Select the month that you will be traveling from the table below to view the packing list:
What Highwood is like to visit throughout the year:
January
Highwood, with its charming small-town feel and stunning natural beauty, is a must-visit destination for any traveler. However, when planning a trip to this picturesque town in January, it’s important to pack appropriately. While the weather can be unpredictable, it’s safe to say that you’ll need to bundle up to stay warm. I recommend bringing a warm winter coat, gloves, a hat, and a sturdy pair of boots. Layering is key, as temperatures can fluctuate throughout the day. A waterproof jacket is also a must, as Highwood is known for its occasional rain and snow showers. When it comes to dressing for indoor activities, such as visiting museums or restaurants, a nice pair of jeans or slacks paired with a sweater or blouse will do just fine. However, don’t forget to pack a dressier outfit for any special events or dinners you may have planned. As for footwear, a comfortable pair of walking shoes is essential for exploring Highwood’s charming streets and hiking trails. Lastly, don’t forget to bring a camera to capture the stunning winter scenery and memories that will last a lifetime. With the right attire and gear, you’ll be able to fully enjoy all that Highwood has to offer in the winter months.
January is a fantastic time to visit the charming town of Highwood, nestled in the heart of the Rocky Mountains. While the snowy landscape may deter some travelers, I highly recommend embracing the winter wonderland and taking advantage of the unique activities this season has to offer. Start your day with a scenic snowshoe hike through the nearby trails, surrounded by towering pine trees and stunning mountain views. After working up an appetite, warm up with a cup of hot cocoa at one of the cozy cafes in town before heading to the famous Highwood Ice Rink, where you can glide across the ice to the sound of traditional Scottish bagpipes. As the sun sets, make your way to the Highwood Winter Festival, a celebration of all things winter. Here, you can try your hand at ice sculpting, take a horse-drawn sleigh ride, and even participate in a polar plunge into the icy waters of the nearby lake. For a more relaxed evening, cozy up by the fire at one of the local pubs and enjoy a hearty meal of traditional Scottish dishes. January in Highwood may be chilly, but with the town’s warm hospitality and endless winter activities, it’s truly a magical time to visit.
February
When traveling to Highwood in February, it’s important to dress in layers to prepare for the unpredictable weather. The temperature can range from chilly to mild, so wearing a warm base layer, a sweater or fleece, and a waterproof jacket is ideal. Don’t forget to bring a hat, gloves, and a scarf to keep your head, hands, and neck warm. Comfortable and sturdy waterproof shoes are a must, as the town’s cobblestone streets can get slippery during rain or snow. And for those planning on exploring the nearby hiking trails, pack a pair of sturdy boots to keep your feet dry and supported. Highwood is a charming town with a bustling outdoor market, so it’s important to dress comfortably and casually. Opt for comfortable pants or jeans, and a light long-sleeved shirt. Layering with a sweater or jacket is key, as the temperature can fluctuate throughout the day. As for accessories, a crossbody bag or backpack is perfect for carrying essentials while keeping your hands free. Don’t forget to bring a reusable water bottle to stay hydrated while exploring the town. And for those planning on visiting the nearby wineries, a nice outfit for a wine tasting is recommended. With these tips, you’ll be ready to explore Highwood in comfort and style.
February is a wonderful time to visit the charming town of Highwood, nestled in the stunning Rocky Mountains of Montana. As the winter season begins to wind down, the town comes alive with a variety of exciting activities and events. One of the must-do experiences in February is to hit the slopes at the nearby Big Mountain Ski Resort. With over 3,000 acres of skiable terrain and breathtaking views, it’s no wonder this resort is a favorite among locals and tourists alike. And don’t worry if you’re not a skier, the resort also offers snowboarding, snowshoeing, and tubing for all ages. After a day of adventure on the slopes, be sure to warm up with a hot cup of cocoa at one of the many charming cafes in town. And for those looking for a cultural experience, February also brings the annual Winter Festival to Highwood. This lively event showcases the town’s rich history and traditions with live music, delicious food, and fun activities for the whole family. Don’t miss the opportunity to join in on the town’s winter festivities and immerse yourself in the local culture. With its beautiful scenery and welcoming community, Highwood is the perfect destination for a winter getaway in February.
