Select the month that you will be traveling from the table below to view the packing list:
What Shelter Island is like to visit throughout the year:
January
When visiting Shelter Island in January, it’s important to dress in layers to combat the chilly weather. Start with a warm base layer, such as thermal underwear or a long-sleeved shirt, and add a sweater or fleece on top. A waterproof jacket or coat is also a must, as the island can experience rain and snow during this time of year. Don’t forget to pack a hat, scarf, and gloves to keep your head, neck, and hands warm. In terms of footwear, be sure to bring a sturdy pair of boots with good traction. The island’s trails and beaches may be slippery and muddy, so it’s important to have shoes that can handle the terrain. And while the temperatures may be chilly, don’t forget to pack a swimsuit for a dip in the hot tub or a soak in a nearby hot spring. Finally, be sure to bring a backpack or day bag to carry all of your essentials, including a water bottle, snacks, and a map of the island. With the right clothing and gear, you’ll be able to fully enjoy all that Shelter Island has to offer in January.
Welcome to Shelter Island, a charming island off the coast of New York’s Long Island. While summer may be the peak season for this idyllic destination, there are still plenty of activities to enjoy during a January visit. Start your day with a stroll along Crescent Beach, taking in the crisp ocean air and admiring the stunning views of the surrounding islands. Then head to the Havens House Museum, where you can learn about the island’s rich history and explore the beautifully preserved colonial-era home. No trip to Shelter Island would be complete without a visit to Mashomack Preserve. This 2,039-acre nature preserve offers a peaceful escape from the hustle and bustle of city life. Bundle up and take a hike through the snowy trails, keeping an eye out for local wildlife such as deer and osprey. After working up an appetite, warm up with a hearty bowl of clam chowder at the cozy Shelter Island Craft Brewery. And don’t forget to end your day with a breathtaking sunset over Shelter Island Sound – a perfect way to end your winter getaway on this charming island.
February
When packing for a February visit to Shelter Island, it’s important to be prepared for the unpredictable weather of the offseason. Layering is key, as temperatures can range from chilly mornings to mild afternoons. A waterproof jacket is a must, as rain is common during this time of year. I also recommend bringing a warm hat, gloves, and a scarf to keep you cozy during your outdoor adventures. Don’t forget to pack comfortable walking shoes, as the island is full of picturesque hiking trails and scenic paths. While Shelter Island may not be known for its fashion scene, it’s important to dress appropriately for the local culture. Opt for casual and comfortable clothing, such as jeans, leggings, and sweaters. Locals are laid-back and friendly, so there’s no need to dress to impress. However, if you plan on dining at one of the island’s upscale restaurants, it’s always a good idea to bring a nice outfit for a special night out. As for accessories, a reusable water bottle and a day pack for hiking are essential to stay hydrated and carry any necessary supplies. With these tips, you’ll be ready to explore and enjoy all that Shelter Island has to offer in February.
February is a wonderful time to visit the charming island of Shelter Island. While the weather may be a bit chilly, the island is still bustling with activities and events to keep visitors entertained. One of the must-do activities in February is to take a hike on the many scenic trails that crisscross the island. From the breathtaking views of Mashomack Preserve to the peaceful serenity of Sylvester Manor, there is no shortage of natural beauty to be explored on Shelter Island. For those looking for a cultural experience, be sure to check out the Shelter Island Historical Society. This small but informative museum offers a glimpse into the island’s rich history, including its Native American roots and its role in the Revolutionary War. February is also the perfect time to sample some of the island’s famous oysters at the annual Oyster Festival. Held every year on President’s Day weekend, this event is a celebration of the island’s maritime heritage and features live music, local vendors, and of course, plenty of delicious oysters to try. Whether you’re a nature lover or a history buff, Shelter Island has something for everyone in February.
March
When packing for a trip to Shelter Island in March, it’s important to dress for the ever-changing weather. The island experiences a mix of cool, crisp mornings and warmer afternoons, so be sure to bring layers. A light jacket or sweater is a must, as well as a rain jacket in case of any unexpected showers. Comfortable walking shoes are also essential for exploring the island’s charming villages and scenic trails. In terms of clothing, I recommend packing versatile pieces that can easily be mixed and matched. A pair of jeans or khakis paired with a button-down shirt and a lightweight jacket is perfect for exploring the island during the day. For more formal occasions, a nice dress or collared shirt with slacks will suffice. Don’t forget to pack a swimsuit, as the island’s beautiful beaches may still be warm enough for a dip in March. And of course, don’t forget to bring a camera to capture the stunning coastal views and quaint towns of Shelter Island.
