Historic Railroad District Travel Guide

Ashland

Road trip food!! I loved the burrito bowl (cafe inside!) and some of their grocery items. ✌️ The only downside was the trip from and back to the freeway... left, right, left, right. Way too many turns! We probably lost 20 minutes driving.
Road trip food!! I loved the burrito bowl (cafe inside!) and some of their grocery items. ✌️ The only downside was the trip from and back to the freeway... left, right, left, right. Way too many turns! We probably lost 20 minutes driving.

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
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

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
Looks more like a little square in Nottingham Hill than Oregon. Lovely town with festive holiday lights at night.

Lithia Park

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Lithia Park

Southern Oregon University

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's entertainment choices and acclaimed theatre scene.

Southern Oregon University

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

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.

Allen Elizabethan Theatre

Top hotels in Historic Railroad District

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
243 4th St Ashland OR
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and a fireplace in reception. Popular attractions Ashland Library and Oregon Cabaret Theatre are ...
9.6/10 Exceptional! (97 reviews)
Couldn't be better. Excellent place to stay.

Reviewed on 19 Jan 2026

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The Peerless Hotel by WanderLodges
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,774 reviews)
Everything from the room to the staff and breakfast everything was amazing! I was so happy!

Reviewed on 15 Jan 2026

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Rogue Regency Inn and Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
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 ...
9.2/10 Wonderful! (1,637 reviews)
Great location in Ashland with a Safeway across the street.

Reviewed on 16 Jan 2026

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Stratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ₹7,109 per night from 6 Feb to 7 Feb
₹7,109
₹9,292 total
6 Feb - 7 Feb
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)
Room was clean, breakfast was excellent, staff was knowledgeable, pleasant, and eager to help. Outstanding stay!

Reviewed on 18 Jan 2026

Ashland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,472 reviews)
Clean room, front desk service, and Luna Cafe, was geeat.

Reviewed on 17 Jan 2026

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Ashland Hills Hotel & Suites
Motel 6 Medford, OR - North

Motel 6 Medford, OR - North

2 out of 5
2400 Biddle Rd Medford OR
The price is ₹3,479 per night from 25 Jan to 26 Jan
₹3,479
₹3,914 total
25 Jan - 26 Jan
includes taxes & fees
Stay at this motel in Medford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.2/10 Good! (1,089 reviews)
Clean room! Big bathroom Needs more pillows though..room only had two

Reviewed on 18 Jan 2026

Motel 6 Medford, OR - North
See all 702 properties in Historic Railroad 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 Railroad District

Ashland is all about the Shakespeare down to the poppy #Red

Historic Downtown District

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Historic Downtown District
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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
Walked across the street from the ER and imagine this was the view from a physician parking lot

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.

Skidmore Academy Historic District

Historic Railroad District Travel Guide