Select the month that you will be traveling from the table below to view the packing list:
What Woodbury is like to visit throughout the year:
January
As you prepare for your trip to Woodbury in January, it’s important to pack the right clothing to stay warm and comfortable in the chilly winter weather. Layering is key, so be sure to bring a warm base layer, a mid-layer like a sweater or fleece, and a waterproof outer layer. Don’t forget a hat, gloves, and a scarf to protect your head, hands, and neck from the cold. And don’t worry about bringing fancy clothes, as the small town of Woodbury is known for its casual and laid-back atmosphere. In addition to warm clothing, I highly recommend bringing a good pair of waterproof boots with good traction. The sidewalks and trails in Woodbury may be slick with snow and ice, so it’s important to have sturdy footwear to avoid slips and falls. And if you plan on spending a lot of time outdoors, don’t forget to pack some hand and foot warmers to keep you toasty. Lastly, be sure to bring a reusable water bottle to stay hydrated, as the dry winter air can be dehydrating. With these items packed and ready to go, you’ll be prepared to explore the charming town of Woodbury and all it has to offer in the winter months.
January is a wonderful time to visit the charming town of Woodbury. Located in the beautiful state of Connecticut, this quaint New England town is full of history, culture, and outdoor activities. One of the highlights of a January visit is the annual Winterfest, a month-long celebration featuring ice carving competitions, sledding, and hot chocolate tastings. It’s the perfect way to embrace the chilly weather and experience the warmth of the local community. Aside from Winterfest, there are plenty of other things to do in Woodbury during January. Take a stroll through the town’s historic district, where you can admire the well-preserved 18th and 19th-century buildings. For art enthusiasts, the Flanders Nature Center and Land Trust offers a variety of winter workshops and events, including watercolor painting and photography classes. And for those looking for a bit of adventure, nearby Mount Tom State Park offers pristine winter hiking trails with stunning views of the surrounding countryside. No matter what your interests may be, Woodbury is the perfect destination for a cozy and memorable January getaway.
February
As you pack for your February trip to Woodbury, it’s important to keep in mind the chilly weather that awaits you. Layers will be your best friend, as temperatures can range from the 30s during the day to the teens at night. Start with a warm base layer, such as thermal underwear, and add on a sweater or fleece. A waterproof and windproof jacket is also essential, as Woodbury can experience rain and snow during this time of year. Don’t forget to pack a scarf, hat, and gloves to keep your extremities warm while exploring the charming streets of this historic town. When it comes to footwear, comfort and warmth should be your top priorities. A sturdy pair of waterproof boots will be perfect for walking on snow-covered sidewalks and hiking through the nearby parks. You may also want to bring a pair of insulated, waterproof shoes for days when the weather is particularly cold. As for accessories, a crossbody bag or backpack will be ideal for carrying your essentials while keeping your hands free. And don’t forget to bring a reusable water bottle, as staying hydrated is important no matter the weather. With these tips, you’ll be well-prepared for a cozy and enjoyable visit to Woodbury in February.
February is a wonderful time to visit the charming town of Woodbury. Located in Connecticut’s Litchfield Hills, this quaint town offers a perfect blend of history, nature, and small-town charm. One of the must-see attractions during this time of year is the Woodbury Ski Area, where visitors can hit the slopes and enjoy some winter fun. With over 20 trails and a variety of terrain, this family-owned ski area is perfect for both beginners and experienced skiers alike. In addition to skiing, February is also a great time to explore the town’s rich history. Take a stroll down Main Street and admire the well-preserved colonial homes and buildings. Make sure to visit the Glebe House Museum and Gertrude Jekyll Garden, where you can learn about the town’s early settlers and their way of life. For a taste of local culture, don’t miss the Woodbury Winter Antiques Show, where you can browse through a variety of unique antiques and vintage items. With its cozy atmosphere and array of activities, Woodbury is the perfect destination for a February getaway.
March
When visiting Woodbury in March, it’s important to dress in layers to be prepared for the unpredictable weather. The mornings can start off chilly, but by midday, the temperature can rise significantly. A light jacket or sweater paired with a scarf and comfortable walking shoes is a good option. Don’t forget to bring a rain jacket or umbrella, as March can bring some spring showers. Also, be sure to pack a hat and sunglasses for those sunny days when exploring the charming streets of Woodbury. As for what to wear, a casual and relaxed style is perfectly acceptable in Woodbury. Avoid dressing too formally, as the town has a laid-back and welcoming vibe. Locals often opt for jeans or khakis paired with a nice top or a button-down shirt. Women can opt for a sundress or skirt with a light jacket. It’s always a good idea to bring a swimsuit as well, as some of the hotels and inns have lovely outdoor pools and hot tubs to relax in after a day of exploring. And don’t forget to pack a reusable water bottle to stay hydrated while taking in the beautiful sights and sounds of Woodbury.
