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 lively festivals 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.
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.
Thomas Theatre
You can get tickets for a performance at Thomas Theatre during your trip to Ashland. Experience the area's acclaimed theatre scene and lively festivals.
Things to do
Top hotels in Historic Downtown District
Ashland Springs Hotel
Just a block from the Shakespeare Festival, this hotel is ideally located. Room was clean as were common areas. Chairs in the room were cute, but could use some stuffing. Breakfast was good deal at $5…a step up from chain hotel breakfasts.
Reviewed on 7 Apr 2026
The Bard's Inn, BW Signature Collection by Best Western
The pros: Friendly staff. Decent hot breakfast. Walkable location to shops and restaurants. The downsides: 1) the place has multiple buildings (our room was across the street), so it's a tad inconvenient to go to the lobby and breakfast lounge when you're in a separate complex. (2) The room is quaint ...
Reviewed on 7 Apr 2026
Winchester Inn
Lovely establishment, made to order breakfast, easy walking to theaters.
Reviewed on 8 Apr 2026
McCall House Boutique Inn
It has a great location, easy to walk to center of town. The breakfasts were very fresh and warm. They had 3 or 4 different EV chargers behind the lovely historic house.
Reviewed on 31 Mar 2026
Stratford Inn
Great stay
Reviewed on 8 Apr 2026
Rogue Regency Inn Medford Airport
No we open the curtains and there was a guy peeing right there and they messed up are reservations gave us the wrong room twice til I found the email then they gave us the right room so was not happy
Reviewed on 6 Apr 2026
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 Thomas Theatre.
