Select the month that you will be traveling from the table below to view the packing list:
What Leesburg is like to visit throughout the year:
January
When visiting charming Leesburg in January, it’s important to dress in layers to prepare for the chilly weather. Start with a warm base layer, such as long-sleeved shirts and pants, and add a sweater or jacket on top. Don’t forget to bring a waterproof and windproof outer layer, as well as a hat, scarf, and gloves to keep yourself cozy while exploring the town. Comfortable and sturdy shoes are a must, as there may be some snow and ice on the ground. And for those planning to do outdoor activities, bring along a pair of waterproof boots to keep your feet dry and warm. In terms of style, Leesburg is a quaint and historic town, so I recommend dressing in classic, timeless pieces. Opt for neutral colors and avoid loud or flashy clothing that may draw unwanted attention. A nice pair of jeans or slacks paired with a simple sweater or button-down shirt will fit right in with the town’s laid-back vibe. And don’t forget to pack a small umbrella or rain jacket, as the weather in Leesburg can be unpredictable in January. With these tips in mind, you’ll be well-prepared to explore all that Leesburg has to offer, from its charming downtown to its picturesque countryside.
January is a wonderful time to visit Leesburg, a charming town nestled in the rolling hills of northern Virginia. Despite the chilly weather, there are plenty of activities to keep any traveler entertained. Start your day with a cup of warm apple cider from a local farmers market, and then head to the historic downtown area for a walking tour. Admire the elegant 18th and 19th century architecture and pop into the quaint shops and galleries along the way. For a taste of local history, visit the Loudoun Museum or take a tour of the nearby Civil War battlefields. And if you’re feeling adventurous, bundle up and take a hike in the scenic Catoctin Mountain Park just outside of town. No visit to Leesburg is complete without indulging in some of the delicious food and wine that the region is known for. In January, many of the wineries in the area offer special tastings and events, perfect for warming up on a cold day. And don’t miss out on the town’s annual Restaurant Week, where you can sample some of the best cuisine Leesburg has to offer at discounted prices. For a unique experience, take a horse-drawn carriage ride through the picturesque countryside, or join in on a traditional barn dance at a local farm. With its rich history, charming atmosphere, and abundance of activities, Leesburg is a must-visit destination in January.
February
February in Leesburg can be a bit chilly, but don’t let that stop you from exploring this charming town. To stay warm and comfortable, I recommend dressing in layers. Start with a base layer of thermal clothing, followed by a sweater or fleece, and top it off with a waterproof jacket. Don’t forget to bring a scarf, hat, and gloves to keep your extremities warm. For footwear, opt for comfortable walking shoes with good traction, as the sidewalks can be slippery in the winter months. And of course, don’t forget to pack an umbrella in case of rain. As for what to wear, Leesburg is a laid-back town, so there’s no need to dress up unless you’re attending a special event. Stick to casual and comfortable clothing, such as jeans and a sweater, or a dress with tights and boots. Layers are key, as the temperature can fluctuate throughout the day. And don’t be afraid to add some color to your winter wardrobe, as Leesburg is known for its vibrant arts and culture scene. When you’re out and about exploring, don’t forget to bring a small backpack or crossbody bag to carry your essentials, like a water bottle, map, and camera. Happy travels!
February is a delightful time to visit the charming town of Leesburg, known for its picturesque streets and historic architecture. As the winter chill begins to thaw, Leesburg comes alive with vibrant festivals and events. One must-do activity in February is to attend the annual Flower and Garden Festival, held in the heart of downtown Leesburg. This event showcases the town’s beautiful blooms and offers a chance to sample local artisan crafts and delicious food. For a more cultural experience, visitors can also catch a performance at the Tally Ho Theatre, a beloved community venue that hosts a variety of shows and concerts throughout the month. And of course, no trip to Leesburg is complete without a stroll through the historic district, where you can admire the town’s well-preserved 19th-century buildings and learn about its rich history.
March
When visiting Leesburg in March, it’s important to dress in layers as the weather can be unpredictable. Bring a light jacket or sweater for cooler evenings, but also pack some t-shirts and shorts for warmer days. Comfortable walking shoes are a must, as Leesburg is a town best explored on foot. Don’t forget to pack a rain jacket or umbrella, as spring showers are common. As for attire, Leesburg is a casual and relaxed town. You’ll fit right in with a pair of jeans and a comfortable shirt. For women, a sundress or flowy skirt is also appropriate. Keep in mind that the town is known for its historic buildings and cobblestone streets, so stiletto heels are not recommended. And don’t forget to bring a hat and sunscreen for when you’re out exploring the charming streets and parks of Leesburg. With the right clothing and gear, you’ll be ready to fully enjoy all that this quaint Virginia town has to offer in the beautiful month of March.
