Select the month that you will be traveling from the table below to view the packing list:
What Oak Bluffs is like to visit throughout the year:
January
When visiting Oak Bluffs in January, it’s important to dress in layers to prepare for the ever-changing weather on the island. Start with a warm base layer, such as a long-sleeved shirt and thermal leggings, and then add a sweater or fleece for extra warmth. A waterproof jacket and sturdy walking shoes are also essential, as the island can get quite windy and rainy during this time of year. Don’t forget to pack a hat, gloves, and scarf to protect yourself from the chill of the ocean breeze. As for what to wear, Oak Bluffs is a laid-back and casual town, so there’s no need to bring any fancy or formal attire. Stick to comfortable and practical clothing, such as jeans, hiking pants, and sweatshirts, which can easily be layered for warmth. Bring a small backpack or crossbody bag to carry essentials like water, snacks, and a map as you explore the charming streets and beaches of Oak Bluffs. And don’t forget to pack a swimsuit and beach towel, as the island’s hot tubs and saunas are a popular way to warm up after a day of adventuring in the winter months.
When visiting the charming town of Oak Bluffs in January, there are plenty of activities to keep you entertained and immersed in the local culture. One must-do activity is to take a stroll along the iconic Ocean Park, where you can admire the stunning views of the Atlantic Ocean and the picturesque gingerbread houses that line the park. This is also a great spot to watch the sunset and take in the peaceful atmosphere of the town. For history buffs, a visit to the Martha’s Vineyard Museum is a must. Located in the former Marine Hospital, this museum showcases the rich history of the island and its people. In January, the museum hosts a variety of events and exhibits, including a special exhibit on the island’s whaling history. After exploring the museum, take a walk through the nearby neighborhood of Camp Ground, known for its colorful cottages and religious tabernacle. This is a perfect way to spend a winter day on the island, learning about its past and admiring its unique architecture.
February
When visiting the charming town of Oak Bluffs in February, it’s important to dress for the unpredictable weather. Layers are key, as the temperature can range from chilly to mild throughout the day. Start with a warm base layer such as thermal underwear or a long-sleeved shirt, and then add a sweater or fleece on top. A waterproof jacket is also a must, as the island can experience occasional rain showers. Don’t forget to bring a warm hat, gloves, and a scarf to protect yourself from the wind off the ocean. Comfortable and sturdy shoes are also essential for exploring the town’s cobblestone streets and rugged shoreline. As for what to wear in Oak Bluffs, the style is casual and relaxed. Locals and tourists alike favor comfortable and practical clothing over fancy attire. Jeans, leggings, and cozy sweaters are all popular choices. For a touch of New England charm, consider packing a pair of duck boots or a wool pea coat. A small backpack is also handy to have for carrying essentials while sightseeing. And don’t forget to bring a camera to capture the picturesque views of the colorful gingerbread houses and picturesque harbor. With the right clothing and gear, you’ll be ready to experience all that Oak Bluffs has to offer in February.
February is a delightful time to visit the charming town of Oak Bluffs on the island of Martha’s Vineyard. Despite being the off-season, there is still plenty to see and do in this picturesque New England town. One of the top highlights is the annual Winter Festival, which takes place in mid-February. This lively event celebrates all things winter with a variety of activities such as ice skating, snowshoeing, and sledding. Local vendors also set up shop, offering delicious hot cocoa and warm treats to keep you cozy while you take in the festive atmosphere. For a more relaxed and cultural experience, head to the Martha’s Vineyard Museum. This small yet informative museum highlights the island’s history, from its Native American roots to its whaling past and present-day tourism industry. In February, the museum hosts a series of lectures and workshops, providing a deeper insight into the island’s fascinating past. It’s a great way to learn and appreciate Oak Bluffs beyond its scenic views and quaint shops. Plus, the cozy fireplace in the museum’s café is the perfect spot to warm up and enjoy a cup of tea after a day of exploring.
March
When visiting the charming town of Oak Bluffs in March, it’s important to dress in layers to prepare for the unpredictable weather on Martha’s Vineyard. The mornings can be chilly, but by midday the sun is shining and the temperature rises. I recommend bringing a light jacket or sweater that can easily be taken off or put on throughout the day. As for footwear, a comfortable pair of walking shoes is a must as the town is best explored on foot. The cobblestone streets can be tricky to navigate, so leave the heels at home and opt for a pair of sneakers or flats. In terms of attire, Oak Bluffs is a casual destination, so leave the formal wear behind. A pair of jeans, a comfortable t-shirt, and a light jacket are perfect for exploring the town and its many shops, restaurants, and beaches. Don’t forget to bring a hat and sunglasses to protect yourself from the bright sun. And of course, don’t leave without a swimsuit as the water may still be a bit chilly, but the beaches are still beautiful and worth a dip. With these essentials, you’ll be ready to enjoy all that Oak Bluffs has to offer in the lovely month of March.
