Historic Downtown District Travel Guide

Ashland

Landmark building in Ashland Oregon.
Ashland is all about the Shakespeare down to the poppy #Red
We had a corner queen on the 8th floor and this is a close look at the neoclassical gothic architecture from our bedroom window
I always check out the local chamber of commerce when I land in a town I haven’t been to before. Ashland Oregon Chamber of Commerce is unique in that it’s beside this amazing bronze Shakespeare statue.
Enjoyed getting to see a screening of Agatha Christie’s “Murder on the Orient Express in this classic old movie theater

Popular places to visit

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

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.

Oregon Shakespeare Festival
USA, Oregon, Mt Ashland. Fresh snow on evergreens.

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.

Mount Ashland Ski Area
A pretty male Wood Duck standing under the shade of a tree on the shoreline of a pond in a city park.

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.

Lithia Park

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.

Oregon Cabaret Theatre

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.

Thomas Theatre

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.

Allen Elizabethan Theatre

Top hotels in Historic Downtown District

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ฿3,134 per night from 31 Mar to 1 Apr
฿3,134
฿4,003 total
31 Mar - 1 Apr
includes taxes & fees
Stay at this spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,006 reviews)
Nice, place breakfast was not worth 5.00 or the trouble.

Reviewed on 22 Mar 2026

Ashland Springs Hotel
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
The price is ฿3,389 per night from 1 Apr to 2 Apr
฿3,389
฿3,779 total
1 Apr - 2 Apr
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,001 reviews)
Great location! Very walkable

Reviewed on 23 Mar 2026

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ฿6,948 per night from 29 Mar to 30 Mar
฿6,948
฿8,176 total
29 Mar - 30 Mar
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (270 reviews)
The room is fantastic!! Highly recommend!

Reviewed on 15 Jan 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ฿6,321 per night from 29 Mar to 30 Mar
฿6,321
฿7,048 total
29 Mar - 30 Mar
includes taxes & fees
Stay at this B&B in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (591 reviews)
Nice job on the room, service.

Reviewed on 16 Mar 2026

McCall House Boutique Inn
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is ฿3,242 per night from 5 Apr to 6 Apr
฿3,242
฿3,615 total
5 Apr - 6 Apr
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the pool in their reviews. Popular ...
9.4/10 Exceptional! (1,727 reviews)
Easy access to everything

Reviewed on 26 Mar 2026

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ฿3,094 per night from 1 Apr to 2 Apr
฿3,094
฿3,645 total
1 Apr - 2 Apr
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.8/10 Excellent! (2,890 reviews)
Absolutely love the rogue Regency!! The only place i will book in the area. Their staff is more than accommodating.

Reviewed on 26 Mar 2026

Rogue Regency Inn Medford Airport
See all 698 properties in Historic Downtown District
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other neighbourhoods around Historic Downtown District

Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Thomas Theatre are some notable places to visit nearby.

Historic Railroad District
Street scene in downtown Ashland Oregon state.

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.

Siskiyou-Hargadine Historic District
Aerial view of Ashland, Oregon

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 Thomas Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District

Historic Downtown District Travel Guide