Select the month that you will be traveling from the table below to view the packing list:
What Chesapeake is like to visit throughout the year:
January
When visiting Chesapeake in January, it’s important to dress for the chilly weather. The average temperature during this time is around 40 degrees Fahrenheit, so be sure to bring warm layers such as a coat, scarf, and gloves. It’s also a good idea to pack waterproof shoes, as there can be rain and snow showers throughout the month. Don’t forget to bring a hat to protect your head from the cold winds blowing off the Chesapeake Bay. As for what to wear, dress in layers to stay comfortable throughout the day. Start with a warm base layer, such as thermal underwear, and then add a sweater or fleece on top. A waterproof and windproof outer layer is essential, as the weather in Chesapeake can be unpredictable. It’s also a good idea to bring a small backpack to carry any extra layers or items you may need throughout the day. And of course, don’t forget to pack a camera to capture the stunning winter landscapes of Chesapeake.
January is a wonderful time to visit the charming city of Chesapeake, located in the heart of coastal Virginia. While the weather may be chilly, the city is full of lively activities to keep you warm and entertained. One of the must-do activities in January is to take a stroll through the Great Dismal Swamp National Wildlife Refuge. This 112,000-acre preserve is home to a diverse range of flora and fauna, making it a nature lover’s paradise. You can also take a guided boat tour through the swamp, learning about the history and ecology of this unique landscape. For those interested in history and culture, a visit to the Chesapeake City Hall and Central Library is a must. The beautiful building is a perfect example of Renaissance Revival architecture and houses a museum with exhibits on the city’s history and heritage. The library is also a great place to escape the cold and cozy up with a good book. In the evening, head to the Chesapeake Jubilee Amphitheater for a concert or performance. With a capacity of 10,000 people, this outdoor venue hosts a variety of events throughout the year, making it a popular spot for locals and tourists alike. So bundle up and come explore all that Chesapeake has to offer in the winter season!
February
February in Chesapeake can be a tricky time to pack for, with potential for both chilly weather and mild temperatures. The key to dressing for this time of year is layering. Start with a base layer of long-sleeved shirts and pants, and then add a sweater or fleece on top. A waterproof jacket is also a must, as the weather can be unpredictable. Don’t forget to bring a warm hat, gloves, and a scarf to keep yourself cozy on colder days. And for footwear, comfortable waterproof shoes or boots are essential for exploring the wetlands and hiking trails. When visiting Chesapeake in February, it’s important to be prepared for any outdoor activities you may encounter. Bring a backpack to carry your layers as the temperature changes throughout the day. A water bottle is also a must, as staying hydrated is crucial when exploring the city’s parks and nature reserves. And don’t forget to pack a camera to capture the beauty of the winter landscape. As always, it’s important to dress in layers, but also be mindful of the local culture and dress respectfully when visiting churches or historic sites. With the right attire and gear, you can fully enjoy all that Chesapeake has to offer in February.
February is a fantastic time to visit the charming city of Chesapeake, nestled in the heart of Virginia’s Tidewater region. Despite the chilly temperatures, there’s still plenty of activities to keep visitors entertained. One of my top recommendations is to take a leisurely stroll along the picturesque Chesapeake Arboretum, where you can admire the beautiful winter landscapes and perhaps catch a glimpse of some early blooming flowers. Another must-see attraction is the Great Dismal Swamp National Wildlife Refuge, where you can immerse yourself in the tranquility of nature and spot some unique wildlife species. For those interested in history and culture, February is the perfect time to visit Chesapeake’s historic district. Take a guided tour of the 18th century St. Brides Church, one of the oldest churches in Virginia, or step back in time at the historic battlefield of Great Bridge. And no visit to Chesapeake would be complete without trying some of the delicious local cuisine. From fresh seafood to hearty southern dishes, the city offers a diverse range of dining options that will satisfy any foodie’s cravings. So bundle up and come experience the charm of Chesapeake in February!
March
When traveling to Chesapeake in March, it’s important to dress in layers. The weather can be quite unpredictable, with chilly mornings and warmer afternoons. I recommend bringing a light jacket or sweater that can easily be removed as the day warms up. A comfortable pair of walking shoes is also essential for exploring the city on foot. The cobblestone streets and uneven sidewalks can be tough on the feet, so make sure to choose footwear that is both stylish and practical. In terms of clothing, I suggest packing items that can easily be mixed and matched to create different outfits. A pair of dark jeans and a few neutral-colored tops are perfect for both casual and more formal occasions. Don’t forget to bring a rain jacket or umbrella, as March can be quite rainy in Chesapeake. And of course, no traveler should leave home without a camera to capture the stunning landscapes and historic buildings of this charming city. With these tips, you’ll be prepared for whatever adventures await in beautiful Chesapeake.
