Ashland Dining and Lodging Hotel Logo Winchester Inn in Ashland Oregon

Explore Ashland's cultural, culinary, and ourdoor gems

What to do in Ashland

Welcome to a year-round destination that never fails to excite.

Ashland is a destination of cultural, culinary, and outdoor experiences that are unmatched.

From performing to visual arts, film, festivals, music and shopping - Ashland's culture offers something for everyone.

Are you a foodie at heart?  Explore the vibrant restaurant scene, boutique food artisans, local farms and abundant wineries.

All minutes from breath taking natural beauty that feature world-class running, biking and hiking trails, with white water rafting, skiing and unmatched vistas all at your fingertips.

Ashland boasts one of the oldest and largest non-profit theaters in the nation with the Oregon Shakespeare Festival. The Tony Award-winning theater is just blocks from the Winchester and presents eight and a half months of plays, back stage tours and educational programs.

Wineries map of Southern Oregon

Southern Oregon, and Ashland, have a wide range of wines and wineries to experience and fall in love with.  With over 70 grape varietals planted and more than 150 wineries spanning from Ashland to Roseburg the area is a wine lovers dream.
Enhance your stay at the Winchester Inn by exploring the Oregon winery map with a detailed guide for your stay in Oregon and Southern Oregon.


Ashland Chamber

The Ashland Chamber of Commerce is a wonderful place to learn all about what Ashland has to offer.  Events, calendars, a visitor's guide as well as friendly staff that can help you plan your visit.  There are few resources as fantastic as the Ashland Chamber.

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Ashland Mystery fest

Join cozy mystery author Ellie Alexander and her mystery writing friends for a weekend of full bookish fun with plenty of of twists and turns. From panels and workshops to an interactive mystery with clues located all around town, this festival is designed to put you in the hot seat.