Select the month that you will be traveling from the table below to view the packing list:
What Winston is like to visit throughout the year:
January
As the cold winter months descend upon Winston, it’s important to dress appropriately for the weather. Layering is key, as temperatures can vary throughout the day. I recommend starting with a base layer of thermal underwear, followed by a warm sweater or fleece. Top it off with a waterproof and windproof jacket to keep out any rain or snow. Don’t forget to bring a hat, scarf, and gloves to protect your extremities from the biting winter chill. When it comes to footwear, make sure to bring sturdy and waterproof boots. The streets of Winston can be slick and slushy, so it’s important to have a good grip. Also, consider bringing a pair of indoor shoes to change into when visiting museums or other indoor attractions. As for what to pack, be sure to bring a mix of both warm and cold weather clothing. While the days may be chilly, the evenings can still be mild. And don’t forget to pack a reusable water bottle and a small daypack to carry all your essentials while exploring this charming city.
Welcome to Winston, a charming city nestled in the heart of North Carolina. While many travelers may shy away from visiting in January due to the colder temperatures, I believe this is the perfect time to experience all that Winston has to offer. One of the highlights of visiting Winston in January is the annual Winterfest celebration. This month-long event features outdoor ice skating, holiday lights, and festive performances. For those looking to escape the cold, the Reynolda House Museum of American Art offers a warm and inviting atmosphere to explore its extensive collection of American art. And don’t forget to warm up with a cup of hot cocoa or coffee at one of the many cozy cafes in the downtown area. No matter how you choose to spend your time in Winston in January, you’re sure to be charmed by its Southern hospitality and winter festivities.
February
When traveling to Winston in February, it’s important to dress in layers to combat the chilly temperatures. Start with a base layer of thermal underwear, followed by a sweater or fleece and a waterproof jacket. Don’t forget to bring a warm hat, gloves, and a scarf to keep your extremities cozy. Comfortable and waterproof shoes are also a must, as the streets can be wet and slippery during this time of year. And for ladies, opt for a pair of stylish yet practical boots that can withstand the rain and add a touch of flair to your outfit. In addition to dressing appropriately, it’s important to bring a few items to enhance your experience in Winston. A small umbrella or rain jacket will come in handy to protect you from the occasional drizzle. A camera is a must to capture the stunning views of the city, especially during the early morning mist or at sunset. And for those planning on exploring the countryside, a backpack with water and snacks is recommended, as well as a map or guidebook to help navigate the winding roads. With the right attire and essentials, you’ll be able to fully enjoy all that Winston has to offer in the month of February.
February is a wonderful time to visit the charming city of Winston. The winter chill is still in the air, but the city is bustling with activities and events. One of the top things to do in Winston during February is to attend the annual Riverwalk Festival. This lively event celebrates the city’s beautiful riverfront with live music, delicious food vendors, and a variety of arts and crafts for sale. It’s the perfect way to immerse yourself in the local culture and enjoy the stunning views of the river. Another must-do activity in Winston during February is to explore the city’s rich history and architecture. Take a stroll through Old Salem, a living history museum that showcases the daily life of the Moravians who settled in the area in the 18th century. Be sure to also visit the Reynolda House Museum of American Art, a beautifully preserved estate that offers a glimpse into the lavish lifestyle of the Reynolds family, one of Winston’s most influential families. With its charming atmosphere and diverse range of activities, Winston in February is a traveler’s dream come true.
March
When visiting Winston in the month of March, it’s important to pack layers as the weather can be quite unpredictable. While the days may start off chilly, it can warm up significantly by midday. I recommend bringing a light jacket or sweater that you can easily take on and off as needed. A waterproof jacket or umbrella may also come in handy as March can bring occasional rain showers. In terms of dressing, Winston is a fairly casual city, so you don’t need to pack anything too fancy. Comfortable walking shoes are a must as there are many beautiful parks and gardens to explore. Jeans or khaki pants paired with a t-shirt or button-down shirt are appropriate for most activities. And don’t forget to bring a hat and sunscreen for those sunny days! Overall, dressing comfortably and for the weather will ensure you can fully enjoy all that Winston has to offer in March.
