Select the month that you will be traveling from the table below to view the packing list:
What New Windsor is like to visit throughout the year:
January
When visiting New Windsor in January, it’s important to dress appropriately for the winter weather. The temperatures can drop below freezing, so it’s important to bring warm and waterproof clothes. I recommend dressing in layers, starting with a base layer made of moisture-wicking material, followed by a warm sweater and a waterproof jacket. Don’t forget to bring a hat, gloves, and a scarf to protect your head, hands, and neck from the cold winds. In addition to warm clothing, make sure to pack sturdy and comfortable shoes as well. You’ll want to explore the charming streets and historic sites of New Windsor, and a good pair of shoes will make all the difference. I also suggest bringing a small backpack to carry any essentials you may need, such as a water bottle, snacks, and a map of the city. And don’t forget to bring a camera to capture the beautiful winter scenery and memories of your trip to New Windsor. With the right clothing and gear, you’ll be sure to have a comfortable and enjoyable visit in this lovely town.
When visiting New Windsor in January, there are a few activities that you simply can’t miss. First and foremost, be sure to explore the rich history of the town by visiting the New Windsor Cantonment State Historic Site. This site was once the final encampment of the Continental Army during the Revolutionary War, and offers a fascinating glimpse into the past. Next, take a stroll down Main Street and admire the beautiful architecture of the historic buildings, many of which date back to the 18th and 19th centuries. For a unique experience, hop on the Hudson Valley Wine Trolley and sample some of the region’s best wines while taking in the picturesque winter scenery. In addition to its historical significance, New Windsor also offers plenty of opportunities for outdoor activities in January. Bundle up and head to Plum Point Park, where you can go ice skating on the frozen lake or take a scenic winter hike. For a more adrenaline-pumping adventure, try snowmobiling at the Orange County Snowmobile Club or hit the slopes at Mountain Creek Ski Resort, just a short drive away. And of course, no trip to New Windsor would be complete without indulging in some hearty comfort food at one of the town’s charming restaurants. So pack your winter gear and get ready for an unforgettable January in New Windsor.
February
When visiting New Windsor in February, it’s important to dress in layers to prepare for the chilly weather. A warm winter coat, gloves, and a hat are essential for exploring the outdoor attractions, such as the historic New Windsor Cantonment State Historic Site. Comfortable and sturdy shoes are also a must, as the sidewalks may be slick with snow and ice. Don’t forget to bring a scarf or neck warmer to protect your neck and face from the biting winds. In terms of clothing, it’s best to stick with warm and cozy fabrics such as wool and fleece. Thermal base layers are also a great addition to keep you warm while exploring the town’s charming streets. For evenings out, bring a nice sweater or dressy jacket to layer over your outfit. But don’t worry, New Windsor is a laid-back town and there’s no need to pack any formal wear. As for accessories, a small backpack or crossbody bag will come in handy for carrying essentials like a water bottle, camera, and map. And of course, don’t forget to bring an umbrella or raincoat in case of unexpected showers. With the right clothing and gear, you’ll be able to fully enjoy all that New Windsor has to offer, even in the winter months.
February is a wonderful time to visit the charming town of New Windsor. Despite the chilly temperatures, there are plenty of activities to keep you warm and entertained. One of the highlights of this month is the annual Winterfest, where locals and tourists alike gather to celebrate the beauty of the season. Bundle up and take a stroll through the town square, adorned with sparkling lights and festive decorations. Enjoy a cup of hot cocoa from one of the many vendors, or indulge in some delicious local cuisine from the food trucks. Don’t miss the ice sculpting competition, where talented artists transform blocks of ice into intricate works of art. For those looking for a more active experience, take a trip to nearby Bear Mountain State Park. This picturesque park is a winter wonderland, with stunning views of the Hudson River and plenty of opportunities for outdoor activities. Lace up your ice skates and glide across the frozen lake, or rent snowshoes and explore the park’s many trails. And for the adrenaline junkies, there’s even a thrilling toboggan ride that will have you zooming down a 400-foot track at exhilarating speeds. So don’t let the cold weather deter you from visiting New Windsor in February, as there’s plenty to see and do for all types of travelers.
March
When visiting New Windsor in March, it’s important to pack for the unpredictable weather that comes with early spring. Layers are key, as the temperature can fluctuate between chilly mornings and warmer afternoons. A waterproof jacket or windbreaker is also essential to have on hand for those occasional rainy days. As for footwear, comfortable walking shoes are a must for exploring the charming streets of this historic town. And don’t forget to bring a hat and sunglasses for those sunny days! As for attire, New Windsor is a quaint and casual town, so there’s no need to dress up unless you have a special event planned. Comfortable jeans or pants paired with a light sweater or long-sleeved shirt will be appropriate for most days. And for a touch of local flair, consider bringing a scarf or hat with a traditional plaid pattern, as it’s a nod to the town’s Scottish heritage. Lastly, don’t forget to pack a small backpack or crossbody bag to carry all your essentials while you’re out and about, including a water bottle and a map of the town. Happy travels!
