Select the month that you will be traveling from the table below to view the packing list:
What Woodside is like to visit throughout the year:
January
When visiting the charming town of Woodside in January, it’s important to dress in layers to combat the chilly weather. Start with a warm base layer such as wool or thermal underwear, topped with a cozy sweater or fleece. Don’t forget to pack a waterproof jacket and sturdy shoes for exploring the great outdoors. Scarves, gloves, and hats are also essential to keep you warm and protected from the elements. Don’t be afraid to mix and match different layers to find the perfect combination for your comfort level. As for what to wear, opt for comfortable and practical clothing that you can easily move around in. Woodside is a haven for outdoor activities, so be sure to pack activewear and comfortable shoes for hiking, biking, and horseback riding. If you plan on dining at any of the town’s upscale restaurants, pack a few dressier outfits for a more formal evening. And don’t forget to bring a camera to capture all the beautiful sights and memories you’ll make in this picturesque town.
Welcome to Woodside, a charming town nestled in the heart of California’s redwood country. Although January may not be the most popular time for tourists, there are still plenty of ways to enjoy all that this town has to offer. Start your day off with a hike through the towering redwoods in nearby Huddart Park. The crisp air and peaceful surroundings will transport you to another world. After working up an appetite, head to Alice’s Restaurant for a hearty breakfast of their famous pancakes and locally sourced eggs. Don’t forget to grab a cup of their freshly roasted coffee to warm you up on a chilly morning. In the afternoon, make your way to the Filoli Historic House and Garden, a 1917 estate with breathtaking gardens and a grand mansion. Take a guided tour to learn about the history of the property and its former owners, or simply wander through the gardens and admire the winter blooms. For a unique experience, visit the nearby San Mateo Arboretum Society, where you can stroll through a collection of over 300 different species of trees and plants. End your day with a cozy dinner at the Village Pub, known for its upscale take on traditional pub fare and extensive wine list. January may be a quieter time in Woodside, but there is still plenty to see and do in this charming town.
February
February is a beautiful time to visit Woodside, with its crisp winter air and stunning scenery. However, the weather can be quite unpredictable, so dressing in layers is key. I recommend bringing a warm coat, gloves, and a hat for those chilly days, but also packing some lighter pieces for when the sun comes out. A waterproof jacket is also a must, as Woodside is known for its intermittent rain showers. When it comes to footwear, a sturdy pair of walking shoes or boots is essential for exploring the many hiking trails in the area. If you plan on visiting any of the charming local villages, I suggest bringing a pair of comfortable yet stylish shoes. And don’t forget to pack a swimsuit! While it may seem counterintuitive for a winter trip, many of the hotels in Woodside have heated outdoor pools and hot tubs, perfect for a relaxing soak after a day of sightseeing. Overall, be prepared for a mix of cold and mild weather, and don’t forget to bring your camera to capture the stunning winter landscapes in Woodside.
February is a wonderful time to visit the charming town of Woodside, nestled in the lush foothills of the Santa Cruz Mountains. While the weather may be a bit cooler, the stunning natural beauty and quaint small-town charm make it the perfect destination for a winter getaway. One of the top things to do in February is to take a stroll through the picturesque Huddart Park. This 900-acre park offers endless opportunities for hiking, birdwatching, and even horseback riding. You can also cozy up by the fireplace at the historic Folger Stable, which now houses a charming restaurant serving up delicious farm-to-table cuisine. After exploring the great outdoors, make sure to check out the local art scene in Woodside. The town is home to several galleries and art studios, showcasing the works of talented local artists. One of my favorites is the Woodside Gallery, which features a diverse collection of paintings, sculptures, and ceramics. And if you’re feeling adventurous, why not try your hand at creating your own masterpiece at one of the many art classes offered in town? With its stunning natural surroundings and vibrant arts scene, Woodside is the perfect destination for a unique and memorable February vacation.
March
When visiting the charming town of Woodside in March, it is important to dress for the changeable weather. Layers are key, as the mornings can be chilly but the afternoons can warm up quickly. A light jacket or sweater, paired with a waterproof outer layer, is a must-have in case of rain. Comfortable walking shoes are also essential, as Woodside is a pedestrian-friendly town with many quaint shops and cafes to explore. And don’t forget to bring a hat and sunglasses, as the California sun can be quite strong even in the spring months. As for what to wear, Woodside has a casual and laid-back atmosphere, so there is no need to dress up. Jeans, t-shirts, and comfortable dresses are all appropriate for exploring the town. However, if you plan on visiting any of the nearby hiking trails or nature reserves, be sure to pack some sturdy shoes and activewear. And of course, don’t forget to bring a camera to capture the stunning views and natural beauty of this charming town. With these tips in mind, you’ll be dressed and prepared for a wonderful visit to Woodside in March.