March is a fantastic time to visit Shelter Island, a hidden gem nestled in the heart of New York’s Long Island Sound. As the winter chill begins to fade and the island comes alive with the promise of spring, there are plenty of activities to enjoy in this charming destination. One must-see attraction in March is the Mashomack Preserve. This 2,039-acre nature reserve is home to a diverse array of wildlife and boasts stunning views of the surrounding waterways. Visitors can take a leisurely hike through the wooded trails, or opt for a guided tour to learn more about the history and conservation efforts of the preserve. Another must-do activity is exploring the island’s quaint villages, such as Shelter Island Heights and Dering Harbor, which offer charming shops, galleries, and restaurants. And for those looking for a taste of local culture, be sure to check out some of the island’s renowned seafood restaurants, where you can sample fresh catches from the surrounding waters. March may not be peak tourist season, but it’s the perfect time to experience Shelter Island’s natural beauty and small-town charm.
April
As you plan your trip to the picturesque Shelter Island in April, it’s important to keep in mind the island’s unique climate and culture when deciding what to wear. The weather in April can be quite unpredictable, with both sunny and rainy days, so it’s best to pack a mix of both warm and lightweight layers. A light rain jacket and comfortable walking shoes are a must, as you’ll want to explore the island’s charming villages and scenic trails. In terms of attire, Shelter Island is known for its relaxed and casual vibe. Think comfortable and practical clothing, such as jeans, shorts, and t-shirts. As the island is surrounded by water, it can get quite windy, so be sure to pack a scarf or hat to keep warm. Also, don’t forget to bring a swimsuit and cover-up, as the island’s beautiful beaches are perfect for a dip in the cool waters. And of course, no trip to Shelter Island is complete without a pair of sunglasses and sunscreen to protect you from the strong island sun. With these essentials, you’ll be ready for a comfortable and stylish stay on Shelter Island in April.
April is a delightful time to visit Shelter Island, a charming oasis nestled between the North and South Forks of Long Island. This picturesque island is known for its stunning beaches, quaint villages, and rich history. In April, the island comes to life with blooming flowers and pleasant temperatures, making it the perfect time to explore all it has to offer. One of the must-do activities in Shelter Island during April is to rent a bike and take a leisurely ride around the island. The roads are quiet and scenic, and you’ll pass by charming homes, historic landmarks, and breathtaking views of the water. Stop by the famous Sunset Beach to catch a beautiful sunset over the bay, or head to Mashomack Preserve for a peaceful hike through nature. April is also a great time to visit the local wineries and taste some of the region’s best wines. And don’t forget to indulge in some fresh seafood at one of the island’s many restaurants, where you can enjoy local favorites like lobster rolls and clam chowder. With its idyllic setting and abundance of activities, Shelter Island in April is a traveler’s paradise.
May
May is a beautiful time to visit Shelter Island, with the spring flowers in full bloom and the warm weather just starting to kick in. As a seasoned traveler, I highly recommend bringing lightweight, comfortable clothing that can easily be layered. The temperature can vary throughout the day, so it’s important to have options. A light jacket or sweater is great for cool evenings, while shorts and t-shirts are perfect for sunny afternoons. Don’t forget to pack a pair of sturdy walking shoes, as there are plenty of scenic trails and beaches to explore on the island. When it comes to dress, Shelter Island is a laid-back and casual destination. Leave your fancy attire at home and embrace the relaxed island vibe. A sundress or khaki pants paired with a collared shirt are perfect for a day of sightseeing or a casual dinner at one of the island’s charming restaurants. And of course, don’t forget to pack a swimsuit and hat for a day at the beach. Oh, and one more thing to bring – a camera! The picturesque views and quaint island charm are just begging to be captured. Happy travels!
Welcome to Shelter Island in the beautiful month of May! This charming island, located just off the coast of Long Island, is the perfect destination for a relaxing and scenic getaway. As the weather warms up and the flowers bloom, there are plenty of activities to enjoy during your stay. One of the highlights of May on Shelter Island is the annual Shelter Island House and Garden Tour. This self-guided tour takes you through some of the most stunning homes and gardens on the island, giving you a glimpse into the local architecture and design. After the tour, be sure to stop by the famous Sunset Beach for a refreshing cocktail and breathtaking views of the sunset over the water. And don’t forget to explore the island’s many nature trails, perfect for a leisurely walk or bike ride. With its small-town charm and beautiful surroundings, Shelter Island is the perfect place to unwind and soak up the beauty of May.
