Select the month that you will be traveling from the table below to view the packing list:
What Shelter Island Heights is like to visit throughout the year:
January
When visiting Shelter Island Heights in January, it’s important to dress for the weather. The island can often experience chilly temperatures and strong winds, so be sure to pack warm layers. Start with a base layer of thermal underwear, followed by a cozy sweater or fleece, and top it off with a waterproof and windproof jacket. Don’t forget to bring a warm hat, gloves, and a scarf to protect your head and extremities from the cold. Comfortable and sturdy shoes with good traction are also a must for exploring the island’s rugged terrain. In addition to dressing for the weather, it’s also important to dress appropriately for the island’s charming and laid-back atmosphere. Shelter Island Heights is a quaint and picturesque town, so leave your flashy and formal attire at home. Opt for comfortable and casual outfits that can easily transition from day to night. Bring a few versatile pieces that you can mix and match, and don’t forget to pack a swimsuit if you plan on taking a dip in the island’s beautiful beaches. Lastly, be sure to pack a reusable water bottle, sunscreen, and a small backpack to carry all your essentials while out and about exploring this charming island.
January is a great time to visit Shelter Island Heights, a charming and historic community located on the eastern end of Long Island. While the summer months may be the most popular time to visit, I highly recommend visiting in January for a more peaceful and authentic experience. One of my favorite things to do in January on Shelter Island Heights is to take a stroll along the picturesque coastline. The crisp winter air and stunning views of the Atlantic Ocean make for a refreshing and invigorating walk. Plus, with fewer crowds, you can truly appreciate the natural beauty of this coastal town. Another must-do in Shelter Island Heights during January is to visit the Havens Farmers Market. This indoor market is a treasure trove of locally grown produce, artisanal goods, and delicious homemade treats. It’s the perfect place to stock up on ingredients for a cozy winter meal or pick up unique souvenirs to bring back home. Plus, the market is a great way to support the local community and get a taste of the island’s culture. Don’t miss out on the opportunity to experience Shelter Island Heights in its quieter and more authentic state during the winter months.
February
When visiting Shelter Island Heights in February, it’s important to remember that the weather can be quite chilly and unpredictable. It’s best to pack layers, such as a warm jacket, scarf, and gloves, as well as a waterproof outer layer. This will ensure that you are prepared for any type of weather that may come your way. Don’t forget to bring comfortable walking shoes, as the island is perfect for exploring on foot. As for attire, Shelter Island Heights is a quaint and laid-back community, so there’s no need to pack your fanciest clothes. Stick to casual and comfortable outfits, such as jeans and sweaters, that can be dressed up or down depending on your activities. And don’t forget to bring a hat and sunglasses, as the sun can still be quite strong even in the winter months. Overall, the key is to be prepared for all types of weather and to dress in layers for maximum comfort and versatility.
February may not be the peak tourist season on Shelter Island Heights, but don’t let that deter you from visiting this charming destination. While the beaches may be too cold for swimming, there are still plenty of activities to enjoy during this time of year. Take a stroll through the quaint downtown area, where you’ll find local shops and restaurants bustling with activity. And don’t miss the annual Winterfest, where you can sample delicious local wines and enjoy live music in the cozy atmosphere of the island. For outdoor enthusiasts, February is the perfect time to explore the hiking trails on Shelter Island Heights. With the trees bare of leaves, you’ll have unobstructed views of the island’s stunning landscapes. For a unique experience, rent a bike and ride along the quiet roads, taking in the picturesque scenery. And when you need a break from the cold, head to one of the island’s many art galleries or museums, where you can appreciate the works of local artists and learn about the rich history of this charming community. February may be the off-season, but Shelter Island Heights has something to offer for every type of traveler.
March
When visiting Shelter Island Heights in March, it’s important to pack for varying weather conditions. The island experiences a mix of sunny days and chilly evenings during this time of year, so it’s best to dress in layers. A lightweight jacket, scarf, and a pair of comfortable shoes are essential for exploring the charming streets and scenic trails. Don’t forget to bring a waterproof jacket in case of rain and a hat to protect you from the sun. As for attire, Shelter Island Heights is a laid-back community, so casual clothing is appropriate for most activities. However, if planning to visit any upscale restaurants or attend a special event, it’s always a good idea to have a dressier outfit on hand. And for those planning to hit the beach, don’t forget to pack a swimsuit and flip flops. Overall, dressing comfortably and being prepared for any weather will ensure a pleasant and enjoyable visit to this quaint island destination in March.
