Select the month that you will be traveling from the table below to view the packing list:
What Great Barrington is like to visit throughout the year:
January
When visiting Great Barrington in January, it’s important to dress in layers to combat the often unpredictable New England weather. Start with a warm base layer, such as long underwear or a thermal shirt, followed by a sweater or fleece, and top it off with a waterproof jacket. Don’t forget a scarf, hat, and gloves to keep your extremities cozy. Comfortable and sturdy waterproof shoes or boots are a must, as the snowy sidewalks can be slippery. And don’t be afraid to add a pop of color to your outfit with a warm, woolen scarf or hat. As for what to bring, be sure to pack a small backpack to carry any essentials for a day of exploring. This could include a water bottle, snacks, a map, and a camera to capture the charming winter scenery. It’s also a good idea to bring an extra pair of socks and gloves, as well as a portable phone charger in case of emergencies. And don’t forget to bring your sense of adventure and willingness to embrace the winter wonderland that is Great Barrington in January. Happy travels!
January is a wonderful time to visit the charming town of Great Barrington. While the winter chill may be in the air, the town is bustling with activities that will warm your heart. One of the must-do activities in January is to visit the annual Winter Festival. This event showcases the town’s unique culture and history through live music, art exhibits, and delicious local food. Don’t forget to take a stroll through the quaint streets of Great Barrington and admire the beautiful holiday decorations that add a magical touch to the town. For outdoor enthusiasts, January offers the perfect opportunity to hit the slopes at the nearby ski resorts. Ski Butternut and Catamount Ski Area are just a short drive away and offer a variety of trails for all levels of skiers. After a day of skiing, warm up by the fireplace at one of the cozy restaurants in town and indulge in some hearty New England cuisine. And for those looking for a more relaxing day, the town’s spas offer a perfect escape with their soothing treatments and tranquil atmosphere. No matter what your interests may be, Great Barrington has something for everyone in January.
February
As February approaches, it’s important to consider the weather when packing for a trip to Great Barrington. This charming town in the heart of the Berkshires experiences chilly temperatures and occasional snowfall during this time of year. To stay warm and comfortable, I recommend dressing in layers. Start with a base layer of thermal clothing, followed by a cozy sweater or fleece, and top it off with a waterproof jacket. Don’t forget to bring a warm hat, gloves, and a scarf to protect your head, hands, and neck from the cold. While staying warm is essential, it’s also important to be prepared for indoor activities. Great Barrington is known for its thriving arts and culture scene, and many of the attractions are indoors. I suggest bringing a nice outfit for a night out at the theater or a visit to one of the many art galleries. Additionally, comfortable walking shoes are a must as you explore the quaint streets and shops of this charming town. Don’t forget to pack an umbrella or waterproof shoes, as February can bring some rain or snow showers. By dressing in layers and being prepared for both indoor and outdoor activities, you’ll be able to fully enjoy all that Great Barrington has to offer during your February visit.
February is a wonderful time to visit the charming town of Great Barrington, nestled in the heart of the Berkshire Mountains in Massachusetts. As the snow blankets the landscape, visitors can experience the winter wonderland of this quaint New England town. Bundle up and take a stroll down Main Street, lined with historic buildings and independent shops. Stop by the local bakery for a warm cup of hot chocolate or indulge in some freshly baked pastries. For a true taste of New England, head to the weekly farmers market where you can sample locally made cheeses, jams, and other delicious treats. For those looking for some outdoor adventure, February is the perfect time for skiing and snowboarding at the nearby Ski Butternut. With over 100 acres of trails and slopes, there is something for every level of skier. And don’t worry if you’re not an expert, the friendly staff at the ski school will have you gliding down the mountain in no time. For a more leisurely experience, take a horse-drawn sleigh ride through the picturesque countryside. And after a day in the snow, warm up with a hearty meal at one of the town’s cozy restaurants, serving up traditional New England dishes like clam chowder and maple syrup drizzled pancakes. February in Great Barrington truly offers something for everyone.
March
When planning a trip to Great Barrington in March, it’s important to pack for the unpredictable New England weather. Layering is key, as the temperature can vary greatly throughout the day. Start with a warm base layer, such as a long-sleeved shirt and pants, and then add a sweater or fleece for extra warmth. Don’t forget a waterproof jacket, as rain is common during this time of year. Comfortable, waterproof shoes are a must for exploring the charming streets and hiking trails of Great Barrington. As for attire, Great Barrington has a casual and laid-back vibe, so there’s no need to dress up. However, if you plan on dining at a fancy restaurant or attending a concert at the Mahaiwe Performing Arts Center, a nice outfit or dress is appropriate. It’s also a good idea to bring a hat, gloves, and scarf for chilly evenings and early mornings. And of course, don’t forget to pack your camera to capture the stunning views of the Berkshire Mountains and quaint New England architecture. With these tips in mind, you’ll be well prepared for your March visit to Great Barrington.