March is a fantastic time to visit Chesapeake, Virginia. The winter chill has started to fade away, and the city is buzzing with excitement for the upcoming spring season. One of my favorite things to do in March is to visit the Chesapeake Arboretum. This 48-acre green oasis is a perfect place to escape the hustle and bustle of the city and enjoy the beautiful scenery. The gardens are beginning to come alive with colorful blooms, and the walking trails are the perfect way to get some exercise while taking in the fresh air. Another must-see in Chesapeake during March is the Dismal Swamp Canal Trail. This historic trail winds through the Great Dismal Swamp, a unique and diverse ecosystem that is home to numerous species of plants and animals. The weather in March is perfect for a leisurely bike ride or a peaceful walk along the canal. Keep an eye out for wildlife such as birds, turtles, and even alligators. And make sure to stop by the visitor center to learn about the fascinating history of the canal and its role in the development of the region. March is the perfect time to explore the great outdoors in Chesapeake and immerse yourself in the beauty of nature.
April
When packing for a trip to Chesapeake in April, it’s important to be prepared for a variety of weather conditions. The temperature can range from cool and breezy to warm and sunny, so it’s best to bring a mix of clothing options. I recommend packing lightweight layers such as a light jacket, long-sleeved shirts, and a sweater. This will allow you to adjust to the changing temperatures throughout the day. Don’t forget to bring a rain jacket or umbrella, as April can bring some showers to the area. A comfortable pair of walking shoes is also a must, as there are many beautiful outdoor areas to explore in Chesapeake. When it comes to dressing in Chesapeake, keep in mind that the area has a relaxed and casual vibe. You’ll fit right in with comfortable and practical clothing choices. For men, a pair of khaki pants or shorts paired with a polo shirt is a classic and versatile option. Women can opt for a sundress or casual pants with a flowy top. Don’t forget to bring a swimsuit as well, as the weather may be warm enough for a dip in the ocean. Lastly, be sure to pack sunscreen and a hat to protect yourself from the strong sun rays. With these items in your suitcase, you’ll be ready to enjoy all that Chesapeake has to offer in April.
April is a fantastic time to visit Chesapeake, the charming coastal city located in the heart of Virginia’s Tidewater region. As the weather warms up and the flowers start to bloom, there is no shortage of things to do and see in this picturesque destination. One of the top attractions in April is the annual Chesapeake Jubilee, a lively celebration of the city’s rich history and culture. From carnival rides and live music to delicious local food and crafts, this event is a must-visit for travelers looking to immerse themselves in the local community. For those seeking a more outdoor experience, April is also the perfect time to explore the Great Dismal Swamp National Wildlife Refuge. This expansive park offers miles of hiking and biking trails, as well as opportunities for birdwatching and wildlife spotting. As the spring migration begins, visitors can expect to see a variety of species, including colorful warblers and majestic bald eagles. And with the weather being just right, it’s the ideal time to pack a picnic and spend a leisurely day surrounded by nature. So come on down to Chesapeake this April and experience all the beauty and excitement this charming city has to offer.
May
May is a lovely time to visit Chesapeake, with warm temperatures and plenty of sunshine. As you pack for your trip, keep in mind that the weather can be unpredictable, so it’s important to pack versatile clothing. I recommend bringing layers, including a light jacket or sweater, as the evenings can get chilly. Comfortable walking shoes are a must, as there are many picturesque trails and paths to explore in Chesapeake. When it comes to fashion, the locals in Chesapeake tend to keep things casual and practical. You’ll see many people sporting shorts, t-shirts, and sandals, especially during the day. However, if you plan on visiting any upscale restaurants or attending a special event, it’s always a good idea to bring a dressier outfit. Also, don’t forget to bring a swimsuit and sunscreen, as the beaches in Chesapeake are not to be missed. With these essentials, you’ll be all set for a comfortable and stylish trip to Chesapeake.
May is a wonderful time to visit Chesapeake, a charming city nestled along the Chesapeake Bay. The weather is mild and pleasant, perfect for exploring the lush greenery and historical sites that this area has to offer. One must-see attraction in May is the Great Bridge Lock Park, where you can watch the boats pass through the historic lock system while enjoying a picnic on the waterfront. The park also has walking trails and a playground, making it a great spot for families to spend a sunny afternoon. For history buffs, a visit to the Chesapeake Arboretum is a must. This 48-acre site is filled with beautiful gardens, walking paths, and historical buildings that showcase the city’s rich past. In May, the gardens are in full bloom, making it the perfect time to admire the colorful azaleas, rhododendrons, and dogwoods. The arboretum also hosts events and workshops, so be sure to check their calendar for any happenings during your visit. And after a day of exploring, don’t forget to indulge in some delicious Chesapeake Bay seafood at one of the many local restaurants. May in Chesapeake truly offers something for every type of traveler.
