Select the month that you will be traveling from the table below to view the packing list:
What Smith Island is like to visit throughout the year:
January
When visiting the charming island of Smith Island in January, it’s important to dress warmly and come prepared for chilly weather. The island is known for its strong winds and frigid temperatures during this time of year, so layering is key. I recommend bringing a warm winter coat, a hat, gloves, and a scarf to keep you cozy while exploring the island. Don’t forget to pack a sturdy pair of boots, as the island can get quite muddy and slippery. It’s also a good idea to bring an umbrella or rain jacket, as January is known for its frequent rain showers. While the weather may be cold, the locals’ hospitality is always warm. When it comes to dressing for activities and attractions, I suggest opting for comfortable and practical clothing. A pair of jeans and a warm sweater are perfect for exploring the charming streets and shops of Smith Island. For those interested in taking a boat ride to explore the surrounding waters, be sure to bring a windbreaker and waterproof shoes. And of course, don’t forget your camera to capture the stunning winter landscape and charming island life. With the right clothing and gear, you’ll be able to fully enjoy the unique experience of visiting Smith Island in January.
As you step off the ferry onto the charming island of Smith Island in January, you’ll immediately be transported back in time. This small island located off the coast of Maryland is known for its rich history and traditional way of life. While it may be chilly outside, there are still plenty of activities to enjoy during your visit. Take a stroll through the quaint streets and admire the colorful homes and local shops, or visit the Smith Island Cultural Center to learn about the island’s fascinating past. For a taste of authentic Smith Island cuisine, be sure to try the famous Smith Island cake. This multi-layered dessert is made with thin, buttery cake layers and decadent chocolate icing. January is the perfect time to sample this sweet treat as it is traditionally enjoyed during the holiday season. You can also take a cooking class and learn how to make this iconic cake yourself. And for nature lovers, don’t miss the opportunity to go birdwatching and spot some of the island’s unique and diverse bird species. With its quiet charm and abundance of activities, Smith Island is the perfect winter getaway.
February
When visiting the charming island of Smith Island in February, it’s important to dress warmly and be prepared for chilly weather. The island is known for its strong winds and low temperatures during this time of year, so be sure to pack plenty of layers and a warm jacket. A waterproof coat and sturdy boots are also essential, as the island can get quite muddy after rain. Remember to bring a hat and gloves as well to keep your head and hands protected from the cold. While the weather may be chilly, the island’s hospitality is always warm. When exploring the quaint towns and meeting the friendly locals, it’s important to dress respectfully and modestly. Avoid flashy or revealing clothing and opt for comfortable, casual attire. A good pair of walking shoes is a must to navigate the island’s uneven pathways and to join in on the traditional crabbing excursions. And don’t forget to bring a camera to capture the picturesque views of the island’s colorful homes and stunning waterways. With these tips in mind, you’ll be prepared for a cozy and enjoyable visit to Smith Island in February.
February is a magical time to visit Smith Island, the quaint and charming getaway off the coast of Maryland. Despite the chilly weather, there is still plenty to see and do on this small island. One of the must-do activities is to take a walk along the island’s famous crabbing docks. Here, you can watch local watermen as they brave the cold waters to bring in the freshest and most delicious blue crabs. Be sure to sample some of the island’s famous crab cakes while you’re there – they are truly a taste of heaven! Another must-see in February is the annual Smith Island Cake Festival. This mouthwatering event celebrates the island’s signature dessert – the multi-layered, decadent Smith Island Cake. Visitors can sample different flavors, learn how to make their own, and even participate in a cake decorating contest. It’s a fun and delicious way to immerse yourself in the island’s culture and community. And don’t forget to take a stroll around the island’s charming streets, lined with colorful Victorian homes and friendly locals. February may be the off-season, but Smith Island’s charm and warmth are still in full bloom.
March
When planning a trip to Smith Island in March, it’s important to dress appropriately for the cool and sometimes unpredictable weather. I recommend packing layers, as temperatures can range from the high 40s to the low 60s. A waterproof jacket is a must, as there is a chance of rain during this time of year. Don’t forget to bring a comfortable pair of walking shoes, as the island is best explored on foot. As for attire, the island has a laid-back and casual atmosphere, so there’s no need to pack fancy clothes. Opt for comfortable and practical clothing such as jeans, long-sleeved shirts, and a light sweater. Scarves and hats also come in handy for those chilly days. And of course, don’t forget to bring a camera to capture the charming and picturesque scenery of Smith Island. With the right clothing and gear, you’ll be well-prepared to enjoy all that this quaint island has to offer in March.
