Select the month that you will be traveling from the table below to view the packing list:
What Ashland is like to visit throughout the year:
January
When visiting Ashland in the month of January, it’s important to dress for both comfort and practicality. The weather can be quite unpredictable, with chilly temperatures and the occasional rain or snow shower. I recommend bringing layers such as a warm sweater or fleece jacket, as well as a waterproof outer layer. Don’t forget to pack a sturdy pair of waterproof boots for exploring the city streets and hiking trails. As for what to wear, the locals in Ashland tend to dress casually and comfortably. It’s perfectly acceptable to wear jeans and a cozy sweater during the day, but if you plan on attending a show at the famous Oregon Shakespeare Festival, you may want to dress up a bit more. And of course, don’t forget to bring a hat, gloves, and a scarf to keep yourself warm while strolling through the charming downtown area. Lastly, make sure to pack a small umbrella or raincoat, as the weather can change quickly and unexpectedly in Ashland. With the right clothing and gear, you’ll be prepared to fully enjoy all that this beautiful city has to offer in January.
January is a fantastic time to visit Ashland, Oregon. While the town is known for its famous Shakespeare Festival, there are plenty of other activities to enjoy during this winter month. Bundle up and take a stroll through Lithia Park, a beautiful 93-acre park with winding paths, a duck pond, and stunning views of the snow-capped Siskiyou Mountains. The park is especially magical in January when it’s dusted with snow and the trees are adorned with twinkling holiday lights. After exploring the outdoors, warm up with some delicious local cuisine. January is the perfect time to try some hearty comfort food, like a piping hot bowl of clam chowder or a savory pot pie, at one of Ashland’s cozy restaurants. For a taste of the town’s history, head to the historic Lithia Springs Hotel, where you can indulge in a traditional high tea experience complete with scones, finger sandwiches, and a variety of teas. No matter how you choose to spend your time in Ashland, January is sure to provide a memorable and charming winter getaway.
February
When visiting the charming town of Ashland in February, it’s important to dress in layers to stay warm and comfortable. The weather can be unpredictable, with chilly mornings giving way to warm afternoons and cold evenings. Start with a base layer of thermal clothing to keep you warm, then add a sweater or fleece on top. A waterproof jacket is also a must, as rain is common during this time of year. Don’t forget to pack a warm hat, gloves, and a scarf for added protection against the cold. As for footwear, a sturdy pair of waterproof boots or shoes is essential for exploring Ashland’s beautiful outdoor areas. The town is known for its scenic trails and parks, and you don’t want to miss out on hiking opportunities due to uncomfortable or inadequate footwear. Additionally, bring along a small backpack to carry your essentials, such as a water bottle, snacks, and a map of the town. With these items in tow, you’ll be ready to fully enjoy all that Ashland has to offer in February.
February is a wonderful time to visit Ashland, a charming town nestled in the heart of Oregon’s Rogue Valley. While most people come to Ashland in the summer for the famous Oregon Shakespeare Festival, February offers a quieter and more off-the-beaten-path experience. One of the highlights of this month is the annual Ashland Independent Film Festival, where you can catch a variety of independent films from all over the world. It’s a great opportunity to escape the winter chill and immerse yourself in the world of cinema. Aside from film, Ashland also boasts a thriving culinary scene. In February, the town hosts the Ashland Culinary Festival, where you can taste some of the best dishes from local restaurants and wineries. You can also attend cooking classes and workshops to learn about the region’s food culture. And if you’re feeling adventurous, why not take a hike in the nearby Siskiyou Mountains or go on a scenic drive through the beautiful countryside? Don’t let the winter weather stop you from exploring Ashland’s many attractions and activities in February.
March
When visiting Ashland in March, it’s important to dress in layers to accommodate the fluctuating temperatures. This quaint town in southern Oregon can experience chilly mornings and warm afternoons, so be prepared with a light jacket or sweater that can easily be taken off as the day progresses. Don’t forget to bring a rain jacket or umbrella as well, as March can bring occasional showers. Comfortable walking shoes are a must, as Ashland boasts beautiful parks and gardens to explore. For those planning to attend the famous Oregon Shakespeare Festival, I recommend bringing something slightly dressier for the evening performances. While the town has a laid-back vibe, the theater is a more formal affair and it’s always a treat to dress up for a night out. As for what to wear, Ashland is known for its bohemian and artsy style, so feel free to embrace your inner hippie and bring flowy skirts or patterned tops. And of course, don’t forget to pack a camera to capture the stunning scenery and charming atmosphere of this charming town. Happy travels!
