Select the month that you will be traveling from the table below to view the packing list:
What Chestertown is like to visit throughout the year:
January
When visiting Chestertown in January, it’s important to dress in layers as the weather can be unpredictable. A warm coat, hat, and gloves are essential for exploring the charming streets of this quaint town. The temperature can range from chilly to below freezing, so bringing a scarf and waterproof boots may also be wise. Don’t forget to pack a sturdy pair of walking shoes for exploring the countryside and historic sites. In terms of attire, Chestertown is a casual town, so there’s no need to pack fancy clothes. A nice sweater and jeans will suffice for most restaurants and activities. However, if you plan on attending any cultural events, such as the Chestertown Jazz Festival, a dressier outfit may be appropriate. And of course, don’t forget to pack a camera to capture the stunning winter landscapes and charming architecture of this delightful town.
January is a wonderful time to visit the charming town of Chestertown, located on Maryland’s Eastern Shore. While the weather may be chilly, the town is alive with a cozy and festive atmosphere. One of the highlights of January in Chestertown is the annual Winterfest celebration, which takes place in the second week of the month. This event features an ice carving competition, live music, and delicious food and drinks from local vendors. It’s the perfect way to experience the town’s community spirit and warm hospitality. For those looking for a more active experience, January is also a great time to explore the beautiful nature surrounding Chestertown. The Chesapeake Bay and its tributaries offer a variety of outdoor activities, from hiking and bird-watching to kayaking and fishing. The nearby Eastern Neck National Wildlife Refuge is a must-visit for nature enthusiasts, with its diverse wildlife and scenic trails. And after a day of outdoor adventure, be sure to cozy up by the fireplace at one of Chestertown’s charming bed and breakfasts, and indulge in some delicious local seafood. January in Chestertown truly has something for everyone.
February
When visiting Chestertown in February, it’s important to dress in layers to combat the unpredictable weather. A warm, waterproof coat is a must, as well as a scarf, gloves, and a hat. The town is known for its charming streets and historic buildings, but be sure to also pack comfortable walking shoes for exploring. As the temperatures can drop below freezing, it’s important to bring warm socks and a few sweaters to stay cozy. While the weather can be chilly, there are still plenty of activities to enjoy in Chestertown during February. Be sure to bring a swimsuit if you plan on taking a dip in the indoor pool at the local community center. And don’t forget to pack a nice outfit for a romantic dinner at one of the town’s cozy restaurants. As always, it’s important to be respectful of the local culture and dress appropriately when visiting any destination. With the right clothes and mindset, you’ll be ready to take on all that Chestertown has to offer in the month of February.
February is a wonderful time to visit the charming town of Chestertown. While the weather may be chilly, the town is full of warm hospitality and a delightful atmosphere. One of the must-see attractions in February is the Chestertown Winterfest. This annual event features a variety of activities, from ice carving competitions to live music performances. It’s a great opportunity to bundle up and explore the town while enjoying the festive winter spirit. Another highlight of visiting Chestertown in February is the opportunity to witness the majestic bald eagles in their natural habitat. The town is located on the Chesapeake Bay and is home to one of the largest populations of bald eagles in the country. Take a scenic boat tour or explore the nearby nature reserves to catch a glimpse of these magnificent creatures in action. February also marks the beginning of the nesting season, so visitors may be lucky enough to see bald eagle pairs building their nests and preparing for the arrival of their young. It’s truly a sight to behold and a unique experience that should not be missed when in Chestertown.
March
When packing for a trip to Chestertown in March, it’s important to keep in mind the unpredictable weather patterns of the Eastern Shore. While the days may start off chilly, they can quickly warm up, so it’s best to dress in layers. A lightweight jacket, scarf, and comfortable walking shoes are essential items to have on hand. Don’t forget to bring a raincoat or umbrella, as March can bring occasional showers. As for what to wear, consider blending in with the locals by opting for a more casual and practical style. This means leaving the high heels and fancy dresses at home and instead opting for comfortable jeans, sweaters, and a warm coat. Locals in Chestertown tend to embrace a “preppy” look, so don’t be afraid to bring your favorite boat shoes or collared shirt. And of course, don’t forget to pack a good pair of binoculars to fully take in the stunning views of the Chesapeake Bay.
