New Milford, Connecticut: What to Bring, what to Pack, and what to Wear


Select the month that you will be traveling from the table below to view the packing list:

JanuaryFebruaryMarchApril
MayJuneJulyAugust
SeptemberOctoberNovemberDecember

What New Milford is like to visit throughout the year:

January

As the winter chill settles in, New Milford transforms into a cozy winter wonderland. But don’t let the frosty temperatures deter you from exploring this charming town. To stay warm and comfortable, be sure to dress in layers. Start with a base layer of thermal underwear, followed by a sweater or fleece, and top it off with a waterproof jacket. Don’t forget to bring a scarf, hat, and gloves to keep your extremities toasty. And for footwear, opt for sturdy snow boots to navigate the snowy sidewalks. In addition to dressing appropriately, it’s important to bring the right gear for exploring New Milford in January. A sturdy pair of hiking boots will come in handy for trekking through the snow-covered hills and trails. A small backpack is also essential for carrying essentials like water, snacks, and a camera. And don’t forget to pack a good pair of sunglasses to protect your eyes from the glare of the winter sun. With the right attire and gear, you’ll be able to fully enjoy all that New Milford has to offer during the winter months.

January is a magical time to visit New Milford, Connecticut. While the chilly weather may keep some travelers away, those who brave the cold are in for a treat. Start your day with a cup of hot cocoa from one of the local cafes, and then head to the town’s charming village green. Here, you’ll find a picturesque winter wonderland complete with ice skating rink and cozy vendors selling warm snacks and handcrafted goods. For an even more immersive experience, join in on one of the community’s ice carving competitions and watch as talented artists transform blocks of ice into stunning sculptures. After a morning of winter fun, warm up at the New Milford Historical Society Museum. This hidden gem offers a fascinating glimpse into the town’s past, with exhibits on everything from the Revolutionary War to the industrial era. In the afternoon, take a stroll along the Housatonic River, which runs through the heart of New Milford. Admire the frozen landscape and keep an eye out for bald eagles, which are known to nest in the area during the winter. End your day with a hearty meal at one of the town’s cozy restaurants, where you can indulge in local specialties like apple cider glazed pork chops or roasted butternut squash soup. January may be cold, but New Milford’s charm will warm your heart.

February

February in New Milford brings chilly temperatures and the possibility of snow, so it’s important to pack accordingly. As a traveler, I always recommend dressing in layers to prepare for any weather changes throughout the day. A warm base layer, such as thermal underwear, is essential. On top of that, a sweater or fleece will provide extra warmth, and a waterproof jacket will keep you dry in case of rain or snow. Don’t forget to bring a hat, gloves, and a scarf to protect your head, hands, and neck from the cold. Comfortable, waterproof shoes with good traction are also a must for navigating the snowy sidewalks. While packing for your trip to New Milford, keep in mind that the town is known for its charming, small-town feel. So leave your fancy clothes at home and opt for casual, comfortable outfits. Jeans or warm leggings paired with a cozy sweater and boots are a great choice for exploring the town’s quaint cafes and boutique shops. And don’t forget to bring a small backpack or crossbody bag to carry your essentials, such as a camera, water bottle, and a map of the town. With the right clothing and gear, you’ll be able to fully enjoy all that New Milford has to offer, no matter the weather.

February in New Milford may be cold, but don’t let that stop you from visiting this charming town. Bundle up and take a stroll through the historic downtown area, where you’ll find quaint shops, cozy cafes, and beautiful architecture. The town also boasts a number of art galleries, perfect for browsing and finding unique souvenirs to take home. If you’re feeling adventurous, head to the nearby Candlewood Lake for some ice fishing or ice skating. The serene winter landscape is truly a sight to behold. And after a day of exploring, warm up with a cup of hot cocoa at one of the local cafes or treat yourself to a delicious meal at one of the many restaurants in town. One of the highlights of visiting New Milford in February is the town’s annual Winter Festival. This week-long event features ice carving demonstrations, live music, and a variety of winter activities for all ages. Bundle up and join the locals in celebrating the beauty of the season. And for a truly unique experience, take a horse-drawn carriage ride through the snowy streets of New Milford. The festival also offers a chance to sample delicious local foods and warm up with a cup of mulled wine or hot cider. Don’t miss out on this festive and charming winter celebration in New Milford.

