Select the month that you will be traveling from the table below to view the packing list:
What Windham is like to visit throughout the year:
January
When visiting Windham in January, it’s important to come prepared for the winter weather. The temperatures can drop well below freezing, so be sure to pack warm layers such as a heavy coat, gloves, and a hat. I recommend investing in a good pair of waterproof boots as well, as the town is known for its snowy terrain. As for clothing, opt for items made of wool or fleece to keep you warm and comfortable during your outdoor adventures. In terms of attire, it’s also important to dress appropriately for indoor activities. Many of the local restaurants and attractions have a casual dress code, so you can leave the fancy clothes at home. However, if you plan on attending any cultural events or performances, it’s always nice to dress up a bit. Lastly, don’t forget to pack a small backpack or bag to carry all of your essentials while exploring the charming town of Windham. This could include a water bottle, snacks, and a map to help navigate through the winding streets. With the right clothing and gear, you’ll be able to fully enjoy all that Windham has to offer in the winter months.
January is a wonderful time to visit the charming town of Windham. While the cold winter weather may deter some travelers, the town truly shines during this time of year. One of the highlights of January in Windham is the annual Winterfest. This festival celebrates all things winter with ice skating, sleigh rides, and even a snowman building competition. It’s the perfect way to embrace the chilly weather and have some fun with the locals. For those looking for a more peaceful experience, a visit to Windham’s Mountain Top Arboretum is a must. While the gardens may be covered in snow, the serene landscape is still a sight to behold. Explore the trails and enjoy the quiet beauty of nature in the winter. And for a taste of local culture, be sure to check out the Windham Local Market, where you can find handmade crafts, delicious food, and live music. January may be a quieter time in Windham, but it’s the perfect opportunity to truly immerse yourself in the town’s cozy and welcoming atmosphere.
February
When visiting Windham in February, it’s important to dress in layers and be prepared for chilly temperatures and possible snow. A warm winter coat, gloves, and a hat are essential items to bring. It’s also a good idea to bring waterproof shoes or boots, as the snow and ice can make sidewalks and roads slippery. Don’t forget to pack a scarf, as it can help protect your face from the cold winds. As for what to wear, comfortable and practical clothing is key. Opt for warm, breathable fabrics like wool or fleece. It’s also a good idea to bring a few pairs of thick socks to keep your feet warm. If you plan on participating in outdoor activities, such as skiing or snowshoeing, make sure to bring appropriate gear and clothing. And don’t forget to pack a swimsuit, as many hotels and resorts in the area have heated indoor pools and hot tubs, perfect for warming up after a day in the cold. With the right clothing and mindset, you can fully enjoy all that Windham has to offer in the winter.
February in Windham is a magical time to visit, with crisp winter air and snow-covered landscapes providing the perfect backdrop for outdoor adventures. For those seeking an adrenaline rush, hit the slopes at Windham Mountain Resort for some world-class skiing and snowboarding. With over 50 trails and a variety of difficulty levels, there’s something for everyone to enjoy. After a day on the mountain, warm up with a cup of hot cocoa and take in the stunning views from the summit. But winter activities aren’t the only thing to do in Windham during February. The town also hosts a variety of events and festivals, including the annual Winter Fest. This lively celebration features ice skating, snow tubing, live music, and delicious food from local vendors. Don’t miss the ice sculptures, created by talented artists from around the region. And for a more relaxed experience, take a scenic drive along the Catskill Mountains and admire the winter wonderland scenery. No matter how you choose to spend your time, February in Windham is sure to be a memorable and enjoyable experience.
March
When visiting Windham in March, it’s important to dress in layers to prepare for the unpredictable weather. A warm and waterproof jacket is a must, as well as a scarf, gloves, and a hat to keep you cozy. The temperature can vary greatly throughout the day, so be sure to bring a mix of short and long-sleeved shirts, along with a pair of comfortable walking shoes. In addition to dressing appropriately, it’s important to bring a few key items to make the most of your visit to Windham. A sturdy backpack is essential for carrying your layers, as well as any souvenirs or snacks you may pick up along the way. Don’t forget to bring a reusable water bottle to stay hydrated while exploring the town. And if you plan on doing any outdoor activities, be sure to pack sunscreen and sunglasses to protect yourself from the bright March sun. With the right clothing and accessories, you’ll be able to fully enjoy all that Windham has to offer.