March is a wonderful time to visit Chestertown, a charming town located on the Eastern Shore of Maryland. As the winter chill begins to fade, the town comes alive with various events and activities. One of the highlights of March in Chestertown is the annual Chestertown Tea Party Festival, which commemorates the town’s role in the American Revolution. Visitors can enjoy a lively parade, reenactments, and a colonial market featuring local artisans and craftspeople. Be sure to try the famous “tea cakes” at the festival, a sweet treat that has been a tradition since 1774. In addition to the Tea Party Festival, visitors can also take advantage of the beautiful spring weather by exploring the charming streets of Chestertown on foot. The town is home to many historic buildings, including the Old Custom House, which now serves as a visitor center. Strolling along the Chester River, visitors can enjoy the picturesque views and stop at one of the many local restaurants for a delicious seafood lunch. March is also a great time to visit nearby historic sites, such as the Washington College campus and the 18th-century plantation home, Washington’s Birthplace. With its rich history, quaint charm, and welcoming community, Chestertown is the perfect destination for a March getaway.
April
As you plan your trip to charming Chestertown in April, it’s important to keep in mind the unpredictable weather of the season. Layers are your best friend when it comes to dressing for this time of year. A light jacket or raincoat, along with a scarf and comfortable walking shoes, will ensure you’re prepared for any situation. As the town is known for its picturesque streets and historic buildings, I recommend bringing a camera to capture the beauty of your surroundings. In terms of attire, Chestertown is a quaint and casual town, so there’s no need to pack anything too fancy. However, if you plan on attending any events or dining at upscale restaurants, it’s always a good idea to have a dressier outfit on hand. As for accessories, don’t forget a hat or sunglasses for those sunny days and a small umbrella for potential showers. And of course, don’t forget to bring a positive attitude and an open mind to fully immerse yourself in the welcoming atmosphere of Chestertown.
Chestertown, a charming town on the eastern shore of Maryland, is a hidden gem that truly shines in the month of April. As the weather warms up and the flowers begin to bloom, this quaint town comes to life with a variety of activities and events. One must-see attraction is the Chestertown Tea Party Festival, held each year in celebration of the town’s rebellious past. Visitors can enjoy live music, tasty treats, and even a reenactment of the infamous tea-dumping protest that took place in 1774. For a more relaxed experience, take a stroll through the historic district and admire the beautiful 18th-century architecture. Stop by the local farmer’s market to sample fresh produce and homemade goodies, or rent a kayak and explore the Chester River. And of course, no trip to Chestertown is complete without a visit to Washington College, the oldest college in Maryland. Take a campus tour and learn about the school’s notable alumni, including George Washington himself. With its charming atmosphere and abundance of activities, Chestertown in April is a must-see destination for any traveler.
May
In May, Chestertown welcomes travelers with warm temperatures and plenty of outdoor activities. It’s important to dress comfortably and prepare for varying weather conditions. I recommend packing light layers, such as a light jacket or cardigan, as the mornings can be cool but the afternoons can warm up quickly. Breathable fabrics like cotton or linen are ideal for the warmer days, and closed-toe shoes are a must for exploring the charming cobblestone streets. Don’t forget to pack a hat, sunglasses, and sunscreen as the sun can be quite strong during the day. And for those planning to spend time on the water, a swimsuit and cover-up are essential for enjoying the nearby beaches and water activities. As always, I recommend bringing a small daypack for your essentials, including a water bottle, camera, and a light rain jacket just in case. With the right clothing and gear, you’ll be able to fully enjoy all that Chestertown has to offer in May.
As you stroll through the charming streets of Chestertown in May, you’ll be greeted with a vibrant burst of colors and a lively atmosphere. This small town in Maryland truly comes alive during the spring season, making it the perfect time to visit. One of the must-do activities in May is to attend the Chestertown Tea Party Festival, a celebration of the town’s colonial history. From reenactments of the famous Boston Tea Party to a street fair filled with local vendors and food, this festival offers a fun and educational experience for all ages. For a more peaceful and scenic experience, take a leisurely bike ride along the Chester River. The town has a designated bike route that takes you through picturesque farmlands and quaint villages, providing a unique perspective of the area. Along the way, you can also stop at local farm stands and pick up some fresh produce for a picnic by the river. As you pedal through the lush green landscape, you’ll understand why Chestertown is known as the “Pearl of the Chesapeake.” So grab a bike and explore this charming town in all its springtime glory.
