10 Best Things to Do in New Milford, Connecticut

© Elephant’s Trunk Flea Market

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.

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

© bouybin/stock.adobe.com

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.

178 Shortwoods Road, New Milford, Connecticut 06776

© Africa Studio/stock.adobe.com

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.

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

© New Milford Historical Society and Museum

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.

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

© Gerard’s Waters Edge Marina

Located at Candlewood Lake, Gerard’s Waters Edge Marina is your gateway to exciting water sports and luxurious afternoons at the lake in New Milford. The marina is home to top notch boats such as those by South Bay Pontoon, Tigè and FourWinns. It also operates as a full-service marina and boat dealer for boating enthusiasts who want to try out different models or take one home for themselves. For travelers, Gerard’s Waters Edge Marina is the perfect place to visit if you simply want to enjoy an afternoon of boating or luxuriating on a yacht as they offer rentals to all the best models of watercrafts out there.

120 Old Town Park Road, New Milford, Connecticut 06776, Phone: 860-350-2628

© Village Center for the Arts

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.

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

© Harris Hill Farm

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.

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

© Merryall Center for the Arts

Nestled along a quiet and narrow back-country road in Litchfield County’s rural community, the Merryall Center for the Arts is best known for being an intimate theater and community center. For more than six decades, this quaint little building has hosted luminaries from all over the country. At Merryall, visitors and local residents alike can enjoy spectacular performance artists in a close knit setting. Despite only having 75 seats in the house, the Merryall Center for the Arts has seen incredible artists grace its stage such as Skitch Henderson, Fredric March, Isaac Stearn, and Margaret Meade. There’s no doubt that that the center will see even more memorable performances in the future.

8 Chapel Hill Road, New Milford, Connecticut 06776, Phone: 860-354-7264

© Ristorante Lucia

Under the watchful eye of its owner and head chef, Antonio Caldareri, the Ristorante Lucia continues to transport its patrons to Northern and Southern Italy through their mouthwatering dishes. Chef Antonio uses all of the culinary expertise and know-how, all of which he learned from his parents, to whip up extraordinary Italian dishes using fresh ingredients and closely guarded family recipes. Patrons of Ristorante Lucia are more than welcome to dine on a truly magnificent menu, enjoy a full bar and their extensive wine list, and even enlist the restaurant’s culinary talents for banquets and catering needs. The only thing left to say is buon appetito!

51 Bank Street, New Milford, Connecticut 06776, Phone: 360-355-5100

© The Cookhouse

If you’re looking for the finest barbeque that New Milford has to offer, you’ll be hard-pressed to find an establishment that does it better than The Cookhouse. Meat eaters all over New Milford have fallen in love with The Cookhouse’s creative and tasty creations, but that doesn’t mean that they don’t have anything for healthy eaters on their menu. In fact, The Cookhouse offers some amazing fresh selections in addition to a number of gluten free menu options. Come check out their menu for yourself and see why and how The Cookhouse went from a neighbor restaurant, to a New Milford institution.

31 Danbury Road, New Milford, Connecticut 06776, Phone: 860-355-4111

© The Iron Rail

There’s nothing simple or unassuming about The Iron Rail’s history. In fact, the history of The Iron Rail can be traced all the way back to 1889 when Thomas F. Young acquired the new Milford House, which houses restaurant. While the location has gone through a lot throughout the years, all of it has led to what The Iron Rail is today, a tasteful restaurant with nothing nut pure food indulgence in mind. The crew behind the restaurant is intent on sating the desires of all the patrons that walk through their doors through their ever changing and seasonally inspired dishes. It goes without saying that that The Iron Rail has tons of amazing food to fill their visitor’s voracious appetites.

10 Railroad Street, New Milford, Connecticut 06776, Phone: 860-799-5606