March

When visiting the charming town of New Milford in March, it’s important to pack layers to prepare for the ever-changing weather. The days can start off chilly, with temperatures in the 40s, but by mid-day, it can warm up to the 60s. I recommend bringing a light jacket, a scarf, and a sweater to easily adjust to the changing temperatures. It’s also a good idea to pack comfortable walking shoes, as New Milford is a pedestrian-friendly town with many beautiful parks and trails to explore. In terms of clothing, it’s always a good idea to dress in layers in New Milford. The town is known for its picturesque New England charm, so it’s common to see locals wearing classic and casual outfits. For women, I suggest packing a mix of jeans, skirts, and dresses, paired with comfortable boots or flats. For men, a nice pair of jeans with a collared shirt and a jacket will fit in perfectly. Don’t forget to bring a rain jacket or umbrella, as March can bring occasional showers. And for those looking to blend in with the locals, don’t forget to pack a baseball cap or knit beanie for those cooler days. With these tips, you’ll be dressed and ready to explore all that New Milford has to offer.

March is a fantastic time to visit the charming town of New Milford. As the weather starts to warm up, the town comes to life with a variety of activities and events. One of the top things to do in March is to take a stroll down the historic Bank Street. Lined with quaint shops, cafes, and galleries, this street is a perfect spot to immerse yourself in the local culture and pick up some unique souvenirs. For outdoor enthusiasts, March is an ideal time to explore the natural beauty of New Milford. Head to Lover’s Leap State Park for a scenic hike with stunning views of the Housatonic River. Or, if you prefer a more leisurely activity, take a walk along the picturesque boardwalk at Candlewood Lake. And don’t forget to stop by the local farmers market, where you can taste some of the freshest produce and sample delicious homemade goods. No matter what your interests may be, New Milford has something for everyone to enjoy in the month of March.

April

When visiting the quaint town of New Milford in April, it’s important to dress in layers to prepare for the changing temperatures. The mornings can be chilly, but as the day progresses, the sun will come out and warm things up. I recommend bringing a light jacket, a scarf, and a pair of comfortable walking shoes. The town is known for its picturesque trails and beautiful parks, so you’ll want to be able to explore without any discomfort. As for attire, the locals tend to dress casually, so leave your fancy clothes at home and opt for comfortable and practical outfits. Don’t forget to bring a raincoat or umbrella, as April showers are common in this part of the country. While packing for your trip to New Milford, be sure to bring a reusable water bottle. The town is eco-friendly and has many water fountains and refill stations to encourage visitors to stay hydrated without the use of single-use plastic bottles. Additionally, don’t forget to pack a camera to capture the stunning scenery and historic buildings. I also recommend bringing a journal to jot down your thoughts and memories as you explore this charming town. And of course, bring your sense of adventure and willingness to try new things. New Milford has a rich culture and friendly locals, so don’t be afraid to immerse yourself in the community and truly experience all that this town has to offer.

New Milford, located in the picturesque Litchfield Hills of Connecticut, is a charming town that offers a plethora of activities for visitors in the month of April. As the weather starts to warm up, this quaint New England town comes to life with blooming flowers and bustling streets. One of the must-do activities in April is to take a stroll along the scenic Housatonic River, which runs through the heart of New Milford. Enjoy the tranquil atmosphere and take in the beautiful views of the river and surrounding nature. For history buffs, a visit to the New Milford Historical Society is a must. Housed in a charming old building, this museum showcases the town’s rich history through engaging exhibits and artifacts. In April, the museum also hosts a special event called “Spring on the Farm”, where visitors can experience what life was like on a traditional New England farm in the 19th century. From sheep shearing demonstrations to blacksmithing workshops, this event is a fun and educational way to spend a day in New Milford. Don’t forget to pick up some freshly made maple syrup from the on-site sugar shack before you leave!

May

As you plan your trip to the charming New England town of New Milford in May, it’s important to consider the changing weather and pack accordingly. The key to comfortable and versatile dressing in this region is layering. Start with a light base layer, such as a tank top or t-shirt, and add a lightweight sweater or jacket on top. This will allow you to adapt to the cool mornings and warm afternoons. Don’t forget to bring a waterproof jacket or umbrella as well, as spring showers are common in this region. When it comes to footwear, opt for comfortable walking shoes as New Milford is a pedestrian-friendly town with many cobblestone streets. If you plan on doing any hiking or outdoor activities, bring a pair of sturdy sneakers or hiking boots. As for accessories, a lightweight scarf or hat can come in handy for both style and warmth. And of course, don’t forget to bring a camera to capture the beautiful blooming flowers and picturesque landscapes of New Milford in May. With these items in your suitcase, you’ll be prepared for any weather and ready to explore this charming town in style.