Welcome to Woodbury, a charming town located in the heart of Connecticut. While many travelers may think of summer or fall as the ideal time to visit, March is actually a wonderful time to experience all that this town has to offer. As the snow begins to melt and the flowers start to bloom, Woodbury comes to life with a variety of unique activities for visitors to enjoy. One of the highlights of March in Woodbury is the annual Maple Festival. This weekend-long event celebrates the town’s rich history of maple syrup production with tastings, demonstrations, and even a pancake breakfast. Another must-see during this time is the town’s famous antique shops, which are plentiful and full of treasures waiting to be discovered. And for nature lovers, the nearby Flanders Nature Center offers guided hikes and birdwatching tours through the beautiful woodlands. No matter your interests, Woodbury has something for everyone to enjoy in the month of March.
April
As April arrives in Woodbury, the weather is finally starting to warm up, making it the perfect time to explore this charming town. When packing for your trip, be sure to bring lightweight layers as the temperature can vary throughout the day. A light jacket or sweater and comfortable walking shoes are essential for comfortable sightseeing. Don’t forget to pack a rain jacket or umbrella, as April showers are common in Woodbury. When it comes to dressing for your visit, keep in mind that Woodbury has a casual and laid-back vibe. This means you can leave your fancy clothes at home and opt for comfortable and practical clothing. A pair of jeans, a t-shirt, and a light jacket will blend in perfectly with the locals. If you plan on visiting any churches or historical sites, it’s always a good idea to bring a scarf or shawl to cover your shoulders as a sign of respect. And of course, don’t forget to bring a camera to capture the beautiful scenery and charming architecture that Woodbury has to offer.
April is a lovely time to visit the quaint town of Woodbury, nestled in the rolling hills of Connecticut. As the weather warms up and the flowers start to bloom, there are plenty of activities to enjoy in this charming New England destination. One must-see attraction in April is the Woodbury Antiques Trail, where you can browse through over 35 antique shops and discover unique treasures from the past. The town also hosts a Spring Fling festival in April, featuring local artisans, live music, and delicious food to indulge in. For those looking to explore the great outdoors, April is the perfect time to visit the Flanders Nature Center and Land Trust. With over 2,000 acres of woodland, meadows, and streams, this nature preserve offers endless opportunities for hiking, birdwatching, and enjoying the peaceful scenery. Another must-do activity in April is a visit to the Woodbury Vineyards, where you can take a tour of the vineyard and sample some of their award-winning wines. And for a taste of local history, don’t miss the Glebe House Museum and Gertrude Jekyll Garden, a beautifully preserved colonial house and garden that will transport you back in time. With so much to see and do, April is the perfect time to experience the charm and beauty of Woodbury.
May
When visiting Woodbury in May, it’s important to dress in layers. The weather can be unpredictable, with chilly mornings and warm afternoons. A light jacket or sweater is necessary for the morning, but can easily be removed as the day warms up. It’s also a good idea to bring a rain jacket or umbrella, as May can bring occasional showers. Comfortable walking shoes are a must, as Woodbury is a pedestrian-friendly town with plenty of shops and attractions to explore on foot. As for what to wear, Woodbury is a casual town. You’ll fit right in with jeans and a t-shirt, but you may want to bring a slightly dressier outfit if you plan on dining at one of the nicer restaurants in town. Don’t forget to pack a swimsuit if you’re planning on taking a dip in the nearby lake or pool. And of course, don’t leave home without your camera to capture the picturesque views and charming streets of Woodbury. With these essentials, you’ll be ready to fully enjoy your May visit to this lovely New England town.
