New Milford, CT

The Elephant’s Trunk Flea Market first began in 1976 with 15 vendors set up on a lawn in front of a 19th century Victorian house. Suffice it to say that since then, the market has ballooned into what can only be described as a New England tradition. A typical Sunday at the Elephant’s Trunk Flea Market sees over 500 vendors offering unique and standout goods to local regulars and out of town visitors alike. A constantly changing mix of food trucks swings by from all over the east coast to dish out delicious meals, while the crowd enjoys hunting down a bargain that they’ll be hard pressed to find elsewhere. One thing that you can be sure of at this flea market is that no weekend is ever the same. Every week sees a new mix of vendors, merchandise and food as interesting and colorful as the people who visit.

Address: 490 Danbury Road (Rte 7 / 202), New Milford, Connecticut 06776, Phone: 860-355-1448

You don’t need to be searching for romance to visit the Lovers Leap State Park, but it wouldn’t hurt to bring your outdoorsy other on a date at this beautiful park either. Lovers Leap is just the place to go if you’re eager for a romantic hike, but it’s also got quite the storied past that might have you thinking twice about staying late at night unless you’ve got a penchant for spooky adventures. The park is home to 127 acres of beautiful oak forest that follows the Housatonic River. Visitors to the park should definitely make it a point to stop by the Lover’s Leap Bridge, an eye-catching red wrought-iron bridge that was originally constructed in 1895. While there, don’t forget to ask someone about the Legend of Lover’s Leap. It might just give you a tingle up your spine to go with the breathtaking views.

Address: 178 Shortwoods Road, New Milford, Connecticut 06776

What to do if you are traveling with kids:

Harrybrooke Park is a gorgeous public park in New Milford, located near Lover's Leap adjacent to a stunning waterfall on the Still River. The park was gifted to the city by its former landowner Frank Harden and stretches for 48 acres along the waterfront, open to the public for walking, hiking, and snowshoeing throughout the year. Visitors can explore the preserved midcentury estate of Frank and Elizabeth Harden, which has been converted into a living history museum showcasing a treasure trove of beautiful historic art pieces, including original copies of master paintings. Guided tours of the home are offered throughout the year, led by volunteer docents. Over two dozen annual special events are hosted at the park each year, including a summer concert series and family-friendly holiday events.

Address: 100 Still River Drive, New Milford, Connecticut 06776, Phone: 860-799-6520

Each city, each town, has its own unique story to tell. Anecdotes from the past, quirky little factoids about how the town started and developed into what it is today. When it comes to New Milford, no place tells the story of the town’s early days and its evolution quite like the New Milford Historical Society and Museum. Guests can peruse the various collections at the museum, which include mementos like a timeline of New Milford, genealogy records, as well as landmarks such as one-room school houses, and the iconic Knapp House. The history of New Milford is just quick car ride away, so history buffs won’t want to miss out on this cultural and historical gem.

Address: 6 Aspetuck Avenue, New Milford, Connecticut 06776, Phone: 860-354-3069

Activities and Attractions for Couples:

There’s no better place in New Milford to explore and discover your creative prowess than the Village Center for the Arts. The center was originally dedicated to promoting and showcasing performance arts but has since branched out to other expressions of art from painting to pottery and more. At the end of the day, the Village Center for the Arts is for people who want to take their inner creativity and channel it into tangible expression through various programs such their popular Open Studio program. Programs are open for the young and old alike with private lessons, summer camps and club activities available to all.

Address: 12 Main Street, New Milford, Connecticut 06776, Phone: 860-354-4318

For over 20 years, the Harris Hill Farm has been operating as the region’s premier pumpkin grower. Given their number one product is their range of pumpkins, the Harris Hill Farm sees a lot of action in October when droves of families arrive to pick pumpkins for the Halloween season. Harris Hill Farm specializes in large jack-o-lantern style pumpkins, but also offer other kinds of fall crops like winter squash varieties, various sized gourds, mini pumpkins and even white and pink pumpkins. Apart from that, the farm also offers rides on their hay wagons, encounters with their farm animals, as well as hearing entertaining corn trivia.

Address: 106 Ridge Road, New Milford, Connecticut 06776, Phone: 860-354-5856