the city’s past at the Danbury Museum and Historical Society, which has a fine main campus on Main Street with five buildings.

Danbury was also a railroad town in the 19th century, at a key junction between a branch of the Metro-North Railroad and the vital Maybrook freight line.

Railroad enthusiasts can visit the former Union Station (1903), now the Danbury Railway Museum, and take a ride on a length of track in the sprawling railyard.

For a relaxing walk in greenery, Tarrywile Park is 722 acres of landscaped parkland in the grounds of the Shingle Style Tarrywile House, dating to 1897 and now rented out for events.

6. White Silo Farm & Winery

Head past the north shore of Candlewood Lake where White Silo Farm & Winery rests in a rollercoaster landscape that takes on a new character with each season.

White Silo’s tasting room is fabulous too, in a dairy barn that has been here since the 18th century.

The winery operates on a boutique level, producing all its bottles in small batches, from grapes like Cayuga, Marquette, Cab Franc and Frontenac, but also a variety of other fruit grown in these fields.

Wine tastings are $8, to be enjoyed below the wooden beams in the old barn, or while savoring the countryside from one of White Silo’s terrace gardens.

The farm has more in its repertoire than wine, and produces a large asparagus crop in spring, all of which goes towards an asparagus festival.

7. Danbury Fair Mall

The second-largest mall in the state is a breeze away in Danbury, and has a location with a compelling past.

As you’ll gather from the name, this was the site of the Danbury Fair, an annual exhibition that took place from 1821 to 1981, drawing 400,000 people in its final year.

The mall opened in 1986 and acknowledges the history of the site with a summer carnival outdoors in June and July.

For a cross-section of Danbury Fair Mall’s 200 upmarket and midmarket tenants, you’ve got Apple Store, Macy’s, Sears, Michael Kors, Old Navy, Gap, H&M, Foot Locker, Clarks and Banana Republic.

Food-wise, chains include Cheesecake Factory, Chipotle, Cosimo’s Pizza, Chick-Fil-A, McDonalds and sweet picks like Cinnabon and Häagen-Dazs.

8. Ives Concert Park

The feted Modernist composer Charles Ives (1874-1954) was born in Danbury, and the city pays tribute to this musical heritage with a sumptuous venue for summer concerts.

The Ives Concert Park is an amphitheater in 40 lush acres next to a pond, staging a program that attracts more than 65,000 people each year.

The line-up reflects the city’s multicultural make-up, and includes classical music, jazz, famous classic rock artists, annual reggae, Irish and Ecuadorian festivals, Shakespeare, live comedy, children’s events and plenty of tribute acts.

9. Richter Park Golf Course

In the 1980s this public course in Danbury was rated by Golf Digest as one of the best in the country.

What Richter Park has going for it is the location, on rolling, wooded terrain beside the ample West Lake Reservoir.

That water comes into play often, with 14 of the 18 holes featuring a water hazard, while the stiff slopes and newly renovated bunkers will punish even the smallest misjudgment.

Safe to say that despite being a public course, Richter Park is a course for people confident in their accuracy.

For non-residents, a full round will cost $73 on weekdays and $83 on weekends (cart complimentary).

10. Sherman Playhouse

Since 1929, this beautiful former church has staged community productions, made with a lot of love and dedication by the Sherman Players (founded 1949). The Greek Revival building used to be the Center Church (1837), which had been abandoned by the 20th century before being rescued in the 1920s by a wealthy couple, Walter and Alice Evans, as a place for their daughter Marianne to enjoy her passion for drama.

Marianne’s daughter, Betsy, has been involved with the Sherman Players (mainly in set design) for over 50 years, while her daughter Phoebe has been making playbills, posters, brochures and more for over two decades.

There are five productions a season at the Sherman Playhouse, and in 2019 this featured Cabaret, The Tempest, The Graduate, Venus in Fur and the Christmas pantomime, Jack and the Beanstalk.

11. Great Hollow Nature Preserve & Ecological Research Center

Only founded in 2016, the Great Hollow Nature Preserve & Ecological Research Center is a non-profit organization dedicated to biodiversity conservation, experiential environmental education, ecological research and passive outdoor recreation.

That last bit will appeal to casual visitors, as you’re free to visit their 825-acre preserve, heading out on more than five miles of walking trails, right here in New Fairfield.

There are also programs to look into, like guided nature walks and monthly “Kids’ Nature Nights”, which are loaded with fun but educational activities and have a different theme each month.

12. New Fairfield Town Park

Open from the start of the school summer break to the Labor Day weekend, New Fairfield has a small but appealing beach on Candlewood Lake.

There’s a designated swimming area in the lake’s clear, gentle waters, as well as a nice patch of soft sand, restrooms, changing areas, an enlarged snack bar and a picnic area.

Residents can purchase seasonal passes for a small fee.

Non-residents can buy daily guest passes, although these do tend to be pricey.

13. Bear Mountain Reservation

One of the best places in the area to go walking if you’re a dog owner, Bear Mountain Reservation has a system of trails on light hills next to Candlewood Lake.

The longest of these is the looping red trail, twisting through open fields and peaceful forest.

On this route you’ll come to a junction with the orange trail, which drops down the rather precipitous slope to Candlwood Lake if you need to work those calves.

South of the property is FCI Danbury, a low-security federal prison, mainly for female inmates.

You may be interested to know that famous conscientious objectors like James Peck and Robert Lowell were imprisoned here in WWII, as was screenwriter Ring Lardner Jr., who was blacklisted in 1947 during the Red Scare.

14. New Fairfield Historical Society

New Fairfield Historical Society, Little Red Schoolhouse

Helping to keep the town’s history alive, the New Fairfield Historical Society meets every 2nd Wednesday of the month in the New Fairfield Library’s Historical Room in the basement.

The society’s main property is the Little Red Schoolhouse, a 19th-century one-room school building on Brush Hill Road.

The schoolhouse opens for programs throughout the year, when you’ll get a taste of education in the days when New Fairfield was a farming community.

In 2019 to celebrate the society’s 50th anniversary there was a letter-boxing treasure hunt Little Red Schoolhouse.

15. Cosier-Murphy House

At 67 Connecticut Route 39 is a sight to take in as you pass through the Miller’s Corner section.

The Cosier-Murphy House is a private residence, but is one of the oldest homes in the town, dating back to 1840 and constructed in the Greek Revival style.

From the road the house seems smaller than it is, as the main entrance is on the side elevation, and has a side-hall plan, so the door is in the right bay.

Above, the second floor windows are unusually squat, to the point where they might be part of an enlarged frieze band below the main facade’s pediment.

Almost everything you see, from the pediment to the shutters to the picket fencing, is original, which, along with the unusual architecture, earned the Cosier-Murphy House listing in the National Register of Historic Places in 1991.