March is a wonderful time to visit the charming town of Oak Bluffs on the island of Martha’s Vineyard. While many travelers flock here during the summer months, those who visit in March will be rewarded with a quiet and peaceful atmosphere as well as some unique activities. One must-do in Oak Bluffs during March is to take a stroll along the beautiful coastline. The crisp sea air and the sound of crashing waves make for a truly rejuvenating experience. For a taste of local culture, be sure to visit the Martha’s Vineyard Museum where you can learn about the island’s history and see fascinating exhibits. And don’t miss out on the opportunity to sample fresh seafood at one of the local restaurants – the lobster rolls are a must-try! With its charming streets, scenic views, and rich culture, Oak Bluffs is the perfect destination for a March getaway.
April
When visiting the charming seaside town of Oak Bluffs in April, it’s important to dress in layers as the weather can be unpredictable. A light jacket or sweater is a must, as well as comfortable walking shoes for exploring the quaint streets. The island breeze can be chilly, so a scarf or hat might also come in handy. And don’t forget your sunglasses for those sunny days on the beach! As for what to wear, keep in mind that Oak Bluffs is a casual and laid-back destination. Opt for comfortable and practical clothing, such as shorts or jeans paired with a t-shirt or blouse. And of course, don’t forget your swimsuit for a dip in the ocean or a relaxing afternoon at the beach. It’s also a good idea to bring a small backpack or tote bag to carry your essentials, like sunscreen, water, and a camera to capture the beautiful scenery. With these tips in mind, you’ll be ready to fully enjoy the charming atmosphere of Oak Bluffs in April.
April is a wonderful time to visit the charming town of Oak Bluffs on Martha’s Vineyard. As the island awakens from its winter slumber, the town bustles with a lively energy and offers a variety of activities for visitors to enjoy. One of the highlights of April in Oak Bluffs is the Annual Spring Festival, where locals and visitors come together to celebrate the start of the season with live music, delicious food, and a colorful parade. Aside from the festival, April is also the perfect time to explore the quaint streets of Oak Bluffs and admire the iconic gingerbread cottages. These whimsical homes are a sight to behold and showcase the unique architectural history of the town. Take a stroll along the Ocean Park, a picturesque green space dotted with historic landmarks and stunning ocean views. And for those looking for a bit of adventure, April is a great month to rent a bike and explore the scenic bike paths that wind through the island. With so much to see and do, April is an ideal time to experience the charming beauty of Oak Bluffs.
May
When visiting the charming seaside town of Oak Bluffs in the month of May, it’s important to dress in layers. The weather can be unpredictable, with cool ocean breezes in the morning and warmer temperatures in the afternoon. I recommend packing a light jacket or sweater, as well as a scarf or shawl to keep you warm during your explorations. Comfortable walking shoes are a must as you’ll want to wander through the quaint streets and along the beachfront. As for what to wear, Oak Bluffs has a laid-back, beachy vibe so you’ll want to dress accordingly. Opt for casual, comfortable clothing such as shorts, sundresses, and t-shirts. Don’t forget to pack a swimsuit as well, as the water may still be a bit chilly but the sun will be shining and the beach is a popular spot for locals and tourists alike. And of course, no trip to Oak Bluffs is complete without a pair of sunglasses and a hat to protect you from the bright sun. With these essentials in your suitcase, you’ll be ready to soak up the beauty and charm of this lovely New England town.
May is a wonderful time to visit the charming town of Oak Bluffs on Martha’s Vineyard. As the summer crowds have yet to arrive, visitors can enjoy a more relaxed and authentic experience. One of the must-see attractions in May is the Flying Horses Carousel, the oldest operating carousel in the United States. Take a ride on one of the beautifully hand-carved horses and feel like a child again. Afterward, stroll along the colorful gingerbread houses in the Campground, a unique community dating back to the 1800s. These whimsical homes are a sight to behold and make for great photo opportunities. For a taste of the local culture, head to the Oak Bluffs Harbor Festival held in May. This lively event celebrates the start of the boating season with live music, delicious seafood, and a variety of activities for all ages. Take a walk around the harbor and admire the stunning yachts and sailboats, or hop on a ferry for a scenic tour of the island. Don’t forget to stop by the Oak Bluffs Arts District, where you can browse through galleries and shops showcasing the work of talented local artists. With its charming atmosphere and laid-back vibe, Oak Bluffs in May is a perfect destination for a tranquil and authentic island experience.