Welcome to Windham, a charming town nestled in the heart of the Green Mountains of Vermont. March is a wonderful time to visit this quaint New England destination, as the snow begins to melt and the town comes alive with the promise of spring. One of the must-see attractions in Windham during this time is the annual Maple Fest, where visitors can experience the process of making delicious maple syrup and sample local treats. It’s a great opportunity to learn about the history and culture of this region, and indulge in some sweet treats while you’re at it. Another activity not to be missed in Windham during March is skiing and snowboarding at the nearby Stratton Mountain Resort. The slopes are still covered in a blanket of fresh powder, making for excellent conditions for all levels of skiers. And after a day on the mountain, be sure to warm up with a cup of hot cocoa at one of the cozy mountain lodges. For those looking for a more relaxed experience, take a leisurely stroll through the town’s charming streets and admire the picturesque colonial architecture. Windham truly has something for everyone in March, so come and experience the magic of this hidden gem in Vermont.
April
When planning a trip to Windham in April, it’s important to keep in mind the unpredictable weather that often comes with the start of spring. Layers are key for this time of year, as mornings can start off chilly but afternoons can warm up significantly. I recommend packing a mix of short and long-sleeved tops, along with a light jacket or sweater for cooler evenings. Don’t forget to bring a rain jacket or umbrella, as April showers are not uncommon in Windham. As for footwear, a comfortable pair of walking shoes is a must. Windham offers plenty of opportunities for outdoor exploration, whether it’s hiking through the lush forests or strolling through charming downtown streets. Be sure to also pack a pair of closed-toe shoes for any outdoor activities, as well as a pair of sandals for warmer days. And of course, don’t forget to bring a hat and sunglasses to protect yourself from the bright spring sun. With these essentials, you’ll be well-prepared for anything that April in Windham may bring.
April is a wonderful time to visit the charming town of Windham in upstate New York. The snow has melted, the trees are beginning to bud, and the town is coming alive with the promise of warmer weather. One of the best ways to experience the beauty of Windham in April is to take a hike on one of the many scenic trails in the area. The Kaaterskill Falls trail offers breathtaking views of the 260-foot waterfall and the surrounding mountains. Another must-see is the Windham Path, a 1.5-mile paved trail that winds through meadows and forests, perfect for a leisurely stroll or bike ride. For those interested in history and culture, don’t miss the Old Blenheim Bridge in North Blenheim, just a short drive from Windham. This iconic wooden covered bridge, built in 1855, is the longest single-span covered bridge in the world and is a fascinating piece of American engineering. April is also a great time to explore the local shops and restaurants in Windham. From handmade crafts to delicious farm-to-table cuisine, there’s something for everyone to enjoy. And be sure to check out the local farmers’ market, where you can find fresh produce, homemade goods, and a taste of the local community. So come and experience the beauty and charm of Windham in April, you won’t be disappointed!
May
May is a lovely time to visit Windham, with warm weather and blooming flowers creating the perfect backdrop for exploring this charming town. When it comes to dressing for your trip, I recommend packing comfortable and versatile clothing that will allow you to fully enjoy all that Windham has to offer. Since the weather can be a bit unpredictable in May, it’s important to bring layers. A lightweight jacket or sweater is essential for cooler evenings, while a pair of comfortable walking shoes will come in handy for exploring the town and its many hiking trails. As for what to wear, I suggest opting for casual and practical clothing that will allow you to blend in with the locals. Windham is a small town, and while it may not be necessary to dress up, it’s always respectful to dress modestly when visiting any new place. Also, don’t forget to bring a rain jacket or umbrella, as May can bring occasional showers. And of course, don’t forget your camera to capture the stunning natural beauty of Windham and the surrounding area. With these tips in mind, you’ll be prepared for a comfortable and enjoyable visit to this charming New England town.
May is a fantastic time to visit the charming town of Windham, nestled in the scenic Catskill Mountains of New York. As the spring flowers bloom and the temperatures rise, there is no shortage of activities to enjoy in this quaint destination. Take a stroll through the historic Main Street, lined with charming shops and delicious eateries. Don’t miss the chance to sample some local delicacies, such as maple syrup or freshly baked apple pie. For outdoor enthusiasts, the nearby Windham Mountain offers excellent hiking and biking trails, with stunning views of the surrounding landscape. One of the highlights of visiting Windham in May is attending the annual Windham Art Festival. This vibrant event showcases the works of local artists and craftsmen, with live music and delicious food to enjoy. As you wander through the booths, you’ll find unique pieces of art, ranging from paintings and sculptures to handmade jewelry and pottery. For a more active experience, rent a kayak or paddleboard and explore the peaceful waters of the Batavia Kill Creek. And don’t forget to take a scenic drive through the picturesque countryside, where you’ll find charming farm stands selling fresh produce and homemade goods. May in Windham truly has something for everyone.
