Select the month that you will be traveling from the table below to view the packing list:
What Chespeake is like to visit throughout the year:
January
When planning a trip to Chesapeake in January, it’s important to keep in mind the unpredictable winter weather. The key to staying comfortable and stylish is to dress in layers. Start with a base layer of thermal underwear or long-sleeved shirts made of moisture-wicking material. Then add a warm sweater or fleece jacket, and top it off with a waterproof and windproof coat. Don’t forget to pack a hat, scarf, and gloves to keep your head, neck, and hands warm. And of course, a sturdy pair of waterproof boots is a must for exploring the wetlands and marshes of the Chesapeake Bay. While it may be tempting to pack your entire winter wardrobe, it’s important to pack strategically to save space and weight. Stick to neutral colors such as black, gray, and navy, which can easily be mixed and matched. Opt for fabrics that are lightweight and easy to layer, such as wool or fleece. Don’t forget to pack a swimsuit as well, as many hotels have heated indoor pools and hot tubs to relax in after a day of outdoor activities. And finally, be sure to bring a good camera to capture the stunning winter landscapes of Chesapeake. With the right clothing and gear, you’ll be able to fully enjoy all that this beautiful region has to offer in the winter months.
January is a wonderful time to visit Chesapeake, Virginia. The coastal city experiences milder temperatures during this time of year, making it the perfect opportunity to explore the great outdoors. Take a stroll along the scenic Chesapeake Bay Bridge-Tunnel, where you can spot migratory birds and even dolphins if you’re lucky. For a more active adventure, head to Northwest River Park for some hiking, biking, or horseback riding through the beautiful winter landscape. After working up an appetite, indulge in some of Chesapeake’s famous seafood. From fresh oysters to mouth-watering crab cakes, the city’s coastal location makes it a seafood lover’s paradise. For a unique experience, visit the Great Bridge Fisherman’s Association Seafood Market, where you can purchase freshly caught seafood and have it cooked to your liking at one of the nearby restaurants. And don’t forget to warm up with a cup of hot clam chowder, a local favorite during the chilly January months. With its charming small-town atmosphere and endless outdoor activities, Chesapeake is the perfect destination for a winter getaway.
February
February is a great time to visit the charming city of Chesapeake, nestled along the beautiful Chesapeake Bay. While the weather may be chilly, there is still plenty to see and do. When packing for your trip, be sure to bring layers to stay warm and comfortable. A waterproof jacket and sturdy walking shoes are a must, as the city is full of picturesque walking trails and parks. Don’t forget to pack a warm hat, scarf, and gloves for those brisk mornings and evenings. As for what to wear, a mix of casual and slightly dressier options will serve you well. A pair of dark jeans paired with a cozy sweater and a light jacket will keep you stylish and warm. For a dressier evening out, a pair of slacks or a dress with tights and boots will fit right in. And don’t forget to bring a swimsuit – some of the hotels in the area have indoor pools and hot tubs, perfect for relaxing after a day of sightseeing. With these tips in mind, you’ll be dressed and prepared for a wonderful February trip to Chesapeake.
February is a great time to explore Chesapeake, Virginia. While the weather may be chilly, the city is still bustling with activities and events. Start your day by strolling along the picturesque Chesapeake Bay, taking in the serene views and watching the local fishermen at work. Then head to the Chesapeake Arboretum, where you can admire the beautiful winter blooms and learn about the local flora and fauna. For history lovers, a visit to the Great Bridge Battlefield and Waterways History Foundation is a must. Here, you can learn about the Battle of Great Bridge, a crucial event in the American Revolution, and explore the museum’s exhibits showcasing the city’s maritime history. In the evening, catch a show at the Chesapeake Conference Center, where you can enjoy concerts, theatrical performances, and more. And don’t forget to indulge in some delicious seafood at one of the many local restaurants – February is the perfect time to try Chesapeake’s famous oysters and crab cakes.
March
When visiting the beautiful Chesapeake region in March, it’s important to dress appropriately for the changing weather. The days can be warm and sunny, while the nights can be chilly and breezy. I recommend bringing layers, such as a light jacket or sweater, to be prepared for any temperature changes. In terms of footwear, comfortable walking shoes are a must, as there will be plenty of opportunities to explore the charming towns and scenic nature trails. As for attire, I suggest dressing in casual and comfortable clothing, as the Chesapeake region has a relaxed and laid-back vibe. A pair of jeans or khakis paired with a light, breathable top would be perfect for a day of sightseeing. Don’t forget to bring a rain jacket or umbrella, as March can bring some rain showers. And of course, don’t leave home without a pair of sunglasses and a hat to protect yourself from the bright sun. With these few essentials, you’ll be ready to fully enjoy all the charms that the Chesapeake has to offer.
