• Skip to main content
  • Skip to header right navigation
  • Skip to after header navigation
  • Skip to site footer
  • Pinterest
  • Instagram
  • Twitter
  • Facebook
  • YouTube
Jaunty Everywhere

Jaunty Everywhere

Travel + Lifestyle

  • Home
  • Blog
  • Podcast
  • About Jaunty
    • Meet Cheri and Jody
    • Meet Brittany and JJ
    • Meet Jordan and Bailey
    • Privacy Policy and Disclosures
  • Destinations
  • Travel Food
  • Outdoors
  • Travel Planning
You are here: Home / Destination / A Weekend in Ashland, Oregon

A Weekend in Ashland: Choose Your Own Adventure

World-class theater

Award-winning breweries and wineries

Outdoor adventure.

Stunning scenery.

Art, culture, and history

Ashland checks all the boxes.

Ashland, Oregon, is 293 miles from Portland, OR, and just 15 miles from the California border.

It’s home to Southern Oregon University and the famed Oregon Shakespeare Festival.

And it’s beautiful!

Related post:

See What is the Pacific Northwest {for travelers}

fountain in Lithia Park, Ashland, Oregon, trees with fall color in the background
Some links below are referral links, meaning, at no extra cost to you, we earn a commission if you make a purchase. Thank you for supporting Jaunty Everywhere in this way! See our full disclosure statement.

We’ve designed the weekend series to take you from Friday – Sunday with suggestions for indoor and outdoor activities and places to find great food.

What sounds like fun to you?

Pick and choose and create your perfect weekend.

Table of Contents
  • A Weekend in Ashland: Choose Your Own Adventure
  • Friday activities in Ashland
  • Saturday in Ashland
  • Saturday morning activities
  • Saturday afternoon activities 
  • Sunday in Ashland
  • Sunday activities 

Some posts on this site contain affiliate links, meaning if you buy something through one of these links, I may earn a small commission at no extra cost to you. Read the full disclosure policy here.

Friday activities in Ashland

Option 1 

See a play

Ashland is home to the Oregon Shakespeare Festival, after all.

The season runs from March to October.

Each season features several Shakespeare plays, musicals, classics, and experimental theater.

Attend a play every morning, noon, and night if you like.

Check out this excellent article by The Atlas Heart – Experiencing the Oregon Shakespeare Festival in Ashland.

Besides OSF, Ashland also boasts the Oregon Cabaret Theater, Camelot Theater, and Ashland Contemporary Theater.

bundled up at the Elizabethan Theater in Ashland, OR
Staying warm at the open-air Elizabethan Theater

Option 2

Enjoy live music

Southern Oregon University is home to the Oregon Center for the Arts, Chamber Music Concerts, and the Rogue Valley Symphony.

Check out the Rogue Scene for live music calendars.

The Chamber of Commerce provides a list of live music venues – restaurants, coffee houses, pubs, etc.

Japanese Garden at Lithia Park in Ashland, OR
Japanese Garden at Lithia Park

Option 3 

Evening stroll

Take an evening stroll through Lithia Park.

The park meanders along Lithia Creek, through woodlands, past duck ponds, a Japanese garden, a rose garden, and a tree arboretum.

The complete trail is approximately 2 miles, but you can turn around anytime.

If you park at the downtown end and walk the loop, you will end up back downtown in time for dinner.

There are 2 guided tours online:

Lithia Park Trail Guide

Historic Lithia Park Tour

Caldera Brewing Ashland, OR
Caldera Brewing has an enormous tap list and delicious food. You won’t be disappointed if you can sit on the patio at sunset.

Dinner in Ashland

Caldera Brewery and Restaurant

The restaurant is located near the freeway, not in the historic district.

But the location has its charms, sitting at the base of the mountains.

The patio is fabulous. I recommend watching the sunset from your picnic table.

Caldera serves ample portions of American-style pub food with a pedigree. Not just mac and cheese, but truffle mac and cheese. Cedar plank salmon. Pulled pork with house-made bread and BBQ sauce.

And with 45 of their beers on tap, the staff will help you pair any meal with the perfect brew.

Thai Pepper

The satay is delicious!

All the food is delicious. But the evening we dined, a wedding rehearsal commandeered downstairs, and we had to sit at the bar.

The charm of Thai Pepper is the location on Ashland Plaza; if the weather is nice, sit next to the creek.

Call ahead for reservations and ensure the creekside seating area is available.

Lithia Creek in Ashland, OR

Oberon’s Restaurant and Bar

The restaurant is fashioned after Shakespeare’s Midsummer’s Night Dream.

They serve home-style food, craft beer, and cocktails. There is live music most evenings.

Happy Hour from 4-6 p.m

View this post on Instagram

A post shared by Oberon’s Restaurant & Bar (@oberonsashland)

Saturday in Ashland

Breakfast

Brothers Restaurant

Brothers offer a full menu of traditional breakfast foods (and lunch).

They also feature corned beef hash, huevos rancheros, and potato pancakes.

View this post on Instagram

A post shared by Brothers’ Restaurant (@brothersrestaurantashland)

The Breadboard

Homemade breakfast served until 2 p.m.

They offer some unique twists on traditional breakfast – try one of their signature scrambles.

Be sure to check out the weekly specials.

Saturday morning activities

Option 1

Indoor/Outdoor – historic neighborhoods

Shop, absorb the vibe, see art, stop for coffee, and enjoy the historic homes.

The Downtown Plaza area and the Historic Railroad District are your best options.

Try the self-guided public art tour.

Option 2 

Outdoors – get wet!

Ashland is Rogue River territory.

Kayaking, river rafting, jet boat excursions, and fishing are abundant.

Try Hellgate Jetboat Excursions or Rogue Jetboat Adventures.

