Select the month that you will be traveling from the table below to view the packing list:
What Bennington is like to visit throughout the year:
January
If you’re planning a trip to Bennington in January, you’ll want to be prepared for the chilly weather. Layering is key for staying warm and comfortable while exploring this picturesque town. Start with a base layer of thermal underwear, followed by a warm sweater or fleece, and top it off with a waterproof jacket. Don’t forget a hat, scarf, and gloves to protect your extremities from the cold. It’s also a good idea to bring waterproof boots or shoes, as snow and slush are common in January. And if you plan on doing any outdoor activities, such as skiing or snowshoeing, be sure to pack appropriate gear and clothing for those as well. As for what to wear while exploring Bennington in January, I recommend sticking to comfortable and practical clothing. Opt for dark colors, as they tend to hide dirt and stains better in case of any spills or messes. You’ll also want to bring a good pair of walking shoes, as there are many charming streets and shops to explore in town. And don’t forget to bring a small backpack to carry your essentials, such as a water bottle, snacks, and a camera to capture the beauty of Bennington in the winter. With the right clothing and gear, you’ll be able to fully enjoy all that this cozy town has to offer in January.
Welcome to beautiful Bennington, Vermont in the heart of winter! January may be chilly, but don’t let that stop you from exploring all that this charming town has to offer. Bundle up and head to the Bennington Museum to immerse yourself in the local history and art scene. From the stunning Grandma Moses collection to the fascinating Battle of Bennington exhibit, there is something for everyone to enjoy. Afterward, warm up with a cup of hot cocoa at one of the nearby cozy cafes. For all the outdoor enthusiasts, January in Bennington means prime skiing conditions. Grab your skis or snowboard and hit the slopes at the nearby Mount Snow or Stratton Mountain. Both resorts offer breathtaking views and a variety of trails for all skill levels. After a day on the mountain, unwind with a soak in the hot tub at one of the many charming bed and breakfasts in town. And don’t forget to try some of the local comfort food, like a hearty bowl of Vermont cheddar soup, to warm you up from the inside out. January in Bennington is a winter wonderland waiting to be explored!
February
When visiting the charming town of Bennington in February, it’s important to dress for the unpredictable weather. While the days may start off chilly, they can quickly warm up and then turn cold again in the evening. I recommend dressing in layers, so you can adjust accordingly. Start with a warm base layer, such as thermal underwear or a long-sleeved shirt, then add a sweater or fleece, and top it off with a waterproof jacket. Be sure to bring a scarf, gloves, and a hat as well, as these can make all the difference in keeping you warm and comfortable. While exploring Bennington, you’ll want to blend in with the locals and dress in a casual, comfortable style. Jeans or leggings paired with a cozy sweater and boots will make for a practical and stylish outfit. Don’t forget to bring a comfortable pair of walking shoes, as you’ll want to explore the town’s charming streets and parks. And of course, don’t leave home without a camera to capture the picturesque New England scenery. Lastly, be sure to pack an umbrella and rain jacket, as February in Bennington can bring rain and snow showers. With these clothing essentials and a sense of adventure, you’ll be well-prepared for your February visit to Bennington.
Welcome to the charming town of Bennington, Vermont! February may be the peak of winter here, but don’t let that stop you from experiencing all this town has to offer. Bundle up and head to the slopes at Mount Snow or Stratton Mountain for some of the best skiing and snowboarding in the Northeast. For a more laid-back winter activity, take a scenic snowshoe or cross-country ski through the picturesque forests and hills of the Green Mountains. After a day of outdoor adventures, warm up with a visit to Bennington’s many art galleries and museums. The Bennington Museum features an impressive collection of American folk art and contemporary works, while the Southern Vermont Arts Center showcases a variety of local and regional artists. And don’t forget to indulge in some delicious Vermont specialties, such as maple syrup and artisanal cheeses. February may be cold, but with its cozy atmosphere and abundance of activities, Bennington is the perfect winter getaway destination.
March
When planning a trip to Bennington in March, it’s important to pack for a variety of weather conditions. While the days can be pleasantly warm, the evenings can still be quite chilly. To stay comfortable, I recommend dressing in layers. Bring a light jacket or sweater to wear during the day and a heavier coat for the evenings. It’s also a good idea to pack a rain jacket or umbrella, as the weather can be unpredictable in March. As for footwear, comfortable walking shoes are a must. Bennington is a pedestrian-friendly town with many historic sites and charming shops to explore. You’ll want to be able to walk comfortably for hours. And don’t forget to pack a pair of sturdy shoes for any outdoor activities you may have planned, such as hiking in the nearby Green Mountains. Lastly, be sure to bring a hat, scarf, and gloves to stay warm during any outdoor adventures. With the right clothing, you’ll be able to fully enjoy all that Bennington has to offer in the beautiful month of March.