March is a magical time to visit the quaint town of Woodside. As the winter chill starts to fade away, the town comes to life with vibrant colors and exciting activities. One of the must-do activities in March is to take a stroll through the beautiful Filoli Gardens. This 654-acre estate boasts stunning gardens, a historic mansion, and breathtaking views of the San Francisco Bay. March is the perfect time to see the gardens in full bloom, with colorful tulips, daffodils, and cherry blossoms creating a picturesque backdrop. Don’t forget to bring your camera and a picnic to fully enjoy this tranquil oasis. Another great way to spend a day in Woodside is by exploring the many hiking trails in the area. With the weather warming up, it’s the perfect time to take a leisurely hike through the redwood forests or challenge yourself with a more strenuous trek up to Skyline Ridge. The views from the top are well worth the effort, and you may even spot some wildlife along the way. After a day of hiking, be sure to stop by one of the local restaurants for a delicious farm-to-table meal and a glass of wine. March in Woodside truly offers something for everyone, making it a perfect destination for any traveler.
April
As the spring season arrives in Woodside, travelers can expect mild temperatures and blooming flowers. To dress for this time of year, I recommend packing layers. A light jacket or sweater will come in handy for the cooler mornings and evenings, while a t-shirt or blouse can be worn during the warmer afternoons. It’s also a good idea to bring a waterproof jacket or umbrella, as April showers are common in this area. When exploring Woodside, comfortable and sturdy shoes are a must. The town is known for its beautiful hiking trails and scenic walks, so be sure to bring a pair of sneakers or hiking boots. For a more formal evening out, a dress or nice pants paired with a blouse for women and slacks and a collared shirt for men would be appropriate. And don’t forget to bring a camera to capture the stunning spring landscapes and charming town atmosphere. With the right attire and gear, travelers can fully enjoy all that Woodside has to offer during the month of April.
Spring is in full bloom in the charming town of Woodside in April. As the weather warms up, the rolling hills and lush greenery make for a picturesque backdrop for outdoor activities. One must-do activity is hiking through the stunning redwood forests in Wunderlich County Park. The fresh air and tranquil surroundings make for a rejuvenating experience. Don’t forget to pack a picnic and enjoy a relaxing lunch surrounded by nature. April also brings the famous Woodside Farmers’ Market, held every Sunday morning. Here, visitors can sample locally grown produce, artisanal cheeses, and freshly baked goods. It’s a great opportunity to immerse yourself in the local culture and support small businesses. After stocking up on goodies, take a stroll through the charming downtown area and browse the quaint boutiques and art galleries. With its small-town charm and beautiful scenery, Woodside is the perfect destination for a springtime getaway.
May
When packing for your trip to Woodside in May, it’s important to remember that the weather can be quite unpredictable. While the days may be warm and sunny, the evenings can be cool and breezy. I recommend bringing light layers such as a sweater or light jacket to throw on when needed. As for footwear, comfortable walking shoes are a must as Woodside is a town best explored on foot. Don’t forget to pack a waterproof jacket or umbrella, just in case of a passing shower. When it comes to dressing for activities such as hiking or outdoor adventures, be sure to wear comfortable and sturdy shoes. The trails in Woodside can be rugged and uneven, so proper footwear is essential. Additionally, for those planning to visit any of the local wineries or restaurants, a nice pair of pants or a dress with a light cardigan will suffice. No need for anything too fancy, as the atmosphere in Woodside is laid-back and casual. With these tips in mind, you’ll be well-prepared to enjoy all that this charming town has to offer in the month of May.
Welcome to Woodside, a charming town nestled in the heart of California’s San Mateo County. May is an ideal time to visit this picturesque destination, with its mild weather and blooming wildflowers dotting the lush landscape. As a traveler, I always seek out authentic experiences, and Woodside offers just that. From outdoor activities to cultural events, here are some must-do activities to add to your itinerary. First, immerse yourself in the natural beauty of Woodside by taking a hike in the nearby Purisima Creek Redwoods Open Space Preserve. This scenic trail meanders through a dense redwood forest and offers stunning views of the surrounding mountains. May is also the perfect time to visit Filoli Gardens, a historic estate with 16 acres of beautifully manicured gardens. Explore the grounds, take a guided tour of the mansion, and enjoy a picnic on the lawn. For a taste of local culture, be sure to check out the Woodside May Day Parade and Festival, featuring live music, food vendors, and a charming parade through the town center. With its small-town charm and natural beauty, Woodside is a gem waiting to be discovered in May.
