Windsor, Vermont: What to Bring, what to Pack, and what to Wear


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

JanuaryFebruaryMarchApril
MayJuneJulyAugust
SeptemberOctoberNovemberDecember

What Windsor is like to visit throughout the year:

January

When visiting the charming town of Windsor in January, it’s important to be prepared for the chilly weather. Layering is key, as temperatures can range from 30 to 50 degrees Fahrenheit. Start with a warm base layer such as thermal underwear or a long-sleeved shirt, and then add a sweater or fleece on top. A waterproof and windproof jacket is a must for those blustery days, along with a scarf, hat, and gloves to keep you cozy. Don’t forget to pack a sturdy pair of boots with good traction, as the sidewalks and cobblestone streets can be slick in the winter months. As for what to wear when visiting popular sites such as Windsor Castle or St. George’s Chapel, it’s important to dress respectfully. This means avoiding revealing or casual clothing, and instead opting for more modest and conservative attire. A nice pair of dark jeans or trousers paired with a button-down shirt and comfortable walking shoes will fit in perfectly. And of course, don’t forget to bring a small backpack or crossbody bag to carry your essentials, such as a camera, map, and water bottle, while exploring the town. With these tips in mind, you’ll be dressed appropriately and comfortably for your January visit to beautiful Windsor.

January is a fantastic time to visit Windsor, the charming town just outside of London. Despite the chilly weather, there are still plenty of activities to keep visitors entertained. One of my top recommendations is to visit Windsor Castle, the oldest and largest inhabited castle in the world. Not only can you explore the grand state apartments and stunning St. George’s Chapel, but you may even catch a glimpse of the Queen herself as she spends her winters at the castle. Plus, the castle is beautifully decorated for the holiday season, making it a must-see in January. After touring the castle, be sure to take a stroll through the quaint streets of Windsor. The town is filled with charming shops, cozy pubs, and delicious restaurants. For a unique experience, take a horse-drawn carriage ride through the town and admire the beautiful architecture and lively atmosphere. And if you’re feeling adventurous, you can even take a boat ride on the River Thames and see Windsor from a different perspective. No matter how you choose to spend your time in Windsor, you’re sure to have a memorable trip in this historic and picturesque town.

February

When visiting Windsor in February, it’s important to pack for the chilly weather. The average temperature during this time is around 40°F (4°C), so be sure to bring layers that you can easily add or remove as needed. A warm, waterproof coat is a must, as well as a scarf, hat, and gloves. If you plan on doing a lot of walking or outdoor activities, consider bringing waterproof boots or shoes with good traction to navigate any potential snow or ice on the ground. Additionally, packing an umbrella or rain jacket is always a good idea, as the weather in February can be unpredictable. As for clothing, I recommend dressing in comfortable and casual layers. Windsor is a charming and laid-back town, and you’ll fit right in with a pair of jeans, a cozy sweater, and a warm jacket. It’s also a good idea to bring a few nicer outfits if you plan on visiting any of the historic sites or attending a special event. And don’t forget to pack some comfortable walking shoes, as there is plenty to explore in this picturesque town. Finally, be sure to bring a camera to capture all the stunning views and historical landmarks that Windsor has to offer.

February is a fantastic time to visit the charming town of Windsor, located just a short train ride from London. While the weather may be chilly, the town is bustling with activity and there are plenty of things to do to keep you entertained. One of the top attractions in Windsor is, of course, Windsor Castle. This magnificent structure is the oldest and largest occupied castle in the world and is home to the British royal family. Take a tour of the castle to see the opulent State Apartments and St. George’s Chapel, where the royal weddings take place. Don’t miss the changing of the guard ceremony, which takes place daily at 11 am and is a quintessential British experience. For a more off-the-beaten-path activity, head to the nearby town of Eton, just across the river from Windsor. Here, you’ll find Eton College, one of the most prestigious schools in the world. Take a stroll through the picturesque campus and marvel at the historic buildings and beautiful architecture. If you’re lucky, you may even catch a glimpse of the students in their signature tailcoats. Afterwards, grab a pint at one of the local pubs or browse the quaint shops for unique souvenirs. February may be the off-season for tourism in Windsor, but with its rich history and charming atmosphere, it’s the perfect time to explore this hidden gem.