Welcome to Bennington, Vermont in the month of March! The snow may still be on the ground, but there is no shortage of things to do in this charming New England town. For a dose of history and culture, be sure to visit the Bennington Battle Monument, a towering structure commemorating the Battle of Bennington during the American Revolution. From the top, you’ll be treated to sweeping views of the surrounding countryside. Afterward, make your way to the Bennington Museum, where you can explore a collection of art and artifacts that showcase the town’s rich history. If you’re in search of outdoor adventures, March is the perfect time to visit Bennington. Head to Mount Anthony for a scenic hike through the snow-covered trails, or rent a pair of snowshoes and explore the picturesque woods. For a taste of local flavor, stop by the Bennington Farmers’ Market, where you can sample fresh produce and homemade goods from the region. And don’t forget to warm up with a cup of hot apple cider from one of the local orchards. No matter what your interests may be, there’s something for everyone to enjoy in Bennington this March.
April
When traveling to Bennington in April, it’s important to be prepared for the unpredictable weather that comes with springtime. The key to dressing for this month is layering. Start with a light base layer, such as a long-sleeve shirt or sweater, and then add a waterproof jacket or windbreaker on top. This will ensure that you stay warm and dry, no matter what the weather may bring. As for footwear, be sure to bring comfortable walking shoes as Bennington is a great town for exploring on foot. Depending on the activities you have planned, you may also want to bring a pair of waterproof shoes or boots for hiking or exploring outdoors. Don’t forget to pack a hat and sunglasses for those sunny days, and a scarf or gloves for the chillier evenings. And of course, an umbrella is always a good idea in case of rain showers. With these tips in mind, you’ll be ready to enjoy all that Bennington has to offer in April!
Welcome to Bennington, Vermont in the beautiful month of April! This charming New England town is full of activities and sights to explore during this time of year. For outdoor enthusiasts, the nearby Green Mountains provide ample opportunities for hiking and enjoying the crisp spring air. A hike up Mount Equinox offers stunning views of the surrounding area and a chance to spot some early wildflowers. Don’t forget to pack a picnic lunch to enjoy at the summit. For those interested in history and culture, a visit to the Bennington Museum is a must. This museum showcases the rich heritage of the town and its surrounding areas, including the famous Battle of Bennington during the American Revolution. April also marks the start of the Bennington Farmers’ Market, where you can sample local produce and handmade goods while supporting the community. And no trip to Bennington is complete without a visit to the iconic covered bridges, such as the Silk Road Bridge, for a quintessential New England experience. So pack your bags and come experience the beauty and charm of Bennington in April!
May
As you prepare for your trip to charming Bennington in May, it’s important to dress appropriately for the weather and local culture. With temperatures ranging from the 50s to 70s, layers are key. Start with a lightweight, waterproof jacket as occasional showers are not uncommon this time of year. Pack a mix of short and long-sleeved shirts, comfortable pants, and a scarf or shawl for chilly evenings. Don’t forget a pair of comfortable walking shoes for exploring the quaint streets and nearby hiking trails. In addition to clothing, be sure to bring a small daypack to carry essentials while sightseeing. This should include a refillable water bottle, sunscreen, and a hat for protection from the sun. A portable phone charger and a camera are also great items to have on hand for capturing memories. As always, it’s important to be respectful of the local culture and dress modestly when visiting religious sites. And don’t forget to throw in a few extra layers for any unexpected changes in weather. With the right clothing and accessories, you’ll be prepared for a comfortable and enjoyable trip to beautiful Bennington.
Welcome to Bennington, a charming town nestled in the heart of Vermont. May is the perfect time to visit, with the warm weather and blooming flowers creating a picturesque backdrop for your adventures. Start your day by strolling through the vibrant Bennington Farmers’ Market, where you can sample local produce and products while chatting with friendly vendors. From there, head to the Bennington Museum to learn about the town’s rich history and admire the impressive collection of artwork, including pieces by Grandma Moses. For a taste of small-town Americana, take a drive along the Covered Bridges Scenic Byway, where you’ll pass by several charming covered bridges and get a glimpse of rural life in Vermont. No trip to Bennington is complete without a visit to the iconic Bennington Battle Monument, a 306-foot tower commemorating the Revolutionary War battle that took place here. Climb to the top for stunning views of the surrounding mountains and countryside. For a more leisurely activity, spend an afternoon exploring the lush gardens at the historic Park-McCullough House. End your day with a delicious farm-to-table dinner at one of Bennington’s many cozy restaurants, where you can savor the flavors of Vermont while chatting with friendly locals. May is the perfect time to experience the laid-back charm and natural beauty of Bennington, and I guarantee you’ll leave feeling refreshed and rejuvenated.