Check out Morrisons Rogue Wilderness Adventures for rafting or Noah’s River Adventures.

View this post on Instagram

A post shared by Hellgate Jetboat Excursions (@hellgatejetboats)

Option 3

Indoor/Outdoor – take a campus tour

During the weekend, this will be a self-guided tour.

Check out the exhibits at Hannon Library.

Southern Oregon University is the home of the Schneider Museum of Art.

Campus Tour Information

Self-Guided Tour

Lunch in Ashland

El Paraiso Mexican

Family-owned.

Extensive menu of Mexican classics

They have a happy hour and weekly specials.

Sammich

Unique sandwich shop right across the street from Southern Oregon University.

You will not leave hungry.

Finding a seat in the small dining room or outdoor patio can be challenging.

You might want to take your sandwich and find a spot under a tree on campus. If so, get extra napkins!

View this post on Instagram

A post shared by Sammich (@sammichashland)

Ashland Food Co-op

The co-op is an excellent choice for a to-go picnic.

The deli serves breakfast burritos and bowls, lunch burritos and tacos, sandwiches, smoothies, coffee, juice, and more.

Saturday afternoon activities 

Option 1

Indoors – Science Works

Science Works is a hands-on science museum.

Exhibits include:

Da Vinci’s Garage for tinkering and inventing

Discovery Island for the 5 and under

The Bubbleology Room

An outdoor climbing wall

A pedal-powered railroad

And more…

blue trail parker on asphalt - Bear Creek, Ashland, OR
Bear Creek Greenway is ideal for a family bike ride. Parks dot the entire trail.

Option 2 

Outdoors – hit a trail 

Bear Creek Greenway, which runs 18 miles from Ashland to Medford, is perfect for biking.

Bring your bike or rent one at Piccadilly Cycles.

For hard-core cyclists, check out the 55-mile Cascade Siskiyou Scenic Bikeway.

If hiking is your style, try Mt. Ashland, Ashland Watershed, or a chunk of the Pacific Crest Trail.

bicyclist on the Bear Creek Greenway in Ashland, OR
Bridge over Bear Creek.

Dinner in Ashland

Agave

Gourmet Mexican

Don’t miss the tamales!

View this post on Instagram

A post shared by ❤️ A G A V E • T A C O ❤️ (@agave_ashland)

Blue Toba

Indonesian food from scratch.

Guy Fieri stopped by on Diners, Drive-ins, and Dives.

Sunday in Ashland

Special breakfast options 

Morning Glory Cafe

Fresh, organic ingredients.

Morning Glory specializes in vegetarian options, skillet breakfasts, and breakfast classics.

It also serves lunch and dinner.

View this post on Instagram

A post shared by Judiaann Woo (@judiaann)

Greenleaf Restaurant

On the Plaza with indoor and outdoor seating on the creek.

They cater to vegetarians, vegans, and carnivores with delicious breakfast options.

Greenleaf offers a full gluten-free menu.

Wild Goose Cafe

Family-owned restaurant – focusing on fresh, local ingredients.

The breakfast menu is extensive.

Made-to-order omelets are a specialty.

Tiny Italian style Macchiatos at Noble Coffee in Ashland, OR
Nobel Coffee Roasting ranks as one of Oregon’s best coffee roasters.

Coffee houses

Noble Coffee Roasting

Large, open coffee house – a great place to hang out.

Coffee is roasted in-house. You can get a peek at the roasting room.

The baristas take their craft seriously.

Bloomsbury Coffee House 

This coffee house is in the back of a charming bookstore.

Can you get more perfect?

View this post on Instagram

A post shared by bloomsburyblends (@bloomsburyblends)

Sunday activities 

Option 1

Indoor – Backstage Tour OSF

Tours run from March to October.

Purchase tickets well in advance.

The tour covers the history, theaters, and behind-the-scenes workings of the Oregon Shakespeare Festival.

Flower farm on the Bear Creek Greenway in Ashland, OR
The Bear Creek Greenway offers interesting things to see. This flower farm was in full fall bloom; We couldn’t help but stop and peek through the trees.

Option 2

Outdoor – Drive the countryside 

The countryside around Ashland is jaw-dropping.

It’s well worth the time to meander the backroads.

Your best bet is to stop at the visitor’s kiosk in the Plaza square. It’s right next to the Lithia Fountain.

Tell them what you’re interested in – waterfalls, wineries, rivers, mountain views – and they will point you in the right direction.

We drove over to Jacksonville for a day. It’s a short drive and well worth the time.

And if you are coming from Portland, this post is worth a look.

Destination:Distance:
Medford, OR13 miles
Cottage Grove, OR157 miles
Eugene, OR178 miles
Bend, OR185 miles
Portland, OR284 miles
Sacramento, CA294 miles
Seattle, WA458 miles
Boise, ID466 miles
Distances to Ashland

More Resources

Planning a Trip to Oregon

A Weekend in Eugene, Oregon: Choose Your Own Adventure

A Weekend in Bend, Oregon – In Summer

Sidebar

Meet the Team

Find a Travel Deal

Legal Information

Jaunty Everywhere is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. Jaunty Everywhere also participates in affiliate programs with CJ, ShareASale, and other sites. Jaunty Everywhere is compensated for referring traffic and business to these companies.

About Jaunty

Privacy

Sitemap

Join our Free Community

Follow on Social

  • Pinterest
  • Instagram
  • Facebook
  • YouTube

Resources

Enneagram and Travel

Road Tripping

Copyright © 2025 · Jaunty Everywhere · All Rights Reserved · Powered by Mai Theme

Pinterest pin about Ashland, Oregon weekend getaway
Pinterest pin about Ashland, Oregon weekend getaway
Pinterest pin about Ashland, Oregon weekend getaway