March is a wonderful time to visit the charming city of Winston. As the weather starts to warm up, locals and visitors alike flock to the bustling downtown area. One of the must-do activities in March is to take a stroll through the historic Old Salem district. This living history museum showcases the daily life of the Moravian settlers in the 18th and 19th centuries. With costumed interpreters, traditional crafts, and delicious Moravian treats, it’s a step back in time that shouldn’t be missed. Another highlight of March in Winston is the annual Piedmont Craftsmen’s Fair. This juried craft show features over 100 talented artists from around the region. From pottery and jewelry to textiles and woodwork, there is something for every taste and budget. It’s a great opportunity to support local artists and find unique souvenirs to take home. And don’t forget to try some delicious southern food at the fair’s food trucks and vendors. With so much to see and do, March is the perfect time to experience the rich culture and traditions of Winston.
April
April in Winston is a beautiful time to visit, with the trees blooming and the weather starting to warm up. However, it’s important to pack appropriately for this transitional season. The key is to dress in layers, as the mornings and evenings can still be chilly while the afternoons can be quite warm. I recommend bringing a light jacket, comfortable walking shoes, and a mix of short-sleeved and long-sleeved shirts. Don’t forget to pack a rain jacket or umbrella, as April showers are common in Winston. As for what to wear, I suggest sticking to comfortable and casual clothing. Winston is a laid-back city, so you won’t need anything too fancy. However, if you plan on visiting any churches or religious sites, it’s important to dress modestly and cover your shoulders and knees. And for those planning on doing some outdoor activities, like hiking in the nearby mountains, be sure to bring sturdy shoes and breathable clothing. Overall, packing a versatile wardrobe and being prepared for any weather will ensure a comfortable and enjoyable trip to Winston in April.
April is a wonderful time to visit the charming city of Winston. With the spring season in full swing, the city is bursting with vibrant colors and plenty of activities to enjoy. One of the must-do activities during this time is to visit the Reynolda Gardens. This 129-acre estate is a tranquil oasis in the heart of the city, with blooming flowers, lush greenery, and peaceful walking paths. It’s the perfect place to soak up the sunshine and relax while admiring the stunning displays of nature. For history enthusiasts, April is the ideal time to explore Old Salem. This living history museum showcases the early days of Salem, with costumed interpreters, traditional crafts, and historic buildings. During this time, the gardens are in full bloom, and the smell of freshly baked goods from the bakery fills the air. Don’t miss the opportunity to taste some authentic Moravian cookies while strolling through the charming streets. Old Salem is a true gem of the city and a must-visit for anyone wanting to immerse themselves in the rich history of Winston.
May
May is a lovely time to visit the charming city of Winston. The weather is mild and pleasant, making it the perfect time to explore the city on foot. When dressing for your trip, I recommend packing comfortable and versatile clothing. A light jacket or sweater is always a good idea, as temperatures can drop in the evenings. As for footwear, a sturdy pair of walking shoes or sneakers will be your best friend as you navigate the cobblestone streets and hilly terrain of Winston. As for what to wear, I suggest packing layers that can easily be mixed and matched. A pair of jeans or khakis paired with a t-shirt or button-down shirt is a great option for both men and women. Ladies, a sundress or skirt with a light cardigan will also be suitable for the warmer afternoons. Don’t forget to bring a scarf or shawl, which can add a touch of style while also keeping you warm on cooler days. Lastly, don’t forget to pack a small day bag to carry your essentials such as a water bottle, camera, and map as you explore the charming streets of Winston. With these tips, you’ll be dressed and ready to fully immerse yourself in the beauty and culture of this lovely city.
May is a wonderful time to visit the charming city of Winston. As the weather starts to warm up, locals and visitors alike flock to the beautiful parks and gardens scattered throughout the city. One must-see spot is the Reynolda Gardens, located on the historic Reynolda Estate. Stroll through the colorful flower beds, admire the tranquil lake, and marvel at the grandeur of the Reynolda House Museum of American Art. Another must-visit is Tanglewood Park, where you can enjoy a picnic, go for a hike, or even play a round of golf. And don’t miss the opportunity to take a scenic drive on the Blue Ridge Parkway, just a short distance from the city. In addition to its natural beauty, Winston is also known for its vibrant arts scene. May is the perfect time to explore the city’s many galleries and museums. The Southeastern Center for Contemporary Art (SECCA) is a must-visit for art enthusiasts, with its constantly changing exhibitions and interactive installations. For a taste of local culture, head to the Winston-Salem Symphony for a performance or the Piedmont Craftsmen Gallery for unique handmade crafts. And no trip to Winston is complete without trying some of the delicious local cuisine. From Southern comfort food to international flavors, there is something for every palate in this charming city. So pack your bags and come experience the best of Winston in May!