March is a wonderful time to visit Ashland, Oregon, where the beautiful outdoors meets a vibrant cultural scene. One of my favorite things to do in Ashland during this time of year is to attend the Oregon Shakespeare Festival. This world-renowned festival runs from February to October, and March is the perfect time to catch some of the early performances. From classic Shakespearean plays to contemporary works, there is something for everyone at this festival. And with the town’s charming streets and local restaurants just steps away from the theaters, it’s easy to make a day out of it. After a day of theater, I love to explore the natural beauty of Ashland. With the arrival of spring, the town is surrounded by lush greenery and blooming flowers. One of my favorite spots is Lithia Park, a 93-acre park with winding paths, stunning gardens, and a peaceful duck pond. It’s the perfect place to take a stroll, have a picnic, or simply relax and take in the beauty of the Pacific Northwest. And for those looking for a bit more adventure, the nearby mountains offer scenic hiking trails and breathtaking views. March truly is a magical time to experience all that Ashland has to offer.
April
When visiting the charming town of Ashland in April, be prepared for varying weather conditions. The days can be warm and sunny, while the nights tend to be cooler. To dress appropriately, I recommend packing layers. Start with a light t-shirt or blouse and add a sweater or jacket for the cooler evenings. It’s also a good idea to bring a rain jacket or umbrella, as April can bring occasional showers. Don’t forget to pack comfortable walking shoes, as Ashland is best explored on foot. As for what to wear, the locals in Ashland have a casual and laid-back style. You’ll fit right in with a pair of jeans or khakis, paired with a button-down shirt or blouse. To blend in with the artistic vibe of the town, consider adding a scarf or statement piece of jewelry. And don’t forget to bring a hat and sunglasses for the sunny days. Lastly, don’t overpack. Ashland offers plenty of unique boutiques and shops where you can find fashionable and locally made clothing items to add to your wardrobe. So leave some room in your suitcase for those special finds.
April is a fantastic time to visit Ashland, a charming town nestled in the foothills of the Siskiyou Mountains. The weather is mild and the spring blooms are in full force, creating a picturesque backdrop for your adventures. One of the highlights of visiting Ashland in April is attending the renowned Oregon Shakespeare Festival. This internationally recognized festival features a variety of plays and performances, ranging from classic Shakespearean works to contemporary pieces. With multiple theaters and a lively atmosphere, the festival is a must-see for any theater enthusiast. Aside from the Shakespeare Festival, there are plenty of other activities to enjoy in Ashland in April. The town is home to numerous wineries and vineyards, offering wine tastings and tours throughout the month. For outdoor enthusiasts, the nearby Rogue River offers excellent opportunities for fishing, rafting, and hiking. And for those looking to relax and unwind, the local spas and wellness centers offer a variety of treatments and services. With its charming small-town vibe and abundance of activities, Ashland is the perfect destination for a spring getaway.
May
When traveling to Ashland in the month of May, it’s important to pack for a variety of weather conditions. The mornings and evenings are typically cool, so bringing a light jacket or sweater is recommended. However, as the day progresses, temperatures can rise significantly, so be sure to also pack some comfortable and breathable clothing like t-shirts and shorts. It’s also a good idea to bring along a rain jacket or umbrella, as May is known for its occasional showers. Don’t forget to pack comfortable walking shoes, as exploring the charming streets of Ashland will surely be a highlight of your trip. In terms of dressing for activities, Ashland is a casual town where you can feel comfortable wearing jeans, shorts, and sundresses. However, if you plan on attending a play at the renowned Oregon Shakespeare Festival, it’s recommended to dress a bit more formally. This can include a nice dress or slacks for women, and a collared shirt and dress pants for men. Sunscreen and a hat are also essential items to bring, as the sun can be quite strong during the day. Finally, don’t forget to bring a reusable water bottle to stay hydrated while exploring this beautiful town. With these tips in mind, you’ll be well-prepared to enjoy all that Ashland has to offer in the lovely month of May.
May is a wonderful time to visit the charming town of Ashland, nestled in the beautiful Rogue Valley of southern Oregon. Known for its world-renowned Shakespeare Festival, there is no shortage of cultural activities to partake in. However, there is so much more to do in this quaint town beyond the stage. One must-see activity in May is the annual Ashland Farmers Market. Held every Saturday morning, this market is a feast for the senses with fresh produce, artisanal crafts, and delicious food vendors. It’s the perfect place to stock up on local goods and get a taste of the community. Another must-do is a hike along the scenic Lithia Park trail, which boasts stunning views of the town and surrounding mountains. For a more leisurely experience, take a stroll through the town’s downtown area, lined with charming shops and restaurants. And don’t forget to stop by the Lithia Water Fountain, where visitors can taste the town’s famous mineral water and take in the historic charm of Ashland.