June
When visiting Chestertown in June, it’s important to dress for both comfort and style. The weather can be quite warm and humid, so lightweight and breathable clothing is a must. Consider packing a few pairs of shorts, t-shirts, and sundresses. It’s also a good idea to bring a light jacket or sweater for cooler evenings. As Chestertown is a charming, historic town, it’s always nice to dress a bit more upscale for dinner or exploring the local shops. A nice blouse or collared shirt with khaki pants or a sundress is appropriate for these occasions. When packing for your trip to Chestertown, don’t forget to bring comfortable walking shoes. The town is best explored on foot and you’ll want to be able to stroll through the quaint streets and along the waterfront without any discomfort. Also, be sure to bring a hat, sunglasses, and sunscreen to protect yourself from the strong sun. Lastly, don’t forget to pack a reusable water bottle and a small backpack for day trips. Chestertown is surrounded by beautiful nature and you’ll want to be prepared for hikes, picnics, and other outdoor activities. With these essentials, you’ll be ready to fully enjoy your June visit to this charming town.
Welcome to Chestertown, a charming town nestled along the banks of the Chester River in Maryland. June is a wonderful time to visit this historic town, as the weather is pleasant and there are plenty of exciting activities to partake in. Start your day with a stroll through the quaint streets lined with beautifully preserved colonial-era homes. Stop by the local farmer’s market to pick up some fresh produce and mingle with the friendly locals. Then head to the waterfront and hop on a river cruise to admire the stunning scenery and learn about the town’s rich maritime history. Next, make your way to the historic Chestertown Tea Party Festival, held every June to commemorate the town’s rebellious past. Join in on the festivities with live music, delicious food, and of course, plenty of tea. Take a break from the crowds and explore the charming shops and art galleries that line High Street. For a dose of culture, visit the Washington College campus and its renowned art gallery. End your day with a leisurely bike ride along the Chester River or a relaxing picnic in one of the town’s picturesque parks. With its small-town charm and lively atmosphere, Chestertown is the perfect destination for a June getaway.
July
When visiting the charming town of Chestertown in July, it’s important to dress for the warm and humid weather. The average temperature during this month is around 85 degrees Fahrenheit, so lightweight and breathable clothing is essential. I recommend packing lightweight tops and bottoms made of natural fabrics like cotton or linen, as they will keep you cool and comfortable while exploring the town. Don’t forget to bring a hat, sunglasses, and sunscreen to protect yourself from the strong summer sun. It’s also a good idea to pack a light jacket or cardigan for the evenings, as temperatures can drop a bit. As for footwear, opt for comfortable walking shoes as Chestertown is a pedestrian-friendly town with many cobblestone streets. And don’t forget to bring a reusable water bottle, as staying hydrated is key in the summer heat. With these tips in mind, you’ll be dressed and prepared to fully enjoy the charming and historic town of Chestertown in July.
July in Chestertown is a time for outdoor adventures and lively festivals. Start your day by strolling through the charming downtown area, admiring the historic buildings and quaint shops. Make sure to stop by the Saturday morning farmers market, where you can sample local produce and handcrafted goods. For a taste of Chestertown’s history, take a tour of the 18th century Schooner Sultana, a replica of a British schooner that played a role in the American Revolutionary War. If you’re feeling adventurous, rent a kayak or paddleboard and explore the Chester River. In the evening, head to Wilmer Park for the Chestertown Jazz Festival, where you can relax with a picnic and enjoy live music under the stars. July is the perfect time to visit Chestertown and experience the best of what this charming town has to offer.
August
When packing for your summer trip to Chestertown, it’s important to keep a few things in mind. The weather in August can be quite hot and humid, so it’s best to dress in lightweight and breathable clothing. Opt for loose-fitting tops and bottoms made of natural fabrics like cotton or linen. And don’t forget a hat and sunglasses to protect yourself from the sun’s rays. While Chestertown may be a quaint and charming town, it’s also a college town, so you’ll want to dress comfortably but still presentable. For women, a sundress or flowy skirt paired with sandals is perfect for exploring the town’s historic streets. Men can opt for a collared shirt and shorts or lightweight pants. And no matter the gender, be sure to bring comfortable walking shoes as Chestertown is best explored on foot. Don’t forget to pack a swimsuit as well, as there are plenty of opportunities to cool off in the nearby rivers and beaches. And lastly, don’t forget to bring a reusable water bottle to stay hydrated while enjoying all that Chestertown has to offer.