March is a fantastic time of year to visit Leesburg, Virginia. The charming town is located in the heart of Loudoun County, known for its beautiful rolling hills and scenic landscapes. As the weather begins to warm up, there are plenty of activities to enjoy in and around Leesburg. First and foremost, I highly recommend taking a stroll through the historic downtown area. With its cobblestone streets and quaint storefronts, it feels like stepping back in time. Stop by the Loudoun Museum to learn about the town’s rich history, and then grab a bite to eat at one of the many locally-owned restaurants. For outdoor enthusiasts, the nearby Appalachian Trail offers stunning views of the surrounding countryside. And of course, no trip to Leesburg is complete without a visit to one of the many wineries in the area. March is a great time to go wine tasting, as the vineyards are starting to come alive after the winter and the spring blooms add a beautiful backdrop to the experience. Cheers to a wonderful trip in Leesburg!
April
April is a beautiful time to visit Leesburg, with the spring flowers in full bloom and the mild temperatures perfect for exploring this charming town. When it comes to dressing for your trip, it’s important to keep in mind the unpredictable weather that April brings. Be sure to pack layers, as the mornings can be cool and the afternoons warm. A light jacket or sweater, comfortable walking shoes, and a rain jacket are all essential items to have on hand. Don’t forget to bring a hat and sunglasses to protect yourself from the sun. As for what to wear, Leesburg is a casual town, so leave your fancy attire at home. Opt for comfortable and practical clothing, such as jeans or khaki pants paired with a t-shirt or light blouse. A sundress or shorts are also appropriate for the warmer days. And if you plan on visiting any of the historic sites, remember to dress respectfully and cover your shoulders and knees. Lastly, don’t forget to bring a reusable water bottle to stay hydrated while exploring the town and a small backpack to carry your essentials. With these tips in mind, you’ll be ready to fully enjoy the beauty and charm of Leesburg in April.
When visiting Leesburg in April, there are plenty of activities to enjoy in this charming Virginia town. One must-see attraction is the annual Flower and Garden Festival, held every year in mid-April. This event transforms the streets of downtown Leesburg into a colorful paradise, with over 150 vendors showcasing their beautiful flowers, plants, and gardening supplies. It’s the perfect opportunity to admire the stunning blooms and maybe even pick up some gardening tips from the experts. For history buffs, April is also a great time to visit Leesburg. The town is home to many historic sites, including the Morven Park Mansion and Gardens. This 1,000-acre estate was once the home of Virginia’s governor and offers a glimpse into the opulent lifestyle of the 19th century. Another must-visit spot is the Ball’s Bluff Battlefield and National Cemetery, where the Civil War battle of Ball’s Bluff took place. Take a self-guided tour of the battlefield and pay your respects to the soldiers buried at the cemetery. April is the perfect time to visit these historic sites, as the weather is pleasant and the crowds are smaller compared to the summer months.
May
When visiting the charming town of Leesburg in May, it’s important to dress for both comfort and style. The weather can be quite unpredictable, so it’s best to dress in layers. Bring a light jacket or sweater for cooler mornings and evenings, but also pack some shorts and t-shirts for warmer afternoons. It’s also a good idea to bring a rain jacket or umbrella, just in case of a passing shower. For footwear, I recommend comfortable walking shoes as Leesburg is a pedestrian-friendly town with plenty of beautiful parks and historic sites to explore. Ladies, leave your high heels at home and opt for a pair of stylish flats instead. As for accessories, a hat and sunglasses are essential for protecting yourself from the strong Virginia sun. And don’t forget to bring a small backpack or crossbody bag to carry your essentials while exploring the town. Overall, the key to dressing in Leesburg in May is to be prepared for any type of weather while still looking fashionable.