Woodbury, located in the charming state of Connecticut, is a delightful destination to visit in the month of May. One of the best ways to experience this quaint town is by taking a stroll down its picturesque Main Street. Lined with boutique shops, cozy cafes, and historic buildings, Main Street offers a glimpse into the town’s rich history and culture. Visitors can also enjoy a scenic hike through the nearby mountains or take a leisurely bike ride along the Farmington River. For a taste of the local produce, be sure to visit the Woodbury Farmers Market, which is held every Saturday in May and offers a variety of fresh fruits, vegetables, and artisanal products. No trip to Woodbury is complete without a visit to the Glebe House Museum and Gertrude Jekyll Garden. This beautifully preserved 18th-century home gives visitors a glimpse into colonial life and features a stunning garden designed by the renowned English landscape architect, Gertrude Jekyll. In May, the garden is in full bloom with vibrant flowers and lush greenery, making it the perfect spot for a peaceful afternoon stroll. For history buffs, the Woodbury Historical Society Museum is also a must-visit, with its collection of artifacts and exhibits showcasing the town’s rich past. With its charming Main Street, stunning natural landscapes, and fascinating museums, Woodbury is the perfect destination for a memorable May getaway.
June
As you prepare for your summer trip to beautiful Woodbury, there are a few key things to keep in mind when it comes to dressing for the warm weather. While the days can get quite hot, the evenings can still be cool, so it’s best to dress in layers. A light jacket or sweater will come in handy when the sun goes down. In terms of clothing, comfortable and breathable fabrics like cotton and linen are your best bet. And don’t forget your sunglasses and a hat to protect you from the bright sun! When it comes to footwear, opt for comfortable walking shoes as you’ll likely be exploring the charming streets of Woodbury on foot. Sandals or flip flops are great for the beach, but not always the best choice for cobblestone streets and uneven sidewalks. And don’t forget to pack a swimsuit, as Woodbury is home to beautiful beaches and lakes perfect for a refreshing dip. Lastly, make sure to bring a reusable water bottle to stay hydrated and a small backpack or tote bag to carry all your essentials while out and about. With these tips in mind, you’ll be dressed and prepared for a wonderful summer adventure in Woodbury. Happy travels!
Welcome to the charming town of Woodbury, nestled in the heart of New England. June is the perfect time to visit this quaint destination, as the warm weather brings the town to life. Start your day with a stroll through the picturesque Main Street, lined with charming boutiques and local cafes. Stop by the renowned Woodbury Kitchen for a delicious breakfast made with locally sourced ingredients. Don’t forget to pick up some handmade crafts and souvenirs at the weekly farmer’s market, held every Saturday in the town center. For history buffs, a visit to the Glebe House Museum is a must. This beautifully preserved colonial house offers a glimpse into the daily life of early settlers in the area. The nearby Quassy Amusement Park is also a great spot for families, with thrilling rides and a water park to cool off in the summer heat. End your day with a scenic hike through the Mattatuck State Forest, where you can take in the stunning views of the rolling hills and lush greenery. With its small town charm and endless activities, Woodbury is the perfect June getaway for any traveler.
July
When visiting Woodbury in the summer month of July, it’s important to dress for warm, sunny weather. The average temperature in July ranges from 70-85 degrees Fahrenheit, so lightweight and breathable clothing is a must. I recommend bringing light-colored clothing to reflect the sun’s rays and a hat to protect your face from the strong UV rays. Additionally, don’t forget to pack a pair of comfortable walking shoes as you’ll likely be exploring the quaint streets of Woodbury on foot. While the days may be warm, the evenings can bring a slight chill, so it’s best to pack a light jacket or sweater for the cooler nights. It’s also a good idea to bring a small umbrella or rain jacket as July can bring occasional showers. As for accessories, a reusable water bottle is a must to stay hydrated while out and about. And don’t forget to bring a camera to capture the picturesque scenery and charming architecture of Woodbury. Overall, dressing in light, comfortable layers and being prepared for any type of weather will ensure a pleasant and enjoyable visit to this charming town.
July is the perfect time to visit the charming town of Woodbury, nestled in the rolling hills of Connecticut. The warm summer weather invites visitors to explore the town’s quaint Main Street, lined with unique shops and delicious eateries. Take a leisurely stroll and admire the beautifully preserved colonial homes, or hop on a bike and pedal along the picturesque country roads. For a taste of local culture, be sure to check out the Summer Concert Series held in Hollow Park, featuring live music and delicious food from the town’s many food trucks. As an avid traveler, I always make it a point to seek out outdoor activities when visiting a new destination. And Woodbury does not disappoint in this regard. July is the perfect time to take a hike in the nearby Flanders Nature Center and Land Trust, where you can explore miles of scenic trails through forests and meadows. For a more challenging adventure, head to the nearby White Memorial Conservation Center and climb to the top of Mount Tom for stunning views of the surrounding landscape. And don’t forget to cool off with a dip in the crystal-clear waters of Lake Quassapaug, a popular spot for swimming, boating, and picnicking. No matter what your interests may be, Woodbury has something for everyone in the month of July.