June
June is a wonderful time to visit the charming town of Chesapeake. As the weather warms up, it’s important to dress in comfortable and breathable clothing. A lightweight, long-sleeved shirt and pants made of quick-drying materials are perfect for exploring the town and its many outdoor activities. Don’t forget to pack a hat and sunglasses to protect yourself from the bright sun rays. And if you plan on visiting the beach, be sure to bring a swimsuit and flip flops for a refreshing dip in the Chesapeake Bay. As for footwear, comfortable walking shoes are a must. Whether you’re strolling through the historic district or hiking in the nearby trails, you’ll want to have a good pair of shoes to keep your feet happy. And since Chesapeake is known for its maritime activities, don’t forget to bring a light jacket or windbreaker in case of a cool breeze on the water. Lastly, be sure to pack sunscreen and insect repellent to protect yourself from the sun and pesky bugs. With these essentials in tow, you’ll be well-prepared for a fantastic June adventure in Chesapeake.
As the summer season begins in Chesapeake, there are plenty of exciting activities to be enjoyed. One of the best ways to immerse oneself in the local culture is by attending the Chesapeake Jubilee, a festival that celebrates the city’s agriculture and maritime heritage. From live music performances to delicious seafood, this event is not to be missed. And for those looking to explore the great outdoors, June is the perfect time to visit the Great Dismal Swamp National Wildlife Refuge. With over 111,000 acres of preserved land, visitors can hike, bike, or even take a guided boat tour through this beautiful and peaceful sanctuary. For history buffs, a visit to the Chesapeake Central Library is a must. This state-of-the-art facility not only offers a vast collection of books and resources, but it also features a special exhibit on the city’s rich history. From the Native American tribes who first inhabited the land to the early colonial settlements, visitors can learn about the diverse past of this charming city. And for a taste of the local cuisine, don’t forget to stop by one of the many seafood restaurants along the waterfront, where you can enjoy fresh crab cakes and oysters while taking in the beautiful views of the Chesapeake Bay. June truly is the perfect time to experience all that Chesapeake has to offer.
July
When visiting Chesapeake in July, it’s important to dress for the hot and humid weather. Lightweight, breathable clothing is a must to stay cool and comfortable. I recommend bringing lightweight, quick-drying fabrics such as cotton or linen. A hat and sunglasses are also essential to protect yourself from the bright sun. As for footwear, comfortable walking shoes or sandals are best for exploring the city and its many outdoor activities. Don’t forget to pack a swimsuit for a dip in the Chesapeake Bay or one of the city’s many beaches. In addition to clothing, be sure to bring sunscreen and insect repellent. The sun can be quite strong in Chesapeake, and it’s important to protect your skin from harmful UV rays. Mosquitoes and other bugs are also prevalent in the summer months, so it’s best to be prepared. Finally, don’t forget to pack a reusable water bottle to stay hydrated throughout the day. There are plenty of water fountains and refill stations throughout the city to help you beat the heat. With the right attire and supplies, you’ll be ready to fully enjoy all that Chesapeake has to offer during your summer visit.
July is the perfect time to visit the charming city of Chesapeake. With warm weather and sunny skies, this coastal town offers endless opportunities for outdoor activities. Start your day with a stroll along the picturesque Chesapeake Bay, where you can take in the breathtaking views of the water and watch the boats sail by. For a more adventurous experience, rent a kayak and explore the bay at your own pace. Don’t forget to pack a picnic and stop at one of the many parks along the way for a scenic lunch break. In the evenings, head to the bustling Town Center area for some delicious seafood and live music. This lively district is full of charming restaurants and bars, offering a taste of local cuisine and a chance to mingle with friendly locals. Don’t miss the opportunity to catch a show at the Chesapeake Performing Arts Center, featuring a variety of performances from theater to music. End your evening with a stroll through the charming streets of Chesapeake, taking in the vibrant atmosphere and admiring the historic architecture. With its laid-back vibe and endless options for fun, July is the perfect time to experience all that Chesapeake has to offer.
