Select the month that you will be traveling from the table below to view the packing list:
What Upperville is like to visit throughout the year:
January
When visiting Upperville in the winter months, it’s important to dress for the cold weather. Layering is key, as temperatures can vary throughout the day. Start with a base layer of thermal underwear, followed by a warm sweater or fleece. Top it off with a waterproof and windproof jacket. Don’t forget to bring a hat, scarf, and gloves to keep your head, neck, and hands warm. Comfortable and waterproof shoes are a must, as the streets can get slippery from snow and ice. And for those planning on hiking, be sure to bring along a good pair of boots. As for what to wear in Upperville, the locals tend to dress in a more relaxed and casual style. Jeans, sweaters, and boots are a common sight. However, if you plan on visiting any of the upscale restaurants or attending a cultural event, it’s best to dress up a bit more. A nice pair of slacks or a dress with tights and boots will do the trick. And remember to always bring a rain jacket or umbrella, as the weather in Upperville can be unpredictable. With these tips in mind, you’ll be prepared for a comfortable and stylish visit to this charming town in January.
January is a wonderful time to visit the charming town of Upperville, nestled in the rolling hills of Virginia’s hunt country. While the weather may be chilly, the town is brimming with activities and events to keep visitors entertained. Start your day with a stroll through the quaint streets, admiring the historic homes and charming shops. Stop by the local bakery for a warm pastry and a cup of coffee to fuel your adventures. For those interested in outdoor activities, Upperville offers plenty of options. Bundle up and take a hike through the picturesque countryside, or visit one of the many nearby vineyards for a wine tasting. January is also the perfect time to attend one of Upperville’s famous fox hunts, where riders in traditional attire and their trusty hounds chase after the elusive fox. And for a taste of local culture, be sure to check out the Upperville Colt and Horse Show, one of the oldest and most prestigious equestrian events in the country. No matter what your interests may be, Upperville has something to offer for a memorable January visit.
February
When visiting Upperville in the chilly month of February, it’s important to dress appropriately for the weather. While the town may be small, it’s full of charm and activities that are best enjoyed when dressed comfortably and warmly. Layers are key, as the mornings can be brisk and the afternoons can warm up. I recommend packing a warm coat, a few sweaters, and a scarf or two. Don’t forget a waterproof jacket or umbrella, as February can bring some rain or even snow. And of course, comfortable walking shoes are a must for exploring the quaint streets and countryside. As for what to wear, Upperville is a casual town so you won’t need any fancy attire. Jeans or khakis paired with a long-sleeved shirt and a jacket will fit right in. However, if you plan on dining at one of the town’s upscale restaurants, a nice dress or button-down shirt would be appropriate. And don’t forget to bring a hat and gloves for those chilly mornings or evenings spent outdoors. Overall, the key to dressing in Upperville in February is to be prepared for any type of weather and to dress comfortably for exploring the charming town and its surroundings.
February is a wonderful time to visit the charming town of Upperville in Virginia. Despite the chilly weather, there are plenty of activities to keep you entertained. One of the highlights of this month is the annual Upperville Winter Classic, a prestigious horse show that attracts equestrian lovers from all over the country. This event showcases some of the finest horses and riders, and spectators can enjoy watching the thrilling competitions while sipping on a cup of hot chocolate. In addition to the Winter Classic, February is also the perfect time to explore the beautiful nature surrounding Upperville. Take a scenic hike through the Blue Ridge Mountains and witness the stunning winter landscapes. Or, for a more relaxed experience, visit one of the local wineries and indulge in a wine tasting while taking in the picturesque views. Don’t forget to also visit the charming shops and restaurants in town, where you can warm up with a delicious meal and shop for unique souvenirs to bring home. February in Upperville truly offers something for everyone.
March
When visiting the charming town of Upperville in March, it’s important to be prepared for the ever-changing weather. As the saying goes, “If you don’t like the weather, just wait five minutes.” In this small town nestled in the rolling hills of Virginia, temperatures can range from chilly to mild within a matter of hours. Therefore, it’s crucial to dress in layers. Start with a light sweater or jacket and bring a waterproof outer layer in case of rain. Comfortable walking shoes are a must, as you’ll want to explore the quaint streets and picturesque countryside. In terms of fashion, Upperville is a mix of classic and casual. You’ll fit right in with a pair of jeans or khakis paired with a nice top and a stylish scarf. For women, a flowy dress or skirt is also a great option. Don’t forget to bring a hat and sunglasses to protect yourself from the strong sun that can peek out in between the clouds. And of course, no visit to Upperville would be complete without a camera to capture the stunning scenery and historic architecture. With these essentials in tow, you’ll be all set to enjoy the beauty of Upperville in March.