June
When visiting the charming town of Ashland in June, it’s important to be prepared for a variety of weather conditions. The Pacific Northwest is known for its unpredictable weather, so it’s best to dress in layers. Start with a light t-shirt or tank top and add a sweater or jacket for cooler evenings. Don’t forget to bring a rain jacket or umbrella, as June is typically a wet month in Ashland. Comfortable walking shoes are a must, as the town is best explored on foot. Keep in mind that the town is known for its hilly terrain, so make sure your shoes have good traction. As for attire, Ashland is a casual town so leave your fancy clothes at home. A pair of jeans or comfortable pants paired with a nice shirt is appropriate for most occasions. If you plan on attending a performance at the famous Oregon Shakespeare Festival, a slightly dressier outfit may be appropriate. However, don’t worry about packing formal wear. It’s more important to be comfortable and able to enjoy all that Ashland has to offer. Lastly, don’t forget to pack a reusable water bottle, sunscreen, and a camera to capture the beautiful scenery and memories of your trip to Ashland in June.
Welcome to Ashland, Oregon, a charming town nestled in the foothills of the Siskiyou Mountains. June is a fantastic time to visit this picturesque destination, as the weather is mild and the town is buzzing with activity. One of the must-do activities in June is to attend the famous Oregon Shakespeare Festival. This renowned event brings together talented actors and playwrights from all over the world to perform in multiple theaters throughout the town. You can catch a matinee or evening show, and even take part in discussions with the actors after the performance. It’s a truly immersive experience that will leave you with a deeper appreciation for Shakespeare and the arts. Aside from the theater, another great way to spend a June day in Ashland is by exploring Lithia Park. This 93-acre park is a local favorite, with its lush greenery, bubbling fountains, and winding trails. Take a leisurely stroll through the park, have a picnic by the creek, or rent a paddleboat to glide across the tranquil pond. The park is also home to a variety of events and festivals throughout the month, such as the Lithia Artisans Market and the Ashland World Music Festival. So grab a blanket, some snacks, and immerse yourself in the natural beauty and community spirit of Lithia Park.
July
When visiting the charming town of Ashland in July, it’s important to dress comfortably and practically. The weather is typically warm and sunny, so be sure to bring lightweight and breathable clothing such as shorts, t-shirts, and sundresses. It’s also a good idea to pack a hat and sunglasses to protect yourself from the strong sun. Comfortable walking shoes are a must, as the best way to explore Ashland is by foot. In addition to clothing, don’t forget to bring a few key items for your trip to Ashland. A small backpack or crossbody bag is perfect for carrying essentials such as water, sunscreen, and a camera. Ashland is known for its outdoor activities, so be sure to pack a swimsuit and towel if you plan on taking a dip in the nearby lakes or rivers. And of course, don’t forget to bring a good book or journal to enjoy while relaxing in one of Ashland’s beautiful parks or gardens. With the right attire and essentials, you’ll be ready to fully immerse yourself in the quaint and picturesque town of Ashland.
As you make your way through the charming streets of Ashland in July, you’ll find yourself surrounded by a vibrant and bustling atmosphere. The town truly comes alive during this time of year, with an array of exciting activities and events for visitors to enjoy. One of the highlights of July in Ashland is the Oregon Shakespeare Festival, which showcases a variety of world-class productions in the iconic outdoor Elizabethan Theatre. From classic Shakespearean plays to contemporary works, there’s something for every theater lover to enjoy. Aside from the theatrical delights, July in Ashland also offers plenty of opportunities to explore the great outdoors. The nearby Lithia Park is the perfect spot for a leisurely stroll or a picnic amidst the stunning scenery of the Rogue Valley. For the more adventurous, the nearby Cascade-Siskiyou National Monument offers breathtaking hiking trails through lush forests and scenic vistas. And don’t forget to cool off in the crystal-clear waters of Emigrant Lake, where you can go swimming, kayaking, or simply relax on the shore. Whatever your interests may be, Ashland in July has something for everyone to enjoy.