May is a wonderful time to visit Leesburg, Virginia. With the arrival of spring, the town comes to life with blooming flowers, bustling farmers’ markets, and lively events. One of the must-see attractions in May is the Leesburg Flower and Garden Festival. This two-day event showcases over 150 vendors selling unique plants, beautiful flowers, and garden accessories. Stroll through the charming streets of Leesburg and admire the stunning displays of colorful flowers and pick up some new additions for your own garden. The festival also features live music, delicious food, and fun activities for the whole family. For history buffs, May is the perfect time to explore the rich heritage of Leesburg. The town is home to numerous historic sites, including the Morven Park estate and Oatlands Plantation. Take a tour of these well-preserved homes and learn about the lives of the families who once lived there. Additionally, the annual Leesburg Airshow takes place in May, where visitors can watch thrilling aerial performances and see historic military aircraft up close. And no trip to Leesburg is complete without a visit to the town’s charming downtown area, filled with quaint shops, delicious restaurants, and a vibrant local art scene.
June
When packing for a June trip to the charming town of Leesburg, it’s important to keep in mind the warm and humid weather. Lightweight and breathable clothing is a must, with a mix of short-sleeved shirts and shorts for exploring during the day, and a light jacket or cardigan for the cooler evenings. Comfortable walking shoes are essential for navigating the town’s cobblestone streets and historic sites. And don’t forget a hat and sunglasses to protect yourself from the bright Virginia sun. As for what to wear, Leesburg has a relaxed and casual vibe so there’s no need to pack your fanciest clothes. Stick to comfortable and versatile pieces that can be dressed up or down. And for women, a sundress or maxi dress is perfect for a day of sightseeing or a romantic dinner in one of the town’s many quaint restaurants. Lastly, don’t forget to pack a reusable water bottle to stay hydrated, as well as a small backpack or crossbody bag to carry your essentials while exploring. With these tips, you’ll be ready to enjoy all that Leesburg has to offer in style and comfort.
June is an excellent time to visit the charming town of Leesburg, nestled in the heart of Virginia’s wine country. One of the must-do activities in Leesburg is to explore the town’s many wineries and vineyards. With the warm summer weather, it’s the perfect time to sip on a glass of local wine while taking in the scenic countryside views. Don’t miss out on a visit to Stone Tower Winery, known for its award-winning wines and stunning panoramic views. For a unique experience, consider taking a wine tour by bike or on horseback, allowing you to fully immerse yourself in the picturesque surroundings. In addition to wine tasting, June also offers a variety of outdoor activities in Leesburg. The town is surrounded by beautiful parks and trails, making it an ideal destination for hiking, biking, and picnicking. Take a stroll through the historic Morven Park, once the home of Virginia’s governor and now a popular spot for outdoor concerts and events. Or head to the C&O Canal Towpath, a scenic trail that follows the Potomac River and offers opportunities for boating, fishing, and birdwatching. With its perfect blend of wine and outdoor adventures, Leesburg is a delightful destination to visit in June.
July
When visiting Leesburg in the month of July, it’s important to dress for the warm and humid weather. Lightweight and breathable fabrics like cotton and linen are your best bet. Opt for loose-fitting clothing to stay cool and comfortable while exploring the charming town. Don’t forget to bring a hat and sunglasses to protect yourself from the bright sun. As for footwear, comfortable walking shoes are a must for exploring Leesburg’s historic streets and parks. Sandals or flip flops are also a good option for the hot weather, but be sure to bring a pair of closed-toe shoes for any outdoor activities. Don’t forget to pack a light jacket or sweater for the evenings, as the temperature can cool down. And of course, always bring a refillable water bottle to stay hydrated throughout your adventures in Leesburg.
Leesburg, a charming town in Virginia’s wine country, is a fantastic destination for a summer getaway. July is the perfect time to visit, as the town comes alive with outdoor activities and events. One must-see attraction is the Leesburg Farmers Market, held every Saturday morning. Here, you can sample the freshest local produce, artisanal cheeses, and homemade baked goods. It’s a great opportunity to support local farmers while also experiencing the vibrant community atmosphere of Leesburg. For history buffs, a visit to Morven Park is a must. This 1,000-acre estate was once the home of Virginia Governor Westmoreland Davis and is now open to the public as a museum and park. In July, the park hosts various events, including concerts, picnics, and even Civil War reenactments. You can also explore the beautiful gardens and tour the historic mansion, filled with original furnishings and artifacts. It’s a perfect way to immerse yourself in the rich history and culture of Leesburg.