If you’re planning to visit Chesapeake in March, you’re in for a treat! This charming city is full of activities and events that will make your trip unforgettable. Start your day with a walk along the beautiful Chesapeake Bay, and take in the stunning views of the water and surrounding nature. March is a great time to visit as the weather is mild and perfect for outdoor activities. You can rent a kayak or paddleboard and explore the bay, or simply relax on the beach and soak up the sun. After a morning spent by the water, head to the Chesapeake Arboretum for a peaceful afternoon. This hidden gem features over 3,000 plants and trees, making it the perfect spot for a leisurely stroll. March is the perfect time to visit as the gardens start to come alive with colorful blooms. If you’re feeling adventurous, you can even sign up for a guided tour to learn more about the different species of plants and their significance. After a day of exploring, end your evening with a delicious seafood dinner at one of the local restaurants. Trust me, you won’t be disappointed with the fresh and flavorful dishes Chesapeake has to offer.
April
As the weather warms up in April, it’s important to dress in layers when visiting the beautiful Chesapeake Bay. Mornings can still be chilly, but by midday, you may find yourself basking in the warm sun. I recommend bringing a light jacket or sweater that can easily be removed as the day progresses. It’s also a good idea to pack a rain jacket or umbrella, as April showers are common in this region. When it comes to footwear, a comfortable pair of walking shoes is a must. The Chesapeake Bay offers many opportunities for exploring on foot, whether it be strolling along the waterfront or hiking through one of the nearby parks. Be sure to also pack a pair of sandals or flip flops for days spent at the beach. And don’t forget to bring a swimsuit – the water may still be a bit chilly, but nothing beats a refreshing dip in the bay on a warm spring day. As always, be sure to pack sunscreen, sunglasses, and a hat to protect yourself from the sun’s rays. With these essentials in tow, you’ll be ready to fully enjoy all that Chesapeake has to offer in the month of April.
April is the perfect time to visit Chesapeake, a charming coastal city located in the heart of Virginia. As the weather begins to warm up, the city comes alive with a variety of activities and events for travelers to enjoy. One of the must-do activities in April is to explore the stunning Chesapeake Bay by boat. Whether you take a leisurely kayak tour or hop on a ferry to explore the nearby islands, the crystal-clear waters and picturesque scenery will leave you in awe. Plus, April is the peak season for dolphin and whale watching, making it an unforgettable experience for nature lovers. In addition to outdoor adventures, April brings a plethora of cultural events to Chesapeake. History buffs will love visiting the Great Bridge Battlefield and Waterways History Museum, where they can learn about the city’s role in the American Revolution and Civil War. Foodies can indulge in the annual Chesapeake Wine Festival, where they can sample local wines and delicious cuisine while enjoying live music and beautiful views. And for those looking for a little retail therapy, April also marks the start of the Chesapeake Farmer’s Market, where you can find fresh produce, homemade goods, and unique souvenirs to take home. With so much to see and do, April is the perfect time to visit Chesapeake and experience all that this charming city has to offer.
May
May is a beautiful time to visit Chesapeake, with mild temperatures and blooming flowers everywhere. As a traveler, it’s important to dress appropriately for the weather and activities you have planned. I recommend packing layers, as the temperature can fluctuate throughout the day. A light jacket or sweater will come in handy during cooler evenings, while a t-shirt and shorts are perfect for exploring the city during the day. When it comes to footwear, comfortable walking shoes are a must. With its charming historic districts and scenic nature trails, Chesapeake is best explored on foot. Plus, you’ll want to be prepared for any spontaneous hikes or walks along the beach. Don’t forget to bring a hat to protect yourself from the sun and sunglasses to enjoy the beautiful views. And of course, don’t leave home without sunscreen – even in May, the sun can be strong here in Chesapeake. With these essentials in your suitcase, you’ll be ready to fully immerse yourself in the sights and sounds of this charming city.
May is a wonderful time to visit the charming town of Chesapeake in Virginia. As the weather warms up, the town comes alive with outdoor activities and events. One must-see attraction is the Great Dismal Swamp National Wildlife Refuge, where visitors can hike, bike, and even take a guided boat tour through the stunning wetlands. For a taste of history, head to the Chesapeake Arboretum, where you can wander through beautiful gardens and learn about the area’s past at the historic farmhouse on site. Foodies will also be delighted by Chesapeake’s culinary scene in May. The town hosts an annual seafood festival, where you can sample some of the freshest and most delicious seafood in the region. And for a more unique experience, take a tour of the local winery and try some of their award-winning wines. Don’t forget to stroll through the charming downtown area, filled with quaint shops and restaurants. With its mix of outdoor adventures and cultural experiences, Chesapeake is the perfect destination for a May getaway.