August
As a seasoned traveler, I always advise my fellow adventurers to dress for comfort and practicality when visiting Ashland in August. The summer months in this charming town can get quite warm, so it’s important to pack lightweight, breathable clothing. Opt for light-colored, loose-fitting tops and bottoms made of natural fabrics like cotton or linen to keep cool in the heat. Don’t forget a wide-brimmed hat and sunglasses to protect yourself from the bright sun. And of course, comfortable walking shoes are a must for exploring Ashland’s picturesque streets and parks. When it comes to evening attire in Ashland, you’ll want to dress up a bit for the town’s renowned Shakespeare Festival. A nice sundress or button-down shirt paired with slacks is appropriate for the outdoor performances. And don’t forget a light jacket or sweater for when the temperatures drop in the evening. As for what to bring, be sure to pack a reusable water bottle to stay hydrated throughout your adventures. And don’t forget to bring a small daypack to carry essentials like sunscreen, a map, and a camera to capture all the beauty and culture Ashland has to offer. Happy travels!
As summer reaches its peak in Ashland, the quaint town comes to life with a plethora of activities for visitors to enjoy. First and foremost, no trip to Ashland is complete without attending a Shakespearean play at the renowned Oregon Shakespeare Festival. With multiple productions running throughout the month of August, theater enthusiasts can immerse themselves in the works of the Bard while surrounded by the stunning natural beauty of Ashland. In addition to the festival, August also brings the annual Ashland Culinary Festival, where foodies can indulge in delicious local cuisine while taking in live cooking demonstrations and competitions. And for those looking to escape the summer heat, a hike to the top of Grizzly Peak offers stunning views of the surrounding mountains and valleys, with the added bonus of a refreshing breeze. With so much to see and do, August is the perfect time to experience all that Ashland has to offer.
September
As you plan your trip to the charming town of Ashland in September, it’s important to consider the weather and pack accordingly. The temperatures in September can range from mild to cool, so it’s best to bring a variety of layers. Start with a light jacket or sweater that you can easily remove if the sun comes out, and also pack a rain jacket or umbrella in case of a passing shower. Comfortable walking shoes are a must, as Ashland is a pedestrian-friendly town with plenty of quaint streets to explore. When it comes to dressing in Ashland, the key is to keep it casual and comfortable. The town has a laid-back vibe, so there’s no need to bring your fanciest attire. Opt for versatile pieces that can be dressed up or down, such as a pair of jeans or a dress with a cardigan. And don’t forget to pack a scarf or hat to add a touch of style to your outfit and keep you warm on cooler evenings. As for accessories, keep it simple with a small crossbody bag or backpack to carry your essentials while you’re out and about. And of course, don’t forget to bring your camera to capture the beautiful scenery and charming streets of Ashland.
September is a wonderful time to visit the charming city of Ashland, nestled in the heart of Oregon’s beautiful Rogue Valley. As summer winds down, the crisp autumn air brings a sense of excitement and energy to this cultural hub. One of the must-see attractions in Ashland is the famous Oregon Shakespeare Festival, which runs from February to October. In September, visitors can catch some of the final performances of the season, including outdoor plays in the stunning Elizabethan Theatre. Be sure to also explore the quaint downtown area, filled with boutique shops, art galleries, and delicious farm-to-table restaurants. For nature lovers, September is the perfect time to explore the stunning outdoor scenery of Ashland. The city is surrounded by the majestic Siskiyou and Cascade mountain ranges, offering endless opportunities for hiking, biking, and kayaking. The crisp fall weather makes for ideal conditions to explore the nearby Lithia Park, a 93-acre oasis filled with colorful foliage and serene walking trails. And don’t forget to stop by the local farmers market, where you can taste the best of Oregon’s fresh produce and mingle with friendly locals. September truly is a magical time to experience all that Ashland has to offer.
October
The crisp autumn air of October in Ashland calls for comfortable yet versatile clothing. As you explore this charming city, be sure to pack layers such as a light jacket or sweater as temperatures can vary throughout the day. It’s also a good idea to bring a waterproof jacket, as October does tend to see some rain. Comfortable walking shoes are a must, as you’ll be strolling through the city’s beautiful parks and gardens, as well as the bustling downtown area. When it comes to dressing for the evenings, Ashland’s culture and arts scene lends itself to a slightly dressier attire. A nice pair of pants or a dress with a sweater or blazer will ensure you’re dressed appropriately for a night at the theater or a fancy dinner. And don’t forget to bring a scarf or hat to keep you warm during those chilly nights under the stars at the Oregon Shakespeare Festival. With these tips in mind, you’ll be dressed and ready for a perfect autumn visit to Ashland.