May is a wonderful time to visit New Milford, a charming town nestled in the scenic Litchfield Hills of Connecticut. As spring blooms in full force, there are plenty of activities to keep you busy while exploring this quaint New England gem. One of the highlights of visiting New Milford in May is experiencing the town’s vibrant farmers market. Held on Saturdays, this market showcases the best of the region’s fresh produce, artisanal goods, and locally made crafts. Take a stroll through the lively stalls, try some of the delicious samples, and chat with the friendly vendors. After stocking up on goodies, head to the nearby town green for a picnic and enjoy the picturesque views of the Housatonic River. It’s the perfect way to spend a sunny day in New Milford.

June

When traveling to New Milford in June, it’s important to be prepared for the warm and humid weather. The temperature can reach up to the high 80s, so you’ll want to pack light and comfortable clothing. I recommend bringing a mix of shorts, t-shirts, and lightweight dresses or skirts for women. For men, a pair of breathable pants and collared shirts would be appropriate. Don’t forget to pack a hat and sunglasses to protect yourself from the strong sun rays. It’s also a good idea to bring a light jacket or sweater for the evenings when the temperature can drop. In addition to packing appropriate clothing, it’s important to bring comfortable walking shoes. New Milford is a charming town with plenty of opportunities for exploring on foot, so you’ll want to make sure you have comfortable footwear. Another essential item to bring is a reusable water bottle. With the high temperatures, it’s important to stay hydrated while out and about. Finally, don’t forget to pack sunscreen and insect repellent, as the warm weather tends to bring out bugs. With these items in hand, you’ll be ready to enjoy all that New Milford has to offer in the beautiful month of June.

June is a wonderful time to visit the charming town of New Milford, located in the scenic Litchfield Hills of Connecticut. As the warm weather arrives, the town comes alive with outdoor activities and events. One of the top things to do in June is to explore the town’s beautiful parks and trails. The Housatonic River flows through New Milford, making it a perfect spot for kayaking, canoeing, or fishing. The Housatonic Meadows State Park offers stunning views of the river and is a popular spot for picnics and birdwatching. For those looking to stretch their legs, the nearby Lover’s Leap State Park offers hiking trails with breathtaking views of the river and surrounding mountains. In addition to outdoor adventures, June also brings a variety of festivals and events to New Milford. The annual Village Fair Days takes place in early June and features local vendors, live music, and delicious food. The town also hosts a weekly farmers market, where visitors can sample fresh produce and homemade goods from local farmers and artisans. And for the history buffs, the New Milford Historical Society offers walking tours of the town’s historic district every Saturday in June. With so much to see and do, June is the perfect time to experience the beauty and charm of New Milford.

July

When visiting the charming and historic town of New Milford in July, it’s important to dress for both comfort and style. The weather can be quite warm and humid, so lightweight and breathable fabrics are a must. I recommend packing a few pairs of shorts or skirts, along with short-sleeved shirts or blouses. For women, a sundress is a great option for exploring the town’s quaint shops and strolling along the Housatonic River. Men can opt for lightweight khaki pants or linen shorts paired with a polo shirt or button-down. A comfortable pair of walking shoes is also essential for exploring the town’s hilly streets and parks. In addition to clothing, be sure to bring along a few essentials to make the most of your trip to New Milford. A small backpack or crossbody bag is perfect for carrying your camera, water bottle, and other necessities while you’re out and about. A light jacket or sweater may also come in handy for cooler evenings. Don’t forget to pack sunscreen and a hat to protect yourself from the strong summer sun. And finally, be sure to bring some cash as many of the town’s charming boutiques and restaurants are cash-only. With the right attire and essentials, you’ll be ready to experience all that New Milford has to offer in the sunny month of July.

July is the perfect time to visit the charming town of New Milford, Connecticut. Nestled in the picturesque Litchfield Hills, this town offers a variety of activities that are sure to please any traveler. One must-see attraction is the New Milford Farmers Market, held every Saturday in the historic town center. Here, local farmers and artisans gather to sell their fresh produce and handmade goods. It’s a great place to grab some delicious snacks for a picnic by the scenic Housatonic River. For history buffs, a visit to the New Milford Historical Society is a must. Housed in a beautifully restored 18th-century building, this museum showcases the town’s rich history through interactive exhibits and guided tours. Another must-visit location is the Harrybrooke Park, a 48-acre park with stunning gardens, hiking trails, and a picturesque waterfall. In July, the park hosts a variety of events, including outdoor concerts and movie nights, making it the perfect place to spend a lazy summer evening. With its small-town charm and abundance of activities, New Milford is the perfect destination for a summer getaway.