March
When traveling to Highwood in March, it’s important to pack for the unpredictable weather of the Pacific Northwest. Layers are key, as the mornings can be chilly and the afternoons warm and sunny. I recommend bringing a waterproof jacket, comfortable walking shoes, and a versatile scarf or shawl to adjust to the changing temperatures. In terms of dress, Highwood is a laid-back and casual town, so there’s no need for fancy attire. However, it’s always respectful to dress modestly when visiting religious sites. Be sure to also pack a swimsuit, as the hot springs in the area are a must-visit experience. And don’t forget a reusable water bottle and a day pack for hiking trips in the beautiful surrounding nature. With these essentials, you’ll be well-prepared for a comfortable and enjoyable trip to Highwood in March.
March is a fantastic time to visit Highwood, a charming town nestled in the heart of the beautiful Illinois countryside. As the winter snow begins to melt away, Highwood comes alive with a sense of rejuvenation and energy. One of the highlights of March in Highwood is the annual Maple Syrup Festival. Held every weekend, visitors can take a guided tour of the maple tree groves and learn about the process of making maple syrup. The festival also offers delicious samples of freshly made syrup and other maple treats, making for a sweet and memorable experience. For those looking for a bit of adventure, March is the perfect time to go hiking in Highwood. The weather is cool and crisp, making it ideal for exploring the numerous trails that wind through the town’s picturesque forests and hills. One of my personal favorites is the Highwood Gorge Trail, which offers stunning views of the Des Plaines River and the surrounding countryside. March is also a great time to spot wildlife, so keep an eye out for deer, foxes, and other creatures along the way. Whether you’re a nature lover or just looking for a peaceful escape, Highwood’s hiking trails are not to be missed in March.
April
When planning a trip to Highwood in April, it’s important to pack layers and be prepared for changing weather. The temperatures can range from cool and crisp in the morning to warm and sunny in the afternoon. Start with a light jacket or sweater that can easily be removed as the day warms up. Comfortable walking shoes are a must, as Highwood is best explored on foot. Don’t forget to bring a rain jacket or umbrella, as April can bring some showers. When it comes to dressing in Highwood, it’s all about blending in with the locals. Casual and comfortable is the way to go, with a focus on practicality. Opt for neutral colors and lightweight fabrics, as they can easily be mixed and matched for different outfits. And don’t be afraid to add a touch of local flair by incorporating some traditional Scottish patterns or prints. Lastly, bring a small day bag to carry your essentials, such as a camera, water bottle, and map. With the right clothing and accessories, you’ll be ready to explore all that Highwood has to offer in April.
April is a wonderful time to visit Highwood, a charming town nestled in the heart of Illinois’ North Shore. As the winter chill begins to fade away, the town comes to life with a vibrant energy and a plethora of activities for visitors to enjoy. One of the best ways to experience Highwood in April is to take a stroll through its picturesque downtown area. With its tree-lined streets, quaint shops, and delicious restaurants, this charming district is a must-visit for any traveler. Be sure to stop by the Highwood Historical Society to learn about the town’s rich history and grab a cup of coffee at one of the local cafes to soak in the small-town charm. For those looking for a more active adventure, April is the perfect time to explore Highwood’s beautiful outdoor spaces. The town is home to several parks and nature preserves, offering scenic hiking and biking trails that are especially breathtaking in the spring. Take a leisurely bike ride along the North Shore Bike Path, which winds its way through Highwood and neighboring towns, or pack a picnic and head to Highwood Beach to soak up the sun and stunning views of Lake Michigan. With its perfect blend of small-town charm and outdoor adventures, Highwood is the ideal destination for a springtime getaway.
May
May is a beautiful time to explore the charming town of Highwood. As you pack for your trip, keep in mind the mild weather that this month brings. The average temperature in Highwood during May ranges from 50-70 degrees Fahrenheit, so be sure to bring layers for varying temperatures. A lightweight jacket, comfortable walking shoes, and a scarf or shawl for cooler evenings are all must-haves. And don’t forget to pack an umbrella or rain jacket, as showers are common this time of year. When exploring the town, you’ll want to dress comfortably and casually. Highwood is a laid-back community, and you’ll fit right in wearing jeans, a t-shirt, and comfortable walking shoes. For a day of sightseeing, I recommend bringing a small daypack to carry essentials such as water, sunscreen, and a camera. And if you plan on visiting any churches or religious sites, be sure to pack clothing that covers your shoulders and knees out of respect. With these tips in mind, you’ll be dressed and prepared for a wonderful trip to Highwood in May.