June
When visiting the charming town of Windham in June, it’s important to dress in layers to prepare for the varying temperatures throughout the day. Mornings and evenings can be cool, while afternoons can be hot and sunny. A light jacket or sweater is a must-have item to bring along. Comfortable walking shoes are also essential for exploring the town’s cobblestone streets and hiking the nearby trails. Don’t forget to pack a hat and sunglasses to protect yourself from the sun during the day. In terms of attire, Windham is a casual town, so there’s no need to bring fancy clothes. Opt for comfortable and breathable clothing, such as loose-fitting pants or shorts and lightweight tops. For women, a scarf can add a touch of style while also providing coverage from the sun. And for those planning to visit any of the local churches, it’s recommended to bring a shawl or cardigan to cover bare shoulders. Lastly, don’t forget to pack a reusable water bottle and sunscreen to stay hydrated and protected while enjoying all that Windham has to offer.
When visiting Windham in June, there are plenty of exciting activities to partake in. The first thing on any visitor’s list should be exploring the beautiful Windham Mountain Resort. Whether you’re an avid skier or simply looking to take in the stunning mountain views, this resort offers something for everyone. In addition to skiing and snowboarding, the resort also offers hiking trails, mountain biking, and a scenic chairlift ride. And if you happen to be in town on a Saturday, be sure to check out the Windham Farmer’s Market for some fresh local produce and artisan goods. Another must-do in Windham in June is taking a scenic drive along the Catskill Mountains Scenic Byway. This 52-mile route offers breathtaking views of the lush green mountains and charming small towns. Along the way, you can stop at various historic sites, including the Thomas Cole National Historic Site and the Mountain Top Historical Society. And for those looking for a bit of adventure, there are also opportunities for zip-lining, tubing, and horseback riding in the area. No matter how you choose to spend your time in Windham, June is the perfect month to experience the beauty and charm of this scenic mountain town.
July
When packing for a July trip to Windham, it’s important to keep in mind the unpredictable weather of the Northeast. Be prepared for hot and humid days, as well as cooler evenings. My advice is to dress in layers, with lightweight, breathable fabrics. A comfortable pair of walking shoes is a must, as you’ll want to explore the charming town and its surrounding nature trails. And don’t forget a rain jacket or umbrella, just in case of a passing shower. As for what to wear, embrace the relaxed and casual vibe of Windham. A pair of shorts or a flowy sundress paired with a t-shirt or tank top will keep you cool and comfortable. And for outdoor activities, be sure to pack a pair of sturdy pants and a long-sleeved shirt to protect against bugs and sun exposure. Lastly, don’t forget to bring a swimsuit for a refreshing dip in the nearby swimming holes or for lounging by the pool at one of Windham’s cozy bed and breakfasts. With these essentials in your suitcase, you’ll be ready to fully enjoy all that this charming town has to offer.
As the summer sun shines down on the charming town of Windham, there are endless opportunities for visitors to soak up the local culture and enjoy the beautiful countryside. July is the perfect time to explore the great outdoors, with hiking trails and bike paths offering stunning views of the rolling hills and picturesque farms. For those looking to cool off, head to the nearby lakes and rivers for a refreshing swim or kayak adventure. But July in Windham isn’t just about nature – it’s also a time for community celebrations and festivals. The annual Windham Summerfest is a must-visit event, with live music, delicious food vendors, and a lively atmosphere that showcases the town’s friendly and welcoming spirit. And for those interested in history, be sure to check out the Windham Historical Society’s July 4th celebration, complete with traditional reenactments and a parade. No matter your interests, Windham in July is sure to offer a memorable and enjoyable experience.