June
When visiting Winston in the month of June, it’s important to dress for warm weather and potential rain showers. Lightweight and breathable clothing is key, as temperatures can reach up to 80 degrees Fahrenheit during this time of year. Opt for shorts, sundresses, and short-sleeved shirts made of natural fibers like cotton or linen to keep you cool and comfortable. Don’t forget to bring a light jacket or raincoat, as the weather can be unpredictable and it’s always better to be prepared. In addition to clothing, it’s important to bring a few key items when visiting Winston in June. First and foremost, sunscreen is a must-have to protect your skin from the strong summer sun. A hat or sunglasses are also recommended to shield your face and eyes. Comfortable walking shoes are a must, as Winston has many beautiful parks and outdoor spaces to explore. And lastly, don’t forget to pack a reusable water bottle to stay hydrated and reduce plastic waste. With these essentials in tow, you’ll be ready to fully enjoy all that Winston has to offer in the lovely month of June.
One of the best times to visit Winston is in the month of June. Not only is the weather warm and pleasant, but there are also many exciting events and activities to partake in. One must-see attraction is the annual June Jubilee, a lively street fair filled with local vendors, live music, and delicious food. It’s a great way to immerse yourself in the local culture and support small businesses. Another must-do activity is to take a stroll through the beautiful Botanical Gardens, which are in full bloom during this time of year. With colorful flowers and fragrant scents, it’s the perfect place to relax and take in the natural beauty of Winston. For the history buffs, June is the perfect time to visit Old Salem, a living history museum that gives visitors a glimpse into the daily life of early American settlers. You can tour the village, interact with costumed interpreters, and even try traditional foods. Another must-visit attraction is the Reynolda House Museum of American Art, which features an impressive collection of American art from the colonial period to the present day. And for those looking for a bit of adventure, head to Pilot Mountain State Park for some hiking and stunning views. June truly is a wonderful time to experience all that Winston has to offer.
July
When visiting Winston in July, it’s important to dress for the warm and humid weather. Lightweight, breathable fabrics such as cotton and linen are ideal for staying cool and comfortable. Ladies may want to bring sundresses or skirts, while men can opt for light-colored button-down shirts and shorts. It’s also a good idea to bring a hat, sunglasses, and sunscreen to protect yourself from the strong summer sun. As for footwear, comfortable walking shoes are a must for exploring the city. Winston has a charming historic district with cobblestone streets, so heels may not be the most practical choice. Additionally, bring a light jacket or sweater for cooler evenings, as summer storms can bring a drop in temperature. Don’t forget to pack a swimsuit as well, as there are plenty of opportunities for swimming and lounging by the pool in Winston’s many parks and gardens. Lastly, be sure to have a small daypack for carrying water, snacks, and any souvenirs you may pick up along the way. With these essentials, you’ll be well-prepared to enjoy all that Winston has to offer in the summertime.
July is the perfect time to visit the charming city of Winston, nestled in the heart of North Carolina’s Piedmont region. As the summer heat begins to settle in, locals and tourists alike flock to the city’s beautiful parks and gardens. Take a stroll through the historic Old Salem district, where you can step back in time and experience the daily life of early Moravian settlers. Don’t miss the opportunity to sample some traditional Moravian treats, like sugar cake and lovefeast buns, at one of the many bakeries in the area. For a taste of Winston’s vibrant arts scene, head to the Downtown Arts District where you can find a variety of galleries, studios, and theaters. Every July, the city hosts the popular RiverRun International Film Festival, showcasing independent films from around the world. After catching a movie, grab a bite to eat at one of the many farm-to-table restaurants in the district, highlighting the region’s fresh and seasonal ingredients. And don’t forget to cool off with a scoop of homemade ice cream from one of the local creameries. With its blend of history, culture, and delicious food, Winston is the perfect destination for a summer getaway.
August
When packing for a trip to Winston in August, it’s important to remember that this charming southern town can get quite hot and humid. Light, breathable clothing is key to staying comfortable while exploring all that Winston has to offer. I recommend packing lightweight cotton tops and bottoms, as well as a wide-brimmed hat to protect yourself from the sun. Don’t forget to bring a comfortable pair of walking shoes as well, as you’ll likely be doing a lot of walking on the city’s cobblestone streets. While the days may be warm, the evenings in Winston can still get a bit chilly. Be sure to pack a light jacket or sweater to throw on when the sun goes down. As for accessories, a stylish scarf can not only add a touch of flair to your outfit but also double as a cover-up if you plan on visiting any churches or other religious sites. And of course, don’t forget your sunscreen and sunglasses to protect yourself from the strong southern sun. With these essentials in your suitcase, you’ll be ready to explore Winston in comfort and style.
