Ashland Itinerary 5 Days: Explore Southern Oregon
If you are planning a trip to Oregon, you do not want to leave out Ashland, a charming city located in the southern part of the state. With numerous attractions and activities, there is no shortage of fun things to do during your stay. This comprehensive guide outlines a 5-day itinerary to help you make the most of your trip to Ashland, Oregon. Whether you are an art enthusiast, an outdoor adventurer, or a foodie, there is something for everyone during your visit to this beautiful city.
With this itinerary, you will discover the must-see attractions that make Ashland the perfect destination for the ultimate American holiday. As you explore the city, you’ll be greeted with amazing experiences that will stay with you for a lifetime. Get ready to experience Southern Oregon with our Ashland Itinerary 5 Days and see everything this magical city has to offer.
Day 1: Arrival and Exploring Downtown Ashland
As you begin your travel plan to Ashland, Oregon, make sure to schedule your first day in the city to explore the downtown area. With its picturesque streets lined with unique shops, art galleries, and cozy cafes, downtown Ashland offers a charming ambiance that’s hard to resist. Be sure to take a stroll around and get immersed in the local culture and vibe of the city.
While exploring the area, you can take the opportunity to have a taste of Ashland’s culinary scene by dining at one of the local restaurants. The city has a diverse culinary selection, with options ranging from farm-to-table restaurants to international cuisines. Make sure to indulge in a culinary adventure for your taste buds!
“Downtown Ashland is a vibrant place that offers a mix of culture, history, and culinary gems, making it a must-see destination in Southern Oregon.”
Day 2: Ashland Shakespeare Festival and Lithia Park
Immerse yourself in the arts on the second day of your Ashland Itinerary 5 Days by attending a performance at the world-renowned Ashland Shakespeare Festival. Founded in 1935, the festival has gained international recognition for its exceptional productions and talented actors. Be sure to check the festival schedule and purchase tickets in advance.
Afterward, take a short stroll to Lithia Park, one of the must-visit things to do in Ashland. This 100-acre park offers stunning gardens, scenic trails, and playgrounds for all ages. Take a peaceful walk through the Japanese garden, relax by the Lithia fountain, or have a picnic with your loved ones.
Make sure to wear comfortable shoes and bring a light jacket, as the evening temperatures in Ashland can get chilly. Day two is an excellent opportunity to stroll and immerse yourself in Ashland’s cultural atmosphere.
Day 3: Outdoor Adventures in Southern Oregon
Start your third day in Southern Oregon with an adventurous spirit and experience the best attractions in Ashland. Here are some of the outdoor adventures you shouldn’t miss:
| Attraction | Description |
|---|---|
| Crater Lake National Park | Marvel at the stunning blue waters of Crater Lake, formed from a collapsed volcano. Take a scenic drive, hike the trails, or even go swimming in the lake. |
| Mount Ashland | Hit the slopes in winter and enjoy skiing and snowboarding an easy 30-minute drive from Ashland. In the summer, go hiking and mountain biking on the many trails. |
| Rogue River Rafting | Hold onto your paddles on a thrilling ride down the Rogue River’s rapids. Take a guided tour with local companies and enjoy stunning views of the surrounding mountains. |
These are just a few of the exciting outdoor adventures you can experience in Southern Oregon. Get ready to explore and make unforgettable memories during your journey.
Day 4: Wine Tasting in the Rogue Valley
After enjoying all the must-see sights in Ashland, it’s time to discover the beauty of the Rogue Valley. On day four of your Ashland itinerary, indulge in the region’s world-famous wine and vineyards by touring the wineries and vineyards.
Discover the unique flavors and rich history of Southern Oregon’s winemaking scene by sampling local wines and learning about the winemaking process. Take a scenic tour of the vineyards and enjoy breathtaking views of the rolling hills that surround the picturesque Rogue Valley.
| Top Wineries to Visit in Rogue Valley | Address |
|---|---|
| Weisinger’s of Ashland | 3150 Siskiyou Blvd, Ashland, OR 97520 |
| Kriselle Cellars | 12956 Modoc Rd, White City, OR 97503 |
| RoxyAnn Winery | 3285 Hillcrest Rd, Medford, OR 97504 |
Don’t forget to appreciate the spectacular views of the surrounding vineyards and mountains. Bring home a bottle of local wine as a unique souvenir of your Ashland trip.
Day 5: Ashland’s Cultural Gems and Departure
On your last day in Ashland, take some time to explore the city’s cultural attractions.
Visit Museums
One of the best ways to immerse yourself in Ashland’s cultural scene is to visit its museums. The Schneider Museum of Art features contemporary works from regional and national artists, while the ScienceWorks Hands-On Museum is perfect for families with interactive exhibits and science-themed activities.
Explore Ashland’s Parks
Take a stroll along the scenic Ashland Creek Greenway or relax at one of the many colorful parks in Ashland. Lithia Park, which you already visited, is a must-see for its stunning trails, playgrounds and Japanese garden.
Departure
Say goodbye to Ashland, check-out of your hotel and depart for your next destination, taking with you unforgettable memories from your 5-day Ashland trip.
“Travel makes one modest. You see what a tiny place you occupy in the world.” -Gustave Flaubert
Where to Stay in Ashland
If you’re planning a five-day exploration of Ashland, you need a comfortable and convenient place to stay. Ashland offers a range of accommodations to suit every preference and budget, from luxury hotels to cozy bed and breakfasts. To optimize your experience, it is advisable to book in advance, especially during peak season.
For luxury seekers, Ashland Hills Hotel & Suites offers spacious rooms and beautiful views of the city. Budget-conscious travelers may find the Flagship Inn of Ashland or the Cedarwood Inn & Suites more appealing. To enjoy a local experience, consider the McCall House Bed and Breakfast or Country Willows Inn, which offer charming amenities and homey touches.