August
As you prepare for your summer visit to the charming town of Windham, located in the picturesque Catskill Mountains of New York, it’s important to pack for warm weather and outdoor activities. August is a popular time to visit, with sunny days and comfortable temperatures in the mid-70s. As you explore the town’s quaint shops and restaurants or venture out into the surrounding nature, you’ll want to dress in comfortable, breathable clothing. Casual and relaxed attire is appropriate for most activities in Windham. Bring along a light jacket or sweater for cooler evenings and early mornings, but for the most part, you’ll want to stick to shorts, t-shirts, and sundresses. Don’t forget to pack comfortable walking shoes for exploring the town and hiking trails. As for accessories, a sunhat and sunglasses are essential for protecting yourself from the bright sun and adding a touch of style to your outfit. And of course, don’t forget to bring a reusable water bottle to stay hydrated while enjoying all that Windham has to offer.
August is a delightful time to visit the charming town of Windham in upstate New York. The town is buzzing with life and there are plenty of activities to keep visitors entertained. One of the highlights of the month is the Windham Mountain Music Festival, where visitors can enjoy live music from a variety of genres while taking in the stunning mountain views. The festival also features local food and craft vendors, making it a perfect way to experience the true spirit of Windham. For those looking to escape the summer heat, a hike to the top of Windham High Peak is a must-do activity in August. The trail is well-maintained and offers breathtaking views of the surrounding Catskill Mountains. On a clear day, visitors can even see all the way to Vermont! The town also offers plenty of opportunities for outdoor adventures, such as mountain biking, fishing, and kayaking. And after a day of activities, be sure to end the night with a delicious meal at one of Windham’s many cozy restaurants, serving up local specialties like farm-to-table dishes and homemade apple pie. August truly is the perfect time to immerse yourself in the beauty and charm of Windham.
September
September is a fantastic time to visit the charming town of Windham. The temperatures are mild, the leaves are just starting to change, and the crowds have dispersed. When it comes to dressing for this time of year, layers are key. I recommend bringing a light jacket or sweater for cooler mornings and evenings, but also packing short-sleeved shirts and pants for the warmer afternoons. Don’t forget to bring a comfortable pair of walking shoes as well, as there are many picturesque paths and trails to explore in Windham. One thing to keep in mind when visiting Windham in September is that the weather can be quite unpredictable. It’s always a good idea to come prepared with a rain jacket or umbrella, just in case. Additionally, be sure to bring a hat and sunglasses to protect yourself from the sun’s rays. And of course, don’t forget the essentials like a camera, sunscreen, and a refillable water bottle. With these items in tow, you’ll be ready to fully enjoy all that Windham has to offer in September. Happy travels!
September is a delightful time to visit the charming town of Windham, nestled in the beautiful Green Mountains of Vermont. As the summer crowds disperse and the leaves begin to change, this quaint town offers a peaceful and authentic New England experience. One of the top activities during this time is hiking the scenic trails of Mount Snow. With cooler temperatures and stunning fall foliage, the views from the summit are simply breathtaking. For a more leisurely stroll, take a stroll through the picturesque town center, where you can browse local shops, sample homemade maple syrup, and admire the historic architecture. Foodies will also find plenty to indulge in during a September trip to Windham. The annual Vermont Wine and Harvest Festival takes place during this month, offering a chance to sample delicious local wines, cheeses, and other artisanal products. For a taste of Vermont’s famous fall flavors, head to one of the many apple orchards in the area and pick your own apples, or stop by a local farmer’s market to sample fresh produce and baked goods. With its charming small-town atmosphere and abundance of outdoor activities and culinary delights, Windham is the perfect destination for a September getaway.
October
As the leaves start to turn and the crisp autumn air settles in, October is a lovely time to visit the charming town of Windham. When it comes to dressing for this picturesque New England destination, layers are key. The temperature can vary greatly throughout the day, so be sure to pack a mix of long-sleeved shirts, sweaters, and a light jacket. And don’t forget a trusty pair of walking shoes as you’ll want to explore the beautiful trails and quaint streets on foot. As for what to wear, you can’t go wrong with classic fall colors like deep reds, oranges, and browns. Embrace the coziness of the season with a warm scarf and a knit hat. And if you plan on dining at one of Windham’s many delicious restaurants, a slightly dressier outfit will fit right in. Don’t forget to bring a rain jacket or umbrella, as October in New England can bring some showers. And of course, a camera to capture the stunning foliage and charming architecture of this quaint town. With these tips, you’ll be dressed to impress and ready to fully immerse yourself in the beauty of Windham in October.