Great Barrington, located in the beautiful Berkshire Mountains of Massachusetts, is a charming town that offers plenty of activities for visitors to enjoy during the month of March. One of my top recommendations is to visit the acclaimed Mahaiwe Performing Arts Center, which hosts a variety of shows and concerts throughout the month. From live music to theater performances, this historic venue is the perfect place to immerse yourself in the local arts scene. For those looking to experience the great outdoors, March is the perfect time to explore the picturesque trails of Monument Mountain. This popular hiking spot offers stunning views of the surrounding mountains and is a great way to get some fresh air and exercise while taking in the natural beauty of the area. And after a day of hiking, be sure to stop by one of the many cozy restaurants in town for a delicious meal and warm cup of locally sourced coffee. Great Barrington truly has something for everyone to enjoy in March.
April
When visiting Great Barrington in April, it is important to dress in layers as the weather can be unpredictable. Mornings can be chilly with temperatures in the 40s, but by midday it can warm up to the 60s. A light jacket or sweater is recommended for the mornings, and a t-shirt or light long-sleeved shirt for the afternoons. It is also a good idea to bring a rain jacket or umbrella, as April showers are common in this area. For footwear, comfortable walking shoes are a must. Great Barrington is a charming town with cobblestone streets and sidewalks, so high heels are not practical. Also, if you plan on hiking or exploring the nearby nature trails, a sturdy pair of sneakers or hiking boots will come in handy. Don’t forget to bring a hat and sunglasses for those sunny days, and a scarf or shawl for the cooler evenings. As for accessories, keep it simple and practical. A crossbody bag or backpack is great for carrying essentials while exploring the town. And lastly, don’t forget to bring your camera to capture the beautiful spring scenery in Great Barrington.
April is a lovely time to visit the charming town of Great Barrington, nestled in the beautiful Berkshire Mountains of Massachusetts. As the winter snow melts away, the town comes to life with a variety of activities and events for travelers to enjoy. One must-see attraction is the annual Great Barrington Arts Market, held every Saturday in April. Local artists and artisans set up booths to showcase their handcrafted goods, from pottery and jewelry to paintings and woodwork. It’s the perfect place to pick up a unique souvenir or gift for loved ones back home. For those looking to explore the great outdoors, April is an ideal month to visit Great Barrington. The weather is mild and the mountains are beginning to bloom with colorful wildflowers. Take a scenic hike along the Appalachian Trail, which runs right through town, or rent a bike and pedal along the picturesque country roads. And don’t miss out on the opportunity to sample some of the town’s famous farm-to-table cuisine. Many of the restaurants in Great Barrington source their ingredients from local farms, providing a delicious and sustainable dining experience. So come visit Great Barrington in April and experience all that this charming town has to offer!
May
As you prepare for your trip to Great Barrington in May, there are a few things to keep in mind when it comes to dressing and packing. The weather in this charming New England town can be quite unpredictable, so it’s important to be prepared for all types of conditions. Layering is key, as temperatures can range from cool mornings to warm afternoons. A light jacket or sweater, along with a scarf and comfortable walking shoes, are essential items to have on hand. Also, don’t forget to pack an umbrella or rain jacket, as showers are common this time of year. In terms of attire, Great Barrington is a casual and laid-back destination. Locals often opt for comfortable and practical clothing, such as jeans, t-shirts, and sneakers. However, if you plan on dining at some of the town’s upscale restaurants, it’s always a good idea to bring a nicer outfit. And for those planning on exploring the surrounding nature, be sure to pack some hiking gear and sturdy shoes. As for accessories, a hat and sunglasses are a must to protect you from the sun’s rays. And of course, don’t forget to bring a camera to capture the beautiful scenery and charming streets of Great Barrington.