Located in the heart of Virginia’s horse country, Upperville is a charming and historic town that offers visitors a delightful escape from the hustle and bustle of city life. And while the town is a popular destination year-round, March is an especially wonderful time to visit. As the winter chill begins to melt away, Upperville comes to life with a variety of activities and events that showcase the town’s rich culture and heritage. One of the must-do activities in Upperville during March is attending the annual Upperville Colt & Horse Show. This week-long event, held at the historic Grafton Farm, brings together equestrian enthusiasts from all over the country to compete in various competitions and exhibitions. Even if you’re not a horse lover, the lively atmosphere and beautiful setting make this event a must-see for anyone visiting Upperville in March. And after a day at the horse show, be sure to stop by one of the town’s charming bed and breakfasts or local restaurants to experience the warm hospitality and delicious cuisine that Upperville is known for.
April
As you prepare for your journey to Upperville in April, be sure to pack layers to accommodate the unpredictable spring weather. The mornings can be crisp and cool, so bring a light jacket or sweater. As the day progresses, the temperature can rise, so make sure to have a t-shirt or short-sleeved shirt underneath. A waterproof jacket or raincoat is also essential, as spring showers are not uncommon in Upperville. When it comes to footwear, opt for comfortable walking shoes or sneakers. The streets of Upperville are cobblestone and can be uneven, so leave the heels at home. As for accessories, a scarf can add a pop of color to your outfit and also come in handy if the weather turns chilly. And don’t forget to bring a small backpack or crossbody bag to carry your essentials while exploring the quaint town. With these tips in mind, you’ll be prepared for whatever the April weather in Upperville may bring.
April is a magical time to visit the charming town of Upperville in Virginia’s picturesque countryside. The rolling green hills are dotted with colorful wildflowers and the trees are just starting to bud, creating a serene and idyllic backdrop for any traveler. One must-do activity during this time is to explore the nearby wineries and take in the stunning views while sipping on a glass of locally produced wine. The Virginia Wine Country Half Marathon also takes place in April, offering a unique way to experience the beauty of the area while getting some exercise. For history buffs, April is the perfect time to visit Upperville as it coincides with the annual Piedmont Races. This traditional steeplechase event dates back to 1843 and is a beloved local tradition. Visitors can don their best attire and join in on the fun of watching the horse races, enjoying delicious food and drinks, and soaking up the lively atmosphere. It’s a wonderful way to immerse oneself in the town’s history and culture while also experiencing the thrill of a classic sporting event. Don’t miss out on this quintessential April activity in Upperville.
May
May is a wonderful time to visit the charming town of Upperville, nestled in the picturesque countryside of Virginia. As the weather warms up, it’s important to dress comfortably and appropriately for all the outdoor adventures this town has to offer. For a day of exploring the quaint streets and visiting the local shops and cafes, a light jacket or sweater paired with comfortable walking shoes will do the trick. But for those planning to hike or bike through the rolling hills, be sure to pack some sturdy hiking boots and breathable layers to stay comfortable in the changing temperatures. For a touch of style and to blend in with the locals, consider wearing some classic preppy attire. A crisp collared shirt, khaki pants or a flowy sundress are all great options for a day in Upperville. And don’t forget to bring a hat and sunglasses to protect yourself from the bright sun. As for what to bring, a camera is a must to capture the stunning views and historic buildings. And if you’re planning to spend some time at the local wineries, be sure to bring a picnic blanket and some snacks to enjoy a leisurely afternoon among the vineyards. With the right clothing and essentials, you’ll be ready to fully experience the charm and beauty of Upperville in May.
As you wander through the charming village of Upperville in May, the scent of blooming flowers fills the air and the town comes alive with the energy of spring. One of the must-do activities during this time is to visit the Upperville Garden Tour, where you can explore some of the most beautiful private gardens in the area. From vibrant tulip fields to tranquil water features, this self-guided tour is a feast for the senses and a chance to see the local community’s passion for gardening. For a taste of local culture, be sure to check out the Upperville Colt & Horse Show, held annually in May. This week-long event draws equestrian enthusiasts from all over the world to watch thrilling horse jumping competitions and browse through the vendor booths selling everything from riding gear to local crafts. You can also take a stroll through the beautiful show grounds and admire the stunning horses and their riders. Whether you’re a horse lover or simply looking for a unique experience, the Upperville Colt & Horse Show is a must-see event in May.
