Historic Downtown District Travel Guide
Ashland
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 lively festivals and entertainment choices.
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 lively festivals.
Top hotels in Historic Downtown District
Ashland Springs Hotel
Lovely music & coffee on the mezzanine in a.m. Beautiful decor. Comfortable bedding. Tea & cookies on the mezzanine in the afternoon. An orientation to amenities on arrival would have been helpful.
Reviewed on 4 Oct 2025
The Bard's Inn, BW Signature Collection by Best Western
Great location and nice room
Reviewed on 18 Oct 2025
Winchester Inn
Lovely room
Reviewed on 15 Oct 2025
McCall House Boutique Inn
Location was very convenient to walking everywhere. Breakfast was fresh and delicious.
Reviewed on 12 Oct 2025
Rogue Regency Inn and Suites
We arrived late from the airport. Very easy check in with a real person. The room was very clean and comfortable. Sinks were outside the toilet and shower. Sheets clean and crisp. Towels white and fluffy. Bed was a little hard. Pillows were large and fluffy. Very nice place to stay.
Reviewed on 18 Oct 2025
Flagship Inn of Ashland
Great room and great service. I'd asked for a scent-neutral room and the Flagship staff came through wonderfully. Comfortable, convenient, everything I needed. I'll be back for sure!
Reviewed on 21 Oct 2025
Check Historic Downtown District hotel availability
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.