Located in the heart of the Chesapeake Bay, Smith Island is a hidden gem that offers a unique cultural experience for travelers. While most tourists flock to this charming island during the summer months, March is actually a great time to visit. The island is less crowded, the weather is mild, and there are plenty of things to do. One of the highlights of a March visit is the annual Smith Island Cake Festival, where visitors can sample the famous local dessert and learn about the island’s rich history. Another must-do activity is taking a boat tour to explore the surrounding marshes and observe the diverse wildlife, including migratory birds and playful dolphins. For those looking for a more active experience, March is the perfect time to go crabbing on Smith Island. Join the locals in their traditional way of catching crabs and learn about the island’s thriving seafood industry. After a day of crabbing, head to one of the island’s quaint restaurants to feast on fresh, delicious crab cakes. And for a cultural immersion, don’t miss the opportunity to visit the island’s famous crab shanties, where you can watch the watermen at work and even try your hand at crab picking. March may not be the traditional tourist season, but for those looking for an authentic Smith Island experience, it’s the ideal time to visit.
April
When visiting Smith Island in April, the weather can be quite unpredictable. The island experiences mild temperatures, but it can also be prone to sudden rain showers. As a traveler, it’s important to dress in layers and be prepared for any weather changes. I recommend bringing a light jacket or raincoat, as well as a hat and sunglasses for those sunny days. Comfortable walking shoes are a must, as the island is best explored by foot. As for clothing, opt for breathable fabrics such as cotton or linen to keep cool during the day, and bring a sweater or scarf for chilly evenings. Don’t forget to pack a small backpack or tote bag to carry your essentials as you explore Smith Island. Sunscreen and bug spray are a must during this time of year, as well as a refillable water bottle to stay hydrated. As a respectful visitor, it’s also important to dress modestly when visiting the island’s small community. Avoid wearing revealing clothing or anything too flashy, and instead opt for comfortable, casual attire. Lastly, don’t forget to bring a camera to capture the stunning views and unique culture of this charming island. With the right clothing and essentials, you’ll be fully prepared to enjoy all that Smith Island has to offer in the month of April.
Welcome to Smith Island, a charming and secluded island off the coast of Maryland. While this island may be small, it is full of unique experiences and friendly locals. If you’re planning a visit in April, you’re in luck as there are plenty of exciting things to do during this time of year. One of the highlights of visiting Smith Island in April is witnessing the annual arrival of migratory birds. The island is a popular stop for many species of birds, making it a paradise for birdwatchers. Take a stroll along the shoreline or rent a kayak to explore the marshes and spot a variety of birds such as herons, egrets, and ospreys. For a truly special experience, join a guided tour with a local expert who can teach you about the different species and their behaviors. Don’t forget to bring your binoculars and camera to capture these beautiful creatures in their natural habitat.
May
When visiting Smith Island in May, it’s important to dress for the changeable weather that comes with springtime on the Chesapeake Bay. Layers are key, as the temperatures can range from cool and breezy to warm and sunny throughout the day. A light jacket or sweater, along with comfortable walking shoes, will serve you well as you explore the island’s charming streets and waterfront. Don’t forget to bring a rain jacket or umbrella, as May can bring occasional showers to the island. As for what to wear, locals on Smith Island tend to be practical and casual in their attire. Comfortable, breathable fabrics like cotton and linen are ideal for the warmer days, while a pair of jeans or khakis will keep you warm on cooler evenings. And of course, no trip to Smith Island is complete without a pair of sturdy, waterproof boots for those muddy marsh walks. As for what to bring, don’t forget sunscreen and a hat for protection from the sun, as well as a reusable water bottle to stay hydrated while exploring the island. And don’t worry about dressing to impress on Smith Island – the true beauty of this place lies in its simplicity and natural charm.