When visiting Winston in August, there are plenty of activities to enjoy. One must-see event is the annual Shakespeare in the Park festival. Held in the beautiful Reynolda Gardens, this festival brings the works of Shakespeare to life in a stunning outdoor setting. From comedy to tragedy, there’s something for every theater enthusiast to enjoy. And the best part? It’s completely free! For those looking to cool off in the summer heat, head to Tanglewood Park for some refreshing fun. The park offers a large lake for swimming, as well as paddle boats and kayaks for rent. And if water activities aren’t your thing, there are also miles of hiking and biking trails to explore. Don’t forget to pack a picnic and spend the day relaxing in this peaceful oasis. August is the perfect time to enjoy all that Tanglewood Park has to offer.
September
As the summer season comes to an end, September in Winston brings cooler temperatures and the beginning of fall foliage. To make the most of your visit, it’s important to dress in layers. Mornings and evenings can be chilly, so a light jacket or sweater is essential. However, as the day progresses, the sun may bring some warmth, making it necessary to shed a layer or two. A comfortable pair of walking shoes is also a must, as there are many historic sites and scenic trails to explore in Winston. To blend in with the locals and fully immerse yourself in the culture, I recommend bringing some traditional Southern attire. For men, a collared shirt and khaki pants will suffice for most occasions. Women may opt for a sundress or flowy skirt paired with a cardigan. Don’t forget to pack a hat and sunglasses for those sunny afternoons. And of course, don’t forget your camera to capture the stunning landscapes and charming architecture of Winston. With the right clothing and gear, you’ll be all set for a comfortable and enjoyable visit to this charming Southern city.
September is a wonderful time to visit Winston, with mild temperatures and fewer crowds compared to the summer months. One of my favorite things to do in September is to explore the historic Old Salem district. This living history museum takes visitors back in time to the 18th and 19th centuries, with costumed interpreters demonstrating daily life in a Moravian settlement. Don’t miss the opportunity to try traditional Moravian sugar cake and purchase handcrafted goods from local artisans. Another must-do activity in Winston during September is attending the Dixie Classic Fair. This annual event has been a local tradition since 1882 and showcases the best of Southern culture, with livestock shows, carnival rides, and delicious fair food. Be sure to catch the nightly fireworks display and indulge in some classic fried treats like funnel cakes and deep-fried Oreos. The fair is also a great place to experience live music and support local vendors selling handmade goods. Don’t forget to bring your appetite and a sense of adventure!
October
When visiting Winston in October, it’s important to dress in layers to adapt to the changing weather. Start with a base layer of comfortable clothing, such as a lightweight long-sleeved shirt and pants. This will provide warmth and protection against the chilly mornings, but can easily be removed as the day warms up. A light rain jacket or windbreaker is also a must-have, as October can bring unpredictable weather. Don’t forget to bring a sturdy pair of walking shoes to explore the city on foot, as well as a hat and sunglasses for protection from the sun. Winston is a charming and historic city, so it’s important to dress respectfully when visiting. Avoid wearing revealing clothing or anything with offensive language or graphics on it. Instead, opt for comfortable and conservative outfits that are appropriate for both city sightseeing and visits to religious and cultural sites. Scarves and shawls are also a great addition to your wardrobe, as they can provide both warmth and coverage when needed. Lastly, don’t forget to pack a small backpack or crossbody bag to carry your essentials, such as water, snacks, and a map of the city. With these tips in mind, you’ll be dressed and prepared for a wonderful October visit to Winston.
