Select the month that you will be traveling from the table below to view the packing list:
What Westchester is like to visit throughout the year:
January
When visiting Westchester in January, it’s important to come prepared for the cold weather. The average temperature during this month is around 32°F, so layers are essential. A warm winter coat, gloves, hat, and scarf are a must. It’s also a good idea to bring waterproof boots as there may be snow on the ground. Don’t forget to pack a few pairs of thick socks to keep your feet warm and cozy while exploring the charming towns of Westchester. While dressing for the cold is important, it’s also important to dress appropriately for the various activities available in Westchester. If you plan on visiting the many historic sites and museums, comfortable and warm clothing is recommended. However, if you’re planning on hitting the slopes at one of the ski resorts, make sure to pack your ski gear and warm, waterproof clothing. No matter what your plans may be, it’s always a good idea to bring a small backpack to carry extra layers, water, and snacks. With the right attire and essentials, you’ll be able to fully enjoy the beauty and charm of Westchester in January.
January is a wonderful time to explore the picturesque county of Westchester, just a short train ride away from the hustle and bustle of New York City. While the chilly temperatures may keep some indoors, there are plenty of activities to keep visitors entertained during this winter month. Start your day with a visit to the historic Kykuit estate, the former home of the Rockefeller family. The stunning gardens may be covered in snow, but the grand architecture and rich history are sure to impress. Afterward, warm up with a hot cup of cocoa at one of the charming cafes in the nearby town of Tarrytown. For those with a love for the arts, January is the perfect time to visit the renowned Caramoor Center for Music and the Arts. This cultural hub hosts a variety of events throughout the month, including classical concerts, art exhibitions, and even a winter festival. And for a taste of local culture, don’t miss the annual Westchester Broadway Theatre’s production of “A Christmas Carol” in nearby Elmsford. January may be a quiet month in Westchester, but it’s certainly not lacking in charm and activities for visitors to enjoy.
February
February is a lovely time to visit Westchester, with the winter chill still in the air but hints of spring on the horizon. As a traveler, it’s important to dress in layers during this time of year. The mornings can be quite chilly, but as the day progresses, the sun may come out and warm things up. Be sure to pack a warm coat, scarf, and gloves to keep you comfortable during your outdoor explorations. I also recommend bringing a waterproof jacket or umbrella, as February can bring a mix of rain and snow. Comfortable and sturdy shoes are a must, as the sidewalks and trails may be slick with ice or snow. In terms of clothing, Westchester is a fairly casual area. You’ll see locals dressed in a mix of styles, from sporty outdoors gear to business casual. As a traveler, it’s always a good idea to blend in with the locals, so I recommend packing a mix of comfortable and versatile clothing. A couple of pairs of jeans, a few sweaters or long-sleeved shirts, and a dress or two for a night out should cover all your bases. And don’t forget to bring a swimsuit, as many hotels and inns in the area have heated pools and hot tubs to enjoy during the chilly evenings. With these essentials in your suitcase, you’ll be well-prepared to explore and experience all that Westchester has to offer in February.
February is a magical time to visit Westchester, New York. While the winter chill may still be in the air, the county is bustling with activities and events that will warm your heart. One must-do experience is the Hudson River EagleFest, where you can witness the magnificent bald eagles as they migrate south. This annual festival also features live bird shows, educational programs, and guided eagle walks. It’s a unique opportunity to get up close and personal with these majestic creatures. For a taste of history and culture, don’t miss out on visiting Kykuit, the Rockefeller estate. This grand mansion was once home to four generations of the Rockefeller family and is now a National Historic Landmark. The estate offers guided tours of the stunning interiors, beautiful gardens, and impressive art collection. February is also the perfect time to visit as the estate is adorned with beautiful winter decorations, creating a charming ambiance. The tour is a fascinating insight into the life of one of America’s most influential families and a must-see for any history lover.
March
When visiting the charming county of Westchester in March, it’s important to dress in layers as the weather can be quite unpredictable. Start with a light sweater or jacket and bring along a raincoat or umbrella just in case. Comfortable walking shoes are a must as you’ll likely spend most of your time exploring the quaint villages and picturesque parks. And don’t forget a scarf or hat to protect against the chilly winds that can still linger in early spring. As for what to wear, opt for casual and comfortable clothing that can easily transition from day to night. Jeans and a nice blouse or button-down shirt are perfect for strolling through the charming towns and villages, while a dress or collared shirt would be appropriate for a nicer dinner out. And don’t forget to pack a swimsuit if you plan on taking a dip in the indoor pool at one of the many luxurious resorts in the area. Overall, Westchester is a laid-back and welcoming destination, so there’s no need to overthink your wardrobe. Just be sure to dress for the weather and you’ll fit right in with the local style.