March

March is a wonderful time to visit the charming town of Windsor, known for its iconic castle and royal history. As the weather can be quite unpredictable during this time of year, it’s important to dress in layers. A waterproof jacket, comfortable walking shoes, and a scarf are essential items to have on hand. It’s also a good idea to pack a small umbrella, as showers can pop up unexpectedly. When visiting Windsor, it’s important to respect the local culture and customs. While the town is quite tourist-friendly, it’s always best to dress modestly. This means avoiding shorts, tank tops, and flip flops, especially when visiting the castle or other religious sites. Instead, opt for comfortable yet appropriate attire, such as jeans and a nice top or a casual dress. And of course, don’t forget to bring your camera to capture the beautiful sights and memories of your trip to Windsor. Happy travels!

March is a fantastic time to visit the charming town of Windsor, located just a short train ride from London. While most tourists flock to Windsor in the summer to catch a glimpse of the Queen at Windsor Castle, the town is equally enchanting in the early spring months. One of my favorite activities in March is taking a stroll along the River Thames, which runs right through the heart of Windsor. The crisp air and blooming flowers make for a picturesque setting, and you can even hop on a boat tour to get a different perspective of the town. Another must-do activity in Windsor during March is to visit the world-renowned Windsor Castle. This iconic fortress is the largest inhabited castle in the world and has been the residence of the British royal family for over 900 years. In March, the castle is less crowded, allowing for a more intimate and leisurely tour. Be sure to check out the State Apartments, Queen Mary’s Dolls’ House, and St. George’s Chapel, where Prince Harry and Meghan Markle tied the knot in 2018. And if you’re lucky, you may even catch a glimpse of the changing of the guard ceremony, which takes place every Tuesday, Thursday, and Saturday in March. Don’t miss the chance to experience the history and grandeur of Windsor Castle during your March visit.

April

As April brings warmer weather and longer days, Windsor is the perfect destination for a springtime getaway. When packing for your trip, be sure to bring layers as the weather can be unpredictable. A light jacket or sweater is essential for cooler evenings, while a t-shirt or blouse will keep you comfortable during the day. Comfortable walking shoes are a must, as you’ll want to explore the charming streets and beautiful parks of Windsor on foot. And don’t forget an umbrella or rain jacket, as April showers are not uncommon in this part of England. As for what to wear, opt for casual and comfortable clothing that can easily transition from day to night. Jeans or khakis paired with a nice shirt or blouse are a great choice for both sightseeing and dinner at one of Windsor’s many excellent restaurants. Keep in mind that the dress code for visiting the royal residences, such as Windsor Castle, is more formal, so be sure to bring a dress or suit jacket if you plan on touring these historic sites. And don’t forget to pack a hat and sunglasses to shield yourself from the sun while strolling around the picturesque town. With these essentials in your suitcase, you’ll be well-prepared to enjoy the beauty and charm of Windsor in April.

April is a wonderful time to visit the charming town of Windsor, nestled in the picturesque countryside of England. As the sun begins to warm up the land and flowers start to bloom, there is no shortage of activities to enjoy in this quaint town. One of the must-see attractions is, of course, the majestic Windsor Castle. This iconic fortress, dating back to the 11th century, is the largest inhabited castle in the world and is still used by the Queen for state occasions. Take a stroll through the beautifully manicured gardens and admire the stunning architecture of this historic landmark. For a more leisurely and scenic experience, I highly recommend taking a boat tour along the River Thames. As you glide through the tranquil waters, you’ll be treated to breathtaking views of the castle and surrounding countryside. If you’re feeling adventurous, you can even rent a rowboat and explore the river at your own pace. April is also the perfect time to sample some of the local cuisine at the Windsor Farmer’s Market. Here, you can taste fresh produce, artisanal cheeses, and delicious baked goods, all while supporting local farmers and businesses. With so much to do and see, Windsor is the perfect destination for a springtime getaway.