March is a fantastic time to visit Shelter Island Heights, a charming village located in the heart of New York’s Shelter Island. As the weather starts to warm up and the crowds of summer tourists have yet to arrive, visitors can truly experience the peaceful and laid-back island lifestyle. One of the top activities to do in March is to take a stroll along the island’s scenic coastline, admiring the picturesque views of the Atlantic Ocean and the surrounding landscapes. Another must-do is to explore the quaint shops and eateries that line the village’s main street, where you can sample local delicacies and pick up unique souvenirs to remember your trip. For those looking to immerse themselves in the island’s rich history, a visit to the Shelter Island Historical Society is a must. This small but informative museum offers a glimpse into the island’s past through its collection of artifacts, documents, and photographs. Additionally, March is the perfect time to participate in some outdoor activities, such as hiking or biking through the island’s many nature trails. The breathtaking views of the island’s forests and wetlands are sure to leave you feeling refreshed and rejuvenated. With its charming atmosphere and plethora of activities, Shelter Island Heights is the perfect destination for a March getaway.
April
As you plan your trip to the charming town of Shelter Island Heights in April, don’t forget to pack layers and comfortable walking shoes. The weather during this time can be quite unpredictable, with chilly mornings and warm afternoons. I recommend bringing a light jacket or sweater that you can easily take off as the day warms up. A rain jacket or umbrella may also come in handy, as April can bring some showers. Be sure to pack comfortable walking shoes, as exploring this quaint town by foot is the best way to take in all its beauty. When it comes to attire in Shelter Island Heights, keep it casual and comfortable. This is a laid-back town, so leave your fancy clothes at home. A pair of jeans or khakis paired with a t-shirt or light sweater is perfect for a day of sightseeing. Don’t forget to bring a hat and sunscreen, as the sun can be quite strong during the day. And for those planning on visiting the beach, a swimsuit and beach cover-up are a must. Lastly, don’t forget to bring a reusable water bottle to stay hydrated and a small backpack to carry all your essentials while on the go. With these items in hand, you’ll be all set for a wonderful April adventure in Shelter Island Heights.
When visiting Shelter Island Heights in April, be sure to take advantage of the beautiful spring weather and explore the island’s many outdoor activities. Rent a bike and ride along the scenic shoreline, taking in the stunning views of the surrounding waters. Stop by the local farmers market to stock up on fresh produce and artisanal goods, perfect for a picnic overlooking the harbor. For a more adventurous experience, try kayaking or stand-up paddleboarding in the calm waters of Coecles Harbor. In addition to outdoor activities, Shelter Island Heights also offers a variety of cultural events in April. Visit the historic Havens House to learn about the island’s rich history and take a guided tour of the beautifully preserved 19th-century home. Don’t miss the annual Daffodil Festival, where the island comes alive with vibrant yellow blooms and a lively parade. And for a taste of local cuisine, be sure to check out the many restaurants participating in the annual Taste of Shelter Island event, showcasing the best of the island’s food and drink. With so much to see and do, Shelter Island Heights is the perfect destination for a springtime getaway.
May
When visiting Shelter Island Heights in May, it’s important to dress in layers to accommodate for the changing weather. The temperatures can range from cool in the mornings and evenings to warm during the day, so I recommend bringing a light jacket or sweater to throw on when needed. A pair of comfortable walking shoes is also a must, as this quaint town is best explored on foot. And don’t forget to bring a hat and sunscreen to protect yourself from the strong sun while strolling along the beach or exploring the charming shops. As for what to wear, I suggest packing comfortable and casual clothing, as the vibe on Shelter Island Heights is laid-back and relaxed. Sundresses, shorts, and lightweight tops are perfect for the daytime, while a nice pair of pants and a button-down shirt can be dressed up for a dinner out. And don’t worry about packing too much, as the island has a casual atmosphere and there’s no need to bring fancy or formal attire. Just remember to bring a swimsuit, as the beaches here are not to be missed!
Welcome to Shelter Island Heights in the month of May! This charming village is the perfect destination for those looking to escape the crowds and experience a slower pace of life. May is a wonderful time to visit as the temperatures are mild and the island is starting to come alive after the winter months. As a traveler, I highly recommend exploring the island on foot or by bike to truly appreciate its natural beauty. Take a stroll along the waterfront and admire the stunning views of the bay or rent a bike and ride through the picturesque streets lined with historic homes. Don’t forget to stop by the local farmer’s market to sample fresh, seasonal produce and mingle with the friendly locals. For those interested in history and culture, Shelter Island Heights has plenty to offer. Visit the Shelter Island Historical Society to learn about the island’s fascinating past or take a tour of the stunning Victorian houses that dot the village. May is also the perfect time to visit the nearby Mashomack Preserve, a nature reserve with over 2,000 acres of protected land. Here you can hike through the scenic trails and spot a variety of wildlife including ospreys, herons, and deer. And of course, no visit to Shelter Island Heights is complete without indulging in some delicious seafood at one of the many local restaurants. So come and explore this hidden gem in May and discover why Shelter Island Heights is the perfect destination for a peaceful and authentic getaway.
