Day Tripping in New Milford


Where you lead, I will follow. Follow me across the Northern Fairfield County border into New Milford in Litchfield County.

Did you know that the New Milford gazebo and town green may have been the inspiration for The Gilmore Girl’s own Stars Hollow?

Spend one day in New Milford, and you will absolutely see its small-town charm. The town green is exactly thirty minutes from my doorstep. I find myself wandering into this town more and more for shopping, dining, and activities with my children.

Here are a few of my many favorite things to see and do in New Milford.

Town Green

In the heart of New Milford sits the town green and its iconic gazebo. The green is home to many town festivals and events.

Bank Street Shopping and Dining

Shop small and eat locally. This is so easy to do on Bank Street and the surrounding blocks. We love to wander The Hunt and find vintage housewares, toys, and clothes. The children beg to stop into Nordica Toys and play, while mom’s favorites are Swank on Bank, Compass Rose, and And Company on Bank.

BD Provisions is a local low/zero waste shopping experience. They stock bulk food, coffee, cleaning supplies, and health and beauty items. I love buying items with no packaging, the mini animal crackers are my kid’s favorites! I often head to their New Milford location and create unique gift baskets.

Bleu on Bank is a one-stop shop for all things gourmet to make the perfect charcuterie board. They also offer cooking classes.

River and Rail Café, Grassroots Ice Cream, Evergreen Juice Bar, Theo’s Downtown Diner, Vega’s Mexican Kitchen & Bar, Johana’s Restaurant, All Aboard Pizza, Al Dente, and Momma’s Tacos are all walkable downtown eateries. Keep your eyes peeled for The Cue – a Danbury BBQ restaurant that will be opening its second restaurant in downtown New Milford.

A short drive from downtown is Kimberly Farm. They make delicious homemade ice cream, meals, and baked goods. Like walking into a classic country store, you’ll surely leave with a bag full of goods! This summer, they have opened a dedicated ice cream storefront, complete with a giant cow statue.

Bank Street Theater

This sweet little downtown theater has been our choice for moviegoing for as long as I have taken my children to movies. The staff is friendly, and the theater clean and comfortable. They play the latest movies, offer special discounted days in the summertime, and often theme the lobby to the current hit movie.

New Milford Public Library

The local library has an enormous children’s selection of books and a replica town green gazebo, perfect for a reading nook.

Harrybrooke Park

Harrybrooke is forever known in our home as the “peacock park” because the park is home to Frank and Liz, a pair of peacocks. We take our bikes to ride the paved and flat loop around the main park, there are hiking trails, a garden maintained by the New Milford Garden Club, and the park offers various events throughout the year. You can catch Scarybrooke Park at Halloween and attend a fun Easter Egg hunt in spring.

Lovers Leap State Park

Lovers Leap has the most picturesque iron bridge that many locals use as a photo op spot. It is a 160-acre park with hiking trails and stunning views.

Candlewood Lake

New Milford is one of five surrounding towns to have shores on Candlewood Lake. Lyn Deming Park is the town beach, and non-residents can pay a daily rate for admittance.

Young’s Field Park

This park is steps from downtown and across the street from the Housatonic River. It has updated FUN play equipment, tennis courts, a basketball court, and a skate park, along with baseball playing fields.

Elephants Trunk

Open seasonally on Sunday, you never know what you will find at this giant flea market. It draws people from all over to buy and sell their goods.

Quiet Rein Farm

When my daughter started watching the Netflix show Spirit Riding Free, she immediately decided she wanted to become an equestrian. After attending camp and taking lessons at other barns, we attended an event at Quiet Rein and knew it was the just right place to learn horsemanship.

Because 4 Paws

Looking to adopt or foster a dog or cat? This rescue works with sister organizations to take dogs out of critical situations and brings them home to Connecticut to be fostered and adopted by loving families. Our family has fostered on and off since 2020, and it has been a rewarding experience for us all. The rescue provides everything you need to care for your foster pup. All you have to do is open your home and enjoy all the joy that comes with a pet.

Have you visited New Milford? What do you love most about this Litchfield County town?

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Jamie is a mom to a daughter (2014) and boy/girl twins (2016). She was born and raised in Westchester County, NY and together with her husband (married in 2011), made Danbury, CT their hometown. Jamie is a real estate agent with Coldwell Banker Realty. In the present day, more than ever before, “home” is an essential and safe place in an ever-changing world. Helping clients achieve their homeownership goals, searching for the home that’s “just right,” or helping them move on from a home that no longer serves them drives Jamie in her real estate career. Home for Jamie is Northern Fairfield County, and she never gets tired of spending time in the community with her family, visiting her favorite parks, and exploring local shops and restaurants. Jamie can be found on the Peloton leaderboard at 6:30 every morning, which fuels her long days of work and momming. Morning workouts are as athletic as she gets, and her favorite thing is tucking her children in at night and catching up on whatever show she is streaming. As much as she loves staying in, she doesn’t pass up a night out with her childhood girlfriends or a date night with her hubby. 


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