When visiting Windham in October, there are plenty of activities and events to enjoy. One of my favorite things to do during this time is to take a scenic drive through the Green Mountain National Forest. The vibrant fall foliage is a sight to behold and the winding roads offer stunning views of the surrounding mountains. Be sure to stop at one of the many roadside farm stands to pick up some fresh apples or pumpkins to take home as a souvenir. For those looking for a more active adventure, October is the perfect time to go hiking in Windham. The cooler temperatures and crisp air make for ideal conditions to explore the trails in the area. There are several options for all levels of hikers, from easy strolls to challenging treks. Don’t forget to pack a picnic lunch and enjoy a scenic meal surrounded by the stunning autumn scenery. And if you’re lucky, you may even spot some wildlife along the way. Just remember to always leave no trace and respect the natural beauty of this charming town.
November
As we approach the picturesque town of Windham in November, it’s important to come prepared with the right clothing and gear. The weather can be quite unpredictable during this time of year, so it’s best to dress in layers. Start with a warm base layer made of wool or synthetic material, followed by a cozy sweater or fleece. Top it off with a waterproof and windproof jacket, as well as a hat, scarf, and gloves to keep you warm and protected from the elements. Don’t forget to bring a sturdy pair of waterproof shoes for exploring the charming cobblestone streets of Windham. In addition to dressing appropriately, it’s also important to bring along a few essential items for your November visit to Windham. It’s a good idea to pack an umbrella, as well as a compact rain jacket, just in case of unexpected showers. Scarves and hats can also come in handy for keeping warm and doubling as a fashion statement. And of course, don’t forget to bring a camera to capture the stunning autumn colors and quaint architecture of Windham. With the right clothing and gear, you’ll be able to fully enjoy all that this enchanting town has to offer in the crisp November weather.
November is a beautiful time to visit Windham, nestled in the heart of the Green Mountains of Vermont. The fall foliage may have passed its peak, but the crisp air and cozy atmosphere make it the perfect time to explore this charming town. One of my favorite activities in November is to take a scenic drive along Route 100, stopping at the many quaint towns and villages along the way. Be sure to stop at the historic Grafton Village Cheese Company for a taste of their award-winning cheddar and a tour of their cheese-making process. For outdoor enthusiasts, November in Windham offers plenty of opportunities for hiking and biking. The West River Trail is a must-do, with its picturesque views of the West River and surrounding mountains. And for those looking for a bit of adventure, Bromley Mountain Resort offers an early ski season, perfect for hitting the slopes before the crowds arrive. After a day of exploring, warm up with a hot cider at one of the local cafes or cozy up by the fire at a charming bed and breakfast. November in Windham truly captures the essence of small town New England and is not to be missed.
December
When visiting Windham in December, it’s important to dress for the cold weather. Temperatures can drop below freezing, so be sure to pack warm, layered clothing. A good winter coat, gloves, and a hat are essential for staying comfortable while exploring the town. Don’t forget to bring a sturdy pair of boots as well, as the sidewalks can get slippery with snow and ice. It’s also a good idea to pack thermal underwear and wool socks to keep you warm during outdoor activities. In addition to warm clothing, don’t forget to bring a raincoat or umbrella. December in Windham can bring unpredictable weather, so it’s important to be prepared for rain or snow. It’s also a good idea to pack a small backpack to carry with you while exploring. This way, you can easily carry any extra layers or items you may need throughout the day. And of course, don’t forget to bring a camera to capture the beautiful winter landscapes of Windham. With the right clothing and gear, you can fully enjoy all that this charming town has to offer in December.
December is a magical time to visit the charming town of Windham, nestled in the foothills of the Green Mountains in Vermont. The town is transformed into a winter wonderland, with snow-covered streets and festive decorations adorning every corner. During this time, there are plenty of activities to keep visitors entertained and feeling the holiday spirit. One must-see attraction in Windham during the month of December is the annual Christmas Tree Lighting Ceremony in the town square. Locals and tourists alike gather to witness the lighting of the towering evergreen tree, accompanied by caroling and hot cocoa. For a more active adventure, visitors can hit the slopes at the nearby ski resorts, which offer breathtaking views and a variety of runs for all levels. And for those looking to warm up and relax, the town’s cozy coffee shops and restaurants offer a perfect respite from the chilly weather. No matter how you spend your December days in Windham, the festive atmosphere and friendly locals will make it a trip to remember.
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.