When visiting Smith Island in May, there are a few must-do activities that can’t be missed. One of the top attractions is taking a boat tour around the island. This allows visitors to get a true sense of the island’s unique culture and way of life. As you cruise along the waters, you’ll see the iconic crab shacks and picturesque marshlands. It’s also a great opportunity to spot some of the local wildlife, such as herons and ospreys. For those interested in history, a visit to the Smith Island Cultural Center is a must. This small but informative museum showcases the island’s history, from its Native American roots to its current fishing industry. Visitors can also learn about the island’s famous Smith Island Cake, a delicious dessert that has become a symbol of the island’s community and resilience. And of course, no trip to Smith Island is complete without indulging in a slice of this scrumptious cake. So come visit in May, when the island is in full bloom and ready to charm you with its quaint beauty and rich history.
June
When visiting Smith Island in June, it’s important to dress comfortably and practically for the island’s warm and humid climate. I recommend wearing light and breathable fabrics, such as cotton or linen, to stay cool and comfortable. A lightweight rain jacket or umbrella may also come in handy, as the island is known for its sudden rain showers. Don’t forget to bring along a comfortable pair of walking shoes, as you’ll likely be exploring the island on foot. In terms of attire, Smith Island is a laid-back and casual destination. You’ll fit right in with a simple t-shirt and shorts, or a sundress for the ladies. However, if you plan on visiting any of the island’s churches or restaurants, it’s best to dress slightly more conservatively. Men should consider packing a collared shirt and pants, while women can opt for a modest dress or skirt. Additionally, don’t forget to bring a swimsuit for the island’s beautiful beaches and a hat or sunglasses to protect yourself from the sun. And of course, don’t leave without packing a camera to capture the island’s picturesque views and charming culture.
When visiting Smith Island in June, travelers are in for a real treat. This charming island, located in the Chesapeake Bay, is known for its rich history and delicious seafood. During this time of year, the weather is warm and sunny, making it the perfect time to explore all that Smith Island has to offer. One of the top things to do is take a bike ride around the island, where you’ll be greeted by stunning views of the bay and quaint, colorful homes. Don’t forget to stop at one of the local crab shacks for a taste of the island’s famous crab cakes. For those interested in history, a visit to Smith Island’s Ewell Museum is a must. Here, you can learn about the island’s past, including its role in the War of 1812 and the oyster industry. The museum also offers guided walking tours of the island, where you can see historic sites such as the Smith Island Schoolhouse and the St. Ann’s Catholic Church. And of course, no trip to Smith Island is complete without indulging in some of the freshest seafood you’ll ever taste. From crab to oysters to rockfish, there’s no shortage of delicious options to satisfy your taste buds. So pack your bags and head to Smith Island this June for a memorable and authentic island experience.
July
When visiting Smith Island in July, it’s important to pack light and dress for warm weather. This small island off the coast of Maryland is known for its hot and humid summers, so be sure to bring plenty of lightweight, breathable clothing. A sun hat or visor is also a must to protect yourself from the strong rays of the sun as you explore the island’s charming villages. In terms of what to wear, opt for comfortable clothing like shorts, sundresses, and lightweight tops. A light rain jacket or umbrella may also come in handy as afternoon showers are common during this time of year. Don’t forget to bring comfortable walking shoes as well, as the best way to explore Smith Island is on foot. And of course, no trip to Smith Island would be complete without a swimsuit, as the island is surrounded by beautiful beaches and crystal-clear water perfect for swimming and water activities. With these essentials in your suitcase, you’ll be ready to fully enjoy all that Smith Island has to offer in the summertime.
When visiting Smith Island in July, be sure to take advantage of the island’s prime location for water activities. The warm summer weather makes it the perfect time for swimming, kayaking, and boating in the Chesapeake Bay. You can also join a local fishing tour and try your hand at catching some of the bay’s famous blue crabs. And don’t forget to take a leisurely stroll along the island’s sandy beaches, where you can collect seashells and take in stunning views of the water. In addition to its water activities, Smith Island is also known for its delicious seafood. July is the peak season for fresh seafood on the island, so be sure to indulge in some of the local specialties like crab cakes, oysters, and rockfish. For a true taste of Smith Island, visit one of the island’s famous seafood restaurants and chat with the friendly locals while enjoying a traditional meal. And for those interested in learning more about the island’s culture and history, be sure to stop by the Smith Island Cultural Center, where you can explore exhibits and artifacts showcasing the island’s unique heritage.