June
When visiting the charming town of Bennington in June, it’s important to dress for both comfort and style. The weather can be unpredictable, so be sure to bring layers that can easily be added or removed. A lightweight rain jacket is also a must, as showers are common in this lush part of Vermont. As for footwear, opt for comfortable walking shoes as you’ll want to explore the quaint streets and historic sites on foot. In terms of attire, a casual and relaxed look is perfectly suitable for Bennington. The locals are welcoming and laid-back, so there’s no need to dress up. Light and airy fabrics such as cotton and linen are ideal for the warmer temperatures, and don’t forget to pack a few items for cooler evenings. A small backpack or crossbody bag is also handy for carrying essentials while exploring, and don’t forget to bring a reusable water bottle to stay hydrated during your adventures. With the right clothing and gear, you’ll be ready to fully immerse yourself in the beauty and charm of Bennington.
June is a wonderful time to visit the charming town of Bennington, located in the beautiful state of Vermont. With the arrival of summer, the town is alive with vibrant energy and plenty of activities to enjoy. One must-see attraction is the Bennington Battle Monument, standing tall at 306 feet and commemorating the Revolutionary War battle that took place here. Visitors can climb to the top for breathtaking views of the surrounding Green Mountains and learn about the history of this significant event. For a taste of local culture, be sure to visit the Bennington Center for the Arts. This museum showcases a diverse collection of art, from contemporary paintings to Native American artifacts. In addition, the center hosts various events and workshops throughout the month, providing a unique opportunity to connect with the local art scene. And don’t forget to stop by the Bennington Farmers Market, held every Saturday, where you can sample delicious local produce and handmade goods while supporting the community. June in Bennington truly offers something for everyone, making it a must-visit destination for any traveler.
July
When visiting Bennington in the month of July, it is important to dress for the warm and sunny weather. Lightweight, breathable clothing is a must to stay cool and comfortable while exploring the quaint town. I recommend packing items such as shorts, t-shirts, and sundresses. Don’t forget to bring a hat to protect yourself from the strong Vermont sun, and a light jacket for cooler evenings. In addition to clothing, it is also important to bring comfortable walking shoes as Bennington is a wonderful town to explore on foot. A sturdy pair of sandals or sneakers will suffice for most activities, but if you plan on hiking or exploring nature trails, I suggest packing a pair of hiking boots. And of course, don’t forget to bring a refillable water bottle to stay hydrated while taking in the beautiful sights of Bennington. With these items in your suitcase, you’ll be ready to fully enjoy all that this charming town has to offer in the summer.
July is a fantastic time to visit the charming town of Bennington, located in the beautiful state of Vermont. This small town is bursting with character and offers a variety of activities for travelers to enjoy. One must-see attraction is the Bennington Battle Monument, a towering 306-foot obelisk that commemorates the Revolutionary War battle of Bennington. Visitors can take an elevator to the top for stunning views of the surrounding countryside. Additionally, the Bennington Museum is a must for history buffs, with its impressive collection of artwork and artifacts from the region’s past. For those looking to immerse themselves in nature, a visit to the Green Mountain National Forest is a must. July is the perfect time to explore the numerous hiking trails and scenic drives in the area, with the trees in full bloom and the weather just right for outdoor activities. And don’t miss out on the local farmers’ market, held every Saturday in July, where you can sample delicious local produce and crafts. Whether you’re interested in history, nature, or simply enjoying the laid-back atmosphere of a charming New England town, Bennington has something for every traveler in the month of July.
August
When packing for a trip to Bennington in August, it’s important to dress for both warm weather and potential rain showers. The average temperature in August ranges from 55-80 degrees Fahrenheit, so light layers are key. Bring a mix of short-sleeved shirts and lightweight long-sleeved options, as well as a light rain jacket or umbrella. Comfortable walking shoes are a must for exploring the charming streets of downtown Bennington and its surrounding countryside. When it comes to dressing for activities, consider the type of outdoor adventures you have planned. If you’re hiking in the nearby Green Mountains, bring sturdy hiking boots and layers for the changing temperatures at higher elevations. For a day of swimming at Lake Paran, pack a swimsuit, towel, and sunscreen. And if you’re planning to attend a performance at the renowned Bennington Center for the Arts, a nice outfit or dress would be appropriate. Overall, be prepared for a mix of warm and cooler temperatures and bring versatile clothing options to fully enjoy all that Bennington has to offer in August.