March is a fantastic time to visit the charming town of New Windsor, located in the heart of the Hudson Valley. As the weather starts to warm up, this picturesque town comes to life with a variety of activities and events for visitors to enjoy. One of the highlights of March in New Windsor is the annual Maple Festival, where you can learn all about the process of making maple syrup while indulging in delicious maple treats. The festival also features live music, crafts, and a pancake breakfast – making it a perfect way to experience the local culture. For those looking to embrace the great outdoors, March is also an ideal time to explore the town’s beautiful parks and hiking trails. The Schunnemunk Mountain State Park offers stunning views of the valley and is a popular spot for hiking, birdwatching, and even rock climbing. And for history enthusiasts, a trip to the New Windsor Cantonment State Historic Site is a must. This site was once a military encampment during the Revolutionary War and now serves as a living museum where visitors can learn about the daily life of soldiers during that time period. With so much to see and do, March is the perfect time to discover all that New Windsor has to offer.
April
As you plan your trip to New Windsor in April, it’s important to keep in mind the unpredictable weather this time of year. The days can range from cool and damp to warm and sunny, so it’s best to dress in layers. A light jacket or sweater, along with a waterproof outer layer, will ensure you’re prepared for any temperature changes. Comfortable walking shoes are a must, as New Windsor’s cobblestoned streets and historic sites are best explored on foot. Don’t forget to pack a few versatile pieces of clothing that can easily be dressed up or down, as you’ll want to be ready for both casual sightseeing and more formal occasions. A pair of dark jeans paired with a nice blouse or collared shirt can easily take you from a day of exploring to a dinner at a local restaurant. And of course, don’t forget to bring a small daypack to carry all your essentials, such as sunscreen, a water bottle, and a camera to capture all the beauty of New Windsor. With these tips in mind, you’ll be well-prepared to make the most of your April visit to this charming town.
April is a wonderful time to visit the charming town of New Windsor, located in the scenic Hudson Valley of New York. As the snow melts away and spring flowers start to bloom, this quaint town comes alive with various activities and events. One of the highlights of April in New Windsor is the annual Hudson Valley Farm & Flea, where visitors can browse through local vendors selling fresh produce, handmade crafts, and delicious food while enjoying live music and entertainment. It’s a great way to support the local community and get a taste of the region’s vibrant culture. For history enthusiasts, April is the perfect time to explore New Windsor’s rich past. Visitors can take a tour of the New Windsor Cantonment State Historic Site, where General George Washington and his troops were stationed during the Revolutionary War. The site offers reenactments, guided tours, and a museum showcasing artifacts from that era. Additionally, April is also the month of the New Windsor Cantonment’s annual Revolutionary War encampment, where visitors can witness demonstrations of 18th-century military drills and daily life in a military encampment. Whether you’re a foodie, a history buff, or simply looking for a relaxing weekend getaway, New Windsor has something for everyone in April.
May
May is a beautiful time to visit New Windsor, with the flowers in full bloom and the warm spring weather inviting you to explore this charming town. As a seasoned traveler, I always make sure to dress appropriately for my destination and New Windsor is no exception. The key is to dress in layers, as the weather can be unpredictable during this time of year. A light jacket or sweater paired with a t-shirt and jeans is a great option for a day of sightseeing. Don’t forget to bring a pair of comfortable walking shoes, as you’ll be doing a lot of walking on New Windsor’s cobblestone streets. When packing for your trip to New Windsor in May, make sure to bring a rain jacket or umbrella. While the weather is generally pleasant, there can be occasional showers that add to the town’s romantic ambiance. Also, don’t forget to pack a hat and sunglasses to protect yourself from the sun while strolling through the town’s picturesque gardens. And for those planning to visit any of the town’s historical sites, I recommend bringing a scarf or shawl to cover your shoulders as a sign of respect. With the right clothing and accessories, you’ll be able to fully enjoy all that New Windsor has to offer in May.