August
When visiting Smith Island in the month of August, it’s important to dress for the warm and humid weather. Lightweight, breathable clothing such as cotton or linen is recommended. This will not only keep you cool, but also protect you from the island’s notorious mosquitoes. A wide-brimmed hat and sunglasses are also essential for shielding yourself from the sun’s rays. As for footwear, comfortable walking shoes or sandals are a must for exploring the island’s charming streets and paths. Don’t forget to pack a swimsuit, as the island’s beaches and waterways offer the perfect escape from the summer heat. And be sure to bring a light jacket or sweater for the evenings, as temperatures can drop slightly. In terms of accessories, a small backpack or crossbody bag will come in handy for carrying your essentials while leaving your hands free to sample the island’s famous crab cakes. Remember to also bring sunscreen, bug spray, and a refillable water bottle to stay hydrated during your adventures on Smith Island.
August is a fantastic time to visit Smith Island, a remote and charming community nestled in the Chesapeake Bay. While this island may be small in size, it is big on character and offers plenty of activities for travelers to enjoy. One of the must-do experiences on Smith Island is taking a boat tour around the surrounding waters. Not only will you get a stunning view of the island’s picturesque landscape, but you’ll also have the chance to see local wildlife like ospreys and blue crabs. Plus, you can’t leave Smith Island without trying their famous layered cake, a mouthwatering dessert made with ten thin layers of buttery cake and fudge frosting. Another top activity in August on Smith Island is attending the annual Crab Festival. This lively event celebrates the island’s seafood culture and features an abundance of fresh crabs, live music, and fun games for all ages. It’s a great opportunity to mingle with the friendly locals and get a taste of their traditional cuisine. And for those looking for a more active adventure, the island offers excellent kayaking and biking opportunities. With its tranquil atmosphere and beautiful scenery, Smith Island is the perfect destination for a relaxing summer getaway.
September
When visiting Smith Island in September, it’s important to dress in layers to prepare for the fluctuating temperatures. The island experiences mild to cool weather during this time, with average highs in the low 70s and lows in the 50s. I recommend bringing a light jacket or sweater for the cooler evenings and mornings, but also packing t-shirts and shorts for the warmer afternoons. It’s always a good idea to bring a rain jacket or umbrella as well, as the island does experience some precipitation during this time. In terms of footwear, I suggest comfortable walking shoes or sneakers as the island is best explored on foot. The terrain can be uneven and rugged, so sturdy shoes will provide the best support. Don’t forget to bring a swimsuit and sandals if you plan on taking a dip in the bay or lounging on the beach. And of course, don’t forget to pack sunscreen and a hat to protect yourself from the sun’s rays. As for accessories, a pair of polarized sunglasses will come in handy for those sunny days out on the water. And lastly, don’t forget to pack a small day bag to carry your essentials while exploring the charming streets of Smith Island.
When visiting Smith Island in September, one can expect to experience the charming island life at its finest. As the summer crowds dissipate, the island takes on a peaceful and more authentic feel. One of the must-do activities during this time is to take a bike ride around the island, stopping at local seafood shacks for a taste of the island’s famous crab cakes and fresh oysters. The cool breeze and stunning views of the Chesapeake Bay make for a perfect day of exploration and indulgence. September also brings the annual Smith Island Crab Festival, a celebration of the island’s most beloved delicacy. The festival features live music, local crafts, and of course, an abundance of delicious crab dishes. This is a great opportunity to mingle with the friendly locals and learn more about the island’s rich history and culture. Don’t forget to try the famous Smith Island Cake, a decadent 10-layer dessert that represents the island’s close-knit community. Visiting Smith Island in September is truly a delight for the senses and a chance to immerse oneself in the island’s laid-back lifestyle.
October
As you make your way to charming Smith Island in October, be sure to pack layers for the ever-changing weather. The island is known for its chilly mornings and warm afternoons, so bring a light jacket or sweater to throw on in the morning and take off in the afternoon. Comfortable walking shoes are a must for exploring the island’s quaint streets and picturesque waterfront. When it comes to dressing for meals, leave the fancy attire at home and opt for casual, comfortable clothing. The island’s famous crab cakes and fresh seafood are best enjoyed while wearing a relaxed outfit. And don’t forget to bring a rain jacket or umbrella, as the island can experience some light rain in the fall. As for accessories, a pair of sunglasses and a sunhat will come in handy for those sunny afternoons spent strolling along the island’s beaches. With the right clothing and gear, you’ll be ready to fully experience the beauty and charm of Smith Island in October.