August
When traveling to the charming town of Woodbury in August, it’s important to dress for both comfort and style. The summer temperatures can get quite warm, so lightweight and breathable clothing is a must. A pair of comfortable walking shoes is also essential, as Woodbury is a pedestrian-friendly destination with many cobblestone streets and charming shops to explore. While the days can be hot, the evenings can cool down, so I always recommend bringing a light jacket or sweater. This will also come in handy if you plan on visiting any of the nearby vineyards or taking a sunset stroll along the Hudson River. And don’t forget to pack a hat and sunscreen to protect yourself from the sun’s rays. As for attire, Woodbury is a quaint and picturesque town, so I suggest dressing in casual yet put-together outfits. Think sundresses, khaki shorts, and linen shirts for a comfortable and stylish look. And don’t forget to bring a camera to capture the beauty of this charming New England town!
August is a fantastic time to visit the charming town of Woodbury, located in the heart of Connecticut. As the summer heat starts to wane and the leaves begin to change, this picturesque town offers a plethora of activities for visitors to enjoy. One of the must-do activities in August is to take a stroll through the beautiful Glebe House and Museum. This historic home, built in 1750, gives visitors a glimpse into colonial life and the history of the town. The gardens surrounding the house are also a sight to behold, with colorful blooms and tranquil pathways perfect for a peaceful afternoon. For a taste of the local culture, head to the Woodbury Farmers Market held every Saturday. Here, you can sample fresh produce, artisanal goods, and even chat with the friendly locals. August also brings the annual Woodbury Antique and Flea Market, where you can browse through unique treasures and snag a bargain or two. And no trip to Woodbury is complete without a visit to the historic Old Woodbury Historical Society, where you can learn about the town’s rich history and admire the well-preserved architecture. With so much to do and see, August is the perfect time to experience the charm and beauty of Woodbury.
September
When visiting Woodbury in September, it’s important to remember that the weather can be quite unpredictable. While it may still be warm and sunny during the day, the evenings can quickly turn chilly. This means it’s important to dress in layers. Bring a light jacket or sweater to throw on when the temperature drops. And don’t forget to pack a scarf or hat to protect yourself from the cool autumn breeze. In terms of footwear, comfortable walking shoes are a must when exploring Woodbury. The town is known for its charming cobblestone streets and historic sites, so you’ll want to be prepared for plenty of walking. Also, consider bringing a small backpack or crossbody bag to carry your essentials while keeping your hands free. And for those planning on visiting any of the nearby parks or nature reserves, don’t forget to pack a pair of sturdy hiking boots. With the right clothing and gear, you can fully enjoy all that Woodbury has to offer in the beautiful month of September.
September is a fantastic time to visit the charming town of Woodbury, located in the heart of Connecticut. As the summer crowds start to dwindle, the town begins to take on a peaceful and serene atmosphere. One of my favorite things to do in September here is to take a leisurely stroll through the historic Main Street, admiring the beautifully preserved colonial architecture and quaint shops. The crisp autumn air and changing leaves provide the perfect backdrop for a relaxing day of exploration. For outdoor enthusiasts, September is the perfect time to take advantage of the many hiking trails in and around Woodbury. The foliage is just starting to turn, creating a stunning display of colors against the rolling hills and picturesque farmland. One of my favorite hikes is the Black Rock State Park trail, which offers panoramic views of the surrounding countryside. And after a day of hiking, be sure to stop by one of the local farm stands for some fresh apple cider and homemade pies – the perfect end to a perfect day in Woodbury.
October
When visiting Woodbury in October, it’s important to dress in layers as the weather can be quite unpredictable. The mornings and evenings tend to be cool, while the afternoons can be warm and sunny. I recommend bringing 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 October is known for its occasional showers. When exploring the charming streets of Woodbury, comfortable shoes are a must. The town is known for its cobblestone sidewalks and hilly terrain, so leave the high heels at home. A pair of sturdy walking shoes or sneakers will be your best friend as you navigate the quaint shops and historic buildings. And don’t forget to bring a small backpack or tote bag to carry your essentials, such as a water bottle, camera, and souvenirs. With these tips in mind, you’ll be prepared for a comfortable and enjoyable visit to Woodbury in October.
