Walk Ashland Walking Tours

Tour Ashland On Foot

Exploring history and art in a new town (or your own town) is fun, meaningful and memorable. Have a new, richer experience of Ashland as you learn about Ashland’s history, art and neighborhoods.

Ashland was founded in 1852 as an agricultural and mill town, but the citizens were committed to culture and education from the early years. Learn what led to Oregon Shakespeare Festival, Southern Oregon University and more.

You can choose from guided walks that focus on history, art, specific neighborhoods – or all of the above! Explore Ashland with a guide and feel the difference.

Custom walking tours or talks can be arranged for your family, group or event.

Thank you for your walking tour. It was fabulous. I have lived in Ashland for nearly 50 years and I learned more from your walk than I had ever known about this town.
M Smith

Ready to go on a Walking Tour?

(NOTE: Tour dates now posted for end of May and all of June!)

Here’s what to do next.

  1. Click the Book Now button for Walking Tour details and reservations.
  2. Choose your preferred Walking Tour. On the calendar page, choose the date you want. Tour dates are in blue. Then click on the time at the bottom of the page. That will take you to the sign-up page.
  3. Please register and pay for only one person at a time.
  4. Pay through the simple, secure payment portal.
  5. You will receive an email confirmation and reminder for your Walking Tour.
Peter leading a walking tour.
Peter leading a walking tour. Photo by Richard Simonds

Here is a brief introduction to each of

my current walking tours.

    1. History walking tour: Plaza & the Founding of Ashland
    2. History walking tour: Impact of the Railroad on Ashland
    3. History+Art walking tour: Plaza to Ashland Library and back
    4. History+Art walking tour: Painted utility boxes in Railroad District
    5. Public Art walking tour: Downtown public art (six artworks)
    6. Public Art walking tour: Bandersnatch trail (three artworks)
    7. Neighborhood Art walking tour: Fordyce Street neighborhood

History tour: Plaza & the Founding of Ashland  

Description: Learn about the founding of Ashland and early Ashland history – people, buildings, stories of triumph and tragedy, and more. Primarily on the Plaza, the walk will also go into Lithia Park and along Winburn Way. See Ashland photos from 100 to 160 years ago.

Time of walk: Approximately 1.5 hours.

Distance of walk: approximately 1 mile. Flat route, mostly paved walking surface with some uneven pavement. A short distance of the walk is on a dirt or wood chips path in Lithia Park.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 12 people.

Route: Plaza, Lithia Park, Winburn Way, back to Plaza.

Meeting spot: Meet at Lithia Park entrance at south end of Plaza.

History tour: Impact of the Railroad on Ashland

Description: Learn about the impact of the railroad on Ashland in the late 1800s and through the 1900s. You will explore historic A Street and Fourth Street in the Railroad District. Hear stories about Ashland’s Chinese community from 1880 to 1930, why Ashland police fed free dinners to hobos in the early 1900s, and much more.

Time of walk: 1.5 to 2 hours

Distance of walk: approximately 1.3 miles. Mostly flat, paved surface, some walking on grass.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 12 people.

Route: Railroad Park, A Street, First Street, B Street, Fourth Street, A Street back to Railroad Park.

Meeting spot: Meet at Golden Connections sculpture in Railroad Park.

History+Art tour: Plaza to Ashland Library and back

Description: In this guided walk through downtown Ashland, you will learn the history of Ashland Springs Hotel, the Hotel Oregon (which was torn down in 1961), the Ashland library from its humble beginning in 1879, Teddy the Elk at the Ashland Elks Lodge, and much more. There will be a brief introduction to eight Ashland public artworks.

Time of walk: Approximately 1.5 hours.

Distance of walk: approximately 1 mile. Flat route on sidewalks, with some uneven pavement.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 10 people.

Route: North end of Plaza, East Main Street, Ashland Carnegie Library, Third Street, return to Plaza along Lithia Way.

Meeting spot: Meet at the flagpole in the Plaza.

History+Art tour: Painted utility boxes in Railroad District

Description: During this tour, we will visit eight painted utility boxes (all part of Ashland’s public art collection) and explore Ashland history through nine stories. Most of our tour will be walking through Ashland’s historic Railroad District.

Time of walk: approximately 1.5 hours

Distance of walk: approximately 1.2 miles. Flat route, mostly paved walking surface with some uneven pavement.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 12 people.

Route: Second Street, Lithia Way, Oak Street, A Street, Third Street, C Street, back to Lithia Way and Second Street.

Meeting spot: Meet in front of U.S. Bank near corner of East Main St and Second St.

Public Art tour: Downtown public art (six artworks)

Description: We will see the artworks Pioneer Mike, “We Are Here,” Rio Amistad, Fall Splendor, Inorganic Compound and Las Calles de Guanajuato. I will give a brief introduction to Native Americans of the Rogue Valley, the founding of Ashland, early Ashland history, and our sister city relationship with Guanajuato.

Time of walk: approximately 1.5 hours

Distance of walk: approximately 1 mile. Mostly on sidewalks. We will walk down one stairway, and walk a very short distance on a level dirt path.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 12 people.

Route: Plaza to North Main Street, south on Granite Street, down Calle Guanajuato stairway, along Calle Guanajuato to the Guanajuato mural.

Meeting spot: Meet at the Pioneer Mike statue in Ashland Plaza.

Public Art tour: Bandersnatch trail

Description: On the Bandersnatch trail art tour we will view three public art pieces: Elevation, Pacific Fisher and Water is Life. You will learn about the artists, how the artworks were created and how the art relates to Ashland’s watershed.

Time of walk: approximately 1 hour

Distance of walk: approximately 0.5 miles. We will be walking on dirt trails. From Pacific Fisher to Water is Life is a somewhat steep uphill and back downhill climb.

Cost is $10 per person, with children 10 years and younger free.

Route: From Glenview Drive parking area along Waterline trail, then up Bandersnatch trail, then back to the starting spot.

Meeting spot: Trail head by parking area on Glenview Drive. Take Granite Street south. At 0.1 miles past point where Granite Street becomes dirt road, turn left on Glenview Drive. You will see two parking areas a little past 0.1 miles on Glenview Drive.

Neighborhood Art tour: Fordyce Street neighborhood

Description: As we walk through the Fordyce Street neighborhood, we will see a dozen colorful, uplifting murals and mosaics. You will learn about the local artists and how they created the artworks.

Time of walk: Approximately 1.5 hours.

Distance of walk: 1 mile. Flat route, mostly paved walking surface with some uneven pavement, short distance on dirt path.

Cost is $15 per person, with children 10 years and younger free. Normally a maximum of 12 people.

Route: East Main Street, through Evergreen Park, Mill Pond Road, Fordyce Street, Orchid Street, Rose Lane, Fordyce Street, Evergreen Lane, through Evergreen Park, back to East Main Street.

Meeting spot: Corner of East Main Street and Wightman Street, on the sidewalk in front of the new National Guard Armory.

The group loved the history and your tour truly gave them a sense of place and appreciation for the town they then explored all week. Thanks again for your participation and sharing your vast knowledge of Ashland!

Not Ready to Schedule a Tour?

If you can’t schedule a Walking Tour now, grab this free PDF download today. It’s filled with quirky Ashland stories and photos that will bring a smile to your face.