June
When visiting Shelter Island Heights in June, it’s important to pack for both warm and cool weather. The island can experience a range of temperatures during this time, so layers are key. I recommend bringing a light jacket or sweater for cooler evenings, as well as breathable clothing for sunny days. Shorts, t-shirts, and comfortable walking shoes are also a must for exploring the charming town and beautiful beaches. Don’t forget to pack a swimsuit and sunscreen for a refreshing dip in the ocean! In terms of dress code, Shelter Island Heights is a relaxed and casual destination. Locals and visitors alike can be seen sporting comfortable and practical clothing, perfect for a day of outdoor activities. 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 don’t forget to pack a hat and sunglasses for protection from the sun. As for what to bring, a reusable water bottle and a small daypack are essential for staying hydrated and carrying any essentials while out and about. With these tips in mind, you’ll be prepared to enjoy all that Shelter Island Heights has to offer in the beautiful month of June.
Welcome to Shelter Island Heights, a charming island escape just a ferry ride away from the bustling city of New York. June is the perfect time to visit this quaint village, as the summer season begins and the island is alive with activity. One of the must-do activities in Shelter Island Heights is to explore the picturesque beaches. From the secluded Crescent Beach to the lively Sunset Beach, there is a beach for every type of traveler. Take a dip in the crystal-clear waters, soak up the sun on the sandy shores, or rent a kayak and explore the island’s coastline. Don’t forget to grab a lobster roll from a local food truck for the perfect beach picnic experience. After a day at the beach, head over to the historic Chequit Inn for some delicious local cuisine. This charming inn, built in 1872, offers a cozy atmosphere with a modern twist. In June, the Chequit Inn hosts a weekly farmers market, where you can taste the freshest produce, meats, and cheeses from the island’s farmers. For a unique experience, take a tour of the inn’s own rooftop garden, where they grow herbs and vegetables used in their dishes. After dinner, take a stroll through the town’s Main Street, lined with charming shops and boutiques, and catch a gorgeous sunset over the bay. Shelter Island Heights is truly a hidden gem, and June is the perfect time to discover its beauty.
July
When traveling to Shelter Island Heights in July, it’s important to remember that this charming village is located on an island and can get quite humid. As such, it’s best to dress in lightweight, breathable clothing to stay cool and comfortable. I recommend packing a few pairs of shorts and t-shirts, as well as a light jacket or sweater for cooler evenings. Don’t forget to bring a hat and sunglasses to protect yourself from the bright sun. In terms of footwear, opt for comfortable walking shoes as you’ll want to explore the village’s quaint streets and beautiful nature trails. And if you plan on spending time at the beach, be sure to pack a swimsuit and beach towel. As for accessories, a small backpack or crossbody bag is ideal for carrying your essentials while on the go. And don’t forget to bring plenty of sunscreen to protect your skin from the strong summer sun. With these tips in mind, you’ll be well-prepared to enjoy all that Shelter Island Heights has to offer during your July visit.
Summer in Shelter Island Heights is a truly magical time. The warm weather, stunning beaches, and charming community make it the perfect destination for a July getaway. One of the must-do activities during this time is to attend a concert at the Perlman Music Program. This renowned music school hosts a series of outdoor concerts featuring talented young musicians from around the world. With the backdrop of the stunning Shelter Island Harbor, it’s an unforgettable experience for music lovers. Another highlight of visiting Shelter Island Heights in July is the annual Fourth of July parade. This small town knows how to celebrate America’s independence in style. The parade features local marching bands, decorated floats, and even a firetruck spray down for kids to cool off in the summer heat. After the parade, head to Crescent Beach for a day of relaxation and swimming, followed by a barbecue and fireworks at sunset. It’s the perfect way to experience the patriotic spirit of this charming island community.