May is a fantastic time to visit the charming town of New Windsor in upstate New York. The weather is mild and the town is bursting with activity. One of the must-see sights is the New Windsor Cantonment State Historic Site, where you can step back in time and experience life in a Revolutionary War era military camp. Take a stroll through the recreated camp, watch musket demonstrations, and even try on a soldier’s uniform for a truly immersive experience. For a taste of local culture, be sure to visit the Storm King Art Center. This outdoor sculpture park is set on 500 acres of rolling hills and features over 100 modern and contemporary sculptures. Take a leisurely walk through the park and admire the unique and thought-provoking pieces, or attend one of the many events and exhibitions held throughout the month of May. And don’t forget to stop by the on-site cafe for a delicious lunch with a stunning view of the Hudson River. With so much to see and do, May is the perfect time to explore all that New Windsor has to offer.
June
June is a lovely time to visit New Windsor, with warm temperatures and plenty of sunshine. But before you pack your bags, it’s important to know how to dress for this charming town. As a seasoned traveler, I always recommend dressing in layers to prepare for changing weather. In June, the mornings and evenings can be cool, so a light jacket or sweater is essential. During the day, you’ll want to wear comfortable and breathable clothing, such as shorts or light pants and a t-shirt. And don’t forget to bring a hat and sunscreen to protect yourself from the strong summer sun. When it comes to footwear, I highly recommend bringing a sturdy pair of walking shoes. New Windsor is a pedestrian-friendly town, with plenty of cobblestone streets and charming alleys to explore. Comfortable shoes will not only keep your feet happy, but also allow you to fully immerse yourself in the local culture. And for any outdoor activities or excursions, such as hiking in the nearby mountains, be sure to pack a pair of closed-toe shoes. Lastly, don’t forget to bring a small daypack to carry your essentials, such as a water bottle, camera, and a map of the town. With these tips, you’ll be well-prepared to enjoy your June visit to New Windsor. Happy travels!
June is a fantastic time to visit the charming town of New Windsor, nestled in the heart of the beautiful Hudson Valley. As the weather warms up and the flowers bloom, this quaint town comes to life with a variety of activities and events for travelers to enjoy. One of the top things to do in June is to attend the New Windsor Community Day, a fun-filled festival that celebrates the local community. With live music, delicious food, and a lively atmosphere, this event is a great way to immerse yourself in the vibrant culture of New Windsor. For history buffs, June is the perfect time to visit the New Windsor Cantonment State Historic Site. This site played a crucial role in the Revolutionary War, serving as the final encampment of the Continental Army before their victory at the Battle of Yorktown. Visitors can explore the recreated camp and learn about the daily life of soldiers during this pivotal time in American history. Additionally, the site hosts special events in June, such as reenactments and demonstrations, providing a truly immersive experience. So whether you’re looking for community festivities or a dose of history, New Windsor has something for everyone in the month of June.
July
When traveling to picturesque New Windsor in July, it’s important to pack light and dress for the warm weather. While the town may be known for its historical sites and quaint charm, it can also get quite hot and humid during the summer months. My top tip for dressing in New Windsor is to bring lightweight, breathable clothing such as cotton or linen shirts and shorts. This will keep you cool while exploring the town’s cobblestone streets and old-fashioned shops. In addition to dressing appropriately for the weather, it’s also important to be respectful of the town’s historical significance. When visiting sites such as the 18th century Washington’s Headquarters or the New Windsor Cantonment State Historic Site, it’s best to dress modestly and avoid wearing revealing or offensive clothing. It’s also a good idea to bring a lightweight scarf or shawl to cover your shoulders when entering churches or other religious buildings. And don’t forget to pack comfortable walking shoes, as you’ll likely be doing a lot of sightseeing on foot. With these tips in mind, you’ll be well-prepared to enjoy the charm and history of New Windsor in the summertime.
July is a fantastic time to visit the charming town of New Windsor, located in the beautiful Hudson Valley region of New York. As the warm summer weather settles in, this quaint town comes to life with a variety of exciting activities and events. One of the top things to do in New Windsor during July is to attend the annual Independence Day celebration. This lively event features a parade, live music, delicious food vendors, and of course, a spectacular fireworks display. It’s a great way to experience the patriotic spirit of America while immersing yourself in the local culture. And if you’re a history buff, be sure to visit the New Windsor Cantonment State Historic Site, where General George Washington and his troops stayed during the Revolutionary War. July truly is a wonderful time to explore all that New Windsor has to offer.
