7 Thing You Can Strike Off Your Bucket List By Visiting Ashland, Oregon

When you hear a town is situated in the Rogue Valley, you might expect it to be an interesting place. Ashland does not disappoint. Despite its small size and proximity to a mountainous wilderness, Ashland boasts one of North America’s biggest cultural attractions.


Here are just 7 of the many things you can cross off your bucket list after a visit to Ashland.


#1. Watch one of Shakespeare’s plays performed live

Ashland is one of the best places in the world to watch a Shakespearean play performed how it would have been 400 years ago in London’s Globe Theatre. From February through October, the Oregon Shakespeare Festival (OSF) performs plays on 3 different stages in Ashland.


If you’re looking for authenticity, head for the Allen Elizabethan Theatre, which has 2 tiers of seating and an outdoor stage. This spectacular building offers the ambiance of a genuine Elizabethan or Jacobean theatre.


The OSF is a renowned repertory theatre founded in 1935. Today they perform between 5 and 11 different plays each day over a 6-day period across their 3 stages. Though Shakespeare’s plays are their forte, they also offer a range of other classic or original plays. Every year, around 400,000 people visit Ashland to watch a play.


#2. Take a hike

Ashland is blessed with the perfect conditions for glorious hiking adventures. Located where the Siskiyou and Cascades Mountain Ranges meet, Ashland boasts spectacular mountain scenery and a wide range of hiking trails.

Whether you want to take the whole family out on a leisurely Sunday walk or scramble up steep trails to near impossible heights, you’ll find a suitable trail within a short distance from town.


If you want to make like Alice, follow the 4½-mile, out-and-back White Rabbit Trail. You’ll find the trailhead in the White Rabbit Parking Area. The trail leads you past gigantic granite boulders and provides stunning views of the Rogue Valley. The White Rabbit Trail takes you into Siskiyou Mountain Park and passes Looking Glass Loop.


From Downtown Ashland, you can access Lithia Park. This 100-acre paradise has not been paved and turned into a parking lot. Instead, it provides a spectacular natural space within easy reach of the town, with a decorative fountain, bandshell, and Japanese Garden. It’s perfect for your family walks, and also provides access to the trailhead for the Bandersnatch Trail (via the Waterline Trail) that provides a steep and challenging route into Siskiyou Mountain Park.


#3. Get on your bike

Many of those wonderful hiking trails headed into Siskiyou Mountain Park are also accessible to mountain bikers. The trails around Ashland offer you a wide choice of terrains and distances, from less than 3 miles to over 30. So, pack your bike into its bike travel case and bring it along.


If you’re looking for a challenge, check out the 4-mile Time Warp Trail that starts at Mount Ashland. This features a high-speed single-track downhill trail. For a slightly easier, fast ride with plenty of jumps, rollers, and berms, head for the Jabberwocky. This 2-mile trail splits off the Caterpillar Trail and heads downhill into Ashland.


Many of Ashland’s biking trails are very challenging and head into remote areas where you’ll have little or no cell phone reception and there’s nobody around to help. While this is great if you want peace and quiet, you should ensure you take your multitool and puncture repair kit.


#4. Get tipsy

Did you know that Southern Oregon is one of the world’s fastest-growing wine regions? There are over 115 wineries within easy reach of Ashland, so you’re in a perfect location for visiting a vineyard and sampling fine wines. In 2017, Forbes Magazine voted Southern Oregon one of the top 12 Underrated Wine Regions To Visit. Within Ashland itself, you can visit the Weisinger Family Vineyards or Eliana Wines.


The Weisinger Family Winery vinifies a variety of different grapes from the Bear Creek Valley, including Malbec, Merlot, Sauvignon Blanc, Syrah, Tempranillo, and Viognier. Their fine wines have won many awards including the 2019 Oregon Wine Experience, 2019 San Francisco Chronicle Wine Competition, 2018 San Francisco International Wine Competition, 2017 Sauvignon Blanc – Double Gold, and 2016 Estate Tempranillo – Double Gold.


Eliana Vineyards has won even more awards. If you go there, you’ll soon learn that Brian, the vintner, focuses on red wines. Brian hails from Zimbabwe and descends from a long line of farmers who have produced fine red wines. Eliana Vineyards is a picturesque winery surrounded by undulating hills threaded through with vines.


#5. Go birdwatching

Some of the best spots to go birdwatching in the US are within easy reach of Ashland. Just 37 miles northeast of Ashland, you’ll find the Lake of the Woods. Around this lake are 2 Forest Service campgrounds aimed at birdwatchers. The lake attracts a range of waterfowl, including gulls, geese, and ducks. Other birds to watch out for are owls, sandhill cranes, gray jays, and Steller’s jays.


If you continue on another 11 miles to Rocky Point, you’ll be on the banks of Upper Klamath Lake. This is not only Oregon’s biggest freshwater lake, but it is also the best place to watch migrating waterfowl. Around the lake, you can see bald eagles, osprey, and heron.


#6. Experience kayaking

There are lots of great places to go kayaking around Ashland. Emigrant Lake is only 6 miles southeast of Ashland town center, and you can kayak across this lake while admiring the surrounding mountain scenery.


You can kayak or paddleboard on Upper Klamath Lake. In fact, birdwatchers often pack inflatable kayaks into their cars’ rooftop cargo boxes and bring them to the lake to enable them to get closer to the waterfowl.


Some 40 miles southwest of Ashland is Applegate Lake. It is actually an 18-mile wide reservoir fed by the Applegate River. This gentle stretch of water is popular with kayakers.


#7. Learn how to ski

Needless to say, during the winter, the trails so popular with hikers and bikers in summer become excellent trails for snowshoeing. And if you’ve ever wanted to learn how to ski, the mountains near Ashland feature many excellent ski slopes.


Mount Ashland Ski Resort is a 20-mile drive south of Ashland. It makes use of the slopes surrounding the tallest peak of the Siskiyou Mountains. There are 23 runs, and you can benefit from affordable lessons and equipment hire.


Mount Ashland Ski Resort also hosts numerous fun winter events. Locals build dummies to enter the Dummy Downhill contest, where they will be launched off a large ski jump on skis or a snowboard.

water gushing down the creek in Lithia Park in downtown Ashland, Oregon