August
When visiting Shelter Island Heights in August, it’s important to pack for warm and sunny weather. The average temperature during this time of year is in the mid-80s, so light and breathable clothing is key. I recommend packing shorts, t-shirts, and sundresses for daytime activities, and a light sweater or jacket for cooler evenings. As the island is known for its beautiful beaches, don’t forget to bring a swimsuit and cover-up for a day by the water. A comfortable pair of walking shoes is also a must, as the island is best explored on foot. In addition to clothing, be sure to bring sunscreen, a hat, and sunglasses to protect yourself from the sun’s rays. It’s also a good idea to pack a small backpack or tote bag to carry essentials while out and about. Other useful items to bring include a refillable water bottle, insect repellent, and a camera to capture the stunning views on the island. And don’t forget to pack a light rain jacket, as occasional showers are not uncommon in August. With these essentials in hand, you’ll be well-prepared for a wonderful and comfortable visit to Shelter Island Heights.
If you find yourself on Shelter Island Heights in August, you’re in for a treat! This charming little town comes alive during the summer months with a variety of activities and events. One of the must-do activities is to take a stroll along the island’s beautiful beaches. With its calm waters and sandy shores, it’s the perfect spot for a relaxing day under the sun. For those seeking a bit more adventure, try renting a kayak or stand-up paddleboard and explore the island’s coastline from a different perspective. In addition to its natural beauty, Shelter Island Heights also offers a rich cultural experience. Don’t miss the weekly farmer’s market where you can sample locally grown produce and homemade goods. For a taste of the island’s history, visit the Shelter Island Historical Society and learn about the town’s past. And for the art lovers, be sure to check out the various galleries and studios showcasing the work of local artists. August is truly the perfect time to visit Shelter Island Heights and immerse yourself in its laid-back island lifestyle.
September
As the summer crowds begin to dissipate and the weather starts to cool, September is a wonderful time to visit Shelter Island Heights. However, with the changing season, it’s important to pack accordingly. The island has a laid-back and casual vibe, so leave the fancy clothes at home and opt for comfortable, practical attire. A light jacket or sweater is a must for the cooler evenings, but don’t forget to pack a few layers as the temperature can fluctuate throughout the day. And of course, don’t forget to bring a sturdy pair of walking shoes to explore the charming streets and scenic trails of the island. In addition to dressing for the weather, it’s important to also consider the activities you have planned during your visit to Shelter Island Heights. If you’re planning on spending time at the beach, be sure to bring a swimsuit, flip flops, and a beach bag to carry your essentials. For those planning on exploring the local restaurants and shops, a nice pair of jeans or casual dress will do the trick. And for any outdoor activities, such as hiking or biking, be sure to pack comfortable and breathable clothing as well as sunscreen and a hat to protect yourself from the sun. With these tips, you’ll be dressed and prepared for a wonderful September visit to Shelter Island Heights.
September is a fantastic time to visit Shelter Island Heights, a charming village located on the eastern end of Shelter Island. As the summer crowds dissipate and the temperatures start to cool down, this quaint community becomes a peaceful oasis for travelers looking for a relaxing getaway. One of the must-do activities during this time is to take a stroll around the village and admire its picturesque Victorian architecture. You can also rent a bike and explore the island’s many scenic trails, or take a leisurely walk along the shores of the bay. For foodies, September in Shelter Island Heights means it’s time for the annual “Taste of the Heights” event. This festival celebrates the local culinary scene with tastings from the area’s top restaurants and wineries. It’s a great opportunity to sample the island’s fresh seafood, locally-grown produce, and award-winning wines. In addition to indulging in delicious food and drink, visitors can also enjoy live music, art displays, and cooking demonstrations. So grab your appetite and head to Shelter Island Heights for a delicious and memorable experience in September.
October
As the leaves begin to change and the air takes on a crispness, October is the perfect time to visit the charming Shelter Island Heights. When it comes to dressing for this time of year, layers are key. Mornings and evenings can be cool, but the afternoons can still have a bit of warmth. I recommend packing a light jacket or sweater, comfortable walking shoes, and a rain jacket, just in case. And don’t forget to bring a scarf and hat to keep warm and add a touch of style to your outfit. While exploring the quaint streets of Shelter Island Heights, you’ll want to blend in with the locals. Opt for a casual and comfortable look, but still put together. Think jeans or khakis paired with a cozy sweater or a button-down shirt. And don’t forget to bring a pair of sturdy shoes for those walks along the beach or through the picturesque nature trails. As for accessories, a cross-body bag is perfect for carrying essentials while keeping your hands free to snap photos. And of course, don’t forget your camera to capture the stunning fall scenery on the island.
