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 traveling to Westchester in the wintertime, it’s important to come prepared for the cold weather. The average temperature in January hovers around 30 degrees Fahrenheit, so be sure to pack plenty of warm layers. Start with a base layer of thermal undergarments, followed by a sweater or fleece. A waterproof and insulated jacket is a must, as well as a scarf, hat, and gloves. Don’t forget to bring a pair of sturdy waterproof boots, as snow and ice can be common in this region during the winter months. In addition to warm clothing, it’s also important to dress appropriately for any indoor activities you may have planned. Many popular attractions in Westchester, such as museums and galleries, require visitors to remove their shoes before entering. Be sure to wear slip-on shoes or easy-to-remove boots to make this process more convenient. You may also want to bring a small bag to carry your shoes in while inside. And don’t forget to bring a reusable water bottle to stay hydrated and reduce your ecological footprint while exploring this beautiful county. With the right clothing and items, you’ll be able to fully enjoy your winter visit to Westchester.
January is the perfect time to explore the charming county of Westchester, located just north of New York City. While the winter chill may be in the air, there are still plenty of exciting activities to enjoy. Bundle up and take a stroll through the quaint town of Tarrytown, where you can admire the historic homes and cozy up in a local cafe for a warm cup of hot chocolate. For history buffs, don’t miss a visit to the Kykuit Estate, the former home of the Rockefeller family. This grand mansion is decorated for the holiday season during January, making it a truly magical experience. For a taste of the great outdoors, head to the sprawling Rockefeller State Park Preserve in Pleasantville. Here, you can hike through scenic trails, spot various wildlife, and take in stunning views of the Hudson River. If you’re feeling adventurous, try your hand at cross-country skiing or snowshoeing in the park. And for a dose of culture, don’t miss a performance at the historic Tarrytown Music Hall, which hosts a variety of concerts, plays, and films throughout the month. January may be chilly in Westchester, but with these exciting activities, you’ll be sure to keep warm and have a memorable visit.
February
When visiting Westchester in February, it’s important to dress in layers to combat the unpredictable weather. The mornings can be chilly, but as the day goes on, the temperature can rise significantly. I recommend bringing a warm coat, a sweater, and a scarf that can easily be taken off or put on as needed. Don’t forget to pack a waterproof jacket or umbrella, as rain showers are common during this time of year. In terms of footwear, comfortable walking shoes or boots are a must. The streets of Westchester are charming but can also be uneven and hilly, so be sure to bring shoes with good traction. If you plan on visiting any parks or hiking trails, pack a pair of sturdy shoes as well. For evenings out, a nice pair of dress shoes will suffice. Lastly, don’t forget to bring a small daypack to carry your essentials like a water bottle, camera, and maps. With the right clothing and gear, you’ll be prepared to explore all that Westchester has to offer in February.
When visiting Westchester in February, there are plenty of activities to keep you entertained and immerse you in the local culture. One must-visit destination is the Rockefeller State Park Preserve, where you can take a tranquil hike through the snowy landscape and admire the stunning views of the Hudson River. For a taste of history, head to Kykuit, the former home of the Rockefeller family, and learn about their legacy and impact on the region. And for a unique culinary experience, don’t miss the annual Hudson Valley Restaurant Week, where you can savor delicious meals at discounted prices from some of the best local restaurants. But February in Westchester isn’t just about outdoor adventures and food. It’s also a great time to appreciate the arts. The Katonah Museum of Art offers a diverse range of exhibits, from contemporary art to traditional folk art. And if you’re a fan of theater, be sure to catch a show at the historic Tarrytown Music Hall, which hosts a variety of performances throughout the month. And for a touch of romance, take a stroll through the charming town of Sleepy Hollow, known for its ties to the famous tale of the Headless Horseman. With so much to see and do, Westchester in February is a perfect destination for any traveler.
March
When visiting Westchester in March, it’s important to dress in layers. The weather can be quite unpredictable, with chilly mornings giving way to sunny afternoons. I recommend bringing a light jacket or sweater that can easily be taken on and off throughout the day. A scarf and hat are also great accessories to have on hand, in case the wind picks up. As for footwear, be sure to bring comfortable walking shoes as you’ll likely be exploring the quaint towns and picturesque countryside on foot. In terms of what to wear, I suggest opting for casual and comfortable clothing. Westchester has a laid-back vibe, so leave the fancy clothes at home. Jeans or khakis paired with a sweater or button-down shirt are suitable for most activities. It’s also a good idea to bring a rain jacket or umbrella, as spring showers are not uncommon in this region. As for what to bring, don’t forget to pack some sunscreen and sunglasses, as the sun can be quite strong in March. And of course, don’t forget your camera to capture the stunning landscapes and charming small towns of Westchester. Happy travels!