August
August in Leesburg is a beautiful time to visit, with warm temperatures and plenty of sunshine. However, it’s important to pack the right clothing and gear to make the most of your trip. In terms of clothing, lightweight and breathable fabrics are key. A comfortable pair of walking shoes is a must, as you’ll likely be exploring the charming downtown area and its many shops and restaurants. A sunhat and sunglasses are also essential for protecting yourself from the summer sun. As for what to wear, casual and comfortable is the way to go in Leesburg. A pair of shorts or a sundress paired with a t-shirt or tank top is perfect for strolling around town. In the evenings, a light jacket or sweater may come in handy as temperatures can cool down. And don’t forget to bring a swimsuit, as many of the area’s hotels and resorts have pools or access to nearby lakes for a refreshing dip. Finally, remember to pack sunscreen and bug spray to protect yourself from the sun and any pesky mosquitoes. With the right clothing and gear, you’ll be able to fully enjoy all that Leesburg has to offer in August.
Welcome to Leesburg, a charming town located in the heart of Virginia’s wine country. As summer winds down, August is the perfect time to visit and experience all that this quaint town has to offer. Start your day by strolling through the historic downtown area, lined with charming shops and restaurants. Take a break from the summer heat with a refreshing scoop of ice cream from The Cone Zone, a local favorite. No trip to Leesburg is complete without a visit to one of the many nearby wineries. August is the perfect time to take a wine tour and sample some of the region’s best vintages. With picturesque views of rolling hills and vineyards, it’s no wonder why this area has become a popular destination for wine lovers. If wine isn’t your thing, head to the nearby Shenandoah River for a day of kayaking, tubing, or fishing. August offers warm weather and clear skies, making it the perfect time to enjoy the great outdoors in Leesburg. So pack your bags, grab a glass of wine, and get ready for a memorable summer vacation in this charming town.
September
When visiting Leesburg in September, it’s important to dress for the changing weather. While the mornings and evenings may be cool, the afternoons can still be quite warm. A light jacket or sweater is a must-have for layering, as well as comfortable walking shoes for exploring the picturesque streets of this charming town. It’s also a good idea to bring a small umbrella or rain jacket, as September is known for occasional showers. As for what to wear, Leesburg is a casual town so there’s no need for fancy attire. Opt for comfortable and breathable fabrics, such as cotton or linen, to keep cool during the day. And don’t forget to pack a hat and sunglasses to protect yourself from the bright sun. In terms of accessories, a crossbody bag or backpack is ideal for carrying essentials while leaving your hands free for taking photos or trying out local treats. And of course, don’t forget to bring a camera to capture the beauty of Leesburg’s historic buildings and vibrant fall colors.
September is a fantastic time to visit Leesburg, a charming town located in the heart of Virginia’s wine country. While the summer crowds have dispersed, the temperatures remain mild and the fall foliage is just starting to make an appearance. This makes it the perfect time to explore the town’s quaint streets and scenic countryside. One of the must-do activities in Leesburg during September is to attend the annual Virginia Wine Festival. Held every year in the first weekend of September, this event brings together over 50 of the state’s best wineries for a weekend of wine tastings, live music, and delicious food. It’s a great opportunity to sample some of the region’s award-winning wines and to learn about the local wine-making culture. And if you can’t make it to the festival, don’t worry – there are plenty of wineries in the area that offer tastings and tours all year round. Cheers to that!
October
When visiting Leesburg in October, be sure to pack layers as the weather can vary greatly. Mornings can be chilly with temperatures in the low 50s, but by midday, it can warm up to the high 70s. I recommend bringing a lightweight jacket and a few sweaters to easily adjust to the changing temperatures. Comfortable walking shoes are also a must as you’ll want to explore the charming town on foot. Leesburg has a casual and relaxed atmosphere, so there’s no need to pack fancy clothes. Jeans, t-shirts, and comfortable dresses are suitable for daytime activities. However, if you plan on attending any upscale events or dining at a fancy restaurant, a nice outfit would be appropriate. Don’t forget to bring a rain jacket or umbrella, as October can bring some showers. And lastly, be sure to pack a camera to capture the beautiful fall foliage and historic buildings that make Leesburg a delightful destination.
Welcome to charming Leesburg, Virginia, a historic town nestled in the heart of the picturesque Loudoun County. October is the perfect time to visit Leesburg, as the crisp autumn air and colorful foliage make for a delightful experience. Start your day by strolling through the quaint streets of downtown Leesburg, admiring the well-preserved 18th and 19th century buildings. Don’t miss the weekly farmer’s market, where you can sample local produce and artisanal goods while mingling with friendly locals. For history buffs, a visit to the nearby Ball’s Bluff Battlefield and National Cemetery is a must. This site played a significant role in the Civil War, and guided tours are available to learn about the brave soldiers who fought here. If you’re in the mood for some outdoor activity, head to the nearby Shenandoah River for a scenic kayak or canoe trip. And of course, no trip to Leesburg is complete without indulging in some local wine. The area is known for its award-winning wineries, and October is the prime season for wine tastings and tours. So grab a glass, sit back, and soak in the beauty of Leesburg in the fall.