May is an ideal time to visit the charming town of Great Barrington, located in the beautiful Berkshires of Massachusetts. The weather is perfect for outdoor activities and the town is bustling with events and festivals. One must-do during this time is to take a scenic hike along the Appalachian Trail, which runs through the outskirts of Great Barrington. The trail offers stunning views of the surrounding mountains and is a great way to immerse yourself in nature and burn off some of that delicious New England cuisine. For a taste of local culture, be sure to check out the Great Barrington Farmers Market. Held every Saturday in May, this market features a wide array of fresh produce, artisanal goods, and live music. It’s the perfect place to pick up some locally made souvenirs and try some delicious homemade treats. Another must-see in May is the Berkshire International Film Festival, a four-day event showcasing independent films from around the world. With screenings, panel discussions, and special guest appearances, this festival is a must-visit for any film enthusiast. So pack your bags and head to Great Barrington this May for a perfect blend of outdoor adventure and cultural experiences.
June
When visiting Great Barrington in June, be sure to pack light and comfortable clothing. The summer months in this charming New England town can be quite warm, so lightweight fabrics such as cotton or linen are ideal. A light jacket or sweater may also come in handy for cool evenings. It’s important to dress in layers, as the weather can be unpredictable, and you may find yourself needing to shed or add on clothing throughout the day. In terms of footwear, comfortable walking shoes are a must. Great Barrington’s quaint streets are perfect for strolling, and you’ll want to be able to explore without any discomfort. If you plan on doing any hiking or outdoor activities, be sure to bring sturdy shoes with good traction. Additionally, don’t forget to pack a hat, sunscreen, and sunglasses to protect yourself from the sun’s strong rays. And of course, don’t forget to bring your camera to capture the picturesque scenery and historic buildings of Great Barrington.
June is a fantastic time to visit the charming town of Great Barrington in the heart of the beautiful Berkshires. With the warm weather and blooming flowers, there is no shortage of outdoor activities to enjoy. Take a stroll through the picturesque downtown area and browse the quaint shops and boutiques, or grab a cup of coffee and people-watch in the town square. For a more active adventure, rent a bike and explore the scenic trails that wind through the surrounding hills and forests. And don’t miss the weekly farmers market, where you can sample delicious local produce and chat with friendly locals. No visit to Great Barrington would be complete without experiencing the rich cultural offerings of the Berkshires. June is the start of the summer season, and the area comes alive with music, theater, and art. Catch a show at the renowned Tanglewood Music Center, where world-class musicians perform in a stunning outdoor venue. Or head to the Norman Rockwell Museum to admire the iconic works of this beloved American artist. And for a taste of history, take a tour of the historic homes and gardens that dot the landscape, offering a glimpse into the town’s past. June in Great Barrington truly has something for everyone.
July
When visiting Great Barrington in July, it’s important to dress for warm weather and sunshine. The average temperature in July is around 80 degrees Fahrenheit, so light and breathable clothing is a must. I recommend packing a few pairs of comfortable shorts or skirts, along with t-shirts and tank tops. A light jacket or sweater may also come in handy for cooler evenings. Don’t forget to bring a hat and sunglasses to protect yourself from the strong summer sun. In terms of footwear, a pair of comfortable walking shoes is essential for exploring the charming streets of Great Barrington. You may also want to bring a pair of sandals for a more casual look. As for accessories, a small backpack or crossbody bag is perfect for carrying essentials while on the go. And don’t forget to pack a swimsuit if you plan on taking a dip in the nearby lakes or visiting the town’s public pool. With the right clothing and gear, you’ll be ready to experience all that Great Barrington has to offer in the beautiful month of July.
July is an ideal time to visit the charming town of Great Barrington, nestled in the rolling hills of the Berkshires. This quaint New England town comes alive in the summer months, offering a variety of activities for travelers of all ages. One of the must-do experiences in July is to attend the town’s annual Fourth of July parade, featuring colorful floats, marching bands, and a lively sense of community spirit. After the parade, head to the town’s picturesque Main Street where you can sample local treats at the farmer’s market or browse the unique boutiques and art galleries. For nature lovers, July is the perfect time to explore the great outdoors in Great Barrington. Take a scenic hike through the lush forests of Monument Mountain or enjoy a leisurely bike ride along the scenic Housatonic River. The town also has several picturesque lakes and ponds where you can cool off with a refreshing swim or try your hand at kayaking or paddleboarding. And don’t miss out on the opportunity to attend one of the many outdoor concerts and festivals that take place in July, showcasing local musicians and artists. From its rich history to its stunning natural beauty, Great Barrington has something for everyone to enjoy in the month of July.