June
When visiting Chesapeake in June, it’s important to dress for the warm and humid weather. Light and breathable fabrics like cotton, linen, and rayon are ideal for staying cool and comfortable. Shorts, t-shirts, and sundresses are all appropriate for daytime activities. However, be sure to bring a light jacket or sweater for the evenings, as temperatures can drop a bit. And don’t forget to pack a hat and sunglasses to protect yourself from the strong sun. In addition to your clothing choices, it’s important to also consider what to bring for outdoor activities. A sturdy pair of walking shoes or sandals are a must for exploring the beautiful parks and trails in Chesapeake. Don’t forget to bring a swimsuit as well, as there are many opportunities for swimming and water sports in the area. And for those planning to spend time on the beach, a beach towel, sunscreen, and a beach bag to carry your essentials are essential items to bring. With the right clothing and gear, you’ll be able to fully enjoy all the outdoor adventures Chesapeake has to offer in June.
June is a delightful time to visit Chesapeake, a charming city nestled along the banks of the Chesapeake Bay. As the warm summer weather sets in, the city comes alive with a plethora of outdoor activities and events. One must-do activity in June is to explore the miles of stunning coastline along the bay. Whether you prefer to lounge on the sandy beaches, take a leisurely bike ride along the waterfront, or go kayaking on the calm waters, there is something for everyone to enjoy. And don’t forget to indulge in some fresh seafood at one of the many waterfront restaurants! For history buffs, June offers the perfect opportunity to delve into Chesapeake’s rich past. Take a stroll through the Historic District, where you can admire beautifully preserved 18th and 19th-century homes. Visit the Chesapeake Bay Maritime Museum to learn about the city’s maritime heritage, or take a tour of the USS Wisconsin, a retired battleship that now serves as a museum. And for a unique experience, hop on a cruise to Smith Island, a small island known for its delicious crab cakes and charming local culture. With so much to see and do in June, Chesapeake is the perfect destination for an unforgettable summer vacation.
July
When visiting the charming Chesapeake region in the month of July, it’s important to dress for both comfort and practicality. With the warm and humid weather, lightweight and breathable clothing is essential. Opt for loose-fitting shirts and shorts made from natural fibers such as cotton or linen to help keep you cool. Don’t forget to bring a hat to protect yourself from the strong sun rays, and a light rain jacket in case of unexpected showers. Comfortable walking shoes are a must, as you’ll want to explore the picturesque towns and scenic trails of the Chesapeake Bay. As for what to bring, make sure to pack plenty of sunscreen and insect repellent to protect yourself from the sun and pesky bugs. A refillable water bottle is also a must, as staying hydrated in the summer heat is crucial. And while the Chesapeake Bay is known for its seafood, it’s always a good idea to bring some snacks and a reusable bag for souvenirs and local produce from the bustling farmers’ markets. With these tips in mind, you’ll be dressed and prepared for a delightful summer adventure in the charming Chesapeake region.
July is a fantastic time to visit Chesapeake, with warm weather and plenty of activities to keep you entertained. One of the top things to do during this month is to explore the great outdoors. The Chesapeake Bay is a popular spot for fishing, boating, and kayaking, and the surrounding parks and trails offer picturesque views and opportunities for hiking and biking. You can also take a scenic drive through the countryside, stopping at charming small towns along the way to sample local cuisine and browse unique shops. For a taste of history and culture, be sure to visit the town of Annapolis in July. This charming colonial town is home to the United States Naval Academy and is bustling with activity during the summer months. Take a stroll down Main Street and admire the historic architecture, or catch a show at the outdoor theater in the park. You can also attend one of the many festivals that take place in Annapolis during July, such as the Annapolis Arts and Crafts Festival or the Annapolis Irish Festival. No matter what your interests may be, Chesapeake has something for everyone in the month of July.
August
When visiting Chesapeake in August, it’s important to dress for the warm and humid climate. Lightweight, breathable fabrics such as cotton or linen are ideal for staying cool while exploring the city. A hat and sunglasses are also essential to protect you from the strong sun, and don’t forget to bring plenty of sunscreen. Comfortable walking shoes are a must, as there are many outdoor activities to enjoy in Chesapeake. In addition to your clothing choices, it’s important to come prepared with the right gear. A reusable water bottle is a must for staying hydrated in the summer heat. You’ll also want to bring a small backpack or crossbody bag to carry your essentials while out and about. I also recommend packing a light rain jacket, as afternoon showers are common in Chesapeake during this time of year. And don’t forget your camera to capture the beautiful landscapes and waterfront views that make Chesapeake such a charming destination.
