Ashland, Oregon
Oregon Shakespeare Festival headquarters with year-round performances. 93-acre Lithia Park and Pacific Crest Trail through town.
Quick Facts
What Makes Ashland Special
- •Oregon Shakespeare Festival with year-round theatrical productions
- •93-acre Lithia Park designed by same architect as San Francisco's Golden Gate Park
- •Farm-to-table dining scene with James Beard-recognized chefs
- •Southern Oregon University contributing to cultural vibrancy
- •Rogue Valley wine country nearby
- •Ashland Independent Film Festival
- •Hiking on Pacific Crest Trail (passes through town)
Things to Do
Oregon Shakespeare Festival
ArtsRenowned theater company performing Shakespeare and contemporary plays year-round.
15 S Pioneer Street, Ashland, OR 97520 ↗Lithia Park
Nature93-acre park with walking trails, creek, Japanese garden, and stunning scenery.
59 Winburn Way, Ashland, OR 97520 ↗Ashland Plaza Shopping
ShoppingCharming downtown with galleries, boutiques, bookstores, and farm-to-table restaurants.
Main Street, Ashland, OR 97520 ↗ScienceWorks Hands-On Museum
MuseumInteractive science museum fun for all ages with outdoor exhibits.
1500 E Main Street, Ashland, OR 97520 ↗Where to Stay in Ashland
The Ashland Inn
Charming historic inn in the heart of Ashland, featuring elegantly appointed rooms with period furnishings and modern amenities. Known for exceptional hospitality and locally-sourced breakfast.
Book on Booking.com ↗💡 Request a room with views of downtown for the best experience
Ashland Bed & Breakfast
Cozy bed and breakfast offering personalized service and comfortable rooms. Homemade breakfast featuring local ingredients. Perfect for couples seeking an intimate getaway.
Book on Booking.com ↗💡 Complimentary breakfast and evening refreshments included
Local Chain Hotel
Reliable national chain hotel with comfortable rooms, free WiFi, pool, and fitness center. Convenient location near major attractions and restaurants.
Book on Booking.com ↗💡 Good option for families and those seeking predictable amenities
Vacation Rentals
Variety of vacation rentals available through Airbnb and VRBO, from cozy cottages to spacious homes. Great for extended stays and families wanting kitchen facilities.
Book on Booking.com ↗💡 Book early for peak season availability
Where to Eat in Ashland
Ashland Bistro
Upscale dining featuring seasonal menus with locally-sourced ingredients. Creative dishes showcasing regional flavors in an elegant atmosphere. Reservations recommended.
Main Street Cafe
Popular local spot serving breakfast, lunch, and dinner. Known for generous portions, friendly service, and comfort food favorites. Great for families.
The Local Pub
Welcoming neighborhood pub with craft beers, burgers, and classic pub food. Live music on weekends. Casual atmosphere perfect for unwinding.
Downtown Coffee House
Cozy coffee shop serving expertly brewed coffee, fresh pastries, and light lunch options. Popular morning gathering spot for locals and visitors.
Ashland Diner
Classic diner offering hearty breakfasts, homestyle cooking, and generous portions. Friendly service and nostalgic atmosphere. Cash-friendly.
Pizza Place
Local favorite for pizza, pasta, and Italian classics. Family-friendly with quick service. Great for takeout after a day of exploring.
Sample Itineraries
Perfect Day in Ashland
Experience the best of Ashland with this carefully planned itinerary covering local attractions, dining, and activities.
Getting Around Ashland
Ashland is a compact, walkable town where most attractions, restaurants, and shops are within easy walking distance of each other. The downtown area is best explored on foot, allowing you to appreciate the historic architecture and discover hidden gems. For longer distances or day trips to nearby attractions, having a car is recommended. Street parking is typically available throughout town, with some areas offering free parking and others requiring meters or permits. Check posted signs carefully. During peak tourist seasons, arrive early to secure parking near popular attractions. Many accommodations offer on-site parking for guests. If you're staying downtown, consider parking once and walking everywhere to avoid the hassle of moving your car. Rideshare services like Uber and Lyft may have limited availability depending on the time of day. Local taxi services are available but should be called in advance. Bike rentals are available seasonally and provide a fun way to explore the area at a relaxed pace.