October is a fantastic time to visit the charming town of Ashland in southern Oregon. The crisp autumn air and colorful foliage make it the perfect setting for outdoor activities. One must-do activity in Ashland during this time is taking a hike in Lithia Park. This 93-acre park is a local favorite, with its winding trails, picturesque creeks, and vibrant fall colors. It’s the ideal spot to immerse yourself in nature and take in the beauty of the season. For a cultural experience, don’t miss the Oregon Shakespeare Festival, which runs from February to October. The festival showcases world-class performances of Shakespeare’s plays and other classic works. In October, you can catch the last few shows of the season and witness the stunning fall backdrop of the outdoor Elizabethan Theatre. After the show, take a stroll through the charming downtown area and stop by one of the local cafes for a warm cup of coffee or a slice of freshly baked apple pie. October is truly a delightful time to explore the vibrant and welcoming town of Ashland.
November
When visiting Ashland in November, it’s important to dress for both comfort and versatility. The weather can be quite unpredictable, with chilly mornings and warmer afternoons. I recommend packing layers, such as a light jacket or sweater, that can easily be added or removed throughout the day. It’s also wise to bring a waterproof outer layer, as November is known for its occasional rain showers. As for footwear, comfortable walking shoes are a must, as Ashland is a pedestrian-friendly town with many hills and stairs to navigate. In terms of what to wear, I suggest opting for casual, practical clothing that can be dressed up or down depending on the occasion. Ashland is a laid-back town, so there’s no need to pack fancy attire. However, if you plan on attending a play at the renowned Oregon Shakespeare Festival, a nice pair of slacks or a dress would be appropriate. And don’t forget to bring a small umbrella or raincoat, as well as a day bag to carry any essentials while exploring the charming streets and shops of Ashland. With the right attire and a sense of adventure, you’ll be ready to fully experience the beauty and culture of this charming town in November.
November is a delightful time to visit the charming town of Ashland in southern Oregon. While most tourists flock to this area during the summer months for the famous Oregon Shakespeare Festival, November offers a more tranquil and authentic experience. Take a stroll through the vibrant Lithia Park, where the autumn foliage paints the landscape in hues of red, orange and gold. The crisp air and peaceful ambiance make it the perfect spot for a leisurely picnic or a scenic hike. No visit to Ashland is complete without indulging in its thriving arts and culture scene. In November, you can catch a variety of performances at the Oregon Shakespeare Festival, from classic Shakespearean plays to modern productions. For a taste of local art, head to the First Friday Art Walk, where you can explore the galleries and studios of talented artists while sipping on a warm cup of apple cider. And don’t forget to savor the delicious flavors of the season at one of the town’s cozy restaurants, serving up hearty dishes made with locally sourced ingredients. November in Ashland truly offers a unique and unforgettable experience for travelers.
December
When visiting Ashland in December, it’s important to dress in layers to prepare for the varying temperatures. The days can be chilly, but the sun often comes out, so having a warm jacket and a few layers underneath is key. Comfortable walking shoes are a must as well, as Ashland is a pedestrian-friendly town with plenty of cobblestone streets to explore. Don’t forget to bring a rain jacket or umbrella, as the winter months can bring some precipitation. In terms of what to wear, Ashland has a laid-back and casual vibe, so leave your fancy clothes at home. Opt for comfortable, yet stylish outfits that can take you from exploring the quaint downtown to enjoying a show at the renowned Oregon Shakespeare Festival. And of course, don’t forget to pack a hat, gloves, and a scarf to keep warm during those brisk winter evenings. Lastly, don’t leave without bringing a camera to capture the beautiful holiday decorations and cozy atmosphere that Ashland is known for during the month of December.
December is a magical time to visit Ashland, nestled in the beautiful Rogue Valley of Southern Oregon. While the town may be best known for its world-renowned Oregon Shakespeare Festival, there is so much more to explore during the holiday season. Bundle up and take a stroll through downtown, where festive lights and decorations adorn the streets and storefronts. Stop by the historic Ashland Springs Hotel for a cup of hot cocoa and a cozy atmosphere that will transport you back in time. No visit to Ashland in December would be complete without experiencing the annual Festival of Light. This beloved tradition features over one million twinkling lights that illuminate the town’s charming Lithia Park. Grab a cup of warm cider and take a leisurely walk through the park, marveling at the dazzling displays and festive music. For an extra special treat, catch a performance of the Nutcracker ballet at the beautiful Craterian Theater. With its small-town charm and festive holiday spirit, Ashland is the perfect destination for a December getaway.
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.