Hello fellow travelers! If you’re planning a trip to Chesapeake in August, you’re in for a treat. This charming city on the east coast of the United States offers a variety of activities for visitors to enjoy during the summer months. One must-do activity is to explore the Great Dismal Swamp National Wildlife Refuge. This 112,000-acre preserve is a nature lover’s paradise, with hiking trails, canoe and kayak rentals, and even guided boat tours. August is the perfect time to visit as the weather is warm and the wildlife is abundant. Keep an eye out for black bears, river otters, and over 200 species of birds. Another must-see attraction in Chesapeake is the Virginia Beach Boardwalk. This three-mile-long boardwalk is a hub of activity in the summer, with street performers, live music, and delicious seafood restaurants. Stroll along the boardwalk and take in the beautiful views of the Atlantic Ocean or rent a bike and explore the surrounding neighborhoods. For a unique experience, visit during the Neptune Festival in late August, where you can witness sand sculpting competitions and a grand parade. No matter what you choose to do in Chesapeake, August is the perfect time to soak up the sun and experience the best this city has to offer. Happy travels!
September
When planning a trip to Chesapeake in September, it’s important to consider the weather and dress accordingly. The temperature in this coastal town can vary greatly, so it’s best to pack layers. A light jacket or sweater is essential for cooler evenings, while breathable and lightweight clothing is ideal for warmer days. Comfortable walking shoes are a must for exploring the charming downtown area and strolling along the water’s edge. Don’t forget to bring a hat and sunglasses for protection from the sun during outdoor activities. As for what to wear, Chesapeake is a casual destination, so leave the formal attire at home. Locals and visitors alike can be seen in shorts, t-shirts, and sundresses. However, if you’re planning on visiting any museums or historical sites, it’s respectful to wear more conservative clothing. In addition, it’s always a good idea to pack a rain jacket or umbrella, as September can bring occasional showers. Lastly, don’t forget to pack a swimsuit and beach gear if you plan on taking a dip in the Chesapeake Bay. With these tips in mind, you’ll be well-prepared and comfortable for your September trip to Chesapeake.
September is a fantastic time to visit Chesapeake, Virginia. The summer crowds have dispersed, the weather is still warm and pleasant, and there are plenty of activities to enjoy. One of my favorite things to do in September is to take a sunset cruise on the Chesapeake Bay. The water is calm and the views of the surrounding coastline are simply breathtaking. You can also try your hand at crabbing, a beloved local pastime, and indulge in some delicious steamed blue crabs for dinner. Another must-do activity in September is to explore the Great Dismal Swamp National Wildlife Refuge. This vast area of wetlands is home to a diverse array of flora and fauna, and offers a peaceful escape from the hustle and bustle of city life. You can hike, bike, or kayak through the refuge, keeping an eye out for rare bird species and maybe even catching a glimpse of a black bear. And if you’re lucky, you might even witness the stunning fall foliage that transforms the swamp into a colorful wonderland. September truly is a magical time to experience all that Chesapeake has to offer.
October
As autumn settles in, so does the crisp air of Chesapeake. October is a wonderful time to visit this charming coastal town, but it’s important to dress appropriately for the changing weather. Layers are key, as the temperature can vary greatly throughout the day. Start with a light sweater or long-sleeved shirt, and add a jacket or raincoat if needed. Comfortable walking shoes are a must for exploring the cobblestone streets and waterfront promenade. And don’t forget to bring a scarf or hat to keep you warm on those breezy boat tours. When it comes to what to wear in Chesapeake, it’s all about embracing the New England vibe. Opt for classic, preppy styles such as striped shirts, khaki pants, and boat shoes. Don’t be afraid to add a pop of color with a bright scarf or statement necklace. And of course, a rain jacket or umbrella is always a smart choice as October can bring some showers. Lastly, make sure to pack a camera to capture the stunning fall foliage and quaint charm of this seaside town. With the right attire and gear, you’ll be ready to fully immerse yourself in all that Chesapeake has to offer.