May

When visiting Windsor in May, it’s important to dress for the changing weather. May can bring a mix of sunshine and rain, so be sure to pack layers and a waterproof jacket. As Windsor is a historic and royal city, it’s always a good idea to dress modestly and respectfully when visiting landmarks and churches. For women, a knee-length skirt or dress paired with a cardigan or scarf is appropriate, while men can opt for pants and a collared shirt. Comfortable walking shoes are a must, as there is much to explore in this charming city. In addition to dressing appropriately, it’s important to bring a few essentials when visiting Windsor in May. A small umbrella or rain jacket will come in handy for any unexpected showers, and a day bag is useful for carrying snacks, water, and other essentials while exploring. Don’t forget to pack a pair of sunglasses and sunscreen, as the sun can be quite strong during this time of year. Lastly, for those interested in touring the magnificent Windsor Castle, remember to bring a camera to capture the stunning views and beautiful architecture. With these items in tow, you’re sure to have a comfortable and enjoyable visit to Windsor in May.

May is a wonderful time to visit the charming town of Windsor, located just a short train ride from London. While the town may be known for its famous castle, there is so much more to see and do here. One of my favorite activities in May is taking a stroll through the beautiful Windsor Great Park. This expansive green space is the perfect place to escape the hustle and bustle of the city and enjoy a peaceful walk among towering trees and blooming flowers. If you’re lucky, you may even catch a glimpse of the Queen’s swans swimming in the nearby lake. Another must-do activity in May is attending the annual Royal Windsor Horse Show. This prestigious event has been a tradition since 1943 and is a great way to experience the British equestrian culture. From dressage performances to show jumping competitions, there is something for everyone to enjoy. The show also features a variety of food and craft stalls, making it a perfect opportunity to sample some local delicacies and pick up some souvenirs. Whether you’re a horse enthusiast or simply looking for a unique cultural experience, the Royal Windsor Horse Show is not to be missed in May.

June

When visiting Windsor in June, it’s important to dress for both comfort and style. The weather can be quite variable, so it’s best to bring layers that can easily be added or removed as needed. A lightweight rain jacket or umbrella is also a must, as occasional showers are common in this region. Additionally, comfortable walking shoes are essential for exploring the charming streets and grand gardens of Windsor. In terms of attire, it’s always a good idea to dress modestly when visiting historical sites such as Windsor Castle. For women, a knee-length dress or pants paired with a blouse is appropriate, while men can opt for trousers and a collared shirt. It’s also a good idea to bring a hat and sunglasses for protection from the sun, as well as a small backpack or crossbody bag for carrying essentials like water and a camera. And don’t forget to pack a nice outfit for an evening out at one of Windsor’s fine dining establishments. With these tips in mind, you’ll be stylish, comfortable, and prepared for your June visit to Windsor.

June is a fantastic time to visit Windsor, England. The weather is usually pleasant and the town is buzzing with energy. One of the must-see attractions during this time is the Changing of the Guard at Windsor Castle. This traditional ceremony takes place every day at 11am and showcases the precision and pomp of the royal guards. It’s a great opportunity to witness a quintessential British tradition and get up close to the palace gates for some great photos. After the ceremony, I recommend taking a stroll through the Castle’s beautiful gardens and enjoying a picnic on the grounds. Another highlight of visiting Windsor in June is attending the Royal Ascot horse races. This annual event brings together the best horses, jockeys, and fashion from all over the world. It’s a fantastic opportunity to experience British culture and witness the excitement of a top-class horse race. Don’t forget to dress to impress and join in on the tradition of wearing a fancy hat or fascinator. If you’re not into horse racing, there are plenty of other events happening around town in June, such as the Windsor Fringe Festival and the Royal Windsor Food Fest. No matter what your interests are, there’s something for everyone in Windsor this June.