November
As the leaves start to change and the temperature begins to drop, November is a beautiful time to visit the charming town of Leesburg. When packing for your trip, be sure to bring layers as the weather can be unpredictable. A light jacket, scarf, and comfortable walking shoes are essential for exploring the historic downtown area. As the town is known for its quaint shops and boutiques, I recommend bringing a reusable bag to carry any treasures you may find along the way. When it comes to dressing for the crisp autumn weather, think cozy and practical. A warm sweater paired with jeans and a pair of boots will keep you comfortable while strolling through the picturesque streets. Don’t forget to bring a rain jacket or umbrella, as November can bring some showers. And for those planning to visit nearby wineries, a stylish yet comfortable outfit is appropriate for wine tasting and taking in the stunning views of the countryside. With the right clothing and accessories, you’ll be able to fully enjoy all that Leesburg has to offer during your November visit.
Leesburg, a charming town in Northern Virginia, is a perfect destination for those looking to experience a bit of American history and culture. And November is an ideal time to visit, as the fall colors are at their peak and the crowds have thinned. Start your day off with a stroll through the historic downtown area, where you can admire the beautifully preserved 18th and 19th century buildings. Don’t miss the Loudoun County Courthouse, a stunning Greek Revival structure that has been in continuous use since 1894. After exploring the town, head out to the surrounding countryside for some outdoor activities. The nearby Blue Ridge Mountains offer fantastic hiking opportunities, with trails of varying difficulty levels. For a more leisurely experience, take a scenic drive along the famous Skyline Drive, which winds through Shenandoah National Park. And for wine enthusiasts, November is the perfect time to visit Leesburg’s many wineries, as it’s harvest season. Sip on some local vintages and take in the stunning views of the rolling hills covered in vibrant autumn foliage. With its rich history, natural beauty, and delicious wine, Leesburg is a must-visit destination in November.
December
When visiting Leesburg in December, it’s important to dress in layers. The weather can be quite unpredictable, with chilly mornings and warmer afternoons. Start with a base layer of thermal undergarments, followed by a sweater or fleece, and top it off with a waterproof jacket. Don’t forget to pack a warm hat, gloves, and a scarf to keep you cozy during any outdoor activities. Comfortable, waterproof shoes are a must, as the town’s cobblestone streets can get slippery when wet. And if you plan on doing any hiking or outdoor exploring, be sure to bring along a sturdy pair of boots. As for what to wear, Leesburg is a quaint and charming town, so a casual and comfortable style is perfectly acceptable. Dress in layers to stay warm and to easily adjust to changing temperatures throughout the day. And don’t be afraid to add a pop of color with a scarf or hat, as the town’s holiday decorations and festive atmosphere make for a picturesque backdrop. Finally, be sure to bring a small backpack or crossbody bag to carry essentials like a water bottle, camera, and map as you explore all that Leesburg has to offer.
December is a magical time to visit Leesburg, Virginia. The town is transformed into a winter wonderland, with charming holiday decorations lining the streets and festive music filling the air. One of the must-see attractions during this time is the annual Christmas and Holiday Parade, a beloved tradition that brings the community together to celebrate the season. The parade features marching bands, colorful floats, and of course, jolly old Saint Nick himself. After the parade, be sure to take a stroll through the historic downtown area, where you’ll find charming shops and cozy cafes perfect for warming up with a cup of hot cocoa. For a truly unique experience, be sure to visit the Leesburg Christmas Tree Maze. This one-of-a-kind attraction features over 1,000 live Christmas trees arranged in a maze for visitors to explore. It’s a fun and festive activity for the whole family, with hot cider and holiday treats available for purchase. Another must-visit spot in December is Oatlands Historic House and Gardens, where you can take a candlelight tour of the beautifully decorated mansion and grounds. And for those looking for a little holiday shopping, the Leesburg Premium Outlets offer great deals on gifts for everyone on your list. With so much to see and do, Leesburg is the perfect destination for a December getaway.
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.