March is a fantastic time to visit Westchester, with plenty of exciting activities and events to enjoy. One must-see attraction is the historic Kykuit estate, home to the famous Rockefeller family. Take a guided tour of the lavish mansion and its stunning gardens, learning about the influential family and their impact on the area. In March, the estate hosts a special spring flower show, showcasing the beautiful blooms that emerge after the winter months. For a taste of local culture, be sure to visit the Hudson River Museum in Yonkers. This multi-faceted museum features art, science, and history exhibits, providing a well-rounded look at the region. In March, the museum hosts a special exhibition on the history of the Hudson River, highlighting its importance in shaping the development of Westchester. After exploring the museum, take a stroll along the riverfront and enjoy the stunning views of the Hudson. March is the perfect time to visit Westchester and experience its rich history and natural beauty.
April
When visiting Westchester in April, it’s important to dress in layers to accommodate for the unpredictable weather. Mornings and evenings can still be quite chilly, so a light jacket or sweater is a must. However, as the day goes on, the sun may come out and it can warm up quickly, making a t-shirt or light blouse a comfortable option. It’s always a good idea to bring a rain jacket or umbrella, as April is known to bring some showers to the area. As for footwear, a sturdy pair of walking shoes is recommended to explore the quaint towns and parks of Westchester. In terms of attire, Westchester is a more casual destination, so there’s no need to pack fancy clothes. However, if you plan on dining at a nice restaurant or attending a show, a business casual outfit would be appropriate. Don’t forget to bring comfortable clothes for outdoor activities such as hiking or biking, as the county has many beautiful trails to explore. And of course, don’t forget to pack a swimsuit if you plan on visiting the beaches or taking a dip in the Hudson River. With the right clothing and gear, you’ll be able to fully enjoy all that Westchester has to offer in April.
April is a fantastic time to visit Westchester, with the warm weather bringing the region to life after the cold winter months. One of the highlights of this season is the annual Cherry Blossom Festival at the New York Botanical Garden. This event celebrates the stunning cherry blossom trees in full bloom with traditional Japanese music, dance performances, and delicious food. It’s a truly magical experience and a must-see for any nature lover. Another must-do activity in April is exploring the charming towns and villages that make up Westchester County. Take a stroll through the historic streets of Sleepy Hollow, the inspiration for Washington Irving’s famous story, or visit the quaint village of Tarrytown, home to the picturesque Lyndhurst Castle. And for those craving some retail therapy, the charming downtown areas of White Plains and Scarsdale offer a variety of unique shops and boutiques to browse. With the beautiful spring weather and a plethora of activities, April is the perfect time to discover the hidden gems of Westchester.
May
When visiting Westchester in May, it’s important to dress in layers as the weather can be unpredictable. The mornings and evenings can be cool, while the afternoons can be warm. A light jacket or sweater is essential for chilly evenings, but can easily be taken off during the day. Also, make sure to bring a light rain jacket or umbrella as there is a chance of showers during this time of year. In terms of clothing, opt for comfortable and casual attire. Westchester is known for its laid-back and relaxed vibe, so leave your fancy outfits at home. A pair of comfortable walking shoes is a must for exploring the charming towns and villages in the area. And don’t forget to pack a swimsuit if you plan on taking a dip in one of the many lakes or pools in the region. As for accessories, a sun hat and sunglasses are perfect for protecting yourself from the bright sun while also adding a stylish touch to your outfit. Lastly, bring a small backpack or tote bag to carry your essentials while out and about. Happy travels!
Welcome to beautiful Westchester, New York in the month of May! As the weather starts to warm up, there are plenty of outdoor activities and events to enjoy in this charming county just north of New York City. One of the must-see attractions in May is the annual Kykuit Garden Tour at the Rockefeller Estate. This is the perfect opportunity to admire the stunning gardens and learn about the history of the Rockefeller family, one of America’s most influential families. Another must-do activity in May is to take a leisurely stroll or bike ride along the Old Croton Aqueduct Trail. This 26.2 mile trail follows the route of the old aqueduct and offers picturesque views of the Hudson River and the surrounding countryside. For those looking for a taste of culture, May is also the perfect time to visit the Caramoor Center for Music and the Arts. This picturesque estate hosts a variety of concerts and performances throughout the month, including classical music, jazz, and opera. If you’re a foodie, be sure to check out the annual Westchester Magazine Wine and Food Festival, where you can sample some of the best food and wine in the county. And for a unique experience, take a hot air balloon ride over the scenic Hudson Valley. No matter what your interests may be, there’s something for everyone to enjoy in Westchester in the month of May. Happy travels!