Welcome to Highwood, a charming town nestled in the heart of the Rocky Mountains. May is an ideal time to visit this picturesque destination, as the winter snow has melted, and the summer crowds have yet to arrive. Start your day by taking a scenic hike through the stunning Highwood National Park, where you’ll be surrounded by lush forests and breathtaking views of the mountains. As you make your way through the trails, keep an eye out for wildlife, including bighorn sheep and elk. After a morning of exploring, head to Main Street for a taste of local culture. Here, you’ll find quaint shops, delicious restaurants, and friendly locals eager to share their love for this hidden gem of a town. For a unique experience, don’t miss the annual Highwood Balloon Festival in May. Watch as dozens of colorful hot air balloons take flight against the backdrop of the majestic mountains. Stay for the lively street fair, where you can sample local treats, shop for handmade crafts, and listen to live music. If you’re feeling adventurous, you can even take a hot air balloon ride yourself and get a bird’s eye view of this stunning landscape. As the sun sets, cozy up by a campfire and gaze at the star-filled sky – a perfect end to a perfect day in Highwood.
June
When traveling to Highwood in June, it’s important to dress for both warm weather and potential rain showers. I recommend packing light, breathable clothing such as shorts, t-shirts, and sundresses for the warm days. A light rain jacket and comfortable walking shoes are also essential for exploring the town and its beautiful parks. Highwood is known for its picturesque hikes, so be sure to bring sturdy hiking boots or sneakers if you plan on hitting the trails. In addition to clothing, don’t forget to bring a few key items to enhance your experience in Highwood. A reusable water bottle is a must for staying hydrated on hikes and walks around town. Sunscreen and a hat are also important to protect yourself from the strong summer sun. And for those planning to visit the farmers’ market, bring a tote bag to carry your purchases. Highwood is a charming and welcoming town, so be sure to dress comfortably and come prepared for a delightful summer adventure.
June is a fantastic time to visit the charming town of Highwood. With the warm weather and longer days, it’s the perfect time to explore all that this hidden gem has to offer. One of the must-do activities in June is to attend the annual Highwood Days festival. This lively event celebrates the town’s diverse culture with delicious food, live music, and a festive parade. It’s a great opportunity to mingle with the friendly locals and get a taste of the community’s vibrant spirit. For those seeking a more active adventure, June is also the ideal time to hike the stunning Highwood Mountains. With the snow melted and the wildflowers in full bloom, the trails offer breathtaking views and a peaceful escape from the hustle and bustle of everyday life. Don’t forget to pack a picnic lunch and enjoy it at one of the many scenic spots along the way. And if you’re feeling up for a challenge, the summit of Mount Highwood offers a rewarding and challenging climb. Whether you’re a foodie or an outdoor enthusiast, June in Highwood has something for everyone.
July
When visiting the charming town of Highwood in July, it’s important to dress comfortably and appropriately for the warm weather. The summer months in Highwood can get quite hot, with temperatures reaching up to 90 degrees Fahrenheit. I recommend packing lightweight, breathable clothing such as cotton or linen shirts and shorts. It’s also a good idea to bring a hat and sunglasses to protect yourself from the sun’s rays. Don’t forget to pack comfortable walking shoes as well, as Highwood is a pedestrian-friendly destination with plenty of cobblestone streets to explore. As a traveler, I always like to blend in with the locals and respect their culture. In Highwood, the dress code is casual and laid-back. However, it’s important to note that the town has a strong Italian influence, so you may want to bring a nice outfit for a fancy dinner at one of the many Italian restaurants. In addition to clothing, don’t forget to bring sunscreen and insect repellent, as well as a reusable water bottle to stay hydrated while exploring the town. With these items in tow, you’ll be well-prepared for a delightful summer visit to Highwood.
When traveling to Highwood in the month of July, there are plenty of exciting activities to enjoy. Start your day off with a stroll through the charming downtown area, where you can browse local shops and grab a delicious breakfast at one of the quaint cafes. Then, head to Highwood Beach to soak up some sun and take a dip in Lake Michigan. For those looking for a bit of adventure, rent a kayak or stand-up paddleboard and explore the beautiful shoreline. In the evenings, be sure to check out the Highwood Evening Market, which takes place every Wednesday night. This outdoor market is a true local gem, offering a variety of artisanal goods, fresh produce, and live music. It’s the perfect place to grab a bite to eat, shop for unique souvenirs, and mingle with the friendly locals. And for the foodies out there, Highwood is known for its diverse culinary scene, with a variety of restaurants serving up everything from Italian to Mexican cuisine. Don’t miss the opportunity to try some of the best food the Midwest has to offer.