June
When packing for a trip to Shelter Island in June, it’s important to keep in mind the unpredictable weather patterns of this charming island. While the days can be warm and sunny, the evenings can bring a cool breeze off the water. To be prepared for any scenario, I recommend packing light layers such as a light jacket or sweater, along with comfortable walking shoes for exploring the island’s quaint streets. Don’t forget to bring a hat and sunglasses to protect yourself from the sun’s strong rays while lounging on the island’s beautiful beaches. As for attire, Shelter Island is known for its laid-back and relaxed atmosphere. You’ll fit right in with casual, comfortable clothing such as shorts, t-shirts, and sundresses. However, if you plan on dining at one of the island’s upscale restaurants, it’s always a good idea to bring a slightly dressier outfit. And of course, don’t forget your swimsuit for a refreshing dip in the ocean or one of the island’s many pools. With these wardrobe essentials and a sense of adventure, you’ll be ready to make the most of your June getaway to Shelter Island.
Shelter Island is a hidden gem in the heart of New York’s Long Island. With its quaint villages, stunning beaches, and rich history, it’s the perfect destination for a summer getaway. And if you’re planning a trip in June, you’re in for a treat. The island comes alive during this time of year with vibrant festivals, outdoor activities, and delicious seafood. One of the must-do activities in June is attending the annual Strawberry Festival. This charming event celebrates the island’s agricultural heritage and features live music, local crafts, and of course, plenty of strawberry-themed treats. For a more active experience, head to the island’s many beaches for some sunbathing, swimming, or kayaking. And for history buffs, a visit to the Havens House Museum is a must. This beautifully preserved 18th-century home offers a glimpse into the island’s past and showcases its unique architecture. No matter what your interests may be, Shelter Island has something for everyone in June.
July
When visiting Shelter Island in July, it’s important to pack for warm and sunny weather. The island offers a perfect mix of outdoor activities and relaxation, so it’s important to dress comfortably and with practicality in mind. Lightweight, breathable fabrics like cotton and linen are ideal for keeping cool in the summer heat. A hat and sunglasses are also essential to protect yourself from the strong island sun. As for footwear, a pair of sturdy sandals or sneakers will be your best bet for exploring the island. In addition to your summer essentials, don’t forget to pack a swimsuit and cover-up for enjoying the island’s beautiful beaches. The water temperature in July is perfect for swimming, and there are many secluded coves and bays to discover. For evenings out, a nice sundress or button-down shirt and khaki shorts will be appropriate for the island’s casual but upscale dining options. And don’t forget to bring a light jacket or sweater for cooler evenings by the water. With these items in your suitcase, you’ll be well prepared to fully enjoy all that Shelter Island has to offer in the summertime.
Shelter Island, located on the eastern end of Long Island, is a charming and picturesque destination for a summer getaway. July is the perfect time to visit this island oasis, with warm weather and endless activities to enjoy. One of the top things to do in Shelter Island in July is to take a stroll along Crescent Beach. This serene stretch of sand offers stunning views of the Atlantic Ocean and is the perfect spot for a peaceful afternoon of sunbathing or a romantic sunset walk. For those looking for a bit more adventure, a kayak tour around Shelter Island is a must-do in July. Paddle through the calm waters, taking in the beautiful scenery and spotting wildlife along the way. After working up an appetite, head to one of the island’s many seafood restaurants for a delicious meal of fresh oysters and lobster, caught locally by the island’s fishermen. And don’t forget to end your day with a spectacular fireworks display on the 4th of July, a beloved tradition on Shelter Island. With its tranquil beaches, outdoor activities, and delicious seafood, July is the perfect time to experience all that Shelter Island has to offer.
August
When visiting Shelter Island in August, it’s important to dress for the warm and sunny weather. The island is known for its beautiful beaches and outdoor activities, so be sure to pack comfortable and lightweight clothing. A t-shirt and shorts or a sundress are perfect for exploring the island. Don’t forget to bring a swimsuit and sandals for a dip in the ocean or a stroll along the shore. It’s also a good idea to bring a light jacket or sweater for the cooler evenings. And of course, don’t leave home without a hat, sunglasses, and sunscreen to protect yourself from the strong summer sun. In terms of what to wear, it’s important to dress modestly when visiting the small towns and villages on Shelter Island. While the island is known for its laid-back and relaxed vibe, it’s still a respectful gesture to cover your shoulders and knees when entering churches or other religious sites. Additionally, be prepared for some outdoor activities by bringing comfortable walking shoes or hiking boots. And for those looking to enjoy the island’s nightlife, a nice outfit for dinner and a light jacket for the cooler evenings will ensure you’re dressed appropriately for any occasion. Remember to also pack a small backpack or tote bag to carry your essentials, such as water, snacks, and a map of the island.