June
When planning a trip to beautiful Oak Bluffs in June, it’s important to pack for the warm, sunny weather that is characteristic of Martha’s Vineyard. Lightweight, breathable clothing is key for staying comfortable while exploring the charming town and its beaches. Bring a mix of shorts, t-shirts, and sundresses for daytime activities, and a light sweater or jacket for cooler evenings. Don’t forget to pack a swimsuit and beach cover-up for a dip in the ocean or lounging on the sand. As for footwear, bring a pair of comfortable walking shoes for exploring the town’s streets and trails. Sandals or flip-flops are also a must for beach visits. Ladies may want to pack a pair of dressier sandals for a night out or a visit to one of the island’s many restaurants. And don’t forget to bring a hat and sunglasses to protect yourself from the strong summer sun. Lastly, be sure to pack a small day bag to carry your essentials while out and about, and don’t forget to bring a reusable water bottle to stay hydrated in the warm weather. With these essentials, you’ll be ready to fully enjoy all that Oak Bluffs has to offer in the month of June.
As you stroll through the charming streets of Oak Bluffs in June, you’ll be greeted with a lively atmosphere and plenty of activities to enjoy. One of the must-do experiences during this month is to attend the annual Oak Bluffs Harbor Festival. This event celebrates the town’s rich maritime history and features live music, delicious seafood, and fun activities for all ages. It’s the perfect way to kick off your visit to this picturesque town. Another highlight of visiting Oak Bluffs in June is exploring the town’s famous gingerbread cottages. These quaint and colorful houses, adorned with ornate Victorian details, are a beloved feature of the town and a sight not to be missed. Take a leisurely walk through the Cottage City Historic District and marvel at the unique architecture, or join a guided tour to learn more about the history and stories behind these charming homes. And don’t forget to snap some photos for your Instagram feed – these cottages are sure to be a hit with your followers.
July
When visiting the charming town of Oak Bluffs in July, it’s important to dress appropriately for the warm and sunny weather. Lightweight and breathable fabrics such as cotton or linen are ideal for staying cool and comfortable while exploring the town. Opt for shorts, sundresses, and short-sleeved shirts to beat the heat. Don’t forget to bring a hat and sunglasses to protect yourself from the strong sun rays. As for footwear, comfortable and sturdy sandals are a must for walking around the town’s colorful streets and sandy beaches. It’s also a good idea to bring a light jacket or sweater for the evenings, as temperatures can dip a bit. And of course, don’t forget your swimsuit for a refreshing dip in the ocean or a day at the beach. Pack light and only bring the essentials, as Oak Bluffs is a casual and laid-back destination. With the right clothing and gear, you’ll be ready to fully enjoy all that this charming town has to offer.
Welcome to beautiful Oak Bluffs, a charming seaside town on the island of Martha’s Vineyard. July is the perfect time to visit and enjoy all that this quaint town has to offer. First and foremost, be sure to take a stroll along the famous Ocean Park, a lovely green space right by the water. This is the perfect spot to relax, have a picnic, and people-watch as locals and visitors alike enjoy the summer weather. Next, make your way to the historic Flying Horses Carousel, the oldest operating carousel in the country. You’ll feel like a kid again as you take a spin on one of the hand-carved horses, all while being serenaded by the charming organ music. No visit to Oak Bluffs is complete without exploring the enchanting gingerbread cottages in the Campground. These colorful and intricately decorated homes are a true sight to behold and offer a glimpse into the town’s rich history. July is also a great time to attend the annual Grand Illumination, a magical event where all the cottages are adorned with thousands of colorful lanterns. For a taste of local culture, be sure to check out the weekly farmers market on the grounds of the historic Grange Hall. Here you’ll find fresh produce, homemade goods, and a lively atmosphere. End your day with a sunset cruise around the island and take in the breathtaking views of the coastline. With so much to see and do, July is the perfect time to experience the charm and beauty of Oak Bluffs. Happy travels!
