A Weekend in Ashland: Choose Your Own Adventure
Award-winning breweries and wineries
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!
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.
Friday activities in Ashland
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.
Enjoy live music
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.
The Rogue Valley Messenger has a complete list of upcoming events in the area.
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:
Dinner in Ashland
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.
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.
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
Saturday in Ashland
Hearty, locally sourced breakfast foods. Breakfast burritos are a specialty.
They suggest you call ahead to order.
Serving breakfast, lunch, and coffee
Brothers offer a full menu of traditional breakfast foods (and lunch).
They also feature corned beef hash, huevos rancheros, and potato pancakes.
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
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.
Outdoors – get wet!
Ashland is Rogue River territory.
Kayaking, river rafting, jet boat excursions, and fishing are abundant.
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.
Lunch in Ashland
Extensive menu of Mexican classics
They have a happy hour and weekly specials.
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!
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
Indoors – Science Works
Science Works is a hands-on science museum.
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
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.
Dinner in Ashland
Don’t miss the tamales!
Indonesian food from scratch.
Guy Fieri stopped by on Diners, Drive-ins, and Dives.
Sunday in Ashland
Special breakfast options
Fresh, organic ingredients.
Morning Glory specializes in vegetarian options, skillet breakfasts, and breakfast classics.
It also serves lunch and dinner.
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.
Family-owned restaurant – focusing on fresh, local ingredients.
The breakfast menu is extensive.
Made-to-order omelets are a specialty.
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.
This coffee house is in the back of a charming bookstore.
Can you get more perfect?
Indoor – Backstage Tour OSF
Tours run from March to October.
The tour covers the history, theaters, and behind-the-scenes workings of the Oregon Shakespeare Festival.
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.
|Medford, OR||13 miles|
|Cottage Grove, OR||157 miles|
|Eugene, OR||178 miles|
|Bend, OR||185 miles|
|Portland, OR||284 miles|
|Sacramento, CA||294 miles|
|Seattle, WA||458 miles|
|Boise, ID||466 miles|