Shelter Island may be a small island off the coast of Long Island, but it packs a punch when it comes to things to do in August. My first recommendation is to take advantage of the beautiful beaches that surround the island. With the warm summer weather, these beaches provide the perfect spot to relax, swim, and soak up the sun. Head to Crescent Beach for a family-friendly atmosphere, or if you’re looking for a more secluded experience, check out Shell Beach. And for those seeking some adventure, there are plenty of water activities available such as kayaking, paddleboarding, and sailing. Another must-do in Shelter Island during August is to attend the annual Shakespeare in the Park event. Set against the stunning backdrop of the island’s nature preserve, this event brings together locals and tourists alike for a night of live theater under the stars. Pack a picnic, bring a blanket, and enjoy a performance of one of Shakespeare’s timeless plays. Not only is it a unique cultural experience, but it also supports the local arts community. And after the show, take a stroll through the preserve and admire the fireflies dancing in the moonlight. It’s a magical evening that truly captures the essence of Shelter Island.
September
When visiting Shelter Island in September, it’s important to pack for unpredictable weather. The island experiences mild temperatures during this time, but it’s not uncommon for a sudden rainstorm to roll in. To be prepared, I recommend bringing layers such as a light jacket or sweater that can easily be removed if the sun comes out. It’s also a good idea to pack a waterproof jacket or umbrella just in case. Comfortable walking shoes are a must for exploring the island’s charming streets and beaches. And don’t forget a hat and sunglasses for protection from the sun. As for attire, Shelter Island is a laid-back and casual destination. You’ll fit right in with a pair of jeans or shorts and a t-shirt or blouse. However, if you plan on visiting any upscale restaurants, it’s always a good idea to bring a slightly dressier outfit. And of course, don’t forget your swimsuit! September is still warm enough to enjoy the island’s beautiful beaches and refreshing waters. Overall, dressing comfortably and being prepared for any weather will ensure a pleasant and enjoyable trip to Shelter Island.
September is a wonderful time to visit Shelter Island, one of New York’s hidden gems. The summer crowds have dispersed, leaving behind a serene island ready to be explored. One of the highlights of visiting Shelter Island in September is taking a stroll through the island’s many nature trails. With the leaves just beginning to change, the scenery is simply stunning. Whether you’re an avid hiker or just looking for a leisurely walk, Shelter Island has trails for all levels and offers breathtaking views of the island’s beaches and lush forests. In addition to its natural beauty, Shelter Island also has a rich history waiting to be discovered. A must-see for history buffs is the Havens House, a restored 18th-century home that now serves as a museum. Here, visitors can learn about the island’s past and get a glimpse into what life was like for early settlers. Another must-visit is the Shelter Island Historical Society, which features exhibits on the island’s Native American heritage and its role in the Revolutionary War. September is the perfect time to explore these historical sites as the weather is mild and the island is less crowded, allowing for a more intimate and immersive experience.
October
When visiting Shelter Island in October, it’s important to dress in layers. The weather can be unpredictable, with chilly mornings and warm afternoons. I recommend packing a lightweight jacket or sweater to wear over a t-shirt during the day. A hat and sunglasses are also essential for protecting yourself from the sun while exploring the island’s beautiful outdoor areas. As for footwear, comfortable walking shoes or sneakers are a must for navigating the island’s quaint streets and trails. In addition to dressing for the weather, it’s also important to be mindful of the island’s laid-back and casual atmosphere. Leave your fancy clothes at home and opt for comfortable, casual outfits. A pair of jeans or khaki pants paired with a button-down shirt or blouse is appropriate for most activities on the island. Don’t forget to bring a bathing suit as well, as the weather in October can still be warm enough for a dip in the ocean. And of course, don’t forget to bring a camera to capture the stunning fall foliage and charming seaside views that make Shelter Island a must-visit destination.