March is a fantastic time to visit Westchester, as the crisp air and budding flowers make for a picturesque experience. One of the must-see destinations in March is the historic Kykuit estate, home to four generations of the Rockefeller family. The stunning gardens and impressive art collection are a sight to behold, and the guided tour offers a fascinating glimpse into the lives of one of America’s most influential families. Plus, with fewer visitors during this time of year, you’ll have plenty of space to wander and take in the breathtaking scenery. For a more active adventure, head to the Hudson River for a scenic bike ride along the famous Croton Aqueduct Trail. This 26-mile trail follows the path of an old aqueduct and offers stunning views of the river and surrounding countryside. Along the way, you’ll pass charming towns and historic sites, including the Lyndhurst Mansion and Sleepy Hollow Cemetery. And if you’re feeling particularly adventurous, you can even continue onto the Old Croton Trailway, adding an additional 14 miles to your journey. No matter what you choose to do in Westchester, March is the perfect time to explore and experience all this beautiful region has to offer.
April
As spring begins to bloom in Westchester, so does the need for appropriate attire for your travels. In April, the weather can be unpredictable, ranging from chilly mornings to warm afternoons, so layering is key. I recommend packing a light jacket or sweater for the cooler mornings, and a t-shirt or blouse for the warmer afternoons. Comfortable shoes are a must, as Westchester is known for its scenic hikes and nature trails. Don’t forget to bring a rain jacket or umbrella, as April showers are common in this region. When it comes to dressing for cultural attractions in Westchester, I suggest opting for smart casual attire. This means avoiding shorts, tank tops, and flip flops, and opting for more conservative clothing such as jeans or slacks and a nice shirt. If you plan on visiting local churches or religious sites, it is important to cover your shoulders and knees out of respect. Additionally, I recommend bringing a hat and sunglasses to protect yourself from the bright April sunshine. And of course, don’t forget to pack a camera to capture the beauty of Westchester in the springtime.
April is a fantastic time to visit Westchester County, just north of bustling New York City. As the weather starts to warm up, the county comes to life with vibrant colors and exciting activities. One of the must-do experiences in April is to visit the Stone Barns Center for Food and Agriculture. This working farm and education center offers visitors a glimpse into sustainable farming practices and the opportunity to taste delicious, fresh produce. It’s a great way to connect with nature and support local farmers. While you’re there, be sure to take a stroll through the beautiful gardens and say hello to the adorable farm animals. For history buffs, April is the perfect time to explore the rich heritage of Westchester. The county played a significant role in the American Revolutionary War, and there are many historical sites to visit, such as Washington’s Headquarters in White Plains and the Philipse Manor Hall in Yonkers. Additionally, April is National Poetry Month, and Westchester has a thriving literary scene. Take a literary tour through the county and visit the homes of famous poets like Edgar Allan Poe and Washington Irving. Don’t forget to attend one of the many poetry readings and events happening throughout the month. April in Westchester is truly a time to embrace nature, history, and culture.
May
May is a wonderful time to visit Westchester, with the warm spring weather and blossoming flowers creating a beautiful backdrop for your travels. As a seasoned traveler, I always recommend dressing in layers when exploring this region. The mornings and evenings can still be a bit chilly, so a light jacket or sweater is essential. However, as the day goes on, the temperatures can rise, so it’s important to have a t-shirt or light blouse underneath for comfort. Jeans or khakis are perfect for bottom wear, as they are versatile and can be dressed up or down depending on your activities. When it comes to footwear, comfortable walking shoes are a must. Westchester is known for its picturesque hiking trails and charming villages, so you’ll want to be prepared for both urban and outdoor adventures. For women, a pair of stylish yet sturdy sandals are also a great option for warmer days. Don’t forget to bring a hat to protect yourself from the sun and a small umbrella in case of a sudden shower. And as always, be sure to bring a reusable water bottle to stay hydrated on your explorations. With these tips in mind, you’ll be dressed for success while experiencing the beauty of Westchester in May.