July

In July, Windsor is a delightful blend of history and modernity, with the stunning Windsor Castle as its centerpiece. As a traveler, it’s important to be prepared for the unpredictable British weather. The key to dressing for this month is layering. Start with a light t-shirt and add a light jacket or sweater for cooler mornings and evenings. As the day warms up, you can easily shed layers and stay comfortable. A waterproof jacket or umbrella is also a must, as the occasional summer shower is not uncommon. And of course, don’t forget comfortable walking shoes for exploring the castle and its surrounding gardens. When visiting Windsor in July, it’s important to dress modestly and respectfully, especially if you plan on entering the castle. This means avoiding revealing clothing and opting for comfortable yet conservative outfits. A nice sundress or khaki pants paired with a blouse would be appropriate for both men and women. Don’t forget to also bring a hat and sunglasses for protection from the sun. And while the summer months in England can be warm, it’s always a good idea to have a scarf or light sweater on hand for cooler evenings. Most importantly, remember to bring a sense of curiosity and adventure as you explore this charming town.

Welcome to Windsor, England in the month of July! This charming town, located just a short train ride from London, offers visitors a delightful mix of history, culture, and outdoor activities during the summer. One of the must-see attractions in July is the annual Royal Windsor Horse Show, a four-day event showcasing world-class equestrian competitions and displays of traditional British horsemanship. This event is particularly special as it takes place in the private grounds of Windsor Castle, the oldest and largest occupied castle in the world. Aside from the horse show, July is also the perfect time to explore the lush gardens and grounds of Windsor Castle. Take a stroll through the Queen’s Garden, a beautiful oasis of colorful flowers and perfectly manicured lawns. The castle also hosts traditional summer garden parties, where you can enjoy a picnic on the grounds while listening to live music and sipping on local beverages. And for those looking for a bit of adventure, take a boat trip down the River Thames or rent a bike and cycle along the scenic paths, offering stunning views of the castle and surrounding countryside. No matter what your interests may be, Windsor in July has something for everyone to enjoy.

August

When visiting Windsor in the month of August, it’s important to dress for both comfort and style. The summer weather can be quite warm, so I recommend wearing lightweight, breathable fabrics such as cotton or linen. A comfortable pair of walking shoes is a must, as Windsor is a city best explored on foot. Ladies, I suggest packing a sundress or a pair of flowy pants, while gentlemen can opt for a nice pair of shorts and a polo shirt. Don’t forget to bring a hat and sunglasses to protect yourself from the sun while enjoying the city’s beautiful sights. As for what to bring, I highly recommend packing a small daypack to carry your essentials while out and about. In addition to the usual items such as a water bottle and sunscreen, I also suggest bringing a light rain jacket, as August can bring occasional showers. It’s also a good idea to have a scarf or shawl on hand, as some indoor attractions may require modest dress. Lastly, don’t forget to bring your camera to capture the stunning architecture and royal landmarks of Windsor. With these tips in mind, you’ll be dressed and prepared for a wonderful trip to this charming English town.

August is a fantastic time to visit Windsor, the charming English town located just outside of London. As summer is in full swing, the town is buzzing with energy and there is no shortage of activities to keep you entertained. One must-see attraction is Windsor Castle, the official residence of the British royal family. Take a tour of the castle and marvel at its grandeur and rich history. Don’t miss the Changing of the Guard ceremony, which takes place daily and is a quintessentially British experience. After exploring the castle, take a stroll through the quaint streets of Windsor and stop for a traditional English cream tea at one of the many charming cafes. For those looking for a more active experience, August is the perfect time to take a boat trip down the River Thames. Enjoy the stunning views of the countryside and get a unique perspective of Windsor Castle from the water. For a more cultural experience, visit the Windsor Great Park, a beautiful expanse of greenery that is perfect for a picnic or a leisurely walk. If you happen to be in town on a Saturday, don’t miss the famous Windsor Farmer’s Market, where you can sample local produce and pick up some souvenirs to take home. No matter your interests, August in Windsor has something for everyone to enjoy.