August
When visiting Highwood in August, it’s important to dress comfortably and appropriately for the warm weather. With average temperatures in the high 70s, a lightweight and breathable outfit is key. I recommend packing light-colored and loose-fitting clothing, such as cotton t-shirts and linen pants, to stay cool in the summer heat. Don’t forget to bring a hat and sunglasses to protect yourself from the sun’s rays while exploring the charming town. In addition to comfortable clothing, it’s important to pack sturdy and comfortable walking shoes when visiting Highwood. With its picturesque streets and abundance of outdoor activities, you’ll want to be prepared to do some exploring on foot. I also suggest bringing a light jacket or sweater for the evenings, as temperatures can drop slightly at night. Lastly, make sure to bring a reusable water bottle to stay hydrated while out and about in this quaint town. With these essentials in tow, you’ll be ready to fully enjoy all that Highwood has to offer in the summertime.
August is a fantastic time to visit the charming town of Highwood, nestled in the beautiful state of Illinois. As summer is in full swing, the town is buzzing with energy and there are plenty of activities to keep visitors entertained. One of the must-see attractions in Highwood during this time is the annual Garlic Fest, where you can sample a variety of garlicky dishes, from garlic-infused ice cream to garlic bread pizza. This unique festival not only celebrates the town’s love for garlic, but also showcases the vibrant local food scene. Aside from the Garlic Fest, August also offers the perfect weather for outdoor activities in Highwood. Take a stroll along the stunning Lake Michigan shoreline, or rent a bike and explore the town’s picturesque streets. For a more active adventure, head to the nearby Fort Sheridan Forest Preserve and hike through its scenic trails. And don’t forget to check out the Ravinia Festival, one of the oldest and most renowned outdoor music festivals in the country, featuring a variety of world-class performances. With so much to see and do, Highwood is the perfect destination for a summer getaway.
September
When packing for your September trip to Highwood, it’s important to keep in mind the unpredictable weather this time of year. The days can be warm and sunny, but the evenings can get chilly. It’s best to dress in layers, bringing a mix of short-sleeved shirts and lightweight jackets. Don’t forget to pack a rain jacket as well, just in case of a sudden shower. And don’t be afraid to add some color to your wardrobe, as September in Highwood is known for its vibrant autumn foliage. As for footwear, comfortable walking shoes are a must for exploring the charming streets and trails of Highwood. Depending on the activities you have planned, you may also want to bring a pair of hiking boots or water shoes. And don’t forget to pack a swimsuit if you plan on taking a dip in one of the many lakes or rivers in the area. Lastly, make sure to bring a daypack for carrying essentials like water, snacks, and a camera to capture the stunning scenery. With the right clothing and gear, you’ll be ready to fully enjoy all that Highwood has to offer in September.
September is a fantastic time to visit the charming town of Highwood, nestled in the scenic forests of northern Illinois. As the summer crowds disperse and the crisp autumn air sets in, this hidden gem becomes the perfect destination for travelers looking to escape the hustle and bustle of the city. One of my favorite things to do in Highwood during this time is to take a leisurely stroll through the quaint downtown area, admiring the unique architecture and stopping at the various local shops and cafes. The colorful foliage and cozy atmosphere make for a truly enchanting experience. For nature lovers, September is also a great time to explore the nearby Lake Michigan shoreline. The beaches are less crowded, and the water is still warm enough for a refreshing dip. I highly recommend taking a sunset hike along the breathtaking bluffs of Fort Sheridan, where you can catch stunning views of the lake and the city skyline in the distance. And don’t forget to indulge in some fresh seafood at one of the many waterfront restaurants – the perfect way to end a day of outdoor adventure in Highwood.
October
October is a beautiful time to visit the charming town of Highwood. As the leaves begin to change and the air turns crisp, it’s important to pack accordingly. The key to dressing for this time of year is layering. Start with a light jacket or sweater and bring a waterproof jacket for rainy days. Comfortable walking shoes are a must, as you’ll want to explore the quaint streets and picturesque parks of Highwood. Don’t forget to bring a scarf and hat for those chilly evenings. When it comes to what to wear in Highwood, it’s all about embracing the cozy fall vibe. Opt for warm, earthy tones like burgundy, mustard, and olive green. A pair of jeans is a versatile choice that can be dressed up or down depending on the occasion. For the ladies, a stylish pair of boots will not only keep your feet warm, but also add a touch of fashion to your outfit. And don’t forget to pack a few sweaters or flannels to stay cozy and stylish during your stay. Lastly, make sure to bring a reusable water bottle to stay hydrated while exploring this charming town.