Welcome to Westchester, a charming county located just north of New York City. May is the perfect time to visit this picturesque destination, with blooming flowers and mild temperatures. As a traveler, I always recommend immersing yourself in the local culture and taking advantage of the outdoor activities that Westchester has to offer. One of my favorite things to do in May is to visit the historic Kykuit estate, once home to the famous Rockefeller family. Walk through the stunning gardens and tour the lavish mansion while learning about the family’s legacy. Another must-do in May is to explore the county’s many hiking trails. With the trees in full bloom, the scenery is simply breathtaking. I recommend hiking the Croton Gorge Park, where you can see the impressive Croton Dam and picturesque waterfalls. Aside from outdoor activities, Westchester also has a bustling food scene that should not be missed. May is the perfect time to indulge in the county’s farmer’s markets, where you can find fresh produce and locally made goods. Be sure to try the famous Hudson Valley apples and artisanal cheeses. For a unique experience, I highly recommend taking a cooking class at the Stone Barns Center for Food and Agriculture. You’ll learn about sustainable farming practices and get hands-on experience in the kitchen using fresh, seasonal ingredients. May in Westchester truly offers something for every type of traveler, so pack your bags and get ready for a memorable trip.
June
When visiting Westchester in June, it’s important to dress for both warm weather and potential rain showers. A lightweight, breathable outfit is ideal for exploring the charming towns and beautiful parks of this region. I recommend packing a few pairs of comfortable walking shoes, as you’ll likely be doing a lot of walking. A light jacket or raincoat is also a must, as the weather can be unpredictable. Don’t forget to pack sunscreen and a hat to protect yourself from the summer sun. As for what to wear, I suggest sticking to casual, comfortable clothing. Locals in Westchester have a relaxed and laid-back style, so there’s no need to dress up. A pair of shorts or a sundress paired with a t-shirt or tank top is perfect for a day of sightseeing. If you’re planning on dining at a nicer restaurant, a nice pair of jeans and a button-down shirt will suffice. Lastly, don’t forget to bring a reusable water bottle, as staying hydrated is key in the summer heat. With these essentials in your suitcase, you’ll be ready to fully enjoy the beauty of Westchester in June.
Westchester may not be the first destination that comes to mind when planning a trip to New York, but let me tell you, June is a fantastic time to visit this charming county. First and foremost, you won’t want to miss the opportunity to explore the historic Hudson Valley. With its picturesque towns, stunning river views, and rich history, this region is a must-see for any traveler. Take a leisurely drive along the scenic Hudson River, stopping at charming towns like Sleepy Hollow and Tarrytown, or visit the grand estates and gardens of Kykuit and the Rockefeller State Park Preserve. June offers the perfect weather to enjoy these outdoor activities and soak up the beauty of the Hudson Valley. In addition to the Hudson Valley, June also brings the start of the summer season in Westchester. This means plenty of outdoor festivals, concerts, and events to enjoy. From the Pleasantville Music Festival to the Clearwater Festival, there is no shortage of entertainment in this county. Art lovers won’t want to miss the annual Armonk Outdoor Art Show, featuring over 300 juried artists and a variety of food and live music. And for foodies, the Westchester Food Truck Festival is a must-visit, with over 50 food trucks serving up delicious eats from around the world. With so much to see and do, June is the perfect time to discover all that Westchester has to offer.
July
When traveling to Westchester in July, it’s important to dress comfortably and appropriately for the warm summer weather. This means wearing light, breathable fabrics such as cotton or linen, and avoiding heavy layers. A lightweight jacket or sweater may come in handy for cooler evenings, but overall, you’ll want to stick to shorts, t-shirts, and sundresses. It’s also a good idea to bring a hat, sunglasses, and sunscreen to protect yourself from the strong sun rays. While the warm weather may be tempting to pack lightly, it’s important to remember that Westchester is known for its upscale and fashionable atmosphere. If you plan on dining at one of the many fine restaurants or attending a cultural event, it’s best to bring along a few dressier options such as a sundress for women or khakis and a collared shirt for men. Additionally, comfortable walking shoes are a must for exploring the charming towns and scenic trails of Westchester. Don’t forget to pack a reusable water bottle to stay hydrated and a camera to capture all the beautiful sights you’ll encounter. With these tips in mind, you’ll be dressed and prepared for a wonderful summer trip to Westchester.
Welcome to Westchester, a charming county just north of New York City. While it may not be as well-known as its famous neighbor, Westchester has plenty to offer visitors, especially in the month of July. With warm weather and longer days, this is the perfect time to explore the natural beauty and cultural attractions of this region. First on the list for July activities is a visit to the historic Philipsburg Manor. This living history museum takes visitors back in time to the 18th century, showcasing life on a working farm during the colonial era. With costumed interpreters, interactive exhibits, and beautiful gardens, this is a must-see for history buffs. Afterward, head to the Hudson River for a scenic boat tour, where you can admire the stunning views of the surrounding mountains and catch a glimpse of the majestic bald eagles that call this area home. End your day with a delicious farm-to-table dinner at one of Westchester’s many acclaimed restaurants, featuring fresh, local ingredients.