October is a wonderful time to visit Shelter Island Heights, a charming and tranquil island located off the coast of Long Island, New York. The autumn foliage is at its peak, creating a stunning backdrop for exploring the island. One of my favorite activities during this time is taking a leisurely bike ride along the picturesque coastline. The island’s many bike paths offer stunning views of the surrounding waters and colorful trees. Along the way, be sure to stop at some of the island’s quaint villages and try some local seafood at one of the many charming restaurants. For history buffs, a visit to the Chequit Inn is a must. This historic hotel, built in 1872, is a true gem of Shelter Island Heights. Take a stroll through its beautiful gardens and admire the Victorian architecture. Inside, you can learn about the fascinating history of the island and its role in the Revolutionary War. If you’re feeling adventurous, you can even book a stay at the inn and experience a taste of old-world charm. No matter what your interests may be, Shelter Island Heights offers something for everyone in the lovely month of October.
November
As you prepare for your November trip to Shelter Island Heights, it’s important to pack for cooler temperatures and potential rain. Layering is key, as the weather can change quickly on this charming island. Bring a waterproof jacket, warm sweaters, and comfortable walking shoes for exploring the quaint streets and nature trails. Don’t forget to pack a scarf and hat for added warmth, as well as an umbrella to protect you from any unexpected showers. When it comes to dressing for the evening, Shelter Island Heights has a relaxed and casual vibe. A nice pair of jeans or slacks paired with a sweater or button-down shirt will be appropriate for most restaurants and bars. However, if you plan on dining at a more upscale establishment, bring a dressier outfit. As for footwear, a pair of dressy boots or flats will be suitable for most occasions. And for those wanting to take a dip in the ocean, don’t forget to pack a swimsuit and beach towel. With the right clothing and gear, you’ll be prepared to fully enjoy all that Shelter Island Heights has to offer in November.
As the autumn leaves begin to fall and the summer crowds dissipate, Shelter Island Heights offers a peaceful and charming retreat for travelers in November. One of the must-see attractions during this time of year is the Shelter Island Historical Society, where visitors can learn about the island’s rich history through interactive exhibits and guided tours. Stroll through the quaint streets of the Heights and take in the beautiful Victorian homes adorned with festive fall decorations. For a true taste of the local culture, be sure to check out the weekly farmers market, where you can sample fresh produce and homemade goods from the island’s farmers and artisans. November is also the ideal time to take advantage of the many outdoor activities that Shelter Island Heights has to offer. With cooler temperatures and less crowds, hiking and biking through the island’s picturesque nature trails is a must-do for nature lovers. Take a leisurely stroll along the coastline and enjoy the crisp ocean air, or rent a kayak and explore the serene waters surrounding the island. And for those looking for a unique experience, hop on a ferry to nearby Greenport and participate in the annual oyster festival, where you can indulge in the local delicacy and enjoy live music and entertainment. No matter what your interests may be, Shelter Island Heights has something for everyone in the tranquil month of November.
December
As you plan your trip to Shelter Island Heights in December, it’s important to consider the weather and pack accordingly. The temperatures in December can range from chilly to cold, so be sure to pack warm layers for your visit. A water-resistant jacket and waterproof boots are must-haves, as well as a scarf, gloves, and a hat to keep you cozy during outdoor activities. Don’t forget to bring an umbrella, as December is known for its occasional rain showers. And while it may be tempting to pack light, don’t forget to also bring a few dressier options for any holiday events or dinners you may attend. When it comes to dressing for the day, comfort and functionality are key. Opt for comfortable walking shoes as you explore the charming streets of Shelter Island Heights. Layering is also important, as the temperature can fluctuate throughout the day. A light sweater or long-sleeved shirt paired with a warm vest and jeans will keep you comfortable and stylish. And don’t forget to bring a backpack or crossbody bag to carry your essentials, such as a water bottle, camera, and map. By packing smart and dressing for the weather, you’ll be able to fully enjoy all that Shelter Island Heights has to offer in December.
Shelter Island Heights may be a small community, but it’s bursting with charm and activities during the month of December. As the holiday season approaches, the streets are adorned with cheerful lights and festive decor, creating a cozy and welcoming atmosphere. Take a stroll through the town and admire the quaint shops and restaurants, each with their own unique holiday displays. One of the highlights of visiting Shelter Island Heights in December is the annual Holiday House Tour. This self-guided tour takes you through some of the most beautiful homes on the island, decorated for the holiday season. Not only will you get to see stunning decorations and architecture, but you’ll also learn about the history and culture of the island. And don’t forget to warm up with a cup of hot cocoa or mulled wine at one of the stops along the way. It’s the perfect way to get into the holiday spirit while exploring this charming town.
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.
