Things To Do In New Milford CT: Top 15 Most Unique Spots | Stanton House Inn

First Congregational Church on the green in New Milford, CT

New Milford is a picturesque farming village by the standards of the CT Gold Coast. Surrounded by lush countryside, the town is right by the Housatonic River. The town green is a charming spot featuring tall Victorian architecture. The downtown area is bustling with local eateries, boutiques, and amenities. But there’s more to New Milford than what first meets the eye. Outdoorsy types will find paradise on the shores of Candlewood Lake, dotted with marinas and beaches. For the adventurous, opportunities to venture off the beaten path and discover some of the town’s lesser-known attractions abound.


Ready to explore the best things to do in New Milford, CT? Let’s get into it:


Quick hits

  • Explore the charming town of New Milford, CT. You’ll find a lively Town Green, a state park with a tragic love story, and a history-rich museum.
  • Enjoy outdoor activities at Harrybrooke Park and Candlewood Lake.
  • Or hunt for hidden treasures at the Elephant’s Trunk Flea Market.
  • For a change of scenery, consider a short drive to nearby Litchfield Hills towns.

New Milford, CT, map of the top things to do, including Elephant's Trunk Flea Market, the New Milford Historical Society, and Lovers Leap State Park
Map design by Stanton House Inn

A Brief History of New Milford, Connecticut

1909 postcard of the Railroad Station in New Milford, CT

The town of New Milford, CT, in Litchfield County, boasts a rich, charming past. Its history stretches back to Native American roots. The town witnessed significant historical events, including the American Revolution, helping shape the nation we know today.


Native Americans

Before the arrival of European settlers, the Wawyachtonoc people inhabited the New Milford area. The Algonquian language was their primary language. This tribe was part of the larger Paugussett Nation and later merged with the Mahican tribe. Their lives centered around farming and fishing. They cultivated crops such as corn, squash, beans, and tobacco. The tribe also fished in the surrounding freshwater bodies. Their main settlement, Weantinock, was near present-day New Milford.


Colonial times

In 1707, John Noble Sr. and his daughter, Sarah Noble, were the first European settlers in New Milford, CT. They were soon followed by others who bought land in the area. The year 1711 marked a significant milestone when a group of families petitioned the Connecticut General Assembly to establish a town. Their request was approved, and the town organized in 1712. Daniel Boardman, a man of faith, was ordained as the minister of the Congregational Church in 1716.


By 1722, most of northwestern Connecticut became a part of New Haven County. Eight years later, the eastern half was transferred to Hartford County. New Milford, Salisbury, and Sharon remained in New Haven County until Litchfield County formed in 1751.


American Revolution

Roger Sherman, a notable figure in the Continental Congress, once called New Milford home. He signed both the Declaration of Independence and the U.S. Constitution. He relocated to New Haven, Connecticut, in 1761. Today, his former homestead serves as the Town Hall. During the American Revolution, New Milford raised its own military unit, known as the 7th Connecticut Regiment or the 19th Continental Regiment. This regiment experienced significant combat at the battles of Brandywine, Germantown, and Monmouth.


19th and 20th centuries

Early 20th century postcard of the Railroad station

In the 19th century, New Milford served as a hub for the Underground Railroad. At least two homes served as part of a network of secret routes and safe houses that guided many slaves to freedom in Canada.


As the century progressed, the town developed new industries. Factories were hopping, producing a wide range of goods from buttons to dairy products. Tobacco became a main crop, leading to the construction of numerous warehouses for storage and processing. In 1942, Buck’s Rock Performing and Creative Arts Camp started and it continues to thrive as a summer camp to this day.


21st century

Today, New Milford has transformed from its past. Work is underway on the New Milford River Trail, which will connect to greenways in adjacent towns.


The town is also home to the Elephant’s Trunk Flea Market. This is the largest weekly flea market in New England, and arguably one of the best flea markets in Connecticut. It operates from April to December.


Today, New Milford remains a classic New England town, complete with a picturesque central green that could be on a postcard. The downtown area is always hopping (for a small town), hosting numerous mom-and-pop shops and hidden gem eateries.


The Best Things to do in New Milford CT

historic buildings in the historic district

From the romance and history of Lovers Leap State Park to the intriguing stories at the New Milford Historical Society and Museum, there’s much to explore. But that’s not all. This guide is your key to unlock the heart of this New England gem.