August
When visiting the charming town of Oak Bluffs in August, it’s important to pack light and dress for the warm, sunny weather. Opt for comfortable, breathable clothing such as cotton or linen shirts and shorts. A light jacket or sweater may come in handy for cooler evenings, but overall, the island is known for its pleasant and mild summer temperatures. As you explore the town, you’ll want to bring a few key items to fully enjoy your experience. A sturdy pair of walking shoes is a must, as many of the streets and paths are cobblestone or uneven. Don’t forget to pack a swimsuit and towel for a dip in the refreshing waters of the Atlantic Ocean. And of course, no trip to Oak Bluffs is complete without a sunhat, sunglasses, and sunscreen to protect yourself from the strong summer sun. With these essentials, you’ll be dressed and prepared for a delightful August getaway in this picturesque New England town.
August is the perfect time to visit Oak Bluffs, a charming town located on the picturesque island of Martha’s Vineyard. As a traveler, I highly recommend taking a stroll along the famous Gingerbread Cottages, a unique neighborhood filled with colorful and intricately designed homes. These whimsical cottages are a true representation of the island’s history and are a must-see for any visitor. For those looking to relax and soak up the sun, head to the Inkwell Beach. This beautiful stretch of sand offers stunning views of the ocean and is the perfect spot for a picnic or a dip in the water. In the evenings, be sure to check out the lively Oak Bluffs Harbor, where you can enjoy fresh seafood, live music, and a vibrant atmosphere. Whether you’re looking for a cultural experience or a day at the beach, Oak Bluffs has something for everyone in the month of August.
September
As September rolls around, the crowds in Oak Bluffs begin to thin out, making it the perfect time to visit this charming New England town. When it comes to dressing for your trip, layering is key. The weather can be unpredictable, with warm afternoons and cool evenings, so be sure to pack a mix of short and long-sleeved shirts, as well as a light jacket or sweater. Comfortable walking shoes are a must, as you’ll want to explore the colorful streets and picturesque beaches on foot. When it comes to fashion in Oak Bluffs, it’s all about casual and comfortable. Leave your fancy dresses and high heels at home and opt for a more relaxed, beachy look. Maxi dresses, shorts, and flowy tops are all popular choices for both men and women. And don’t forget to bring a swimsuit, as the ocean waters are still warm enough for a dip in September. As for accessories, a sunhat and sunglasses are a must for sunny days, and a light scarf can come in handy for cooler evenings. And of course, don’t forget your camera to capture all the beautiful sights and memories of your trip to Oak Bluffs.
As summer comes to a close, the charming town of Oak Bluffs on Martha’s Vineyard transforms into a serene and peaceful retreat. September is the perfect time to visit this picturesque town, as the crowds dissipate and the island takes on a more relaxed atmosphere. One of the must-do activities in Oak Bluffs during this time is to take a stroll along the iconic gingerbread cottages in the Campground. These whimsical and colorful homes, dating back to the 19th century, are a unique sight to see and offer a glimpse into the island’s history. Another fantastic way to spend a September day in Oak Bluffs is by exploring the town’s beautiful beaches. While the water may be a bit cooler, the sandy shores are less crowded, making it an ideal time for a peaceful walk or a picnic with a view. For those feeling more adventurous, renting a bike and cruising along the scenic bike paths that wind through the island is a must. You can also take a short ferry ride to neighboring Chappaquiddick Island and discover its secluded beaches and stunning views. No matter how you choose to spend your time in Oak Bluffs in September, the crisp air and beautiful surroundings will leave you feeling refreshed and rejuvenated.
October
October is a beautiful time to visit the charming town of Oak Bluffs on Martha’s Vineyard. As the leaves change color and the summer crowds dissipate, the island takes on a peaceful and cozy atmosphere. When packing for your trip, keep in mind that the weather can be quite unpredictable in October. It’s best to dress in layers, as the mornings and evenings can be cool while the afternoons can still be quite warm. A light jacket or sweater and a scarf are essential items to have on hand. As you stroll through the quaint streets of Oak Bluffs, you’ll want to blend in with the locals and embrace the island’s laid-back style. Opt for comfortable and casual clothing, such as lightweight pants or jeans, and breathable tops. Don’t forget to bring a pair of comfortable walking shoes for exploring the town and its beautiful beaches. And of course, no visit to Oak Bluffs is complete without a visit to the iconic gingerbread cottages, so be sure to bring a camera to capture the charming architecture. Finally, don’t forget to pack a rain jacket or umbrella, just in case the weather decides to take an unexpected turn. With these tips, you’ll be dressed and prepared for a wonderful October getaway in Oak Bluffs.