October is a fantastic time to visit the charming oasis of Shelter Island. With the summer crowds gone and the crisp autumn air settling in, this small island off the coast of New York offers a peaceful and picturesque escape. One of the must-do activities during this time of year is to take a stroll along the island’s serene beaches. Whether you’re looking to bask in the warm sun or take a refreshing dip in the cool waters, the beaches of Shelter Island offer a tranquil setting for relaxation. And if you’re feeling adventurous, you can even rent a kayak or paddleboard and explore the island’s shoreline from a different perspective. Another highlight of October in Shelter Island is the abundance of fall festivals and events. From the annual Harvest Festival, featuring local food and crafts, to the popular Pumpkin Walk where hundreds of carved pumpkins light up the town, there’s something for everyone to enjoy. And for those looking to get a taste of the island’s history, October is the perfect time to visit the historic Sylvester Manor. This 17th-century estate offers guided tours and special events during the fall season, giving visitors a glimpse into the island’s past. No matter what your interests may be, Shelter Island in October is sure to delight and leave you with lasting memories.
November
When visiting Shelter Island in November, it’s important to dress in layers to prepare for the changing weather. The island experiences cool temperatures in the fall, with highs in the 50s and lows in the 40s. I recommend packing a waterproof jacket, as November can bring rain and wind. Don’t forget to bring a warm sweater or fleece to stay cozy during outdoor activities. Scarves, gloves, and hats are also essential for keeping warm during chilly walks on the beach. As for footwear, comfortable walking shoes are a must for exploring the island’s scenic trails and charming towns. A pair of waterproof boots would also come in handy for those planning to go kayaking or paddleboarding. And of course, don’t forget to bring a swimsuit for a dip in the island’s heated pools or hot tubs. Overall, packing versatile, weather-appropriate clothing and comfortable shoes will ensure a pleasant and enjoyable trip to Shelter Island in November.
Shelter Island, a small island located off the coast of Long Island, is a hidden gem perfect for a November getaway. While the summer months may bring crowds and sunbathers, November offers a quieter and more authentic experience on this charming island. One of the top things to do in November is to take a leisurely bike ride around the island. With fewer cars on the road, you can enjoy the stunning views of the harbor, quaint cottages, and lush greenery without the distractions of traffic. Stop by the Island’s End Golf Course for a game of golf with a view, or explore the island’s many hiking trails for a peaceful and scenic outdoor experience. For history buffs, Shelter Island’s Havens House is a must-see attraction. This beautifully preserved 18th-century home offers a glimpse into the island’s past and showcases the lifestyles of its early settlers. In November, you can also visit the Havens Farmers Market, held every Saturday, where you can sample local produce and homemade goods while chatting with friendly locals. And of course, no visit to Shelter Island is complete without indulging in some fresh seafood. November is the perfect time to savor a warm bowl of creamy clam chowder or a plate of steamed lobster while enjoying the crisp autumn air. With its charming ambiance and array of activities, Shelter Island is the perfect destination for a November adventure.
December
When visiting Shelter Island in December, it is important to pack for cold and potentially wet weather. Be sure to bring a warm, waterproof jacket and comfortable walking shoes for exploring the island’s charming towns and beautiful nature trails. Layers are key, as the temperature can fluctuate throughout the day. A hat, scarf, and gloves are also essential for staying cozy in the chilly island breeze. In terms of attire, Shelter Island is a casual destination, so there’s no need to pack fancy clothes. Opt for comfortable and practical clothing that you can easily move around in. A pair of jeans or leggings paired with a sweater or long-sleeved shirt is a great option for both sightseeing and dining at the island’s delicious seafood restaurants. Don’t forget to bring a swimsuit as well, as some of Shelter Island’s hot tubs and saunas offer a perfect way to warm up after a day of exploring in the cool December weather. And of course, don’t forget your camera to capture the island’s picturesque landscapes and charming holiday decorations.
When visiting Shelter Island in December, there are plenty of festive activities to enjoy. Start your day with a stroll through the charming town center, adorned with holiday decorations and twinkling lights. Stop by the local bakery for a warm cup of hot cocoa and a freshly baked treat. Then, head over to the annual Christmas Market, where you can browse through artisanal crafts, sample seasonal delicacies, and listen to live music. For a unique experience, take a guided tour of the island’s historic homes, all dressed up in their holiday best. Learn about the island’s rich history and admire the beautiful architecture while getting into the holiday spirit. In the evenings, cozy up by the fire at one of the island’s many bed and breakfasts, or catch a live performance at the local theater. No matter what you choose to do, Shelter Island in December is sure to be a magical and memorable experience.
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.