Elephant’s Trunk Flea Market

Every Sunday, from April to December, over 500 vendors set up their stalls for the Elephant’s Trunk Flea Market. They showcase a variety of items – trinkets, antiques, handcrafted goods. This market promises you’ll stumble upon treasures you never knew you needed. Bargaining over prices is part of the fun. The Elephant’s Trunk Flea Market is an adventure. Each stall is a surprise waiting to be discovered. Each item has a tale to share.


Historic Downtown New Milford

St Peter's Temple

Let’s turn our attention to downtown New Milford. The stretch from Railroad Street to the green is quaint, with charming brick-front shops. One standout is The Hunt, a secondhand boutique with a stylish, well-curated collection. Then there’s Nutmeg on Main, where you can sample a variety of flavored oils. Got a sweet tooth? Grassroot’s Ice Cream is a must-try. For movie buffs, there’s the Bank Street Theatre. Its art deco facade is hard to miss.


New Milford Town Green

Gazebo in the center of town

But the standout here is the heart of New Milford – the Town Green. This place paints a vivid picture in your mind. In the center of this tree-lined green space, there’s a gazebo that has been the backdrop for countless stories (and likely inspiration for one in Gilmore Girls). The changing seasons of New England are celebrated with events like Village Fair Days and the Christmas tree lighting ceremony.


New Milford Historical Society and Museum

Immerse yourself in New Milford’s past at the New Milford Historical Society and Museum. Explore the story of Roger Sherman, a key figure in drafting the United States’ founding documents. Uphill from the north end of the Town Green, the museum campus is a complex of buildings. These structures house and interpret objects and documents related to the area. The main gallery, attached to the historic Knapp House, showcases a wide range of exhibits. These displays cover topics like Black Life in New Milford’s History, the town’s Pre-Colonial Peoples, and the evolution of local industries. You’ll also find the ‘A Rough Road To Freedom’ monument here. It honors the struggles and victories of one of the darkest chapters of American history.


Village Center for the Arts

Village Center for the Arts, facing the green

The Village Center for the Arts is a haven for the creative spirit. This sanctuary welcomes people of all ages. Beginners and seasoned artists will find countless opportunities to learn and express yourself through art. The Center offers a variety of mediums, from painting and pottery to drawing and sculpture.


TheatreWorks New Milford

This cozy little theater is known for its captivating performances, stirring a range of emotions. TheatreWorks New Milford is an ideal spot to spend an evening. You can immerse yourself in a story and feel as though you’ve lived a hundred lives within a few hours. It’s a remarkable place, and a visit is highly recommended.


Parks in New Milford, Connecticut

View from the summit at Lovers Leap State Park

Home to some of the best CT state parks for hiking, as well as some more accessible and charming spots along the river, New Milford is a haven for outdoor activities in CT.


Lovers Leap State Park

Red bridge at Lovers Leap State Park

Lovers Leap State Park overlooks the banks of the Housatonic River and boasts a charming old red bridge. The breathtaking views are not the only attraction here. The park is steeped in a love story, a tale of passion and tragedy that lingers in your memory long after your visit.


Princess Lillinonah, daughter of Chief Waramaug, fell in love with a white man she found in the woods. She took him to her village near the Housatonic falls, where he stayed until winter. Despite his promise to return, he didn’t, leaving Lillinonah destitute. Chief Waramaug decided to marry her to Eagle Feather, a member of their tribe. Before her wedding, Lillinonah boarded a boat to the falls and certain death. It was at that moment that the young man returned and threw himself into the water to accompany her. Both perished.


Make sure you don’t miss the Tea House Trail and Castle Loop. These paths through the woods offer a journey through history. And the Lovers Leap Bridge and the Yellow Cat Tea House are integral parts of the park’s story.


Harrybrooke Park

Harrybrooke Park is a peaceful haven spread across 48 acres. It features a waterfall, a well-preserved mid-century estate, and gorgeous gardens. You can enjoy a leisurely walk by the river, admire the well-kept grounds, or simply soak in the calm ambiance of this hidden treasure.


The park also hosts over two dozen events each year. This makes it a perfect spot for a day of relaxation or a lively gathering with your loved ones. It also features a skate park.


Candlewood Lake

Candlewood Lake, the largest lake in Connecticut, is a popular destination for water sports enthusiasts. With breathtaking views, marinas, and clean waters, it’s no wonder people are drawn to it. At Gerard’s Marina, you can rent a kayak or a motorboat for a day on the lake. If you prefer to relax, the public beach at Squantz Pond State Park is a great spot to catch some sun.


Lynn Deming Park

Thinking about a summer splash at Candlewood Lake in New Milford? It’s a sight to behold from Memorial Day weekend through Labor Day weekend. Lynn Deming Park features a large sandy beach that gently slopes into the lake’s calm waters. And it’s all framed by lush woods.