August
When visiting Great Barrington in August, it’s important to dress in layers as the weather can be quite unpredictable. The mornings and evenings can be cool, while the afternoons can be quite warm. I recommend bringing a light jacket or sweater that can easily be taken off or put on as needed. As for footwear, comfortable walking shoes are a must, as Great Barrington is a charming town perfect for exploring on foot. Be sure to also pack a hat and sunglasses for protection from the sun. In terms of attire, the locals in Great Barrington tend to dress casually and comfortably, so there’s no need to pack any formal or fancy clothing. Light, breathable fabrics such as cotton and linen are ideal for the summer weather. And of course, don’t forget to bring a swimsuit if you plan on taking a dip in the nearby lakes or rivers. Lastly, be sure to pack a reusable water bottle to stay hydrated while out and about, and don’t forget your camera to capture the picturesque scenery of the Berkshires. Happy travels!
August is a wonderful time to visit Great Barrington, a charming town nestled in the Berkshires of Massachusetts. One of the must-see attractions during this time is the annual Berkshire Arts Festival, which showcases the works of over 200 artists from all around the country. This lively event takes place in the beautiful grounds of Ski Butternut, where visitors can not only admire and purchase unique pieces of art, but also enjoy live music, delicious food and drinks, and fun activities for the whole family. For those looking to escape the summer heat, a hike to the top of Monument Mountain is a perfect activity. This moderate hike offers stunning views of the surrounding mountains and valleys, and the lush greenery and wildflowers in August make it even more picturesque. At the summit, travelers can also learn about the fascinating history of this mountain, including its connection to famous writers such as Herman Melville and Nathaniel Hawthorne. With its refreshing breeze and peaceful atmosphere, Monument Mountain is a great way to spend a summer day in Great Barrington.
September
When visiting Great Barrington in September, it’s important to pack for all types of weather. The temperature can range from warm and sunny to cool and rainy, so it’s best to bring layers. A lightweight jacket or sweater is a must, as well as a raincoat or umbrella. Don’t forget to pack comfortable walking shoes, as the town is best explored on foot. In terms of attire, Great Barrington is a casual and laid-back town. Jeans and a t-shirt or a sundress are appropriate for most occasions. However, if you plan on dining at a nicer restaurant or attending a show, it’s always a good idea to bring a dressier outfit. As always, be mindful of the local customs and dress respectfully when visiting places of worship. And don’t forget to bring a reusable water bottle and tote bag, as Great Barrington is a green town and encourages sustainable practices. Happy travels!
Welcome to Great Barrington, a charming town nestled in the picturesque Berkshires of Massachusetts. While this town is a popular summer destination, September offers the perfect time for a quieter and more authentic experience. As the leaves begin to change and the crowds thin out, visitors can truly appreciate the natural beauty and local charm of this New England gem. One of the top things to do in September is to explore the many outdoor activities Great Barrington has to offer. Take a leisurely hike through the enchanting forests of Monument Mountain or hit the nearby Appalachian Trail for a more challenging adventure. For a more relaxing experience, rent a kayak and paddle along the Housatonic River, taking in the stunning fall foliage. And don’t miss the local farmers market, where you can sample delicious seasonal produce and mingle with friendly locals. With its idyllic setting and abundance of outdoor activities, Great Barrington is the perfect September destination for nature lovers and outdoor enthusiasts.
October
When visiting Great Barrington in October, it’s important to dress in layers to prepare for the changing weather. The days can be warm and sunny, but the evenings can get quite chilly. I recommend bringing a light jacket or sweater to throw on when needed. Also, don’t forget to pack a raincoat or umbrella as October can bring some rainy days. As for what to wear, Great Barrington is a charming New England town and has a casual and laid-back vibe. Comfortable walking shoes are a must as you’ll want to explore the quaint streets and shops. Locals tend to dress in layers as well, with jeans or khakis and a nice shirt for men, and a sundress or leggings paired with a cozy sweater for women. And don’t forget to bring a warm scarf or hat to keep you cozy as you take in the beautiful fall foliage. With these tips in mind, you’ll be dressed perfectly for a memorable visit to Great Barrington in October.