Welcome to Woodbury, a charming town located in the heart of Connecticut. If you’re planning a trip here in October, you’re in for a treat. With the leaves changing colors and a crispness in the air, this is the perfect time to explore the outdoors. One of the top activities to do in October is to take a scenic drive on the Litchfield Hills Loop. This 100-mile route takes you through picturesque small towns, past stunning views of the fall foliage, and up to the top of Mount Tom for a panoramic view. Don’t forget to stop at local farm stands along the way to pick up some fresh apples and pumpkins. For history buffs, Woodbury is home to the famous Glebe House Museum & Gertrude Jekyll Garden. This 18th-century house museum was once a Revolutionary War-era parsonage and is now filled with period furnishings and artifacts. The Gertrude Jekyll Garden, designed by the renowned British horticulturist, is a tranquil oasis with beautiful colors and scents in the autumn. And if you’re feeling adventurous, take a hike on the nearby Mattatuck Trail, which offers stunning views of the fall foliage and takes you through the historic Hollow Park and Nature Preserve. October in Woodbury truly offers something for everyone.
November
November in Woodbury is a beautiful time to visit, with the changing leaves and crisp autumn air. However, the temperatures can vary greatly during this month, so it’s important to pack accordingly. Layers are key to staying comfortable throughout the day. Start with a light base layer, like a long-sleeved shirt or sweater, and then add on a warmer mid-layer, such as a fleece or light jacket. Top it off with a waterproof outer layer, as November can also bring some rain. Don’t forget to pack a scarf, hat, and gloves for those chilly mornings and evenings. As for footwear, comfortable walking shoes are a must. Woodbury is a charming town with many cobblestone streets, so leave the high heels at home. A good pair of sneakers or boots will do the trick. And don’t forget to bring a small backpack or crossbody bag to carry your essentials while exploring. In terms of style, Woodbury is a laid-back and casual town, so leave the fancy clothes at home and opt for comfortable and practical outfits. And don’t worry about bringing too much, as there are plenty of charming shops and boutiques in town where you can pick up any items you may have forgotten. Happy travels!
As November comes around, the charming town of Woodbury transforms into a winter wonderland. The streets are lined with twinkling lights and the crisp air is filled with the scent of hot apple cider. One of the must-do activities during this time is to visit the annual Pumpkin Festival at Hollow Park. Here, you can wander through rows of pumpkins, taste local treats, and even take a hayride through the picturesque countryside. It’s the perfect way to embrace the cozy fall vibes of Woodbury. After indulging in pumpkin treats, take a stroll through the historic Main Street. Admire the beautiful colonial homes and browse through the quaint shops, filled with unique gifts and souvenirs. For a taste of local history, stop by the Glebe House Museum and explore its fascinating collection of artifacts and exhibits. And if you’re feeling adventurous, head out to the nearby Quassy Amusement Park for some thrilling rides and games. November in Woodbury offers a perfect blend of seasonal festivities and small-town charm, making it an ideal destination for travelers looking to escape the hustle and bustle of city life.
December
When planning a visit to Woodbury in the month of December, it’s important to pack warm and versatile clothing. The weather in this charming town can be quite chilly this time of year, so be sure to bring layers such as sweaters, scarves, and a sturdy winter coat. It’s also a good idea to pack waterproof shoes or boots, as there may be some snow on the ground. Don’t forget to bring gloves, a hat, and a warm pair of socks to keep your extremities toasty while exploring the town. As for what to wear while exploring Woodbury, opt for comfortable and casual attire. This is a quaint and laid-back town, so leave your fancy dresses and high heels at home. A pair of jeans, a cozy sweater, and a comfortable pair of shoes will be perfect for wandering the streets and visiting the local shops. And don’t forget to bring a small umbrella or rain jacket, just in case the weather takes a turn for the worse. Overall, the key is to dress comfortably and be prepared for all types of weather while enjoying the charming town of Woodbury in December.
Hey there travelers, if you find yourself in Woodbury during the month of December, fear not as there are plenty of fun and festive activities to enjoy. One of the must-do’s during this time of year is to visit the Woodbury Winter Wonderland. This charming village transforms into a magical wonderland with twinkling lights, holiday decorations, and an ice-skating rink. It’s the perfect place to get into the holiday spirit and take some memorable photos. Another great activity for December visitors is to take a horse-drawn carriage ride through the quaint streets of Woodbury. Snuggle up under warm blankets as you trot through the town, admiring the festive decorations and taking in the crisp winter air. After the ride, be sure to stop by one of the local cafes for a cup of hot cocoa or mulled wine. It’s a wonderful way to experience the charming town of Woodbury during the holiday season.
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.