As a traveler, I have had the pleasure of exploring the charming town of Chestertown in the month of August. One of the must-do activities during this time is attending the annual Chestertown Tea Party Festival. This event commemorates a colonial protest against British taxation and features a reenactment of the historic event, as well as live music, food vendors, and a parade. It’s a fun and educational way to experience the town’s history and culture. Another highlight of visiting Chestertown in August is taking a leisurely stroll along the Chestertown River Walk. This scenic path follows the banks of the Chester River and offers stunning views of the water and surrounding nature. Along the way, you’ll find quaint shops, restaurants, and art galleries to peruse. And if you’re lucky, you may even catch a glimpse of the local wildlife, including bald eagles and ospreys. It’s the perfect way to spend a summer afternoon and get a taste of small-town life in Maryland.
September
September is a lovely time to visit the charming town of Chestertown. The summer crowds have dispersed, the temperatures are mild, and the autumn foliage is just starting to emerge. When packing for your trip, be sure to bring layers to accommodate the changing temperatures. A light jacket or sweater is essential for the cooler evenings, while a t-shirt or dress will keep you comfortable during the warmer afternoons. As for footwear, a pair of comfortable walking shoes is a must, as you’ll want to explore the town’s historic streets and scenic waterfront. When in Chestertown, it’s always a good idea to dress in layers and wear items that can easily be mixed and matched. This will not only keep you comfortable, but will also allow for more versatility in your wardrobe. In addition to your clothing, be sure to bring a hat and sunglasses for protection from the sun. And don’t forget to pack a reusable water bottle, as staying hydrated is key when spending time outdoors. Lastly, be sure to leave room in your suitcase for any souvenirs you may want to bring home, as Chestertown is known for its charming shops and local artisanal goods.
September is a fantastic time to visit the charming town of Chestertown, nestled on the banks of the Chester River in Maryland. As summer fades away and the crisp autumn air starts to creep in, the town comes alive with a variety of exciting events and activities. One of the highlights of September is the annual Chestertown Jazz Festival, where talented musicians from all over the country gather to showcase their skills. Whether you’re a jazz aficionado or simply appreciate good music, this festival is not to be missed! Aside from the jazz festival, September also brings the popular Chestertown RiverFest, a celebration of the town’s maritime heritage. Visitors can take part in boat races, enjoy live music and delicious seafood, and even take a ride on a traditional skipjack. The town’s historic streets and charming shops are also perfect for an afternoon stroll, and don’t forget to stop by the farmers’ market to sample some local produce. With its picturesque setting and lively atmosphere, September in Chestertown is a traveler’s dream come true.
October
As you plan your trip to charming Chestertown in October, it’s important to consider the weather and pack accordingly. While the days may still be pleasantly warm, the nights can get quite chilly, so it’s best to dress in layers. A light jacket or sweater paired with a scarf and comfortable walking shoes will keep you comfortable as you explore the quaint streets and historic buildings. Don’t forget to bring a rain jacket or umbrella, as October can bring some occasional showers. When it comes to attire, Chestertown is a laid-back town, so there’s no need to dress up. You’ll fit right in with casual, comfortable clothing. However, if you plan on visiting any of the local restaurants or attending a performance at the Garfield Center for the Arts, you may want to bring a nice outfit. And of course, don’t forget to pack a camera to capture the beautiful fall foliage and picturesque views of the Chesapeake Bay. With the right clothing and gear, you’ll be all set to fully enjoy the charm and beauty of Chestertown in October.