Great Barrington is a charming town nestled in the beautiful Berkshire mountains of Massachusetts. While it may be known for its stunning fall foliage, there are plenty of other activities to enjoy in October. One of my favorite things to do in this quaint town is to take a scenic drive along the Mohawk Trail. The winding roads offer spectacular views of the colorful autumn leaves, and there are plenty of pull-off spots to take in the scenery and snap some photos. After the drive, head to the Berkshire Botanical Garden for their Harvest Festival, where you can sample local cider, pick pumpkins, and enjoy live music. For history lovers, October is the perfect time to visit Great Barrington’s historic homes and sites. The town is home to the oldest home in Berkshire County, the Bidwell House Museum, which dates back to the 1750s. Another must-see is the Great Barrington Historical Society Museum, where you can learn about the town’s role in the Revolutionary War and its famous residents, including writer and activist W.E.B. Du Bois. And if you happen to be in town on Halloween, be sure to check out the Ghost Walk, a guided tour through the town’s haunted spots and spooky tales. October in Great Barrington truly offers something for everyone.
November
When visiting Great Barrington in November, it’s important to dress in layers as the weather can be quite unpredictable. I recommend bringing a warm coat, scarf, and gloves for those chilly New England evenings. It’s also a good idea to pack a waterproof jacket in case of rain. Comfortable walking shoes are a must, as the town is best explored on foot. Don’t forget to bring a hat to keep your head warm and protected from the brisk winds. In terms of what to wear, I suggest opting for casual and comfortable clothing. Great Barrington is a laid-back town, so there’s no need to dress up. A pair of jeans or leggings paired with a cozy sweater will fit right in with the locals. Don’t forget to bring a swimsuit, as some hotels in the area have heated outdoor pools and hot tubs that are perfect for relaxing after a day of exploring. Lastly, make sure to pack a camera to capture the beautiful fall foliage that blankets the town in November. With the right clothing and gear, you’ll be ready to fully enjoy the charming and picturesque town of Great Barrington.
November is a lovely time to visit Great Barrington, a charming town nestled in the beautiful Berkshire Mountains of Massachusetts. While the leaves may have fallen and the air may be crisp, there is still plenty to see and do in this quaint New England town. One must-see activity in November is a visit to the Norman Rockwell Museum, located just a short drive from Great Barrington. This museum pays tribute to the iconic American artist and showcases a vast collection of his original paintings and illustrations. It’s the perfect place to spend a cozy afternoon, admiring Rockwell’s heartwarming and nostalgic depictions of small-town life. And for those who enjoy the outdoors, November is a great time to take a hike on one of the nearby trails, such as the Monument Mountain Trail. The autumn colors may have faded, but the peacefulness and beauty of the Berkshire Mountains are still worth exploring. Plus, the cooler temperatures make for a refreshing and invigorating hike. No matter what your interests may be, Great Barrington has something to offer in November.
December
Great Barrington is a charming New England town that exudes small-town charm and warmth, especially during the winter months. As you plan your visit in December, it’s important to be prepared for the chilly temperatures and occasional snowfall. I recommend packing layers of clothing to stay comfortable throughout the day. Start with a warm base layer like thermal underwear, then add a sweater or fleece and top it off with a waterproof jacket. Don’t forget a cozy hat, gloves, and scarf to keep your extremities warm. And of course, a good pair of waterproof boots will be your best friend for exploring the town on foot. When it comes to dressing for the quaint shops and restaurants of Great Barrington, opt for casual and comfortable attire. A pair of warm jeans or leggings paired with a comfortable sweater and boots will fit in perfectly. Don’t be afraid to add some festive touches like a plaid scarf or a knitted hat to embrace the holiday spirit. And if you plan on taking a stroll through the countryside, be sure to bring some sturdy shoes to navigate the snowy trails. Finally, don’t forget to pack a reusable water bottle and a small backpack to carry your essentials as you explore this charming New England town.
December is a magical time to visit Great Barrington, nestled in the heart of the beautiful Berkshires. The town comes alive with festive lights and holiday cheer, making it the perfect destination for a winter getaway. One of the must-do activities during this time is to visit the Berkshire Botanical Garden’s Winter Lights Festival. This enchanting event features thousands of twinkling lights illuminating the garden’s pathways, creating a truly magical atmosphere. Visitors can also enjoy hot cocoa and seasonal treats while strolling through the gardens, making it a perfect evening out for the whole family. For those looking for a more cultural experience, December is also the perfect time to catch a show at the Mahaiwe Performing Arts Center. This historic theater showcases a variety of performances, from live music to theater productions, and is the perfect place to escape the cold and be entertained. After the show, take a stroll down Main Street and admire the charming storefronts decorated for the holiday season. And don’t forget to stop by one of the many local restaurants for a warm and cozy meal, using locally sourced ingredients and showcasing the best of the Berkshires’ culinary scene. With so much to do and see, December is the perfect time to experience the charm and warmth of Great Barrington.
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.