September

When visiting Windsor in September, it’s important to dress in layers. The weather can be quite unpredictable, with cool mornings and evenings and warmer afternoons. I recommend packing a light jacket or sweater, as well as a scarf or shawl that can easily be removed or added depending on the temperature. Comfortable walking shoes are a must, as you’ll likely be exploring the town on foot. And don’t forget to bring a rain jacket or umbrella, just in case of a passing shower. As for what to wear, it’s always a good idea to dress modestly when visiting a historic town like Windsor. This means avoiding shorts and tank tops, especially when visiting religious sites. Opt for lightweight, breathable fabrics that will keep you comfortable throughout the day. And if you plan on visiting any of the royal palaces, a more formal outfit may be required. Finally, don’t forget to bring a small daypack to carry your essentials, such as a water bottle, sunscreen, and a camera to capture all the stunning sights of Windsor.

Welcome to Windsor, a charming town situated on the River Thames just outside of London. September is a wonderful time to visit this historic town, as the summer crowds begin to dissipate and the weather is still pleasant enough for outdoor activities. One of the top must-sees in Windsor is the majestic Windsor Castle, the largest and oldest inhabited castle in the world. Take a stroll through the State Apartments and admire the grandeur of the Queen’s official residence. Don’t miss the Changing of the Guard ceremony, a quintessential British tradition that takes place every day at 11 am. And for a unique experience, book a tour of the castle’s underground tunnels and see where the royal family took refuge during World War II. After exploring the castle, head over to the Windsor Great Park for a leisurely walk or bike ride. This sprawling park is home to stunning gardens, lakes, and forests, and is the perfect place to escape the hustle and bustle of the city. In September, the park is also a popular spot for picnics and outdoor concerts, so be sure to check the schedule and plan accordingly. For a taste of local life, visit the Windsor Farmer’s Market held every Saturday in the town center. Here, you’ll find an array of fresh produce, baked goods, and artisanal crafts, all while mingling with the friendly locals. And of course, no trip to Windsor is complete without indulging in a traditional afternoon tea at one of the many quaint tea rooms scattered throughout the town. September in Windsor truly offers something for everyone, making it the perfect destination for a fall getaway.

October

When visiting Windsor in the month of October, it’s important to keep in mind the unpredictable weather. The temperatures can range from cool and crisp to mild and sunny, so layering is key. I recommend bringing a light jacket or sweater, along with a raincoat or umbrella, to be prepared for any type of weather. Comfortable walking shoes are also a must, as there is much to explore in this charming town. In terms of attire, it’s best to dress in layers that can easily be added or removed depending on the weather. A pair of jeans or khakis with a light long-sleeved shirt or blouse is a versatile and practical option. For women, a scarf can add a touch of style and keep you warm on chilly days. Men may want to consider bringing a blazer or sports coat for a more formal evening out. And don’t forget to pack a hat and sunglasses for those sunny days exploring the beautiful gardens at Windsor Castle. With these items in your suitcase, you’ll be well-prepared for a comfortable and stylish visit to Windsor in October.

October is a fantastic time to visit Windsor, the charming town situated on the banks of the River Thames. As the leaves start to change colors and the air gets crisp, there’s a certain magic in the air that can only be experienced during this time of year. While Windsor is known for its famous castle, there are plenty of other activities to enjoy during this autumn month. One must-do activity in October is to take a stroll through the beautiful Windsor Great Park. This sprawling park covers over 4,800 acres and is home to stunning landscapes, wildlife, and even a deer park. It’s the perfect place to escape the hustle and bustle of the town and immerse yourself in nature. Another must-see is the Eton College, one of the most prestigious boarding schools in the world. Take a guided tour of the campus and learn about its rich history and famous alumni, including Prince William and Prince Harry. And of course, no trip to Windsor would be complete without a visit to the iconic Windsor Castle, the oldest and largest occupied castle in the world. With fewer crowds in October, it’s the ideal time to explore the grandeur and history of this royal residence.