June
When visiting the charming town of Woodside in June, it’s important to pack for a variety of weather conditions. The coastal location means that the weather can be unpredictable, so it’s best to come prepared with layers. A light jacket or sweater is a must, as temperatures can drop in the evenings. It’s also a good idea to bring a pair of comfortable walking shoes, as the town is known for its beautiful hiking trails and scenic walks. Be sure to pack a hat and sunglasses for protection from the sun, as well as a raincoat or umbrella for any unexpected showers. As for attire, Woodside is a casual and laid-back town, so there’s no need for fancy or formal clothing. Plan to dress comfortably in breathable fabrics, such as cotton or linen, to stay cool in the summer heat. A pair of shorts or a sundress is perfect for exploring the town during the day, and you can dress up a bit more for a nice dinner at one of Woodside’s charming restaurants. And don’t forget to bring a swimsuit if you plan on taking a dip in the nearby beaches or pools. With the right clothing and gear, you’ll be ready to enjoy all that Woodside has to offer in June.
Welcome to Woodside, a charming town nestled in the rolling hills of California’s Peninsula region. June is a fantastic time to visit this quaint destination, as the weather is warm and the town is buzzing with outdoor activities. One of the must-do experiences in Woodside is to hike the scenic trails at the beautiful Wunderlich County Park. With over 1,200 acres of lush greenery and towering redwood trees, this park offers stunning views and a peaceful escape from the hustle and bustle of city life. Pack a picnic and spend a day exploring the trails, or join a guided tour to learn about the local flora and fauna. For a taste of local culture, be sure to visit one of Woodside’s charming farmer’s markets. Held every Sunday in the town center, these markets offer a wide array of fresh produce, artisanal goods, and delicious food vendors. Stroll through the stalls, chat with the friendly vendors, and savor the flavors of the season. Afterward, head to the nearby Filoli Historic House and Garden for a tour of the stunning estate and its blooming gardens. With its rich history and picturesque setting, Woodside is the perfect destination for a June getaway.
July
When visiting the charming town of Woodside in July, it’s important to dress for both comfort and style. The summer months can bring warm temperatures, so lightweight and breathable fabrics are a must. A comfortable pair of walking shoes is also essential as you’ll want to explore the quaint streets and scenic trails. For the ladies, a sundress or maxi skirt paired with a light cardigan is a great option, while men can opt for lightweight pants and a collared shirt. In addition to clothing, be sure to bring a hat, sunglasses, and sunscreen to protect yourself from the sun’s rays. A small backpack or crossbody bag is also useful for carrying essentials like a water bottle, camera, and guidebook. As Woodside is known for its beautiful parks and outdoor spaces, don’t forget to pack a pair of comfortable shoes for hiking or a swimsuit if you plan on visiting the nearby beaches. And of course, don’t forget to bring along your sense of adventure and willingness to immerse yourself in the small-town charm of Woodside.
Woodside, nestled in the scenic Redwood forests of Northern California, is a charming town that offers plenty of activities for visitors in the month of July. One of the must-do experiences is exploring the famous Woodside Farmers Market, held every Sunday in the town center. Here, travelers can sample fresh, locally grown produce and mingle with friendly locals while enjoying live music and delicious food. For outdoor enthusiasts, July is the perfect time to hike the beautiful trails of Huddart Park. This expansive park offers stunning views of the surrounding mountains and is filled with lush greenery and towering redwood trees. Visitors can also go horseback riding or have a picnic in one of the many scenic spots. And for those looking to escape the summer heat, a short drive will take you to the picturesque beaches of Half Moon Bay, where you can relax and soak up some sun. With its small-town charm, natural beauty, and a variety of fun activities, Woodside is the perfect summer destination for travelers.