August is a wonderful time to visit the charming town of Bennington, located in the beautiful Green Mountains of Vermont. This time of year, the town is bustling with activity and offers a plethora of things to do. One of the must-see attractions is the Bennington Battle Monument, a towering 306-foot structure that commemorates the Battle of Bennington during the American Revolutionary War. Visitors can climb to the top of the monument for stunning views of the surrounding mountains and learn about the town’s rich history at the on-site museum. Another must-do activity in Bennington is exploring the local farmers market, held every Saturday in the heart of town. Here, you can find a variety of fresh produce, artisanal goods, and local crafts. It’s a great way to support the community and get a taste of the region’s delicious offerings. And while you’re in town, be sure to take a stroll down Main Street and stop by the many quaint shops and galleries. August is also the perfect time to enjoy outdoor activities such as hiking, biking, and kayaking in the nearby parks and lakes. With its charming atmosphere and abundance of things to do, Bennington is the perfect summer destination for travelers looking for a mix of history, culture, and outdoor adventure.
September
When traveling to Bennington in September, it’s important to pack for unpredictable weather. The autumn season in Vermont can bring a mix of warm and cool temperatures, as well as occasional rain showers. I recommend dressing in layers, so you can easily adjust to the changing weather throughout the day. A light jacket or sweater, along with a waterproof outer layer, will ensure you stay comfortable while exploring the charming town of Bennington. In terms of footwear, comfortable walking shoes are a must. Bennington is a pedestrian-friendly town, and you’ll want to be prepared for strolling along its quaint streets and scenic trails. Additionally, packing a small umbrella or rain jacket is always a good idea, as the weather can change quickly. And don’t forget to bring a camera to capture the beautiful autumn foliage that blankets the surrounding hills. With these essentials in your suitcase, you’ll be well-prepared to enjoy the charming town of Bennington in September.
September is the perfect time to visit the charming town of Bennington, Vermont. As the leaves begin to change and the air turns crisp, this small town comes to life with autumnal festivities. One must-do activity during this time is to take a drive along the scenic Route 7, known as the “Moose Trail”. This winding road boasts stunning views of the colorful foliage and is the perfect way to take in the beauty of the Vermont countryside. In addition to admiring the fall foliage, September in Bennington also offers a plethora of cultural experiences. Don’t miss the annual Bennington Arts Weekend, where local artists showcase their talents through a variety of exhibits, performances, and workshops. And for history buffs, a visit to the Bennington Battle Monument is a must. This towering structure commemorates the Battle of Bennington, a pivotal moment in the American Revolution. September truly is a special time to visit Bennington, where you can soak up the beauty of nature and immerse yourself in the rich culture and history of this charming town.
October
October in Bennington is a magical time to visit. The leaves are changing colors, the air is crisp, and the town is bustling with fall festivities. When preparing for your trip, be sure to pack layers as the weather can be unpredictable. A light jacket, scarf, and comfortable walking shoes are a must. Don’t forget to bring a raincoat or umbrella, as well. The key to dressing for October in Bennington is to be prepared for all types of weather. As for attire, Bennington is a laid-back, casual town. You’ll fit right in with a pair of jeans, a cozy sweater, and a flannel shirt. If you plan on exploring the many hiking trails in the area, be sure to bring sturdy shoes and a waterproof jacket. And don’t forget to pack a hat and gloves to keep you warm during those chilly autumn nights. Trust me, you’ll want to spend as much time as possible outdoors, taking in the beautiful fall foliage. So pack smart and be ready to enjoy all that Bennington has to offer in October.
October is a magical time to visit the charming town of Bennington. As the leaves change into vibrant shades of red, orange, and yellow, the town comes alive with cozy fall activities. One of the must-do experiences in October is to take a scenic drive along the famous Route 7. This picturesque route offers stunning views of the rolling hills and colorful foliage, making for the perfect fall road trip. Along the way, be sure to stop at local farm stands to pick up some fresh apples and pumpkins, a quintessential autumn treat. For history buffs, a visit to the Bennington Battle Monument is a must. This 306-foot-tall obelisk commemorates the site of a Revolutionary War battle that took place in 1777. Climb to the top for a breathtaking view of the surrounding countryside and learn about the significant role this small town played in American history. Afterward, head over to the Bennington Museum to explore their eclectic collection of art and artifacts, including works by local artists and the iconic Grandma Moses. October is the perfect time to soak up the rich history and natural beauty of Bennington.