August

When visiting the charming town of New Milford in August, it’s important to dress comfortably and appropriately for the warm summer weather. The average temperature during this time is around 80 degrees Fahrenheit, so lightweight and breathable clothing is key. Opt for shorts, skirts, and light-colored tops to stay cool while exploring the town. Don’t forget to bring a hat and sunglasses to protect yourself from the sun’s rays. As for footwear, comfortable walking shoes are a must. New Milford is a pedestrian-friendly town with plenty of sidewalks and trails to explore, so be sure to have a good pair of walking shoes to keep your feet happy. Additionally, don’t forget to bring a light sweater or jacket for cooler evenings, as well as a swimsuit if you plan on taking a dip in the nearby rivers or lakes. And of course, don’t leave home without a camera to capture the beautiful scenery and quaint charm of New Milford.

August is a fantastic time to visit the charming town of New Milford, Connecticut. With its picturesque setting on the banks of the Housatonic River and its rich history, there’s no shortage of things to do here in the summer months. One of my favorite activities is to take a stroll along the historic New Milford Green, a lovely park surrounded by beautifully preserved colonial homes. The Green also hosts a weekly farmer’s market, where you can sample some delicious local produce and chat with friendly locals. For outdoor enthusiasts, August is the perfect time to explore the natural beauty of New Milford. I highly recommend taking a hike on the scenic New Milford River Trail, which winds its way along the Housatonic River and offers stunning views of the surrounding countryside. You can also rent a canoe or kayak and paddle your way down the river, taking in the peaceful atmosphere and spotting wildlife along the way. And don’t miss the chance to cool off at Candlewood Lake, where you can swim, fish, or simply relax on the sandy shores. With its small-town charm and plethora of outdoor activities, New Milford is the perfect destination for a summer getaway.

September

As the summer months come to an end and the leaves start to change, September is a beautiful time to visit New Milford. The weather is mild and comfortable, making it the perfect time to explore the charming town and its surrounding areas. When packing for your trip, it’s important to remember to bring layers. The temperature can vary throughout the day, so having a light jacket or sweater on hand will ensure you stay comfortable no matter where your adventures take you. A pair of comfortable walking shoes is also a must, as New Milford is a pedestrian-friendly town with many sidewalks and trails to explore. When it comes to dressing for New Milford, think casual and comfortable. Locals here have a relaxed and laid-back style, so leave your fancy attire at home. Opt for jeans or khakis paired with a comfortable shirt or blouse. And don’t forget to pack a hat and sunglasses to protect yourself from the sun while strolling through the town’s charming streets. As for accessories, a small backpack or crossbody bag is perfect for carrying your essentials while leaving your hands free to snap photos of the picturesque scenery. With these tips in mind, you’ll be dressed for a perfect September visit to New Milford.

September is a fantastic time to visit the charming town of New Milford. As the summer crowds begin to dissipate, the crisp autumn air settles in and the changing leaves paint the town in vibrant hues. One of the highlights of this season is the annual New Milford Village Fair and Car Show, which takes place in the first week of September. This lively event brings together locals and visitors alike to enjoy classic cars, live music, and delicious food from local vendors. It’s a perfect way to get a taste of the town’s warm community spirit while also admiring some beautiful vintage automobiles. Another must-see attraction in September is the Harrybrooke Park and Harden House. This picturesque park offers a peaceful escape from the hustle and bustle of everyday life. Stroll through the serene gardens, hike the scenic trails, and take in the stunning views of the Housatonic River. The historic Harden House, built in the late 18th century, is also open for tours during this time and provides a fascinating glimpse into the town’s past. September in New Milford is a time to slow down, appreciate the simple pleasures of life, and immerse yourself in the rich history and natural beauty of this charming town.

October

When planning a trip to New Milford in October, it’s important to pack for the changing weather. As the leaves start to turn and the temperatures drop, dressing in layers is key. Bring a mix of sweaters, long-sleeved shirts, and a lightweight jacket that can easily be taken off or added on depending on the weather. Comfortable walking shoes are also a must as there are many beautiful hiking trails and quaint streets to explore in this charming town. In terms of what to wear, I recommend sticking to neutral colors and avoiding flashy or bright patterns. This will not only help you blend in with the locals, but also allow you to easily mix and match your outfits. Don’t forget to also bring a rain jacket or umbrella, as October in New Milford can bring occasional showers. And of course, no trip to New Milford is complete without a cozy scarf and hat to keep you warm while strolling through the picturesque autumn scenery. With these wardrobe essentials, you’ll be well-prepared to fully enjoy the charming atmosphere of this delightful New England town in October.