October is a wonderful time to visit the charming town of Oak Bluffs on Martha’s Vineyard. The summer crowds have dissipated, but the town is still buzzing with activity and the autumn foliage adds a beautiful backdrop to the vibrant streets. One of my favorite things to do in October is to take a stroll along the famous gingerbread cottages, which are adorned with festive Halloween decorations. These whimsical homes were built in the late 1800s and are a must-see for any visitor to Oak Bluffs. Aside from admiring the gingerbread cottages, October is also the perfect time to explore the island’s natural beauty. The State Beach, located just a short walk from the town center, offers stunning views of the ocean and is a great spot for a leisurely bike ride. For a more challenging hike, head to the Manuel F. Correllus State Forest, where you can wander through the colorful foliage and spot wildlife such as deer and turkeys. And of course, no trip to Oak Bluffs would be complete without trying some of the local seafood, so be sure to stop by one of the many seafood shacks for a delicious lobster roll or clam chowder. With its charming atmosphere and abundance of outdoor activities, October is the perfect time to visit Oak Bluffs.
November
When visiting the charming town of Oak Bluffs in November, it’s important to dress for the cool autumn weather. Layering is key, as the temperature can fluctuate throughout the day. Start with a warm base layer, such as a long-sleeved shirt and pants, and add a sweater or jacket on top. Don’t forget to bring a waterproof outer layer in case of rain. Comfortable, closed-toe shoes are a must for walking around the town and exploring the beaches. And don’t forget to bring a scarf, hat, and gloves for extra warmth! In terms of what to wear in Oak Bluffs, embrace the casual and laid-back vibe of the island. Opt for comfortable and practical clothing, such as jeans, leggings, and cozy sweaters. And don’t be afraid to add some fun and colorful pieces to your wardrobe, as the town is known for its vibrant and quirky atmosphere. As for what to bring, make sure to pack a reusable water bottle, as well as a camera to capture the picturesque views of the town. And of course, don’t forget your sense of adventure and willingness to try new things – that’s the best thing to bring to any destination!
November is a delightful time to visit the charming town of Oak Bluffs, located on the picturesque island of Martha’s Vineyard. As the busy summer crowds have dispersed, the town takes on a more relaxed and peaceful atmosphere. One of the top activities during this time is to take a leisurely stroll along the colorful gingerbread cottages in the historic Campground neighborhood. Built in the 1800s as a Methodist summer retreat, these whimsical homes are adorned with intricate details and pastel hues, making for a delightful sight to behold. For those seeking a taste of the island’s rich history, a visit to the Martha’s Vineyard Museum is a must. Housed in a former marine hospital, the museum offers a fascinating glimpse into the island’s past through its collection of artifacts, photographs, and interactive exhibits. In November, the museum also hosts a variety of events and workshops, including cooking classes that showcase the local flavors and traditional dishes of the island. It’s a perfect way to immerse oneself in the culture and traditions of Oak Bluffs during the chilly autumn months.
December
When visiting Oak Bluffs in December, it’s important to dress warmly and prepare for chilly weather. The average temperature during this time is around 40 degrees Fahrenheit, so it’s best to bring a heavy coat, warm layers, and a hat and gloves. However, don’t forget to also pack a few lighter layers as the temperature can fluctuate throughout the day. It’s also a good idea to bring waterproof shoes or boots in case of rain or snow. In addition to warm clothing, it’s important to dress appropriately for the holiday season. Oak Bluffs is known for its festive decorations and events in December, so don’t be afraid to bring a few dressier outfits for special occasions. Many restaurants and shops also require a dress code, so it’s a good idea to pack a nice outfit or two for those occasions. And of course, don’t forget to bring a camera to capture all the magical holiday moments in this charming New England town.
December is a wonderful time to visit Oak Bluffs, a charming seaside town on the picturesque island of Martha’s Vineyard. Despite the cooler temperatures, there is still plenty to see and do in this quaint New England destination. One of the highlights of December in Oak Bluffs is the annual Christmas in Edgartown celebration. This festive event includes holiday-themed activities such as a parade, caroling, and a holiday market featuring local artisans. Visitors can also enjoy the beautifully decorated gingerbread cottages and take part in a tree lighting ceremony. It’s a truly magical experience that captures the essence of small-town New England during the holiday season. And for those looking for a bit of adventure, December is also a great time to explore the island’s scenic hiking trails or take a leisurely stroll along the peaceful beaches. No matter how you choose to spend your time in Oak Bluffs, you’ll be sure to leave with a deeper appreciation for this charming town and its unique island 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.
