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Find Off-Season Revelry in Southern Oregon’s Cultural Hub

Oregon Shakespeare Festival Ashland retreat

This spring, make a trip to Ashland, a cultural and outdoors hub in the heart of Southern Oregon.

Lithia Park Ashland Retreat
Lithia Park. Photo by Sean Bagshaw

My daughters run through the sycamore grove in Lithia Park, our first stop during our three-day Ashland getaway. The grove is one of my favorite places in Ashland, Southern Oregon’s cultural hub. Home to the world-famous Oregon Shakespeare Festival, we visit Ashland each year to see live theater and music, eat amazing meals, take a backstage tour, do a little shopping and wander in urban nature.

Ashland in the summer means packed streets, hot weather and the Oregon Shakespeare Festival at full tilt. But OSF actually fires up in March, and this year, we decided to make Southern Oregon our spring break trip. The scene is quieter, temperatures are high 60s instead of high 80s, and while we won’t be hitting the hotel pool, it’s still at least ten degrees warmer than back home in Bend. It feels great to get out of town, soak up some culture, and of course, walk in Lithia Park—ninety-three acres of landscaped paradise on Ashland Creek, featuring a Japanese garden, two duck ponds, a formal rose garden and a children’s playground.

After the park, we wander along the creek downtown and explore the Lithia Artisans Market, a little outdoor shopping experience featuring art, clothing and trinkets. Then it’s dinner at Standing Stone Brewery, which uses as many local products as possible, even in their beer (try the I Heart Oregon Ale, which is 100 percent Oregon-sourced).

Oregon Shakespeare Festival Ashland retreat
Oregon Shakespeare Festival. Photo by T Charles Erickson

It’s busy before play time, and after our meal we walk with others up the hill to the Angus Bowmer Theatre to see a contemporary drama. While the festival was founded eighty years ago as a Shakespeare-only troupe, today OSF presents plays of all eras and genres. This early in the season, the outdoor theater isn’t open yet, and the nightly free entertainment known as the Green Show hasn’t begun either, but the tradeoff is that we got great seats, second row, and the girls are riveted throughout the romantic, Elizabethan, sometimes-bawdy story of Shakespeare in Love.

On the agenda the next morning is the backstage tour, led by an OSF company member and a great way to learn more about festival history, the amazing effort that goes into productions and get a glimpse behind the curtain, from the dressing rooms to the set to stories of when things went wrong on stage (unscripted vomiting, anyone?).

A long weekend in Ashland is these experiences on repeat: another play, another meal, some shopping, another walk in the park. Our three days in Ashland pass quickly, and we return home with a lingering taste of the culture and flavor of Southern Oregon.


Larks restaurant in Ashalnd, Oregon

Larks, in the Ashland Springs Hotel, serves fresh fine dining focusing on local products and produce. The light and lovely space is the perfect place for a nice meal accompanied by great cocktails and an extensive Oregon-based wine list. Brother’s Restaurant serves delicious breakfast and lunch and is a great option for brunch before a matinee. The food here is plentiful and extremely tasty, and best accompanied by one of their incredible bloody marys.


Ashland Springs Hotel in Ashland, Oregon
Ashland Springs Hotel

Ashland Springs Hotel is the crown jewel. This luxurious landmark hotel first opened in 1925 and underwent a restoration and reopening in 2000. Rooms are modest in size but beautiful and comfortable. The lobby is a little natural history museum, with bird taxidermy, eggs and seashells on display. Bard’s Inn is another great lodging option, located within easy walking distance of theaters. With many rooms including suites, and a swimming pool, this is a great destination for families. Jacksonville Inn, built in 1861 during the gold rush, is a good choice for extremely charming lodging and dining in nearby Jacksonville.

Nearby Attractions

Crater Lake National Park near Ashland, Oregon
Crater Lake National Park

Crater Lake is between Bend and Ashland. The road from the south doesn’t open until summer season, but a stop is well worth the effort in season. Applegate Valley offers wine tasting and scenery galore in this valley with over a dozen wineries. Jacksonville began as a gold rush town in the 1850s and is home to the Britt Festival, a summer-long lineup of concerts in a very pretty and unique outdoor venue in the hills just to the west of downtown. The Rogue River is one of America’s original Wild and Scenic Rivers, and a terric destination for whitewater rafting, fishing and hiking.

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