Historic Downtown District Travel Guide
Tourist Guide
Visit Historic Downtown District
Popular places to visit
Oregon Shakespeare Festival
You can get tickets for a performance at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
Mount Ashland Ski Area
Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.
Oregon Cabaret Theatre
You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Allen Elizabethan Theatre
You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.
Thomas Theatre
You can get tickets for a performance at Thomas Theatre during your trip to Ashland. Experience the area's entertainment choices and acclaimed theatre scene.
Angus Bowmer Theatre
You can make plans for a show at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.
Activities
Our pick of the best Historic Downtown District Hotel Deals
Ashland Springs Hotel
Loved everything however we are allergic to cats and our room on the 5th floor had some pet allergies that set off an allergic reaction we didn't expect. We had understood pets were only allowed on the 3rd floor. Additionally the room across the hall had several dogs that barked...not a huge issue ...
Reviewed on 5 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western
Thus is our go to hotel every time we visit Ashland. It is quiet and extremely close to downtown.
Reviewed on 2 Jan 2026
Winchester Inn
Property was beautiful. Room was large, clean and nicely appointed. The only disappointment was not getting to sample the highly rated breakfast as we learned after we made our booking that the kitchen and restaurant were shut down for a yearly deep clean.
Reviewed on 4 Jan 2026
McCall House Boutique Inn
Limited iptions for breafast
Reviewed on 4 Jan 2026
Rogue Regency Inn and Suites
The room was clean, had plenty of towels. The restaurant onsite had very good food for dinner. I wasn't too impressed with the free breakfast. The liquid eggs and processed sausage wasn't my favorite. The front desk staff was very pleasant and friendly.
Reviewed on 6 Jan 2026
Stratford Inn
Fantastic place to stay
Reviewed on 5 Jan 2026
Other neighbourhoods around Historic Downtown District
Historic Railroad District
While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.
Siskiyou-Hargadine Historic District
If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.
Skidmore Academy Historic District
While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Oregon Shakespeare Festival.
