If you’re planning a road trip along the Pacific Northwest, then you must include a visit to Ashland because it is by far the best place to stay between San Francisco and Portland or visa versa.

Ashland is not like other towns in Oregon. Surrounded by the Cascade & Siskiyou mountain range, it has fantastic views and tons to do outside in nature for people who love the great outdoors. We often have three seasons in one day, depending on which part of town you’re in. Sometimes, I leave my house located on the south side of Ashland to head to the Inn, which is located on the north and I am in the fog! I can’t see anything until I drive 5 blocks down to Main Street when the fog subsides and there is gorgeous sunshine. The west side of town is hilly and loaded with great hikes & bike trails, and the east side is more flat with railroad tracks running from north to south.

woman sitting on top of pilot rock


If you like to explore wild flowers and take long walks, Ashland has it all. Besides the hundreds of hikes that shoot off from the fantastic Lithia Park, we have one of the most gorgeous hiking trails on the edge of town called Grizzly Peak. At the top of the trail (it’s not a difficult hike) there are spectacular views of Mount Ashland, Mount Shasta & Mount McLoughlin. The wild flowers are amazing too, especially in the spring and fall. Another place with amazing wild flowers is Pilot Rock. This too is not a very difficult hike except for the very top. Climbing to the top of the messa, can be rather harry & technical. You will need good shoes if you want to attempt making it to the top. Both of these are half-day hikes, which will get you back in time to enjoy one of Ashland’s mouth watering restaurants.

pacficic crest trail

For a small town, we have some amazing restaurants. MAS is a phenomenal restaurant serving ‘Cascadian Cuisine,’ and has a unique farm-to-table menu by chef Josh Dorcak, who happens to also be the Iron Chef of Oregon.  Peerless Restaurant is another truly inspiring restaurant that has a great locally sourced menu. We love their lavish tuscan style garden located in the quaint Railroad District.

friends drinking champagne and having a picnic at a winery in southern oregon

Ashland is located in the heart of Southern Oregon which is the fastest growing wine region in the world, so it is only right that our top restaurants offer a large selection of local wines. We happen to agree with Vogue when they wrote, ‘Why This Oregon Town Could Be The Next Napa.’ One of our favorite restaurants with a great wine list that never disappoints is Ostra’s Tapas & Bottleshop. They serve traditional Spanish Tapas Bar and are in the heart of downtown Ashland with tables outside on the Ashland Creek. If you try one of our local wines and fall in love, you can purchase a bottle from their bottleshop!

colorful fresh food on a white plate

Apart from being the most picturesque gorgeous little town, Ashland is a cultural mecca. Home to the Oregon Shakespeare Festival, which goes from March until November with 3 different sessions, the crescendo being the high summer months when the outdoor Elizabethan Theatre opens from June until late October. A lot of people are surprised to learn that OSF has two shows a day for most of the week, a matinee at 1:30 and an evening show at 8:00 p.m. and they are closed on Mondays.

oregon shakespeare festival elizabethan theatre at night

If you like music, we have the fabulous Brava Opera, great local choirs as well as the Oregon Cabaret Theatre which is a fantastic small theatre company that performs live dinner shows inside an old church in downtown Ashland. Our bars & wineries almost always have live music, especially during summer. Did I mention the Bayberry Inn hosts live bluegrass & jazz musicians on Sunday evenings during the warmer months in our back garden? Enjoy a view of Mt. Ashland while you listen to live music with a glass of local wine; it’s blissful.

hands holding red grapes

Ashland is the perfect half-way-point between San Francisco & Portland so it’s not only convenient, but it’s also not to be missed for all the reasons mentioned above!

womens feet wearing blue jeans and red and white shoes sticking out of white car driving on road with green trees