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4 Days in Ashland, Oregon

  • Day 1: Lithia Park
    0 minutes (Located in Downtown Ashland)

    Lithia Park is a 93-acre park in downtown Ashland, known for its beautiful gardens, hiking trails, and playgrounds. Stroll around the park, take in the scenery or have a picnic.

  • Day 2: Oregon Shakespeare Festival
    10 minutes (5 miles) from Lithia Park

    The Oregon Shakespeare Festival is a world-renowned theater event that runs from February to October. Watch one of the amazing Shakespearean productions in one of the festival's theaters or the outdoor theater.

  • Day 3: Cascade-Siskiyou National Monument
    35 minutes (17 miles) from Oregon Shakespeare Festival

    Cascade-Siskiyou National Monument is a protected area full of local wildlife, gorgeous scenery and numerous hiking trails. Enjoy the stunning views or go for a short hike.

  • Day 4: Ashland Vineyards & Winery
    20 minutes (8 miles) from Cascade-Siskiyou National Monument

    Take a tour of the Ashland Vineyards & Winery, renowned for its award-winning wine. Enjoy the scenery and indulge in a tasting session of some of Ashland's finest wines.

Time and Costs Estimates

  • Lithia Park (2 hours, Free)
  • Oregon Shakespeare Festival (3 hours, $115/person)
  • Cascade-Siskiyou National Monument (4 hours, Free)
  • Ashland Vineyards & Winery (2 hours, $25/person for tastings)
  • Total Estimated Costs: $165/person

Transportation

It’s best to rent a car for this trip, as most of the destinations require some driving. The estimated car rental cost is around $40/day. The estimated distance traveled on this trip is about 30 miles per day.

Useful Tips

For those with more time, consider adding a day trip to Crater Lake National Park to your itinerary. For those with less time, we recommend dropping Cascade-Siskiyou National Monument from your itinerary.

Airports

Rogue Valley International-Medford Airport (MFR) is the main airport for Ashland, located 16.4 miles northeast from the city center. Airlines that fly to MFR include Alaska Airlines, Delta, and United Airlines.

When are you going?
Add your start date and we'll check in at two weeks out, one week out, and the day before — bookings, packing, and a day-one brief. Reply to any of them if plans change.
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