Lifeguards are on duty, typically from 11:00 to 18:00. You’ll find bathrooms, a pavilion, and picnic tables in the woods behind the beach. But there’s a catch: the park is only open to residents with a car pass. If you’re visiting family in New Milford, ensure you get in when you all ride in one car.


Young’s Field

Young’s Field is a breath of fresh air in the heart of town. It’s a large, grassy area by the Housatonic River. It features a skate park and a playground for the kids. Sports enthusiasts will find a basketball court, two baseball fields, and tennis courts. There’s also a pavilion for gatherings.


Across Young’s Field Road, you’ll find a kayak ramp. If you’re up for a longer outing, the New Milford River Trail starts here. It’s a paved path that meanders along the river for five miles, stretching from Boardman Road to Gaylordsville.


Barn Quilt Trail

Over many visits to New Milford over the years, this writer had noticed quilt patterns on local barns, but didn’t understand their meaning. Thanks to researching for this guide, they’re all points on the Barn Quilt Trail, a self-guided tour. As you meander past historic barns, you’ll notice each one is adorned with vibrant quilt patterns. These patterns pay homage to New Milford’s farming roots and recognize its lively arts and crafts scene.


Housatonic River Brewing Company

The Housatonic River Brewing Company truly understands beer. With a wide array of craft beers on tap, they keep the selection fresh by rotating them with the changing seasons. The knowledgeable staff is always ready to guide you through the various flavors and styles to savor. There’s an inviting warmth to this top pick among the best breweries in CT, making it easy to sit down, enjoy a drink, and lose track of time.


Harris Hill Farm

Harris Hill Farm is an exciting destination for families to experience the authentic farm life. Activities include picking pumpkins in one of the best pumpkin patches in CT, hayrides, and visiting with farm animals. Located in the open country, this working farm offers both fun and educational experiences for all ages. Harris Hill Farm is an unforgettable destination, ideal for a wholesome family outing.


Hunt Hill Farm

Hunt Hill Farm was a beloved local spot known for its art, music, and cooking classes at the Silo. It’s also the birthplace of the New York Pops. The largest independent pop music orchestra in the U.S. was an initiative of Ruth and Skitch Henderson. Unfortunately, it closed its doors in the summer of 2019 after over forty years of operation. That said, new owners, Alessandro and Daniele Piovezahn, are determined to preserve Hunt Hill’s legacy. For current concerts, art shows, and events, check their Facebook page. And if you’re on the Barn Quilt Trail, don’t miss the two quilt blocks at Hunt Hill Farm.


Restaurants in New Milford, Connecticut

American flag on the green where the New Milford Farmer's Market is held

The food scene in New Milford is diverse for the Litchfield Hills of Connecticut, and delicious.


Craving Italian? Head to Lucia Ristorante. Cozy cafes and food trucks with tasty offerings are scattered around town.


Established in 2017, The Abbey Restaurant and Bar is a cozy haven for family dining. Its unique charm is highlighted by a copper-top Irish American horseshoe bar and multiple flat screen TVs. Irish-themed menus are its specialty. The restaurant also offers Happy Hour deals and a Bottomless Sunday Brunch. On weekends, The Abbey comes alive with Singo, trivia, and live music events. St. Patrick’s Day brings special celebrations to the venue.


Once you’ve satisfied your palate, the New Milford River Trail is ready for you. It’s time for a walk!


Hotels, Inns, and Places to Stay in New Milford, CT

Front sign of the Homestead Inn Bed & Breakfast

New Milford makes a fantastic CT day trip from our Connecticut, bed and breakfast in Greenwich, CT. It’s especially beautiful as a CT fall foliage driving route for a day heading deeper into the Litchfield Hills. But if you want to stay around a little longer and explore more of the area, you have a few charming options.


Homestead Inn

If you’re looking for a place to stay in downtown New Milford, the Homestead Inn is ideal. It’s filled with charm and history, and within walking distance to the center of town’s main attractions. The rooms are equipped with modern amenities such as Wi-Fi, flat-screen HD TVs, and private bathrooms.


One of the best parts of your stay will be waking up to a complimentary gourmet breakfast. And if you’re worried about parking, rest easy – they have it covered. The Homestead Inn offers a blend of class and comfort in the heart of New Milford.


Candlelight Farms Inn

Located in the rolling hills, Candlelight Farms Inn in New Milford, CT is a sight to behold. This serene spot is the perfect place to unwind. The inn’s warm hospitality and stunning surroundings make it feel like a home away from home.