As the leaves begin to change and the crispness of autumn fills the air, Chestertown becomes a charming destination for travelers in October. Walking through the quaint streets lined with historic homes and shops, visitors can take in the beauty of the season and immerse themselves in the small town charm. One must-do activity in October is to visit the annual Chestertown Fall Festival. This lively event features local vendors selling crafts, delicious food, and live music. It’s the perfect opportunity to sample some of the region’s specialties and support small businesses. Plus, with the vibrant colors of fall as the backdrop, it’s a picturesque experience. For those looking to get a taste of Chestertown’s history, a visit to the Washington College is a must. Founded in 1782, this liberal arts college has a rich history and stunning campus. October is the perfect time to visit as the campus is adorned with colorful foliage and the weather is mild. Take a stroll through the campus and admire the historic buildings, or attend one of the many events and lectures that take place during the month. Don’t forget to stop by the Rose O’Neill Literary House, where you can attend readings and workshops with renowned authors. It’s a great way to learn about Chestertown’s past while also indulging in the beauty of the present.
November
As you plan your visit to charming Chestertown in November, it’s important to keep in mind the seasonal weather. As the temperatures start to cool down, it’s essential to dress in layers. A light jacket or sweater paired with a scarf and hat will keep you cozy during the day, while a heavier coat will be necessary in the evenings. Don’t forget to pack comfortable walking shoes, as you’ll want to explore the quaint streets of Chestertown on foot. When it comes to what to wear in Chestertown, a classic and casual style is best. Think comfortable jeans, a button-down shirt, and a pair of boots. This will allow you to blend in with the locals and be prepared for any weather changes. Additionally, be sure to bring a small umbrella or rain jacket, as November can bring some rainy days. As for what to bring, don’t forget your camera to capture the stunning fall foliage and historic architecture. And of course, a sense of adventure and an open mind to fully immerse yourself in the charming culture of Chestertown.
Chestertown, located on the serene Eastern Shore of Maryland, is a charming small town with plenty to offer travelers in the month of November. The crisp autumn air and colorful foliage make for the perfect backdrop to explore this historic town. Start your day with a stroll through the charming streets, admiring the well-preserved 18th and 19th century homes. Don’t miss the opportunity to visit the famous Schooner Sultana, a replica of an 18th century ship that played a significant role in American history. Take a tour of the ship and learn about its fascinating past, or even set sail on a sunset cruise along the Chester River. After working up an appetite, head to the Farmer’s Market in Fountain Park, where you can sample fresh local produce, homemade goodies, and chat with friendly locals. For a taste of Chestertown’s rich cultural heritage, make sure to visit the Garfield Center for the Arts, where you can catch a play, concert, or art exhibit. And don’t forget to stop by the renowned Washington College, the tenth oldest college in the United States, and take in the beautiful campus. Whether you’re interested in history, nature, or simply enjoying the charm of a small town, Chestertown has something for everyone in the lovely month of November.
December
As the holiday season approaches, Chestertown transforms into a winter wonderland with charming lights, festive decorations, and a cozy feeling in the air. However, with the colder temperatures, it is important to dress appropriately for your visit. Layering is key in December, as the weather can be unpredictable. I recommend bringing a warm coat, gloves, and a hat to keep you comfortable while exploring the town. Scarves are also a stylish and practical addition to your outfit. Don’t forget to wear comfortable walking shoes, as Chestertown’s cobblestone streets can be slippery in the winter. When packing for your trip to Chestertown in December, be sure to include some festive attire. The town hosts many holiday events, such as the annual Christmas parade and tree lighting ceremony, so bringing a holiday sweater or scarf is a great way to get into the holiday spirit. Additionally, Chestertown’s quaint shops and boutiques are perfect for finding unique gifts and souvenirs, so leave room in your suitcase for any special finds. And don’t forget to bring a camera to capture the beauty of Chestertown during the holiday season. Happy travels!
December is a magical time to visit the charming town of Chestertown. As the leaves fall and the air becomes crisp, this quaint town transforms into a winter wonderland. One of the must-do activities during this time of year is to take a stroll through the historic downtown area. The streets are adorned with festive decorations and the shops are filled with unique holiday gifts. I highly recommend stopping by the local bakery for a warm cup of hot cocoa and a freshly baked gingerbread cookie. It’s the perfect way to soak in the holiday spirit. For those seeking a bit of culture, be sure to catch a performance at the Garfield Center for the Arts. This intimate theater hosts a variety of shows during the month of December, from holiday concerts to classic plays. It’s a great way to support the local community and get into the holiday spirit. And don’t miss the annual Chestertown Christmas parade, where you can watch festive floats and hear carolers singing traditional holiday tunes. With so much to see and do in Chestertown during December, it’s no wonder it’s a favorite destination for holiday travelers.
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.