November
When visiting the charming town of Bennington in November, it’s important to dress for the unpredictable weather. The days may start off chilly, but as the sun rises, you may find yourself shedding layers. My advice is to dress in layers, with a warm base layer and a waterproof jacket on top. It’s also a good idea to bring a scarf, gloves, and a hat to keep you warm during any sudden drops in temperature. As for footwear, a comfortable pair of walking shoes or boots will be your best friend when exploring the town’s cobblestone streets. In addition to dressing for the weather, it’s also important to dress respectfully when visiting Bennington. This is a small town with a strong sense of community, so it’s important to dress in a modest and conservative manner. Opt for comfortable yet modest clothing, such as jeans or slacks paired with a nice sweater or blouse. When visiting any religious sites, make sure to cover your shoulders and knees out of respect. And don’t forget to bring a day pack to carry your essentials, such as a water bottle, camera, and guidebook as you explore the charming sights of Bennington.
Welcome to Bennington, a charming town located in the southwestern corner of Vermont. November is a lovely time to visit, as the crisp fall air and changing leaves provide a picturesque backdrop for exploring this historic town. One must-see attraction is the Bennington Battle Monument, standing tall at 306 feet and commemorating the Battle of Bennington during the American Revolution. Climb to the top for stunning views of the surrounding countryside. Another must-do activity is to take a drive along the famous Covered Bridges Scenic Byway, where you can admire the quaint covered bridges that dot the landscape. Be sure to stop and take a stroll through the charming village of Arlington, with its classic New England architecture and cozy cafes. When you’re ready for a break from sightseeing, head to the Bennington Museum to learn about the town’s rich history and admire its impressive collection of regional art. For a taste of local flavor, visit the Bennington Farmer’s Market, open every Saturday in November. Here you can sample delicious Vermont cheeses, fresh produce, and homemade goods. And don’t forget to warm up with a hot cup of apple cider at one of the many cozy coffee shops around town. With its small-town charm and endless autumn activities, Bennington is the perfect destination for a November getaway.
December
As you plan your trip to Bennington in December, it’s important to remember that the weather can be quite unpredictable. The key to dressing for this time of year is to layer up. Start with a warm base layer, such as long-sleeved shirts and pants, and add on a sweater or fleece for extra warmth. A waterproof and windproof jacket is a must-have, as well as a hat, gloves, and a scarf to protect against the chilly winds. Don’t forget to pack a pair of waterproof shoes or boots to keep your feet dry while exploring the town. When it comes to what to wear in Bennington in December, it’s all about comfort and practicality. The town has a casual and laid-back vibe, so leave your fancy clothes at home and opt for comfortable, versatile pieces. You’ll want to bring a mix of both warm and cool weather clothing, as temperatures can range from below freezing to mild. Be sure to pack some warm socks and pajamas for cozy nights indoors. And don’t forget to bring a reusable water bottle and a daypack for carrying all your essentials while out and about. With these tips in mind, you’ll be well-prepared to enjoy all that Bennington has to offer in December.
Welcome to beautiful Bennington, Vermont in the month of December! This charming New England town is the perfect place to get into the holiday spirit. Start your day by strolling through the historic downtown area, decorated with twinkling lights and festive wreaths. Stop by the Bennington Potters store to browse their unique pottery and pick up some handcrafted gifts for your loved ones. Next, head over to the Bennington Museum to view their collection of Norman Rockwell paintings and learn about the town’s rich history. For a taste of local flavor, grab a hot cider and a maple cream donut at the Apple Barn and Country Bake Shop. And don’t forget to snap a photo with the iconic Bennington Battle Monument, lit up for the holiday season. In the evening, catch a performance at the Oldcastle Theatre Company, a beloved local theater that puts on a variety of shows throughout the year. For a cozy dinner, head to the South Street Cafe where you can warm up with a bowl of homemade chili and listen to live music. And no trip to Bennington in December is complete without a visit to the Annual Bennington Festival of Trees. This magical event features dozens of beautifully decorated Christmas trees, each sponsored by a local business or organization. It’s the perfect way to end your day and get into the holiday spirit in this charming Vermont 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.