August
When visiting Westchester in August, it’s important to dress appropriately for the warm and humid weather. Light and breathable clothing is key, such as shorts, t-shirts, and sundresses. It’s also a good idea to bring along a hat and sunglasses to protect yourself from the bright sun. However, it’s important to keep in mind that many attractions and restaurants in Westchester have a more formal dress code, so it’s always a good idea to pack a nice outfit for evening activities. In addition to clothing, it’s essential to bring along sunscreen and insect repellent. Westchester is known for its beautiful parks and outdoor activities, but with that comes the potential for sunburns and bug bites. Be sure to reapply sunscreen throughout the day, especially if you plan on spending a lot of time outdoors. As for footwear, comfortable walking shoes are a must as there are many scenic hiking trails and charming villages to explore. And don’t forget to pack a swimsuit if you plan on taking a dip in the Hudson River or one of the many lakes in the area. With the right clothing and supplies, you’ll be ready to fully enjoy all that Westchester has to offer in the summertime.
Welcome to Westchester, New York in the month of August! As the summer heat starts to cool down, there are plenty of exciting activities to enjoy in this beautiful county. From exploring historic sites to indulging in delicious local cuisine, Westchester has something for every type of traveler. First on the list is to take a stroll through the charming town of Sleepy Hollow. Known for its spooky legends and rich history, this quaint town is perfect for a leisurely walk along the Hudson River and a visit to the famous Sleepy Hollow Cemetery, where you can pay your respects to the legendary author, Washington Irving. Next, head over to the Rye Playland Amusement Park for a day of thrilling rides and classic carnival games. End your day with a delicious dinner at one of the many waterfront restaurants in the area, where you can savor fresh seafood while enjoying stunning sunset views. In Westchester, there’s never a dull moment in August!
September
As you plan your trip to the charming county of Westchester in September, it’s important to consider the weather and the local culture when packing your wardrobe. The temperatures in September can vary greatly, with warm days and cool nights. I recommend dressing in layers, so you can adjust accordingly throughout the day. A light jacket or cardigan is a must-have for the cooler evenings. In terms of footwear, comfortable walking shoes are essential for exploring the picturesque towns and villages of Westchester, but also pack a pair of dressier shoes for any upscale dinners or events you may attend. When it comes to clothing, the style in Westchester is generally casual yet refined. Opt for classic, neutral pieces that can easily be mixed and matched. A pair of jeans or khakis paired with a nice top or blouse is a great choice for both men and women. Don’t forget to bring a versatile dress or two for a fancier evening out. As for accessories, a scarf or hat can add a touch of personality to your outfit while also keeping you warm on cooler days. And of course, no trip to Westchester is complete without a pair of sunglasses to protect your eyes from the bright September sun. Lastly, don’t forget to bring a reusable water bottle to stay hydrated while exploring this beautiful county. Happy travels!
When visiting Westchester in September, there are plenty of activities to enjoy in this charming region of New York. One of the top things to do is to take a stroll through the beautiful Hudson River Valley, where you can admire the vibrant fall foliage and take in the stunning views of the rolling hills and quaint towns. For history buffs, a visit to Kykuit, the Rockefeller estate, is a must. This grand mansion offers a glimpse into the lavish lifestyle of one of America’s wealthiest families. And don’t miss out on the charming towns of Tarrytown and Sleepy Hollow, where you can explore the legend of the Headless Horseman and visit the Sleepy Hollow Cemetery, the final resting place of Washington Irving. September is also a great time to indulge in some delicious food and wine in Westchester. The region is known for its farm-to-table dining, and many restaurants offer seasonal menus using fresh, local ingredients. You can also visit one of the many wineries in the area for a tasting and tour. And for outdoor enthusiasts, there are plenty of hiking trails and parks to explore, such as the Rockefeller State Park Preserve and the Croton Gorge Park. So whether you’re looking for a relaxing getaway or an adventure-filled trip, Westchester in September has something for everyone.
October
As you plan your trip to Westchester in October, it’s important to pack clothing that will keep you comfortable in the changing autumn weather. The temperatures can range from cool and crisp in the mornings to warm and sunny in the afternoons, so it’s best to dress in layers. Start with a lightweight, long-sleeved shirt and bring a sweater or jacket to add on top. Don’t forget to pack a waterproof jacket or umbrella, as there may be some rain showers during your trip. For footwear, comfortable walking shoes are a must. With the beautiful fall foliage in Westchester, you’ll want to spend plenty of time exploring the outdoors. A pair of sturdy sneakers or hiking boots will be perfect for hiking trails and strolling through parks. And don’t forget to bring a hat and sunglasses for those sunny afternoons. As for accessories, a scarf can add a touch of warmth and style to your outfit, and a small backpack or crossbody bag will be useful for carrying essentials while you explore. With these tips, you’ll be dressed and prepared for a wonderful autumn adventure in Westchester.
