Ashland October Shakespeare Festival – October 2-5, 2024




Tour Type


Embark on a captivating four-day cultural retreat at the world famous Ashland Shakespeare Festival. During the entire excursion, we will be staying in the cozy and historic Ashland Springs Hotel, which is on the same block as the Thomas Theater and one block from the Allen Elizabethan Theatre and Oregon Cabaret Theater. This tour incorporates two Oregon Shakespeare Festival performances, Much Ado About Nothing and Macbeth, and a dinner performance of Sherlock Holmes and the Study in Scarlet at the Oregon Cabaret Theater. Enjoy wonderful meals in award-winning locally-owned restaurants and venture into neighboring historic Jacksonville for some small town Oregon charm and sampling of wines from a local vineyard. Unforgettable memories await at every turn!

Day 1 – Wednesday, October 2

The luxury motor coach will head down the Willamette Valley after its stops in Tualatin, Woodburn, and Salem, stopping at a local vineyard in route to Ashland for lunch and a wine tasting – what a nice start to the trip! After checking into the Ashland Springs Hotel, guests will take part in a 30 minute preface to set the stage so to speak for the performance of Much Ado About Nothing. Over a delightful dinner we will anticipate the performance and then make our way to the Allen Elizabethan Theatre to round out our first day with a true Shakespearean classic in the open air theater.


Day 2 – Thursday, October 3

After breakfast we will make a mid-morning start for historic Jacksonville, Oregon for some free leisure time in their quaint downtown before settling in for a local lunch. A quick excursion to one of the area’s vineyards to sample the latest vintages will give travelers a chance to enjoy the fruits of the unique southern Oregon microclimates, and then a bit of cheese! After a relaxing day, enjoy dinner and a classic Sherlock Holmes mystery at the Oregon Cabaret Theater.


Day 3 – Friday, October 4

A morning tour of the Oregon Shakespeare Festival performance areas and campus will prime travelers for the afternoon performance of William Shakespeare’s classic tragedy, Macbeth. Our last night out in Ashland will be at a delectable local restaurant prior to the performance. A wonderful evening to reminisce over the memorable productions, incredible food, and unparalleled company. After dinner, we will make our way to the Angus Bowmer Theatre for our final performance of the trip.


Day 4 – Saturday, October 5

A leisurely morning to enjoy the last bits of Ashland will be punctuated by brunch prior to departure from the Ashland Springs Hotel. We will retrace our steps up to Salem, Woodburn, and Tualatin and look forward to the next cultural and culinary adventure.


Click Here for a Flyer for this Trip

Booking Tour

Tour Information

Max Guests


Min Age


Tour Location

Languages Support