When visiting Smith Island in October, be sure to take advantage of the island’s annual Oyster Festival. This traditional event celebrates the island’s history and culture of oyster harvesting. Visitors can sample fresh oysters, watch demonstrations of shucking and learn about the island’s oyster industry. It’s a great opportunity to support the local community and indulge in some delicious seafood. For those seeking a bit of adventure, October is the perfect time to explore the marshes and wetlands of Smith Island. Rent a kayak or join a guided tour to discover the diverse wildlife and stunning scenery of this unique environment. Keep an eye out for migratory birds and maybe even catch a glimpse of the famous Smith Island ponies. With the crisp autumn air and colorful foliage, October is the ideal time to experience the natural beauty of Smith Island.
November
When visiting Smith Island in November, it’s important to dress for the cool and windy weather. Be sure to pack layers, including a warm jacket, scarf, and gloves. The island is often windy, so a hat or beanie is also a good idea. Comfortable walking shoes are a must, as the island is mostly unpaved and you’ll want to explore all the nooks and crannies. Don’t forget to bring rain gear, as November can bring unpredictable showers. While the weather may be chilly, the hospitality on Smith Island is always warm. It’s a casual and laid-back place, so don’t worry about packing fancy clothes. Opt for comfortable and practical outfits, such as jeans and a sweater. And of course, don’t leave without trying the local delicacy, Smith Island Cake. Just be sure to bring some stretchy pants to accommodate all the delicious food you’ll be indulging in during your stay. Overall, the key is to dress for the weather and embrace the relaxed island vibe. Happy travels!
November is a magical time to visit Smith Island, a small community nestled in the Chesapeake Bay. As the leaves turn golden and the air becomes crisp, the island takes on a peaceful and serene atmosphere. One of the best things to do during this time is to take a leisurely bike ride around the island. With little traffic and stunning views of the water, you’ll feel like you’ve been transported back in time. Don’t forget to stop by the local bakery for a slice of their famous Smith Island cake – a decadent 10-layer dessert that is a must-try for any visitor. For those who are looking to immerse themselves in the culture of Smith Island, November offers the perfect opportunity. Join the locals for the annual Oyster Festival, where you can sample the freshest oysters straight from the bay and learn about the island’s rich history of oystering. After indulging in some delicious seafood, take a stroll through the charming streets of Ewell, the main village on the island. With its colorful houses and friendly locals, you’ll feel like you’re part of the community in no time. November truly is a special time to experience the beauty and charm of Smith Island.
December
Smith Island, located off the coast of Maryland, is a charming destination with a unique island culture. In December, the island is a bit chilly, but still a quaint and cozy place to visit. When packing for your trip, be sure to bring warm layers to bundle up in. A waterproof jacket or coat is essential for exploring the island, as well as a sturdy pair of shoes for walking on the uneven cobblestone streets. Don’t forget to pack a hat, gloves, and a scarf to keep yourself warm while strolling along the waterfront or taking a boat tour. As for attire, the island has a casual and laid-back atmosphere. Locals often opt for comfortable and practical clothing, such as jeans and a warm sweater. As a visitor, you can blend in by dressing similarly and embracing the island’s relaxed vibe. However, if you plan on dining at one of the island’s famous seafood restaurants, a slightly dressier outfit would be appropriate. And of course, don’t forget to bring a camera to capture the beautiful scenery and unique traditions of Smith Island. December is a magical time to visit, with festive holiday decorations adorning the island and cozy fires crackling in the local bed and breakfasts. So pack smart, dress for comfort and warmth, and get ready to experience the charm of Smith Island in the winter.
December is a magical time to visit Smith Island, a small island community located in the Chesapeake Bay. While the summer months may be bustling with tourists, December brings a sense of tranquility and a unique opportunity to experience the island’s charm in a different light. One must-do activity during this time is to take a stroll through the island’s quaint streets, adorned with twinkling lights and festive decorations. As you wander, be sure to stop by the local shops and bakeries, where you can find delicious treats like Smith Island Cake, a traditional dessert made with multiple layers of yellow cake and chocolate fudge. And don’t forget to pay a visit to the island’s oldest church, where you can join in on the community’s holiday services and immerse yourself in the island’s rich history and traditions. December truly is a special time to visit Smith Island and experience its warm hospitality and unique culture.
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.