Directions to New Milford, CT from Greenwich, CT

Fall day in a New England town

Considering a day trip from Greenwich, Connecticut to New Milford, CT? The most direct route is through the Hudson River Valley. You’ll pass rolling hills, charming towns, and stunning countryside. Start by heading north on I-684 from Greenwich. Then, take I-84 west. Stay on I-84 until you reach exit 7 for US-7 towards New Milford. The entire drive should take just under an hour. It’s a quick trip if you’re staying in Greenwich.


If you’d rather stay in Connecticut, drive up the Merritt Parkway to Route 7, then meander your way through the towns along this road. It only adds about another 16 minutes or so to the route, and offers more stops along the way, like:





More Towns and Cities to Explore Near New Milford, Connecticut

Church in Kent, Connecticut

Located in the heart of Litchfield County, New Milford is as a gateway to a collection of unique towns and cities in northwest Connecticut. Together, they paint a picture of the rich tapestry of New England.


Kent, CT

Kent Falls State Park in the summer

Just a short distance from New Milford, is Kent, a small town with a lot to offer.


Kent Falls State Park is a sight to behold with cascading waterfalls and winding trails. It’s a major draw , as it’s nature at its finest.


If you’re interested in history, the Eric Sloane Museum & Kent Furnace, and Connecticut Antique Machinery Museum is worth a visit. The exhibits take you back in time, narrating tales of the area’s past. And Bull’s Bridge is on the National Register of Historic Places.


Danbury, Connecticut

Old ad on a wall in Danbury, CT

If you’re visiting New Milford from our way, you’ll have to pass through Danbury, Connecticut. You can explore the past at the Danbury Railway Museum or the Danbury Museum and Historical Society. If you love the outdoors, Tarrywile Park & Mansion and the hike to ruins of an old mansion on a hill is for you.


Southbury, CT

Bridge in Southbury, Connecticut

If you’re yearning for the wild, open, and untouched, Southbury, CT, has it in spades. Places like Shepaug Eagle Observation Area, Kettletown State Park, and Southbury Dog Park showcase the raw beauty of nature.


Litchfield, Connecticut

Topsmead State Forest in Litchfield, CT

Last but not least, Litchfield, Connecticut, is the town people expect to see when they go looking for New England charm in our state.


The White Memorial Conservation Center is a must-visit for a good hike, though watch out for horseback riders. If you enjoy a good drink, the Litchfield Distillery is a haven. For outdoor enthusiasts or photographers, Topsmead State Forest is a sight to behold.


Feeling hungry? Litchfield won’t disappoint. From The Saltwater Grille to Arethusa Al Tavolo and West Street Grill, you’re in for a treat.



New Milford, Connecticut is a true gem of a New England town. With its rich history, charming culture, and stunning natural beauty, it’s one of the most unique places to visit in Connecticut. There’s plenty to see and explore, from historic sites to state parks. The food scene is top-notch, and the accommodations are as cozy as can be. So pack your car and get ready for an unforgettable CT road trip to New Milford.


Frequently Asked Questions


What is New Milford CT known for?

New Milford is known for its picturesque parks, a stunning bridge, and a historic village. The landscape is dotted with farms and the town green stretches wide. The charm of New Milford is unique and hard to find elsewhere.


What is Milford CT known for?

Let’s turn our attention to Milford. This place is teeming with charm that’s impossible to ignore. The downtown area is vibrant, brimming with life and steeped in history. The town’s roots are deeply embedded in shipbuilding and trade. Furthermore, the leather industry here is as dynamic as it gets. The beautiful beaches and the state park are a feast for the eyes.


Is New Milford CT a city or town?

New Milford, CT is a town located in Litchfield County, Connecticut. It’s in close proximity to New York and boasts the beautiful Candlewood Lake along its northeastern shores.


Is New Milford CT a good place to live?

New Milford is the place to be if you’re seeking tranquility and a host of activities. The residents are welcoming, fostering a robust sense of community. The town boasts excellent schools, and ample open spaces for children to frolic. Life here is simple, with homes filled with happy families. The town’s steady rhythm is reminiscent of a reliable old clock. In essence, New Milford is a small town with a big heart.


What are some of the top attractions in New Milford?

Consider a journey to New Milford. You’ll have the chance to explore Lovers Leap State Park. You can also visit the New Milford Historical Society and Museum, where the past is preserved. Don’t miss the Elephant’s Trunk Flea Market, a treasure trove of unique finds. Lastly, spend some time at Harrybrooke Park, a true haven. These are the gems that make New Milford special.


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