August
When visiting the charming town of New Windsor in August, it’s important to dress appropriately for the warm summer weather. Lightweight, breathable clothing is essential, such as cotton or linen tops and bottoms. Opt for loose-fitting clothing to help keep you cool and comfortable while exploring the town’s many sights. Bring a sun hat and sunglasses to protect yourself from the strong summer sun, and don’t forget to pack comfortable walking shoes for all the walking you’ll do. In addition to your summer wardrobe, be sure to bring a light jacket or sweater for the evenings, as the temperature can drop slightly at night. Also, it’s a good idea to bring a small umbrella or rain jacket, as August can bring occasional showers to New Windsor. Don’t forget to pack sunscreen and insect repellent as well, as you’ll likely be spending a lot of time outdoors. And of course, a camera is a must to capture the beauty of New Windsor’s historic buildings, picturesque streets, and stunning views. With these essentials packed, you’ll be ready to fully enjoy all that this charming town has to offer in the month of August.
August is a fantastic time to visit the charming town of New Windsor. Located in the heart of the beautiful Hudson Valley, this historic town offers a plethora of activities for visitors to enjoy. One of the highlights of August in New Windsor is the annual Storm King Art Center Summer Solstice Celebration. This event features live music, delicious local food, and a magical atmosphere as visitors can explore the stunning outdoor sculptures by world-renowned artists. It’s a perfect way to spend a warm summer evening in New Windsor. For history buffs, a visit to the New Windsor Cantonment State Historic Site is a must. This site served as the final encampment of the Continental Army during the Revolutionary War and is now a fascinating museum that showcases the daily life of soldiers during that time. In August, the site hosts various reenactments and demonstrations, giving visitors a unique opportunity to step back in time and experience a piece of American history. Don’t miss the chance to learn about the brave men who fought for our independence while admiring the beautiful Hudson Valley scenery.
September
When visiting New Windsor in September, it’s important to pack for both warm and cool weather. The beginning of September can still be quite warm, while towards the end of the month, the temperatures start to drop. I recommend bringing lightweight, breathable clothing such as t-shirts, shorts, and sundresses for the warmer days. However, be sure to also pack some layers such as long-sleeved shirts, sweaters, and a light jacket for the cooler evenings. It’s always a good idea to check the weather forecast before your trip to get a better idea of what to expect. As for footwear, comfortable walking shoes are a must. New Windsor has many historical sites and beautiful parks to explore, so you’ll want to be prepared to do a lot of walking. I also suggest bringing a pair of closed-toed shoes for any outdoor activities or hikes you may want to do. Additionally, don’t forget to bring a rain jacket or umbrella, as September can bring some showers. Lastly, a hat, sunglasses, and sunscreen are essential for protecting yourself from the strong sun rays. With these tips, you’ll be dressed and prepared for whatever September may bring in New Windsor.
As summer fades into fall, the charming town of New Windsor comes alive with a variety of activities perfect for a September visit. Start your day with a stroll through the historic district, taking in the beautiful architecture and learning about the town’s rich history. Then, head to the farmers market where you can sample local produce and handmade goods while chatting with friendly locals. For a unique experience, hop on a hot air balloon ride and take in the stunning views of the changing leaves from above. In the evening, catch a live performance at the renovated New Windsor Opera House, a must-visit for any culture enthusiast. September is the perfect time to explore all that New Windsor has to offer, with its pleasant weather and festive atmosphere. For outdoor enthusiasts, September is an ideal time to visit New Windsor. Take advantage of the mild temperatures and head to the nearby Storm King State Park for a scenic hike or bike ride. The park offers breathtaking views of the Hudson River and the surrounding mountains, making it the perfect spot for a picnic lunch. If you’re feeling adventurous, try your hand at kayaking or stand-up paddleboarding on the river. For a more leisurely activity, spend an afternoon picking apples at one of the town’s many orchards, followed by a stop at a local cidery to sample some of the best hard ciders in the region. With so much to see and do, September is the perfect time to explore New Windsor and all it has to offer.
October
As October brings cooler temperatures and changing leaves to New Windsor, it’s important to dress appropriately for the season. I recommend layering your clothing, as the weather can be unpredictable. A light jacket or sweater paired with a scarf and comfortable shoes will keep you warm and stylish as you explore the charming town. Don’t forget to bring a waterproof jacket or umbrella, as showers are common during this time of year. When packing for your trip to New Windsor in October, be sure to include items that will keep you comfortable while sightseeing. Comfortable walking shoes are a must, as many of the town’s attractions are best explored on foot. Bring a hat and sunglasses to protect yourself from the sun on warmer days, and a warm hat and gloves for chilly mornings and evenings. And of course, don’t forget your camera to capture the beautiful fall foliage and historic monuments!