June
When visiting Westchester in June, it’s important to dress for the warm and humid weather. Light, breathable clothing is essential, such as cotton shirts, shorts, and dresses. Layers are also key, as the temperature can fluctuate throughout the day. A lightweight jacket or sweater can come in handy for cooler evenings. Don’t forget to bring a pair of comfortable walking shoes for exploring the quaint towns and parks of Westchester. In addition to clothing, it’s important to bring sunscreen, a hat, and sunglasses to protect yourself from the strong summer sun. A reusable water bottle is also a must-have, as staying hydrated is crucial in the hot weather. For those planning to spend time at the beach or pool, a swimsuit and towel are essential. And of course, don’t forget to pack a camera to capture the picturesque landscapes and charming villages of Westchester. With the right clothing and essentials, you’ll be able to fully enjoy your June visit to this beautiful region.
June is a fantastic time to visit Westchester, as the summer season is just beginning and the weather is perfect for outdoor activities. One must-see attraction is the historic Kykuit estate, the former home of the Rockefeller family. The expansive grounds and gardens are a delight to explore, and the guided tour of the mansion gives a fascinating glimpse into the opulent lifestyle of this influential family. For a more active experience, head to the Croton Gorge Park where you can hike along the picturesque Croton Dam and take in the stunning views of the Hudson River. Foodies will be in heaven in Westchester in June, as the local farmers’ markets are overflowing with fresh produce. One of my favorite spots is the Pleasantville Farmers’ Market, where you can sample delicious locally-grown fruits and vegetables, artisanal cheeses, and homemade baked goods. For a taste of Westchester’s rich history, make sure to visit the Philipsburg Manor, a restored 18th-century farm where you can learn about the traditional methods of farming and even try your hand at churning butter. And of course, no visit to Westchester is complete without indulging in some of the region’s famous apple cider donuts, which are a perfect treat on a warm June day.
July
When packing for a summer trip to Westchester, it’s important to keep in mind that this region experiences warm and humid weather in July. To dress comfortably and stay cool, I recommend packing lightweight and breathable fabrics such as cotton and linen. A comfortable pair of walking shoes is a must, as many of the attractions in Westchester are best explored on foot. In addition to clothing, it’s important to bring along some essential items to make your trip to Westchester more enjoyable. Sunscreen, a hat, and sunglasses are essential for protecting yourself from the summer sun. For outdoor activities, a reusable water bottle and insect repellent are also recommended. Don’t forget to pack a small umbrella or rain jacket, as afternoon showers are common in this area. And lastly, don’t forget to bring a camera to capture the beautiful scenery and charming towns of Westchester. Happy travels!
As you explore the charming towns and picturesque landscapes of Westchester in July, be sure to take advantage of the many outdoor activities available. Start your day with a hike through the beautiful Rockefeller State Park Preserve, where you can spot various wildlife and enjoy stunning views of the Hudson River. Then, head over to one of the local farmers’ markets to taste fresh fruits and vegetables grown in the fertile soil of the Hudson Valley. In the evening, catch an outdoor concert at Caramoor Center for Music and the Arts, where you can relax with a picnic while listening to world-class music performances. For a taste of history and culture, visit Kykuit, the grand estate of the Rockefeller family. Take a guided tour through the opulent mansion and gardens, and learn about the family’s influential role in shaping Westchester’s landscape. For a more interactive experience, visit Philipsburg Manor, a living history museum where you can step back in time and see how life was like in a 17th century farming community. And don’t miss out on the annual Clearwater Festival in Croton-on-Hudson, a celebration of music, art, and environmental activism that draws in thousands of visitors every year. With so much to see and do, July is the perfect time to immerse yourself in the beauty and culture of Westchester.