August
When visiting Woodside in the month of August, it’s important to dress for both warm weather and potential rain. The average temperature during this time is around 80 degrees Fahrenheit, but it’s not uncommon for brief showers to occur. To be prepared, I recommend packing lightweight, breathable clothing such as shorts, t-shirts, and sundresses. It’s also wise to bring a light rain jacket or umbrella, just in case. Comfortable walking shoes are a must, as Woodside offers plenty of opportunities for exploring the beautiful outdoors. In addition to clothing, it’s also important to consider what items to bring with you while visiting Woodside. As a nature lover’s paradise, be sure to pack sunscreen, insect repellent, and a water bottle to stay hydrated during your adventures. If you plan on visiting the many parks and hiking trails, a backpack to carry these items is essential. And don’t forget your camera to capture the stunning views and wildlife that Woodside has to offer. With the right attire and supplies, you’ll be well-equipped to fully enjoy your trip to this charming town.
Welcome to Woodside, a charming town nestled in the heart of California’s stunning redwood forests. If you find yourself here in the month of August, you’re in for a treat. This is the perfect time to explore the great outdoors and soak up the warm summer weather. Start your day with a hike through the majestic redwood groves at Huddart Park, just a short drive from the town center. You’ll feel like you’ve stepped into a fairy tale as you wander through the towering trees and listen to the soothing sounds of nature. After your hike, head to the charming downtown area for some shopping and dining. August is the peak of farmers market season, so be sure to check out the Woodside Farmers Market for fresh, locally grown produce and artisanal goods. For lunch, grab a sandwich from one of the many quaint cafes and have a picnic in one of the town’s beautiful parks. In the evening, catch a show at the Woodside Community Theater, where you can enjoy live music, theater, and film under the stars. August truly is a magical time to experience all that Woodside has to offer.
September
As summer fades into fall, September is a beautiful time to visit the charming town of Woodside. The weather is still warm and pleasant, but with a slight chill in the air. When it comes to dressing for your trip, I recommend packing layers. A light jacket or sweater will come in handy for cooler evenings, but you’ll still want to have some short-sleeved shirts and shorts for the warm days. Comfortable walking shoes are a must for exploring the quaint streets and nature trails of Woodside. As for what to wear, I always suggest dressing modestly and respectfully when visiting small towns. Locals appreciate visitors who make an effort to blend in. For women, a simple sundress or nice blouse and skirt combo will be appropriate. Men can’t go wrong with a nice collared shirt and khaki pants. Don’t forget to bring a hat and sunscreen for those sunny days. And of course, you’ll want to pack a camera to capture the picturesque scenery and charming architecture of Woodside. With these tips in mind, you’ll be dressed and ready to fully enjoy all that this lovely town has to offer.
Woodside, known as the “Town of Trees,” is a charming destination in September. This is the perfect time to visit as the crowds have dispersed and the weather is still pleasant. Immerse yourself in nature with a hike through the majestic redwood forests. The Purisima Creek Redwoods Preserve offers a variety of trails with stunning views and the opportunity to spot wildlife. For a unique experience, take a horseback ride through the redwoods with the Folger Stable. And don’t forget to stop by the Woodside Store, a historic general store that has been in operation since 1854. September in Woodside also offers a chance to indulge in the local food scene. The town’s Farmers Market is in full swing, with fresh produce and artisanal goods from local vendors. Be sure to try the famous Woodside Bakery’s apple turnovers, a perfect treat for the crisp fall weather. For a taste of the town’s history, visit the Alice’s Restaurant, a local favorite since 1960. This iconic spot serves up delicious burgers and live music on the weekends. And don’t miss the opportunity to sample some of the award-winning wines from the nearby Santa Cruz Mountains at the Thomas Fogarty Winery. With its small-town charm and endless activities, Woodside is the perfect destination for a September getaway.
October
When visiting the charming town of Woodside in October, it is important to come prepared with the right clothing and accessories. The weather can be variable during this time of year, so it’s best to dress in layers. A lightweight jacket or sweater is essential for cooler mornings and evenings, while comfortable walking shoes are a must for exploring the town’s scenic trails. Be sure to bring a waterproof jacket or umbrella as well, as rain showers are not uncommon in October. As for what to wear, Woodside is a casual town so there’s no need for formal attire. Opt for comfortable and practical clothing that can take you from hiking in the morning to strolling through the town’s quaint shops in the afternoon. A good pair of jeans, a light long-sleeved shirt, and a hat for sun protection are all great options. Don’t forget to bring a small backpack to carry essentials like water, snacks, and a camera to capture the stunning fall foliage. And for those planning to visit any of the nearby wineries, be sure to pack a nice outfit for a more upscale dining experience.