October is a fantastic time to visit the charming town of New Windsor, located in the picturesque Hudson Valley region. As the leaves turn vibrant shades of red, orange, and gold, visitors can fully immerse themselves in the beauty of the fall season. One of the must-see attractions during this time is the New Windsor Cantonment State Historic Site, where you can learn about the role this area played in the American Revolution. Take a tour of the encampment and imagine what life was like for the soldiers who fought for our independence. Don’t miss the reenactments and demonstrations that bring history to life. For a more leisurely activity, head to the Storm King Art Center, a sprawling outdoor sculpture park that showcases the works of renowned artists. The fall foliage provides a stunning backdrop for these unique and thought-provoking pieces. And if you’re feeling adventurous, take a hike along one of the many trails that wind through the park. The crisp autumn air and stunning views are sure to rejuvenate your soul. And after a day of exploring, be sure to stop by one of the local farms for some fresh apple cider and homemade apple cider donuts – the perfect way to end a perfect October day in New Windsor.
November
When visiting New Windsor in November, it’s important to dress in layers. The weather can be quite unpredictable during this time, with chilly mornings and evenings, but warm afternoons. I recommend bringing a light jacket or sweater to wear during the day, and a heavier coat for the cooler evenings. Don’t forget to pack a scarf, hat, and gloves to keep yourself warm and comfortable while exploring the charming streets of New Windsor. As for footwear, I suggest bringing a pair of comfortable walking shoes or boots. New Windsor’s cobblestone streets can be quite uneven, so it’s important to have sturdy shoes to navigate them. You may also want to bring a pair of dressier shoes for a night out at one of the town’s fine restaurants. In terms of what to pack, be sure to bring versatile clothing that can be easily mixed and matched. This will save space in your suitcase and allow you to create different outfits for each day of your trip. And don’t forget to pack a camera to capture the beautiful fall foliage that blankets the town in November. Happy travels!
November is a fantastic time to visit the charming town of New Windsor, nestled in the beautiful Hudson Valley. As the leaves begin to change and the air turns crisp, this quaint town comes alive with a variety of activities for visitors to enjoy. One of the highlights of November in New Windsor is the annual Holiday Market, where local vendors gather to sell their wares, from homemade jams to handcrafted jewelry. This is the perfect place to find unique gifts for your loved ones or to simply soak up the festive atmosphere. For those looking to immerse themselves in the rich history of New Windsor, a visit to the New Windsor Cantonment State Historic Site is a must. This was the final encampment of General George Washington’s Continental Army during the American Revolution, and visitors can explore the recreated structures and learn about the daily life of the soldiers. November also marks the anniversary of the famous “Farewell Orders” given by Washington to his troops, making it an especially poignant time to visit. So come to New Windsor in November and experience the perfect blend of history, culture, and holiday cheer.
December
When visiting the charming town of New Windsor in December, it’s important to come prepared for the chilly weather. The average temperature during this time of year is around 40 degrees Fahrenheit, so I recommend dressing in layers. A warm base layer, such as a thermal shirt or long-sleeved sweater, is essential. On top, a cozy jacket or coat will keep you warm while exploring the town’s picturesque streets. Don’t forget to pack a scarf, gloves, and a hat to protect your extremities from the cold. Comfortable walking shoes with good grip are also a must, as you’ll want to explore the town on foot and may encounter some slippery sidewalks. As for what to wear in the evenings, New Windsor has a range of restaurants and pubs perfect for a cozy night out. A nice pair of jeans or pants paired with a sweater or collared shirt is appropriate attire for these establishments. And for those planning to attend any holiday events or performances, a dressier outfit will be needed. A nice dress or slacks with a festive top will fit right in with the holiday spirit. Finally, don’t forget to pack a waterproof jacket or umbrella, as December can bring some rain and snow to this charming town. With these tips in mind, you’ll be well-prepared and comfortable during your December visit to New Windsor.
Welcome to New Windsor, a charming town nestled in the Hudson Valley of New York. While many travelers may think of summer as the ideal time to visit, December brings its own unique charm to this picturesque destination. Here are a few activities that are sure to make your December visit to New Windsor memorable. First, take a stroll through the historic downtown area, adorned with twinkling lights and festive decorations. Stop by the local shops and boutiques to find the perfect gifts for your loved ones. And don’t forget to warm up with a cup of hot cocoa from one of the cozy cafes. Next, bundle up and head to the Storm King Art Center, where you can experience larger-than-life sculptures set against a backdrop of snowy landscapes. And for a truly magical experience, visit the United States Military Academy at West Point during their annual “Christmas at West Point” event, featuring holiday concerts and a festive light display. No matter what you choose to do in December, New Windsor is sure to enchant you with its small-town charm and festive spirit.
Hey there! I’m Jason, a total travel junkie who is always on the go. I live for discovering new places, meeting cool people, and experiencing different cultures. I’m here to help you with your travels.
