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.
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.
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.
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
Rogue River Family Float & Discovery Park-Rafting and Kayaking
Rogue River Whitewater Rafting- Mid Day
Rogue River Whitewater- Morning Rafting Adventure
Our pick of the best Historic Downtown District Hotel Deals
The Bard's Inn, BW Signature Collection by Best Western
"The staff was excellent! Room was nice and the breakfast was great."
Reviewed on 18 May 2026
Ashland Springs Hotel
"We stayed here because it was in downtown Ashland, which was convenient for our planned activities. Our room, while on the top floor and with a nice view, was not as clean as expected. There was popcorn clearly visible on the floor near the sofa from a previous guest; there were visible stains on ..."
Reviewed on 16 May 2026
Winchester Inn
"A lovely place to land. Beautiful Victorian with a garden to relax in. The room was so comfortable (even had a window seat) and the food was great. As was each member of the staff."
Reviewed on 2 May 2026
McCall House Boutique Inn
"McCall House was a perfect place to stay for an overnight trip to Ashland. The location was perfect and easy walking distance to many restaurants. The property was very quite. The breakfast was delicious."
Reviewed on 27 Apr 2026
Rogue Regency Inn Medford Airport
"Check in and out were easy. Very friendly staff for airport shuttle. Has a restaurant lounge we were too late to use. Included breakfast was ok. It’s clean but very outdated"
Reviewed on 18 May 2026
Prospero's Flagship Inn
"Was a very cute spot to stay the night at. I like that they had all the amenities. Mini fridge, hair dryer, iron, microwave, because I really needed to warm up left overs and my baby's water for his formula. Breakfast area could use some work. Waffle maker was a bit troublesome. And there wasn't ..."
Reviewed on 18 May 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 Oregon Shakespeare Festival.