Woodside, located in the heart of California’s stunning Redwood region, is a hidden gem waiting to be explored. During the month of October, the town comes alive with autumnal colors and a plethora of activities to enjoy. One must-see event is the Woodside Art & Wine Festival, where local artists showcase their work and visitors can sip on delicious wines from the region. This charming festival is the perfect way to spend a sunny October afternoon. For nature lovers, a hike through the nearby Redwood Regional Park is a must-do activity in Woodside. The towering redwood trees, some of the oldest and tallest in the world, create a magical atmosphere that is truly unforgettable. October is the perfect time to visit, as the temperatures are cool and the leaves are changing colors. Don’t forget to pack a picnic and enjoy a tranquil lunch surrounded by the beauty of nature. Whether you’re a wine connoisseur or an outdoor enthusiast, Woodside offers something for everyone in October.
November
As the crisp autumn air settles over the charming town of Woodside, it’s important to dress in layers to stay comfortable throughout the day. November temperatures can range from cool mornings to warm afternoons, so I recommend packing a light jacket and a sweater that can easily be tied around your waist. Don’t forget to bring a sturdy pair of walking shoes for exploring the town’s picturesque streets and trails. Woodside is a quaint and casual town, so there’s no need to pack formal attire. Instead, opt for comfortable and practical clothing such as jeans, leggings, and long-sleeved shirts. A light rain jacket or umbrella might also come in handy, as November can bring occasional showers. And of course, don’t forget to bring a camera to capture the beautiful fall foliage and charming architecture of this idyllic town. With these essentials in tow, you’ll be ready to fully enjoy all that Woodside has to offer.
Woodside, a charming town nestled in the foothills of the Santa Cruz Mountains, is the perfect destination for a November getaway. As the leaves turn golden and the air becomes crisp, the town takes on a cozy and inviting atmosphere. One of the must-see attractions in November is the Filoli Estate, a stunning country home surrounded by acres of gardens. Take a leisurely stroll through the autumnal foliage and admire the grandeur of the estate, or warm up by the roaring fireplace in the drawing room. For a fun and unique experience, visit on November 10th for the annual Filoli Holiday Traditions event, where the house is decked out in festive decorations and visitors can enjoy live music, refreshments, and holiday shopping. For outdoor enthusiasts, November is an ideal time to explore the numerous hiking trails in Woodside. The weather is mild and the crowds have thinned out, making it the perfect time to immerse yourself in the beautiful natural surroundings. One of the most popular trails is the Purisima Creek Redwoods Open Space Preserve, where you can hike through towering redwoods and catch glimpses of wildlife such as deer and wild turkeys. After a day of hiking, be sure to stop by Alice’s Restaurant, a local favorite known for its hearty American fare and cozy atmosphere. With its stunning autumn scenery and welcoming community, Woodside is the perfect November destination for travelers looking to relax and recharge.
December
When visiting the charming town of Woodside in December, it’s important to dress in layers to combat the chilly weather. Start with a warm base layer such as a long-sleeved shirt and add a sweater or fleece on top. Don’t forget to bring a waterproof jacket or coat to protect against any rain or snow. As for pants, opt for comfortable and durable options such as jeans or khakis. Finish off your outfit with sturdy shoes or boots to keep your feet warm and dry while exploring the town. In addition to dressing appropriately, make sure to pack a few essentials for your December visit to Woodside. A warm hat, scarf, and gloves will keep you comfortable while wandering the streets or taking a scenic hike. Don’t forget to bring a small backpack or tote bag to carry any extra layers or souvenirs you may pick up along the way. And of course, a camera to capture the charming holiday decorations and beautiful winter scenery is a must. With the right clothing and gear, you’ll be able to fully enjoy the festive atmosphere of Woodside in December.
When December rolls around in Woodside, California, the holiday spirit is in full swing. Take a stroll through the charming downtown area and admire the festive decorations adorning the storefronts and tree-lined streets. You may even catch a glimpse of the annual Christmas parade, complete with marching bands and colorful floats. After a day of exploring, warm up with a cup of hot cocoa at one of the town’s cozy cafes. For a more active experience, head to the nearby Filoli Gardens for their annual Holiday Traditions event. This historic estate is transformed into a winter wonderland, with thousands of twinkling lights, festive decorations, and even an ice skating rink. Take a guided tour of the grand mansion, or simply wander through the beautifully lit gardens and enjoy the holiday ambiance. And don’t forget to stop by the gift shop for some unique holiday gifts and decorations to take home with you.
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.
