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.
Lithia Park
Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and lively festivals in this family-friendly 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.
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.
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 acclaimed theatre scene.
Top hotels in Historic Downtown District
Ashland Springs Hotel
Great breakfast, beautiful but small rooms for the price.
Reviewed on 29 Mar 2026
The Bard's Inn, BW Signature Collection by Best Western
There were a lot of different buildings so maybe some were different but my room was dark and depressing.
Reviewed on 28 Mar 2026
Winchester Inn
The room is fantastic!! Highly recommend!
Reviewed on 15 Jan 2026
McCall House Boutique Inn
Amazing stay in the Anthony room. Lovely staff with 24/7 amenities such as a water fill station, extra towels, hot coffee, and tea. Being an historical house you can definitely hear your neighbors but everyone was respectful of quiet hours. Yummy chef selected breakfast in the morning.
Reviewed on 29 Mar 2026
Stratford Inn
Fantastic location, convenient to walk downtown. Kids loved the pool. Staff were very kind.
Reviewed on 29 Mar 2026
Rogue Regency Inn Medford Airport
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.