October is a fantastic time to visit the charming town of Chesapeake, located in the heart of Maryland’s Eastern Shore. As the leaves start to change color and the temperatures begin to cool, this scenic destination offers a variety of activities for travelers to enjoy. One must-see attraction is the Chesapeake Bay Maritime Museum, which features interactive exhibits and demonstrations on the region’s rich maritime history. Visitors can also take a relaxing stroll along the waterfront and admire the picturesque views of the bay. For outdoor enthusiasts, October is the perfect time to explore the many outdoor activities that Chesapeake has to offer. From kayaking and paddleboarding on the bay to hiking and biking along the scenic trails, there is no shortage of ways to enjoy the beautiful fall weather. And for those looking for a taste of local culture, make sure to check out the charming farmer’s market, where you can sample delicious Chesapeake Bay seafood and other regional specialties. No matter what your interests may be, October is a wonderful time to experience all that Chesapeake has to offer.
November
When packing for a trip to Chesapeake in November, it’s important to be prepared for both chilly weather and potential rain. The key to dressing appropriately in this region during the fall season is to layer your clothing. Start with a base layer of a lightweight long-sleeved shirt made of moisture-wicking material to keep you warm and dry. Then add a sweater or fleece for insulation, followed by a waterproof and windproof jacket. Don’t forget to bring a hat, gloves, and a scarf to keep your extremities warm. It’s also a good idea to pack a pair of waterproof shoes or boots, as the city can be quite damp during this time of year. As for what to wear while exploring Chesapeake, comfort is key. Bring a pair of sturdy walking shoes or boots that you can wear all day while exploring the city’s charming streets and parks. Opt for dark-colored clothing to blend in with the locals and avoid standing out as a tourist. And don’t forget to pack a small umbrella or rain jacket, as November in Chesapeake can be unpredictable when it comes to weather. Finally, be sure to bring a small backpack or crossbody bag to carry your essentials while sightseeing, such as a water bottle, map, and camera. With the right clothing and gear, you’ll be ready to fully enjoy all that Chesapeake has to offer in November.
November is a wonderful time to visit Chesapeake, as the summer crowds have dissipated and the fall colors are in full display. One of my favorite things to do in November is to take a stroll along the Chesapeake Bay Bridge-Tunnel. This engineering marvel connects the Eastern Shore to the mainland and offers stunning views of the bay and the surrounding foliage. On a clear day, you can even see the Atlantic Ocean from the bridge. It’s a great way to get some fresh air and appreciate the natural beauty of the area. If you’re a history buff like me, you won’t want to miss the opportunity to visit Colonial Williamsburg in November. This living history museum takes you back in time to the 18th century and showcases what life was like in colonial America. In November, the town is decorated for the holiday season and there are special events and activities to enjoy. You can also warm up with a cup of hot cider and chat with costumed interpreters as they go about their daily tasks. It’s a unique and immersive experience that shouldn’t be missed during your visit to Chesapeake.
December
When visiting Chesapeake in December, it’s important to remember that the weather can be quite unpredictable. While it may be chilly, it’s not uncommon for temperatures to rise unexpectedly, so it’s best to dress in layers. A warm sweater or jacket paired with a scarf and hat will keep you comfortable while exploring the charming streets of this coastal town. Don’t forget to bring a waterproof jacket and sturdy shoes, as rain and snow are not uncommon in December. As for what to wear, I recommend sticking to comfortable and practical clothing. Chesapeake is a laid-back destination, so leave your fancy outfits at home. Opt for clothing made from breathable fabrics and bring a few pairs of comfortable walking shoes. A good pair of waterproof boots will come in handy if you plan on venturing out for a hike. And of course, don’t forget to pack a swimsuit, as the indoor pools and hot tubs at many hotels are perfect for warming up on a chilly December day. Lastly, be sure to bring a camera and some binoculars to take in the stunning views of the Chesapeake Bay and its wildlife.
December in Chesapeake is a magical time of year, with festive lights twinkling and cheerful holiday music filling the air. One of my favorite things to do during this time is to stroll through the charming downtown area, taking in the delightful decorations and popping into the local shops for some unique gifts. The Chesapeake Christmas Market is a must-see, featuring over 40 vendors selling everything from handmade crafts to delicious treats. And for a taste of local tradition, don’t miss the annual Parade of Lights, where boats decked out in colorful lights glide across the waterway in a dazzling display. But don’t let the holiday spirit distract you from the natural beauty of this coastal city. December is a great time to explore Chesapeake’s outdoor offerings, such as hiking through the picturesque Great Dismal Swamp or birdwatching at the Great Bridge Lock Park. And for a one-of-a-kind experience, take a sunset cruise on the Elizabeth River, where you can admire the stunning views of the city skyline while sipping on hot cocoa. No matter how you choose to spend your December days in Chesapeake, you’ll be sure to feel the warmth and charm of this charming city.
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.