August
When visiting the charming town of Chesapeake in August, it’s important to dress for the warm and humid weather. Lightweight and breathable clothing is key, such as cotton or linen shirts and shorts. A hat and sunglasses are also essential to protect yourself from the bright sun. And don’t forget to bring a comfortable pair of walking shoes for exploring the town’s charming streets. In addition to your clothing, make sure to bring a light jacket or rain jacket as there may be occasional showers during this time of year. It’s also a good idea to pack a swimsuit, as there are many beautiful beaches and swimming spots in the area. And don’t forget to bring a reusable water bottle to stay hydrated while exploring the town. With these essentials, you’ll be sure to have a comfortable and enjoyable trip to Chesapeake in August.
When visiting Chesapeake in August, there are plenty of activities to enjoy in this charming coastal city. One must-see attraction is the Chesapeake Arboretum, a beautiful green space filled with native plants and trees. Take a leisurely stroll through the gardens and learn about the different species of flora that thrive in this region. The arboretum also hosts special events and workshops throughout the month, making it a great place to immerse yourself in local culture. For a taste of Chesapeake’s history, head to the Great Bridge Lock Park. This historic site played a significant role in the American Revolutionary War and is now a popular spot for picnics and outdoor activities. Take a tour of the lock or rent a kayak to explore the waterways. The park also has a playground and picnic areas, making it a perfect spot for a family outing. August is the perfect time to visit as the weather is warm and sunny, making it ideal for outdoor adventures. So grab your sunscreen and camera, and get ready to make some unforgettable memories in Chesapeake.
September
September is a lovely time to visit the charming town of Chesapeake. The weather is mild and the autumn foliage is just beginning to show its vibrant colors. As a traveler, it’s important to dress appropriately for the season and the activities you have planned. A light jacket or sweater is a must for the cooler evenings, but be sure to pack some layers as the temperature can fluctuate throughout the day. A pair of comfortable walking shoes is also essential for exploring the quaint streets and historic sites of Chesapeake. When it comes to dressing for outdoor activities, such as hiking or boating, it’s important to keep in mind the unpredictable weather. A waterproof jacket and sturdy shoes are a must, as well as a hat and sunglasses to protect from the sun. And don’t forget to bring a swimsuit, as September is still warm enough for a dip in the Chesapeake Bay. As for what to bring, be sure to pack a camera to capture the stunning fall scenery, as well as a reusable water bottle to stay hydrated. And of course, don’t forget to bring an adventurous spirit and an open mind to fully experience all that Chesapeake has to offer.
As the summer crowds begin to dwindle and the crisp autumn air settles in, September is the perfect time to visit the charming city of Chesapeake. Located in the heart of Coastal Virginia, this hidden gem offers a variety of activities for travelers of all ages. One must-see attraction is the Great Dismal Swamp National Wildlife Refuge, where visitors can hike, bike, or take a scenic boat tour through the lush wetlands. The cooler temperatures in September make it an ideal time to explore this natural wonder and spot some of the diverse wildlife that call it home. For history buffs, a visit to the Chesapeake Arboretum is a must. This beautiful botanical garden features over 48 acres of native plants and trees, as well as a historic farmhouse dating back to the 1700s. In September, the arboretum is alive with the vibrant colors of fall foliage, making it the perfect spot for a leisurely stroll or a picnic lunch. And for those looking for a taste of the local culture, the Chesapeake Farmers Market is a must-visit. Here, you can sample fresh produce, homemade goods, and even catch a live music performance while mingling with friendly locals. With its charming atmosphere and abundance of activities, September is the perfect time to experience all that Chesapeake has to offer.
October
As autumn sets in and the leaves begin to change, the charming city of Chesapeake, Virginia offers the perfect destination for a fall getaway. However, with fluctuating temperatures and unpredictable weather, it’s important to pack wisely for your trip. When visiting Chesapeake in October, it’s best to dress in layers to be prepared for any changes in temperature. A light jacket or sweater is essential, as well as a rain jacket or umbrella, as the city is known for its occasional showers. Comfortable walking shoes are also a must, as you’ll want to explore the city’s picturesque parks and historic sites. In terms of clothing, the key is to dress comfortably and casually. Chesapeake has a relaxed and welcoming atmosphere, so there’s no need to dress up. Opt for light, breathable fabrics such as cotton or linen, and avoid heavy materials like wool. Don’t forget to bring a hat and sunglasses for those sunny days, and a scarf for added warmth on cooler evenings. And of course, be sure to pack a camera to capture the beauty of the city’s fall foliage. With these tips in mind, you’ll be well-equipped to enjoy all that Chesapeake has to offer in the lovely month of October.