October is the perfect time to visit the charming city of Winston. As the leaves change color and a chill fills the air, there is a cozy and festive atmosphere that is just waiting to be explored. One of my favorite activities in October is to take a walk through the farmers market, where you can taste the season’s best produce and warm up with a cup of hot apple cider. The market is also a great place to pick up some unique souvenirs, such as handcrafted pottery or homemade jams. After the market, take a stroll through the historic downtown area and admire the beautiful fall foliage. Don’t forget to stop by one of the local cafes for a slice of pumpkin pie – a must-try in October! For history buffs, a visit to Old Salem in October is a must. This living history museum brings to life the colonial days of the Moravian settlers who founded the town in the 1700s. During October, the town hosts a variety of special events, including candlelight tours and traditional harvest festivals. It’s a great opportunity to learn about the customs and traditions of the early settlers while enjoying the crisp autumn weather. And for those looking for a little spooky fun, the Ghost Walk through the historic district is sure to give you a thrill! October in Winston is a time of celebration, history, and charm – a perfect combination for an unforgettable trip.
November
As you prepare for your November trip to Winston, it’s important to pack appropriately for the season. While the weather can be unpredictable, one thing is for sure: it will be chilly! Be sure to bring warm layers, including a waterproof jacket, as well as comfortable walking shoes. You’ll also want to pack a scarf, hat, and gloves for those brisk mornings and evenings. Don’t forget to bring an umbrella too, just in case of rain. And for those planning to explore the beautiful countryside, sturdy hiking boots are a must. When it comes to dressing in Winston in November, the key is to layer up. Start with a base layer, such as a long-sleeved shirt or sweater, then add a warm coat or jacket on top. Pair with jeans or trousers and you’ll be ready to tackle the day’s adventures. And don’t worry about dressing too fancy, as Winston has a relaxed and casual vibe. Just be sure to bring a few nicer outfits if you plan on dining at some of the city’s upscale restaurants. Lastly, don’t forget to pack a camera to capture the stunning autumn colors that adorn the city during this time of year. Happy travels!
November is a wonderful time to visit the charming city of Winston. The crisp autumn air and changing leaves make for a picturesque setting, and there are plenty of activities to keep you entertained. One must-do activity is to take a stroll along the Salem Lake Trail. This 7-mile loop around the serene lake offers beautiful views of the surrounding mountains and is a great way to get some exercise and take in the fall foliage. For history buffs, a visit to Old Salem is a must. This living history museum showcases the town’s Moravian roots and is especially enchanting during the holiday season when the streets are decked out in festive decorations. No trip to Winston is complete without indulging in some delicious Southern cuisine. November is the perfect time to try some hearty comfort food, like chicken and waffles or a bowl of piping hot shrimp and grits. For a taste of the local craft beer scene, head to the foothills of the Blue Ridge Mountains where you’ll find several breweries offering seasonal brews. And for those looking to get into the holiday spirit early, the annual Christmas tree lighting ceremony in downtown Winston is not to be missed. With festive music, hot cocoa, and a visit from Santa himself, it’s a magical way to kick off the holiday season.
December
When packing for a December trip to Winston, it’s important to be prepared for both chilly temperatures and potential rain. I recommend bringing layers, such as a warm sweater and a waterproof jacket, to stay comfortable in the changing weather. Opt for comfortable and sturdy walking shoes, as the city’s cobblestone streets can be slippery when wet. Don’t forget to pack a scarf, gloves, and a hat to keep you cozy while exploring the city. When it comes to dressing for Winston, I suggest opting for a mix of stylish and practical. The locals here have a laid-back yet chic fashion sense, so you’ll fit right in with a pair of dark jeans, a nice blouse or sweater, and a statement coat. Don’t be afraid to add some pops of color to your outfit, as the city is known for its vibrant street art. And of course, don’t forget to bring a camera to capture all the beautiful sights you’ll encounter in Winston!
December is a magical time to visit Winston, a charming city in the heart of North Carolina. As you walk down the cobblestone streets, the smell of roasted chestnuts fills the air and holiday lights twinkle from every storefront. The city comes alive during the festive season, with a variety of activities to enjoy. One of my favorite things to do in December is to visit the Old Salem Christmas Market. This outdoor market is filled with local vendors selling handcrafted goods, delicious treats, and traditional holiday decor. It’s the perfect place to find unique gifts for your loved ones and soak up the holiday spirit. Another must-do activity in December is to attend the annual Tanglewood Festival of Lights. This drive-through light show is a true winter wonderland, with over a million lights twinkling in intricate displays. It’s a great way to experience the beauty of the season while staying warm and cozy in your car. After the light show, make sure to stop by the Tanglewood Gift Village for some hot cocoa and holiday treats. Whether you’re strolling through the Christmas market or admiring the twinkling lights, visiting Winston in December is sure to be a merry and memorable experience.
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.