October is a wonderful time to visit the quaint town of New Milford, nestled in the picturesque Litchfield Hills of Connecticut. As the leaves begin to change and a crispness fills the air, the town comes alive with fall festivities. One of the highlights of this month is the annual Harvest Festival, where visitors can sample local foods, peruse handmade crafts, and enjoy live music. It’s a great opportunity to immerse yourself in the vibrant community and get a taste of authentic New England culture. For outdoor enthusiasts, October is the perfect time to explore the natural beauty of the area. The nearby Candlewood Lake offers stunning views of the colorful foliage and is a popular spot for fishing and boating. Hiking trails, such as the scenic Steep Rock Preserve, are also a must-visit for those looking to experience the stunning fall foliage up close. And after a day of outdoor adventure, be sure to stop by one of the charming local restaurants for a hearty meal and a warm cup of apple cider. Fall is truly a magical time to visit New Milford.

November

As the leaves turn to vibrant shades of red, orange, and yellow, November is a beautiful time to visit the charming town of New Milford. With crisp temperatures and potentially chilly winds, it’s important to dress appropriately for your visit. I recommend dressing in layers, starting with a comfortable base layer such as a long-sleeved shirt or sweater. Bringing a warm jacket or coat is a must, as well as a scarf, gloves, and a hat to keep you cozy while exploring the town’s picturesque streets and parks. When it comes to footwear, comfortable walking shoes or boots are essential for navigating New Milford’s hilly terrain. I also suggest bringing a waterproof option, as November can bring some rain showers. As for what to pack, don’t forget to bring a camera to capture the stunning fall foliage, as well as a reusable water bottle to stay hydrated on your adventures. And of course, don’t forget to pack a sense of curiosity and a willingness to immerse yourself in the local culture and charm of this lovely town. Happy travels!

November is a magical time to visit the charming town of New Milford. As the leaves change colors and the air turns crisp, it’s the perfect opportunity to enjoy the great outdoors. A favorite activity during this time is to take a scenic drive along the Housatonic River, where you can witness the stunning fall foliage and maybe even spot some local wildlife. For a more active adventure, lace up your hiking boots and explore the trails at Harrybrooke Park, where you can immerse yourself in the natural beauty of the area. But it’s not all about nature in New Milford. November also brings with it a lively arts scene. The town hosts its annual New Milford Film Festival, showcasing the works of up-and-coming filmmakers. This is a great opportunity to support local artists and catch some thought-provoking films. For a taste of the local culture, visit the historic downtown area and check out the quaint shops and art galleries. And don’t forget to grab a warm cup of apple cider from one of the many charming cafes – it’s the perfect way to warm up on a chilly November day.

December

When visiting New Milford in December, it’s important to dress in layers to stay warm and comfortable. The weather can be unpredictable at this time of year, with potential for chilly temperatures and snow. A warm base layer, such as thermal underwear, is essential. On top of that, wear a cozy sweater or fleece and a waterproof jacket. Don’t forget a hat, gloves, and a scarf to protect your head, hands, and neck. Comfortable, waterproof shoes or boots with good traction are a must, as the streets can get slippery with ice and snow. And of course, don’t leave home without a sturdy umbrella to shield you from any unexpected rainfall. As for what to bring, it’s always a good idea to pack a compact umbrella, a portable charger for your phone, and a reusable water bottle. New Milford is a charming town with plenty of quaint shops and delicious restaurants, so be sure to bring some spending money for souvenirs and tasty treats. And if you’re planning on doing some outdoor activities, such as hiking or skiing, be sure to bring appropriate gear and clothing. Finally, don’t forget to pack a positive attitude and a sense of adventure, as New Milford has plenty to offer in terms of beautiful scenery, friendly locals, and cozy holiday vibes.

December is a magical time to visit the charming town of New Milford. The holiday spirit is in full swing, with festive decorations adorning the streets and cheerful carolers spreading joy throughout the town. One of the must-do activities during this time is to visit the iconic Christmas Village. This beloved tradition has been around for over 70 years and features charming displays, a Santa’s workshop, and a chance to meet the man himself. It’s the perfect place to get into the holiday spirit and make some cherished memories with loved ones. For a taste of local culture, be sure to check out the New Milford Winter Farmers Market. Held every Saturday in December, this market showcases the best of the town’s produce, crafts, and artisanal goods. You can pick up unique gifts for your loved ones, sample delicious homemade treats, and mingle with friendly locals. The market also hosts live music and entertainment, adding to the festive atmosphere. It’s a great way to support the community and experience the warm hospitality of New Milford. So bundle up, grab a cup of hot cocoa, and enjoy the cozy winter vibes of this charming town.

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