October is a fantastic time to visit the charming town of Highwood. As the leaves begin to change and the air becomes crisp, this quaint town comes alive with autumn festivities. One must-see activity is the Highwood Pumpkin Fest, where the community comes together to carve and display thousands of pumpkins. It’s a sight to behold and truly captures the spirit of the season. Aside from the Pumpkin Fest, Highwood also offers a variety of outdoor activities in October. The nearby Moraine State Park is the perfect place to take a scenic hike and admire the fall foliage. And for the more adventurous traveler, the park also offers horseback riding and canoeing on the lake. After a day of outdoor exploration, be sure to stop by one of the local restaurants for some delicious comfort food, like a hearty bowl of homemade soup or a warm apple cider. October in Highwood is a magical time, filled with festive events and beautiful scenery.
November
When visiting the charming town of Highwood in November, it’s important to dress in layers to prepare for the changing weather. The temperatures can range from cool and crisp in the morning to mild and sunny in the afternoon. Bring a warm jacket or coat, as well as a scarf and gloves for those chilly evenings. Comfortable walking shoes are a must, as Highwood is a pedestrian-friendly town with many cobblestone streets and sidewalks to explore. As for what to wear, I recommend sticking to comfortable and casual clothing that is appropriate for the season. A pair of jeans or leggings paired with a cozy sweater and a waterproof jacket will keep you warm and stylish. Don’t forget to pack a hat to keep your head warm and protect yourself from any unexpected rain showers. And of course, don’t forget to bring a camera to capture the beautiful fall foliage and quaint architecture of Highwood. With these tips in mind, you’ll be well-prepared to enjoy all that this charming town has to offer in the month of November.
November is a wonderful time to visit Highwood, a charming town nestled in the beautiful state of Illinois. With the leaves changing colors and a crisp chill in the air, it’s the perfect time to explore this quaint town and all it has to offer. One of the must-do activities in Highwood during November is to visit the annual Fall Fest. This lively event features local vendors, delicious food, and live music, making it the perfect way to experience the town’s community spirit. Plus, with the holiday season just around the corner, it’s a great opportunity to get a head start on your gift shopping. After the festival, take a stroll through the picturesque downtown area and admire the festive decorations, you’ll feel like you’ve stepped into a winter wonderland. And don’t forget to warm up with a cup of hot cocoa from one of the many charming cafes in town. Highwood truly shines in November, making it a must-visit destination for any traveler.
December
When planning a visit to the charming town of Highwood in December, it’s important to dress for both comfort and practicality. The weather can be quite chilly, so layers are a must. Start with a warm base layer such as long underwear or a thermal shirt, then add a sweater or fleece on top. A waterproof and windproof jacket or coat is essential for staying dry and warm. Be sure to bring a hat, gloves, and a scarf to keep your extremities cozy. And don’t forget to pack comfortable and sturdy shoes for exploring the town’s cobblestone streets and hilly terrain. As for what to wear in Highwood, I recommend opting for a cozy and casual style. Locals in this town value comfort over fashion, so feel free to leave your fancy attire at home. A pair of jeans or leggings paired with a warm sweater or flannel shirt is a perfect outfit for a day of sightseeing. And if you plan on participating in any winter activities such as skiing or snowshoeing, be sure to bring appropriate gear such as waterproof pants and insulated boots. Lastly, don’t forget to bring a small backpack to carry all your essentials, including a water bottle, snacks, and a map of the town.
If you find yourself in Highwood during the month of December, you are in for a treat! This small town, located in the beautiful state of Illinois, truly comes alive during the holiday season. One of the must-do activities is to take a stroll down Sheridan Road, where you will be greeted with charming storefronts decked out in festive decorations. Make sure to stop by the famous Highwood Star, a 50-foot-tall holiday tree that is lit up every night, creating a magical atmosphere. And don’t forget to warm up with a cup of hot chocolate from one of the local cafes! For a unique experience, head to the Annual Highwood Holiday Market. This European-style market is held every weekend in December and features local vendors selling handmade gifts, delicious treats, and festive drinks. It’s the perfect place to find a one-of-a-kind souvenir to bring back home. And if you’re feeling adventurous, try some traditional German mulled wine, or Glühwein, while enjoying live music and holiday performances. The Highwood Holiday Market truly captures the spirit of the season and is a must-visit for any December traveler in Highwood.
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.