June
When visiting the charming town of Upperville in June, it’s important to pack light and comfortable clothing. The weather during this time is typically warm and sunny, so be sure to bring plenty of shorts, t-shirts, and sundresses. However, it’s also wise to bring a light jacket or sweater for cooler evenings. Upperville is known for its picturesque countryside, so be sure to bring a sturdy pair of walking shoes to explore the scenic trails and cobblestone streets. When it comes to dressing for Upperville, it’s important to keep in mind the town’s laid-back atmosphere. Locals here value simplicity and comfort over fashion trends, so leave your high heels and fancy attire at home. Instead, opt for a casual yet put-together look with a pair of jeans or a flowy skirt paired with a comfortable blouse. And don’t forget to pack a hat and sunscreen to protect yourself from the strong summer sun. With these essentials in tow, you’ll be ready to fully immerse yourself in the relaxed and charming vibe of Upperville.
When traveling to Upperville in June, visitors are in for a treat. This small town, nestled in the rolling hills of Virginia’s horse country, comes alive with vibrant events and activities during this summer month. One must-do activity is attending the annual Upperville Colt & Horse Show, the oldest horse show in the United States. Here, spectators can witness skilled riders and their majestic horses competing in various equestrian events. The charming town also hosts a lively street fair during this time, where visitors can browse local crafts and indulge in delicious food and drinks. With the warm weather and picturesque scenery, June is the perfect time to explore Upperville’s outdoor offerings, such as hiking in the nearby Shenandoah National Park or picnicking at the picturesque Sky Meadows State Park. In addition to its outdoor attractions, Upperville also has a rich history waiting to be discovered. A visit to the Aldie Mill Historic Park is a must for history buffs. Here, visitors can tour the restored 19th-century gristmill and learn about its role in producing flour for the Confederate army during the Civil War. For a taste of Upperville’s cultural side, head to the Middleburg Film Festival, held in June, where independent films from around the world are screened in unique venues throughout the town. And of course, no trip to Upperville is complete without savoring the local cuisine. From farm-to-table restaurants to quaint cafes, this town offers a range of dining options that are sure to satisfy any palate. So pack your bags and head to Upperville in June for an unforgettable experience filled with history, nature, and charm.
July
As you plan your summer trip to Upperville, Virginia, it’s important to consider the warm and humid weather that awaits you. In July, temperatures in this charming town can reach up to the high 80s, so be sure to pack light, breathable clothing. A comfortable pair of walking shoes is a must, as Upperville is best explored on foot. I recommend opting for light, airy fabrics such as cotton and linen to keep you cool and comfortable throughout the day. When it comes to dressing for activities in Upperville, it’s important to consider the local culture and etiquette. While the town has a relaxed and casual vibe, it’s always respectful to dress modestly when visiting churches or historical sites. For outdoor adventures, don’t forget to bring a sun hat, sunglasses, and sunscreen to protect yourself from the intense summer sun. And of course, don’t forget to pack a swimsuit for a refreshing dip in the nearby Shenandoah River! With these essentials in tow, you’ll be ready to fully enjoy all that Upperville has to offer in the month of July.
Welcome to the charming town of Upperville, nestled in the rolling hills of Virginia’s countryside. July is the perfect time to visit this quaint town, as it is filled with outdoor activities and local events that showcase the beauty of this region. One of the must-do activities in Upperville is to take a leisurely hike through the lush countryside. The countryside is dotted with picturesque farms, meandering streams, and stunning views of the Blue Ridge Mountains. It’s a great way to immerse yourself in nature and get a sense of the slow-paced lifestyle of the locals. Another highlight of visiting Upperville in July is the annual Upperville Colt & Horse Show. This prestigious event brings together world-class equestrians and their magnificent horses for a week-long competition. Even if you’re not a horse enthusiast, this event is worth attending for its lively atmosphere and charming small-town feel. You can browse the vendor booths, sample local cuisine, and watch as the graceful horses compete in various events. So come to Upperville in July and experience the best of Virginia’s countryside and equestrian culture.