August
When visiting Westchester in the month of August, it’s important to pack light and comfortable clothing. The weather is typically warm and humid, so lightweight fabrics such as cotton and linen are ideal. A light jacket or sweater may also be necessary for cooler evenings. As for footwear, a pair of comfortable walking shoes or sneakers will be your best friend as you explore the charming streets and parks of this suburban county. Don’t forget to pack a hat and sunglasses to protect yourself from the strong summer sun. In terms of dress code, Westchester is a fairly casual destination. Locals typically opt for comfortable and practical clothing, especially when spending time outdoors. However, if you plan on dining at a fancy restaurant or attending a special event, it’s always best to bring along a nicer outfit. Additionally, it’s important to be respectful of religious sites and dress more conservatively when visiting places of worship. Overall, just remember to dress comfortably and be prepared for any outdoor activities with appropriate clothing and gear.
August is the perfect time to visit Westchester, with the warm summer weather and an abundance of outdoor activities. One must-see destination is the historic Kykuit estate, the former home of the Rockefeller family. Take a tour of the grand mansion and explore the beautiful gardens, or hike through the surrounding Rockefeller State Park Preserve. For a taste of local culture, head to the Hudson Valley Shakespeare Festival and catch a performance in the picturesque outdoor theater. And of course, no trip to Westchester is complete without a visit to the charming town of Sleepy Hollow, where you can learn about the legend of the Headless Horseman and enjoy a scenic stroll along the Hudson River. But Westchester offers more than just beautiful scenery. For foodies, August is the perfect time to visit the annual Westchester Magazine Wine & Food Festival, featuring local restaurants and wineries. And for history buffs, a visit to the historic Philipsburg Manor is a must. This fully restored colonial farm offers a glimpse into life in the 18th century, with costumed interpreters and hands-on activities. So whether you’re looking for outdoor adventures, cultural experiences, or a taste of local cuisine, Westchester has something for everyone in the month of August.
September
September is a beautiful time to visit Westchester County, with the colors of fall starting to emerge and the cooler temperatures making outdoor activities all the more enjoyable. When packing for your trip, be sure to bring layers as the weather can be unpredictable. A light jacket or sweater, along with a scarf and comfortable walking shoes, are essential for exploring the charming towns and countryside of Westchester. When it comes to dressing in Westchester, comfort and practicality are key. Opt for casual, yet stylish attire that will allow you to blend in with the locals while still being comfortable. A pair of jeans or khakis paired with a button-down shirt or sweater is a great choice for both men and women. Don’t forget to bring a rain jacket or umbrella, as there may be some showers during your visit. And of course, don’t forget your camera to capture the stunning fall foliage and picturesque landscapes of Westchester.
When visiting Westchester in September, there are plenty of activities to keep travelers busy and entertained. One must-see destination is the Kykuit estate, the former home of the Rockefeller family. This sprawling property boasts stunning gardens, grand architecture, and incredible views of the Hudson River. Visitors can take a tour of the mansion and learn about the history of the Rockefellers and their impact on the local community. In addition, September is the perfect time to visit the estate as the weather is mild and the fall foliage is starting to show its vibrant colors. For those looking to immerse themselves in the local culture, a trip to the Hudson Valley Wine and Food Festival is a must. This annual event, held in September, showcases the best of the region’s wineries, breweries, and food vendors. Visitors can sample delicious wines, craft beers, and gourmet food while taking in the beautiful scenery of the Hudson Valley. The festival also features live music, cooking demonstrations, and activities for all ages. It’s a great way to support local businesses and get a taste of the flavors of Westchester.
October
When visiting Westchester in October, it’s important to dress in layers to be prepared for the changing weather. The mornings can be crisp and cool, but by midday, the temperature can rise significantly. I recommend packing a light jacket or sweater that you can easily take on and off, as well as a scarf for those chilly mornings. Comfortable walking shoes are a must, as you’ll likely be exploring the charming towns and scenic trails that Westchester has to offer. In terms of what to wear, opt for casual and comfortable clothing that is appropriate for the autumn season. Jeans or leggings paired with a cozy sweater or flannel shirt is a classic and practical choice. Don’t forget to bring a rain jacket or umbrella, as October in Westchester can bring occasional showers. And for any outdoor activities, such as hiking or apple picking, be sure to pack a pair of sturdy shoes and a hat to protect against the sun. With these essentials, you’ll be ready to fully enjoy the beauty of Westchester in the fall.