When visiting Chesapeake in October, there are plenty of activities to keep any traveler entertained. Start your day by taking a leisurely stroll along the scenic Chesapeake Bay Trail. This 22-mile trail offers stunning views of the bay, as well as opportunities for birdwatching and fishing. After working up an appetite, head over to the Chesapeake Farmers Market, where you can sample fresh local produce and artisanal goods. From there, take a drive down to the charming town of Cape Charles, where you can spend the afternoon browsing through quaint shops and enjoying a delicious seafood lunch at one of the many waterfront restaurants. As the sun sets, make your way to the Great Dismal Swamp National Wildlife Refuge, where you can take a guided boat tour through the eerie and mysterious swamplands. October is also the perfect time to visit the Chesapeake Arboretum, where you can admire the vibrant fall colors and learn about the diverse flora and fauna of the region. End your day by attending a local oyster festival, where you can indulge in fresh, juicy oysters and experience the lively culture of Chesapeake. With its beautiful scenery and charming small towns, October is a fantastic time to explore all that Chesapeake has to offer.
November
As the leaves begin to change and the temperature starts to drop, November is a beautiful time to visit Chesapeake. However, it’s important to pack accordingly to fully enjoy your trip. Layering is key in this transitional month, as the weather can be quite unpredictable. I recommend bringing a waterproof jacket, a few sweaters, and a scarf to stay warm in the cool mornings and evenings. During the day, you can shed layers and enjoy the pleasant autumn weather. When it comes to footwear, comfortable walking shoes or boots are a must. The sidewalks and trails can be slippery from fallen leaves, so be sure to choose shoes with good traction. Additionally, pack a pair of waterproof shoes if you plan on exploring the nearby wetlands or taking a boat tour. As for accessories, a hat and gloves may come in handy on particularly chilly days. Don’t forget to bring a camera to capture the stunning fall foliage and a reusable water bottle to stay hydrated while out and about. With these tips in mind, you’ll be prepared for a comfortable and enjoyable visit to Chesapeake in November.
November is a wonderful time to visit the charming city of Chesapeake. As the fall foliage begins to change, the city takes on a cozy and inviting vibe. One of the best ways to experience Chesapeake in November is by taking a stroll through the Great Dismal Swamp National Wildlife Refuge. This 111,000 acre preserve is home to a diverse array of wildlife and offers breathtaking views of the changing leaves. Visitors can also enjoy hiking, bird watching, and even canoeing through the peaceful waters of the swamp. For history enthusiasts, November is the perfect time to explore the many historic sites in Chesapeake. The city played a significant role in both the Revolutionary and Civil Wars, and there are numerous battlefields and museums to visit. One must-see attraction is the Chesapeake Planetarium, which offers a fascinating look at the night sky and its connection to the city’s history. And for a taste of local culture, be sure to check out the Chesapeake Farmers Market, where you can sample delicious regional specialties and pick up some unique souvenirs to take home. With so much to see and do, November is an ideal time to experience the charm and history of Chesapeake.
December
When visiting Chesapeake in December, it’s important to dress in layers to stay warm and comfortable. The weather can be unpredictable, with chilly mornings and evenings, but mild temperatures during the day. I recommend bringing a warm coat, scarf, and gloves for exploring outdoors, as well as a few sweaters or long-sleeved shirts for layering. Don’t forget comfortable walking shoes and socks to keep your feet warm while strolling through the charming streets of Chesapeake. In addition to dressing appropriately for the weather, don’t forget to bring a rain jacket or umbrella. December in Chesapeake can be quite rainy, so it’s best to be prepared. I also recommend packing a small daypack to carry with you during your adventures. This will come in handy for storing any extra layers, as well as a water bottle, snacks, and a map of the area. And of course, don’t forget your camera to capture the beautiful holiday decorations and festivities happening in Chesapeake during this time of year. With the right clothing and gear, you’ll be able to fully enjoy all that this charming coastal city has to offer in December.
December is a magical time to visit Chesapeake, with its charming small-town feel and festive holiday spirit. One of the must-do activities during this time of year is strolling through the Chesapeake City Park, which is transformed into a winter wonderland with twinkling lights and holiday decorations. Take a horse-drawn carriage ride through the park and sip on a warm cup of hot cocoa while listening to carolers serenade you. It’s the perfect way to get into the holiday spirit and experience the community’s tight-knit atmosphere. For a taste of local culture, don’t miss the Chesapeake Christmas Market held at the Towne Place at Greenbrier. This open-air market features over 50 vendors selling unique gifts, crafts, and delicious treats. You’ll also find live music, holiday-themed workshops, and a visit from Santa himself. It’s a great place to pick up some souvenirs for loved ones back home and get a feel for Chesapeake’s vibrant arts and crafts scene. Plus, with the chilly weather, the market offers the perfect opportunity to cozy up with a warm drink and enjoy the festive ambiance.
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.