Fall is a magical time to visit Westchester County, located just north of New York City. The vibrant colors of the changing leaves, crisp air, and charming small towns make for a perfect autumn getaway. In October, there are plenty of activities to enjoy in this picturesque region. Nature lovers will be in heaven in Westchester during October. Take a hike through the scenic trails of Rockefeller State Park Preserve or explore the historic grounds of Kykuit, the Rockefeller estate. For a unique experience, head to Croton Point Park for the Great Jack O’Lantern Blaze, where over 7,000 hand-carved pumpkins are lit up in elaborate displays. And don’t forget to visit local farmers’ markets for fresh apple cider and pumpkin picking. History buffs will also enjoy visiting the historic sites of Philipsburg Manor and the Old Dutch Church, both offering special events and tours during this time of year. October is the perfect time to immerse yourself in the natural beauty and history of Westchester County.
November
As November approaches, the weather in Westchester can be quite unpredictable. While you may experience some crisp autumn days, be prepared for chilly temperatures and the occasional rain shower. To stay comfortable while exploring this charming region, I recommend dressing in layers. Start with a light sweater or long-sleeved shirt, and add a windproof jacket or raincoat on top. A pair of sturdy walking shoes or boots will also come in handy for navigating the uneven terrain of the historic villages. When packing for your trip to Westchester, be sure to bring a hat, gloves, and scarf to keep warm on colder days. It’s also a good idea to have an umbrella on hand, just in case. As for clothing, stick to versatile pieces that can easily be mixed and matched. A pair of dark jeans or khaki pants paired with a neutral-colored sweater or blouse can be dressed up or down depending on your daily itinerary. And don’t forget to bring a backpack or tote bag to carry any extra layers or souvenirs you may pick up along the way. With these tips in mind, you’ll be prepared to enjoy all that Westchester has to offer in November.
November in Westchester offers travelers a unique blend of cozy autumn charm and bustling holiday preparations. Start your day with a leisurely stroll through the quaint villages of Tarrytown and Sleepy Hollow, where the colorful leaves and crisp air create a picturesque setting. As you wander, don’t miss the opportunity to stop by local bakeries for a taste of freshly made apple cider donuts and pumpkin spice treats. For history buffs, a visit to Kykuit, the Rockefeller Estate, is a must. This magnificent mansion offers a glimpse into the lavish lifestyle of one of America’s wealthiest families. And with the holiday season just around the corner, make sure to check out the elaborate Christmas decorations at the nearby Lyndhurst Mansion. And for a taste of the local culture, head to the Hudson River Museum where you can explore the works of renowned artists and take in the stunning views of the river. November in Westchester truly has something for everyone.
December
When packing for a December trip to Westchester, it’s important to consider the chilly weather that the region experiences during this time of year. Layering is key, as temperatures can vary greatly throughout the day. Start with a warm base layer, such as a thermal top and leggings, and build up with a sweater or fleece and a waterproof jacket. Don’t forget to pack a hat, scarf, and gloves to keep your extremities cozy. Comfortable walking shoes with good traction are also a must, as Westchester is full of charming villages and scenic trails waiting to be explored. As for what to wear, the locals in Westchester tend to dress casually yet stylishly. Opt for comfortable clothing that can easily be dressed up or down, as you may find yourself strolling through a quaint town one minute and attending a holiday party the next. Dark jeans or trousers paired with a nice blouse or button-down shirt is a versatile and practical outfit choice. And of course, don’t forget to bring a camera to capture the beautiful holiday decorations and festive atmosphere that Westchester has to offer in December.
As the holiday season approaches, Westchester becomes a cozy and festive destination for travelers. The crisp air and charming towns make it the perfect place to enjoy the winter season. One must-do activity is to visit the historic Philipsburg Manor, which transforms into a magical winter wonderland during December. The manor is adorned with twinkling lights, a roaring fire, and festive decorations, making it a picturesque spot for a holiday photo. Visitors can also participate in traditional holiday activities such as candle making and gingerbread house decorating. Another must-see in Westchester during December is the Winter Wonderland at Kensico Dam Plaza. This annual event features an outdoor ice-skating rink, festive light displays, and holiday market stalls. It’s the perfect place to get into the holiday spirit and enjoy some hot cocoa while browsing for unique gifts. The highlight of the event is the dazzling fireworks show on New Year’s Eve. With its charming holiday activities and festive atmosphere, Westchester is the ideal destination for a December getaway.
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.