November

When visiting Windsor in the month of November, it’s important to be prepared for the cooler temperatures and potential rain. Layering is key, as the weather can fluctuate throughout the day. Start with a base layer of thermal clothing, then add a sweater or fleece, and top it off with a waterproof jacket. Don’t forget to bring a scarf, gloves, and a hat to keep yourself warm and protected from the elements. Comfortable walking shoes are a must, as there are many cobblestone streets and sidewalks to navigate while exploring this charming town. As for what to wear, aim for a casual yet put-together look. Locals in Windsor tend to dress in a classic and preppy style, so a few nice sweaters and a pair of dark jeans will fit right in. Bring a few dressier options for evenings out, but don’t worry about being too fancy. Leave the high heels at home and opt for a comfortable pair of flats or boots instead. And don’t forget to pack an umbrella or raincoat, as showers are common in November. With these tips in mind, you’ll be ready to fully enjoy all that Windsor has to offer, rain or shine.

As the crisp autumn air sets in, November is the perfect time to visit Windsor, England. Located just a short train ride away from London, this charming town is full of history, culture, and royal splendor. One must-see attraction in November is the famous Windsor Castle. This magnificent fortress is the oldest and largest inhabited castle in the world and offers a unique insight into the lives of the British monarchy. Visitors can tour the State Apartments, see the stunning St. George’s Chapel, and even catch a glimpse of the Changing of the Guard ceremony. For a more tranquil experience, take a stroll through the beautiful Windsor Great Park. This sprawling park is home to the stunning Savill Garden, where November brings a burst of autumn colors. Take a leisurely walk through the park, admire the lush greenery and colorful foliage, and perhaps even spot some deer grazing in the distance. Afterward, warm up with a cup of tea and some delicious scones at one of the quaint cafes nearby. November in Windsor is a delightful escape from the hustle and bustle of city life, offering visitors a chance to immerse themselves in the beauty and tranquility of the English countryside.

December

When visiting Windsor in December, it’s important to dress in layers to combat the chilly temperatures. Start with a warm base layer, such as thermal underwear, and then add a sweater or fleece on top. A waterproof jacket is also a must-have, as the weather can be unpredictable. Don’t forget to bring a scarf, hat, and gloves to keep your extremities warm. Comfortable and sturdy shoes are essential, as you’ll be doing a lot of walking on uneven cobblestone streets. As for what to wear when exploring Windsor, I recommend dressing in comfortable yet stylish clothing. The locals have a sophisticated sense of fashion, so leave the sweatpants and sneakers at home. Opt for a nice pair of jeans or trousers paired with a cozy sweater or blouse. For women, a dress with tights and boots is a classic and practical choice. And don’t forget to bring a small crossbody bag to keep your belongings safe while you’re out and about. Lastly, be sure to bring a camera to capture the stunning views of Windsor Castle and the surrounding countryside.

December is a wonderful time to visit the charming city of Windsor, located in the heart of England’s countryside. One of the top attractions during this time is the enchanting Windsor Castle, which is beautifully decorated for the holiday season. Visitors can take a tour of the State Apartments and witness the stunning Christmas decorations, including a grand Christmas tree in the luxurious St. George’s Hall. The castle also hosts a traditional Christmas market, where you can find unique gifts and sample delicious holiday treats. It’s truly a magical experience that shouldn’t be missed. Another must-see in December is the St. George’s Chapel, located within the grounds of Windsor Castle. This stunning Gothic church is the site of many royal weddings and funerals, and during the holiday season, it becomes even more special. The chapel is adorned with festive decorations and hosts traditional carol services, making it the perfect place to get into the holiday spirit. You can also attend the famous Christmas Eve service, which is attended by members of the royal family. Don’t forget to stop by the quaint town center, where you can find charming shops and cozy cafes to warm up with a cup of hot cocoa. December in Windsor truly offers a magical and unforgettable experience.

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