October is a fantastic time to visit Westchester, New York. The crisp autumn air, vibrant fall foliage, and charming small towns make for a quintessential New England experience. One of my top recommendations is to take a scenic drive along the Hudson River, stopping at the various historic sites and quaint villages along the way. I highly recommend visiting Kykuit, the Rockefeller family’s grand estate, and exploring the charming town of Sleepy Hollow, known for its spooky legends and quaint Main Street. For those interested in history, Westchester is home to some of the most important Revolutionary War sites in the country. Take a tour of Washington’s Headquarters in White Plains, where the general spent the winter of 1778-1779. You can also visit Philipsburg Manor, a working 18th-century farm that offers a glimpse into colonial life. And don’t miss out on the charming farmers’ markets, where you can sample local produce, artisanal cheeses, and homemade goods. October truly is a delightful time to visit Westchester and experience all it has to offer.
November
When visiting Westchester in November, it’s important to dress in layers to combat the changing temperatures. Mornings can be chilly, but afternoons can warm up significantly. I recommend bringing a warm coat, a scarf, and a hat for the colder moments of the day. It’s also a good idea to have a waterproof jacket or umbrella on hand, as November can bring some rainy days. Comfortable walking shoes are a must, as Westchester is a great place to explore on foot. As for what to wear, I suggest opting for comfortable and casual clothing. Westchester has a laid-back vibe, so there’s no need to pack formal attire. A pair of jeans or leggings paired with a cozy sweater and boots will fit right in. And don’t forget to pack a few outfits suitable for indoor activities, such as visiting museums or dining at a nice restaurant. Lastly, be sure to bring a camera to capture the beautiful fall foliage that blankets the area in November. With these tips, you’ll be prepared to fully enjoy your visit to Westchester during this lovely autumn month.
November is a wonderful time to visit Westchester, as the crisp autumn air and changing leaves create a beautiful backdrop for exploring this charming county. One of the must-see attractions during this time of year is the Kykuit Estate, the former home of the wealthy Rockefeller family. Take a guided tour of the grand mansion and its impressive gardens, while learning about the history of this influential family. And for a taste of the local culture, head to the Hudson Valley Center for Contemporary Art, where you can browse through thought-provoking exhibits and interact with local artists. For outdoor enthusiasts, November in Westchester offers a variety of activities to enjoy. Lace up your hiking boots and take a scenic stroll along the Old Croton Aqueduct Trail, a 26-mile path that follows an old water supply system and passes through charming towns and stunning landscapes. Or, for a more leisurely experience, hop on the Hudson River Skywalk, a pedestrian bridge that connects the historical estates of Kykuit and Lyndhurst. And don’t forget to indulge in some seasonal treats, such as apple cider donuts and pumpkin spice lattes, at the local farmers’ markets and cafes. November in Westchester truly has something for everyone to enjoy.
December
As you pack your bags for your December trip to Westchester, be sure to dress in layers. The weather can be quite unpredictable during this time of year, with chilly mornings and evenings and potentially warmer afternoons. A good rule of thumb is to bring a warm coat, scarf, and gloves, as well as a few sweaters or long-sleeved shirts that can be easily layered. Don’t forget to pack comfortable walking shoes, as there are many outdoor activities to enjoy in Westchester, from hiking to strolling through charming villages. When it comes to what to wear in Westchester, consider the local style. While it’s always a good idea to dress comfortably and casually, you may want to bring a few nicer outfits if you plan on dining at some of the area’s upscale restaurants. In terms of what to bring with you, don’t forget to pack a camera to capture the stunning winter landscapes and historic sites. And if you’re planning on visiting any of the outdoor markets or holiday festivals, be sure to bring a reusable shopping bag to carry your purchases. With the right clothing and a few essential items, you’ll be well-prepared to explore all that Westchester has to offer this December.
December is a magical time to visit Westchester County, with its quaint New England charm and festive holiday spirit. One of the top things to do during this time is to visit the famous Winter Wonderland at Kensico Dam Plaza. This annual event features ice-skating, holiday light displays, and even a visit from Santa himself. It’s the perfect way to get into the holiday spirit and experience the local culture. For a more low-key activity, take a stroll through the charming town of Hastings-on-Hudson and enjoy the festive decorations and window displays. This small town is known for its picturesque Main Street, lined with locally-owned shops and restaurants. During December, the town comes alive with holiday cheer and is the perfect place to shop for unique gifts and try some delicious winter treats, like hot chocolate and gingerbread cookies. Don’t miss the annual tree lighting ceremony and caroling event, where you can join in on the local holiday traditions.
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.