Hotels and Resorts
| Hotel Name | Rating | Price Range |
|---|---|---|
| Flagship Inn of Ashland | 3.7/5 | $89-$129 |
| Ashland Springs Hotel | 4.6/5 | $140-$280 |
| Ashland Hills Hotel & Suites | 4.4/5 | $149-$299 |
| Plaza Inn & Suites at Ashland Creek | 4.5/5 | $169-$259 |
Bed and Breakfasts
| Bed and Breakfast Name | Rating | Price Range |
|---|---|---|
| The McCall House Bed and Breakfast | 4.9/5 | $209-$289 |
| Country Willows Inn | 4.9/5 | $220-$355 |
| Chanticleer Inn Bed and Breakfast | 4.7/5 | $175-$305 |
| Bayberry Inn | 4.8/5 | $219-$289 |
Choose the accommodation that suits your needs, whether you’re seeking proximity to downtown or a more secluded and tranquil location. Whatever your preference, Ashland has something to offer for every type of traveler.
Dining in Ashland
While exploring Ashland, you will surely work up an appetite. Luckily, the city has a diverse culinary scene with options to fit all tastes and budgets. From farm-to-table restaurants to international cuisine, Ashland has something to satisfy every palate.
For a taste of the local cuisine, try the huckleberry milkshake at Northwest Raw or the organic, grass-fed beef burgers at Smithfields. If you’re in the mood for Italian, head to Pasta Piatti for homemade pasta and wood-fired pizza. For a special occasion, treat yourself to a fine dining experience at Alchemy Restaurant and Bar.
| Restaurant Name | Cuisine | Price Range |
|---|---|---|
| Northwest Raw | Organic, vegetarian | $ |
| Smithfields | American, steakhouse | $$ |
| Pasta Piatti | Italian | $$ |
| Alchemy Restaurant and Bar | American, fine dining | $$$ |
Make sure to check out the local farmers’ market (link to Section #11: Weather and Best Time to Visit Ashland) to stock up on fresh produce and artisanal goods. If you have dietary restrictions, don’t worry – many restaurants offer vegan, gluten-free, and other allergy-friendly options.
With so many delicious options, it can be hard to decide where to eat. Use these Ashland travel tips to plan ahead, make reservations, and enjoy the local cuisine to the fullest!
Getting Around Ashland
Getting around Ashland is easy and convenient, with a range of transportation options at your disposal. Here are some Ashland travel tips to help you choose:
Renting a Car
Renting a car is a great option in Ashland, especially if you plan to explore the surrounding areas. There are several car rental companies in Ashland, including Avis, Enterprise, and Hertz. You can also rent a car at the nearby Rogue Valley International-Medford Airport. Make sure to book your car in advance, especially during peak season.
Public Transportation
Ashland has a reliable public transportation system, including buses and shuttles. The Rogue Valley Transportation District (RVTD) operates bus routes throughout Ashland and the surrounding areas. The Ashland Connector shuttle provides service to the downtown area, including the Ashland Oregon Shakespeare Festival theaters. Plan your trip in advance and check the RVTD website for schedules and fares.
Pedestrian and Bike-Friendly City
Ashland is a pedestrian-friendly city, with many attractions and amenities within walking distance. You can also rent a bike from one of the local bike rental shops and explore the city on two wheels. The Bear Creek Greenway connects Ashland with neighboring towns and is a popular route for cyclists.
Whatever your preferred mode of transportation, these Ashland travel tips will help you explore the city and its surrounding areas comfortably and conveniently.
Weather and Best Time to Visit Ashland
When planning your itinerary for exploring Ashland in 5 days, it’s important to consider the weather patterns. The climate in Ashland is characterized by hot summers and cool winters. If you want to avoid extreme temperatures and have a comfortable trip, then the best time to visit is during spring or fall.
Peak tourist season in Ashland falls between June and August. While the warm weather attracts many visitors during this time, it also means larger crowds and higher prices. If you’re traveling on a budget and want to avoid the crowds, then plan your trip for the off-season months of April, May, September, or October. Not only will you have more affordable options, but you’ll also have more opportunities for sightseeing without having to navigate through bustling crowds.
| Month | Average Temperature |
|---|---|
| January | 41°F (5°C) |
| February | 45°F (7°C) |
| March | 51°F (11°C) |
| April | 58°F (14°C) |
| May | 66°F (19°C) |
| June | 74°F (23°C) |
| July | 83°F (28°C) |
| August | 82°F (28°C) |
| September | 76°F (24°C) |
| October | 62°F (16°C) |
| November | 49°F (9°C) |
| December | 41°F (5°C) |
Keep in mind that the weather in Ashland can be unpredictable, so it’s a good idea to pack a variety of clothing options to accommodate changing temperatures and weather conditions.
Conclusion
In conclusion, planning a travel itinerary for 5 days in Ashland, Oregon is the perfect way to explore the must-see sights and attractions, including the Ashland Shakespeare Festival, Lithia Park, and wineries in the Rogue Valley. With our travel plan Ashland Oregon guide, you’ll be able to make the most of your trip and indulge in delicious local cuisine, outdoor activities, and cultural gems.
Make sure to book your accommodations in advance and consider renting a car or using public transportation to get around Ashland. With mild weather throughout the year, any time is perfect for exploring Ashland in 5 days. Plan your trip now and embark on a memorable journey in Southern Oregon.
Thank you for choosing our Ashland Itinerary 5 Days guide and we hope you have a wonderful time exploring all that Ashland, Oregon has to offer.