August
When visiting Upperville in the month of August, it’s important to dress for the warm and sunny weather. I recommend wearing lightweight, breathable clothing such as shorts, sundresses, and t-shirts. It’s also a good idea to bring a hat and sunglasses to protect yourself from the strong UV rays. While the days may be hot, the evenings can cool down so I suggest bringing a light jacket or sweater. Comfortable walking shoes are a must, as Upperville is a charming town to explore on foot. In addition to dressing for the weather, it’s important to consider the activities you have planned in Upperville. If you’re planning on visiting any of the local vineyards, a dressier outfit may be more appropriate. However, if you’re spending the day hiking or biking through the beautiful countryside, more casual attire is suitable. Don’t forget to bring a swimsuit if you plan on taking a dip in the nearby Shenandoah River. And as always, be sure to pack plenty of sunscreen to keep your skin protected while enjoying all that Upperville has to offer.
August is the perfect time to visit the charming town of Upperville, nestled in the foothills of the Blue Ridge Mountains. This historic town comes alive with outdoor activities and events during the summer months, making it an ideal destination for travelers. One of the must-do activities in August is a visit to the Upperville Colt and Horse Show, one of the oldest and most prestigious horse shows in the United States. Here, you can witness some of the world’s best equestrian athletes compete in various events, and even get up close and personal with these majestic animals. For those seeking a more relaxed and cultural experience, a visit to the Buchanan Hall is a must. This 19th-century building now serves as a community center and hosts a variety of events, including art exhibitions, live music performances, and even a farmers market. Strolling through the historic halls and gardens of Buchanan Hall is a delightful way to spend a summer afternoon and get a taste of the local culture. And don’t forget to try some of the delicious fresh produce from the farmers market – the perfect way to support the local community and indulge in some delicious treats.
September
When visiting Upperville in September, it’s important to come prepared for the changing weather patterns. The mornings and evenings can be cool, so it’s best to dress in layers. A light jacket or sweater paired with a long-sleeved shirt will keep you warm while exploring the charming streets of this small town. As the day progresses and the sun comes out, you can easily shed the layers and soak up the warm sunshine. Don’t forget to bring a waterproof jacket or umbrella, as September can also bring some unexpected rain showers. As for footwear, comfortable walking shoes are a must for exploring Upperville. The town is known for its scenic nature trails and historic sites, so be sure to bring a sturdy pair of shoes that you can comfortably walk in for extended periods of time. And if you plan on attending any outdoor events or festivals, a pair of waterproof shoes will come in handy. Lastly, don’t forget to pack some sunscreen and a hat to protect yourself from the strong September sun. With the right attire and gear, you’ll be ready to fully enjoy all that Upperville has to offer in the beautiful month of September.
September is a fantastic time to visit the charming town of Upperville, nestled in the rolling hills of Virginia’s horse country. The weather is still warm, but the leaves are starting to change and the crowds have thinned out, making it the perfect time to explore this quaint town. Start your visit with a stroll down Upperville’s main street, lined with historic buildings and quaint shops. Be sure to stop by the local farmers’ market, held every Saturday, to sample some delicious fresh produce and artisanal goods. For outdoor enthusiasts, September in Upperville offers endless opportunities for hiking, biking, and horseback riding. The nearby Blue Ridge Mountains boast some of the most scenic trails in the country, with breathtaking views of the surrounding countryside. Horse lovers will also delight in the annual Upperville Colt & Horse Show, one of the oldest and most prestigious shows in the country. Here, you can watch some of the world’s best horses and riders compete, while also enjoying local food and entertainment. With so much to see and do, September is truly the perfect time to experience the beauty and charm of Upperville.
October
As you plan your trip to Upperville in October, be sure to pack layers and comfortable walking shoes. This charming town in Virginia’s horse country offers a mix of outdoor activities and small-town charm, making it the perfect destination for a fall getaway. The weather in October can be unpredictable, so it’s important to dress in layers to stay comfortable throughout the day. A light jacket or sweater paired with a scarf and hat will help you stay warm during crisp mornings and evenings, while a t-shirt or light blouse will keep you cool during the warmer afternoons. When exploring Upperville, be sure to wear comfortable walking shoes as the town is best explored on foot. The quaint streets are lined with historic buildings, boutique shops, and charming cafes, making it a delight to wander around. As you stroll through the town, you’ll also want to bring a small day bag to carry any souvenirs or snacks you may pick up along the way. Don’t forget to also pack a camera to capture the picturesque fall foliage and the charming local architecture. With the right attire and essentials, you’ll be ready to fully enjoy all that Upperville has to offer in October.