When to Visit Ashland: Seasonal Guide
Spring (March-May)
Spring brings mild temperatures and blooming flowers to the area. It's a quieter time to visit with fewer crowds.
- •Mild weather perfect for hiking and outdoor activities
- •Spring flowers and fresh greenery
- •Lower accommodation rates before peak season
- • Local farmers markets begin
- • Spring festivals and events
Summer (June-August)
Peak tourist season with warm weather and long daylight hours. All attractions and restaurants operate on full schedules.
- •Warm, sunny days ideal for outdoor recreation
- •All seasonal businesses and attractions open
- •Festivals, concerts, and community events
- • Summer concert series
- • Fourth of July celebrations
- • Art fairs and markets
Fall (September-November)
Autumn is spectacular with colorful foliage and pleasant temperatures. Popular season with moderate crowds.
- •Beautiful fall foliage and crisp weather
- •Harvest festivals and seasonal activities
- •Excellent hiking conditions
- • Harvest festivals
- • Fall foliage tours
- • Halloween events
Winter (December-February)
Winter brings cold temperatures and potential snow. Quieter season with holiday charm and winter activities.
- •Peaceful, uncrowded atmosphere
- •Holiday decorations and festivities
- •Winter sports and activities nearby
- • Holiday celebrations
- • Winter festivals
- • New Year's events
Best Photography Spots
Historic Downtown
The main street and historic district offer excellent architectural photography opportunities. Best captured in early morning or late afternoon light.
📸 Best time: Golden hour (sunrise or sunset)
Town Center
The heart of Ashland features charming streetscapes and local character. Look for interesting storefronts and street scenes.
📸 Best time: Morning for fewer crowds
Scenic Overlook
Find elevated vantage points for panoramic views of the town and surrounding landscape. Stunning during fall foliage season.
📸 Best time: Sunset for dramatic lighting
Local Landmarks
Iconic buildings, monuments, or natural features that define Ashland. Research specific landmarks before your visit.
📸 Best time: Blue hour for illuminated buildings
Day Trips from Ashland
Nearby State Park
Explore pristine natural areas with hiking trails, scenic viewpoints, and wildlife viewing opportunities. Perfect for nature lovers and outdoor enthusiasts.
Historic Town
Visit a neighboring historic town with unique shops, galleries, and restaurants. Many areas have complementary attractions worth exploring.
Eugene, OR
Take a day trip to the nearest major city for museums, shopping, dining, and urban attractions. Provides a nice contrast to small-town charm.
Practical Tips for Visiting Ashland
- •Book accommodations well in advance during peak season, especially for weekends and holidays
- •Most restaurants accept credit cards, but some local establishments may be cash-only
- •Dress in layers as weather can change throughout the day, especially in spring and fall
- •Wear comfortable walking shoes for exploring downtown and visiting attractions
- •Check attraction hours before visiting, as some locations have seasonal schedules
- •Bring a reusable water bottle - many establishments offer water refill stations
- •Download offline maps in case of spotty cell service in rural areas
Frequently Asked Questions
What is the best time of year to visit Ashland?
June to October for Shakespeare Festival and outdoor performances
How many days should I spend in Ashland?
2-3 days (theater weekend)
Is Ashland walkable?
Yes, Ashland is very walkable with most downtown attractions, restaurants, and shops within easy walking distance. However, having a car is useful for reaching outlying attractions and taking day trips to nearby areas.
Are there family-friendly activities in Ashland?
Absolutely! Ashland offers various family-friendly activities including parks, museums, outdoor recreation, and special events throughout the year. Many restaurants and attractions cater specifically to families.
What should I pack for a trip to Ashland?
Pack comfortable walking shoes, layers for changing weather, sunscreen, and a camera. Depending on the season, bring weather-appropriate clothing. The climate is mediterranean with southern oregon; warm dry summers, mild winters; perfect for theater season; rogue valley wine country.
Where is the nearest airport to Ashland?
Rogue Valley International-Medford (15 min)
Are pets allowed in Ashland?
Many outdoor areas and some accommodations in Ashland are pet-friendly. However, policies vary by establishment, so always call ahead to confirm. Most restaurants with outdoor seating welcome well-behaved dogs.
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