October is a fantastic time to visit the charming town of Upperville, nestled in the heart of Virginia’s horse country. As the leaves change colors and the temperatures begin to cool, this quaint town comes to life with a variety of activities and events. One must-do experience is taking a scenic drive through the rolling hills and admiring the picturesque fall foliage. You’ll feel like you’ve stepped into a postcard as you wind your way through the countryside, passing by historic farms and estates. For a taste of local culture, be sure to visit the Upperville Colt & Horse Show, held annually in October. This prestigious event brings together the best equestrians in the country for a week of thrilling competitions and elegant displays of horsemanship. Even if you’re not a horse enthusiast, the lively atmosphere and stunning displays are not to be missed. Plus, with food vendors, craft booths, and live music, there’s something for everyone to enjoy. And for those looking for a taste of the region’s famed wine, October is also harvest season, making it the perfect time to visit nearby wineries and sample some of Virginia’s finest vintages. So pack your sweater and join us in Upperville this October for a delightful autumn getaway.
November
When traveling to Upperville in November, it’s important to dress in layers to prepare for the unpredictable weather. The mornings may start off chilly, but by midday, the sun may be shining and temperatures rising. I recommend bringing a light jacket or sweater that can easily be removed if needed. It’s also a good idea to pack a waterproof jacket or umbrella, as Upperville is known for its occasional rain showers. As for footwear, comfortable walking shoes are a must as many of the town’s attractions are best explored on foot. In terms of attire, Upperville is a quaint and charming town, so I suggest dressing in casual yet stylish clothing. Locals tend to dress in preppy or equestrian-inspired outfits, so don’t be afraid to embrace the country chic look. For the ladies, a pair of stylish boots and a scarf will add a touch of sophistication to any outfit. And for the gentlemen, a collared shirt and a pair of khakis will fit right in with the town’s aesthetic. Remember to also bring a hat and sunglasses for those sunny days, and don’t forget to pack a camera to capture the beautiful fall foliage that adorns the town in November.
November is a wonderful time to visit the charming town of Upperville, nestled in the rolling hills of Virginia’s horse country. As the leaves change to vibrant hues of red and gold, the town takes on a cozy and quaint atmosphere. One of the must-see attractions in November is the annual Upperville Colt and Horse Show, which has been a local tradition since 1853. This prestigious event showcases some of the most beautiful and talented horses in the country, and offers a unique glimpse into the equestrian culture of the region. For those looking to immerse themselves in the local history and culture, a visit to the historic Oak Hill Estate is a must. This 19th-century plantation, once owned by President James Monroe, offers guided tours of the stunning mansion and its grounds. November is also the peak season for wine tasting in Upperville, and visitors can enjoy a leisurely afternoon sampling the award-winning wines at nearby vineyards. And for outdoor enthusiasts, the surrounding countryside offers endless opportunities for hiking, biking, and horseback riding, providing a perfect way to take in the beautiful autumn scenery.
December
When visiting Upperville in December, be sure to pack for cold and potentially snowy weather. Layers are key, as the temperature can fluctuate throughout the day. Bring a warm, waterproof jacket, a hat, gloves, and a scarf to keep you cozy while exploring the charming town. Comfortable walking shoes with good traction are also a must, as the streets can be slick with snow or ice. In terms of attire, Upperville is a small town with a laid-back vibe, so there’s no need to dress up. However, if you plan on dining at one of the upscale restaurants or attending a holiday event, it’s always nice to have a dressier outfit on hand. As for cultural considerations, Upperville is a welcoming and diverse community, so there is no specific dress code to adhere to. Just be respectful and dress comfortably for the weather. And don’t forget to bring your camera to capture the picturesque winter scenery and holiday decorations that make Upperville a truly magical destination in December.
December is an enchanting time to visit Upperville, a quaint town nestled in the rolling hills of Virginia’s horse country. The crisp winter air and festive decorations add to the charm of this small town. One of the must-see attractions during this time is the Upperville Christmas Market. Held on the first weekend of December, this market features local artisans selling their handcrafted gifts, delicious seasonal treats, and live music. It’s a great opportunity to support small businesses and find unique gifts for loved ones. For outdoor enthusiasts, December is the perfect time to explore the many hiking and biking trails in the area. The cooler weather and beautiful scenery make for an invigorating experience. One of the most popular trails is the Upperville Heritage Trail, which takes you through historic sites and offers stunning views of the countryside. And if you’re feeling adventurous, you can even go horseback riding through the picturesque landscapes. End your day with a cozy meal at one of the town’s charming restaurants, where you can warm up with a hearty bowl of soup and a glass of mulled wine. December in Upperville truly offers something for everyone.
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.
