Itching to get out of town, Portlanders? Skip those pesky airport security lines and jump in your car for a road trip to Ashland instead. From theatrical performances at the world-renowned Oregon Shakespeare Festival to the famous chicken soup at Brothers’ Restaurant — we’re spilling all the details on how to have an unforgettable time in the 541.

📍 Essential info

Drive time: ~4.5 hours
Year city was established: 1852
Est. population: 21,607

Take a romantic moonlit stroll on a pleasant evening along the many pedestrian pathways. | Photo by Cambrie Juarez, PDXtoday

🎟️ Experience

Oregon Shakespeare Festival
What started in July of 1935 with performances of William Shakespeare’s “Twelfth Night” and “The Merchant of Venice” is now an 11-program festival running every February-November. It’s often referred to as the “Broadway of the West Coast,” has won multiple Tony Awards, and is one of Time magazine’s top five regional theater companies in the US. A show at the festival’s flagship Allen Elizabethan Theatre can transform even the hardest heart into one replete with thankfulness.

Lithia Park
Portlanders who love having access to one of the largest urban natural areas in the country will feel right at home in Ashland, thanks to the 100-acre park that reaches into the heart of downtown. Visitors will find undeveloped woodlands, a Japanese garden, two duck ponds, athletic courts, a swimmable reservoir, picnic areas, and walking trails.

First Friday Art Walk
Time your visit to coincide with the first Friday of the month, year-round, to take advantage of this beloved community where you can listen to live music, meet artists and browse their creations, watch demonstrations, and stop for lunch at one of many nearby eateries. Learn about the current exhibits by downloading an Art Walk Map.

Try a unique herbal elixir at Elder Apothecary. | Photo by Cambrie Juarez, PDXtoday

🍴 Eat

The Black Sheep
Are you really getting the full Shakespearean experience if you don’t stop for a meal at a traditional British pub? Feast on a tried-and-tested favorite like bangers and mash, fish and chips, or shepherd’s pie while listening to live music or watching acrobats defy gravity.

Greenleaf Restaurant
Located just a few steps from Lithia Park, this popular restaurant inside an 1879 building prides itself on treating each customer like a regular. You’ll find a range of PNW-inspired dishes for breakfast, lunch, and dinner — as well as a daily happy hour menu — and plenty of indoor, outdoor, and creekside seating.

Dobrá Tea
This downtown tea room and cafe serves teas made with organic and wild-grown loose-leaf teas in a cozy atmosphere. Pair your drink with a vegetarian bowl, salad, or small plate (like dolmas, pita bread with goat cheese and tomatoes, or hummus and olives) — or go for something sweet with a housemade baked treat (like pistachio baklava, mochi, or brown butter tea cake).

Brothers’ Restaurant
Conveniently situated along North Main Street, this casual eatery with patio seating serves all-day breakfast for those who stayed up too late the night before at The Black Sheep — just be sure to get there before it closes at 1:30 p.m. You’ll also find sandwiches, soups, cocktails, teas, and a full range of espresso drinks.

The Ashland Springs Hotel has 100 rooms. | Photo by Joe Mabel

🏨 Stay

Ashland Springs Hotel
Billed as “one of the most prominent landmarks in Southern Oregon,” the building originally known as Lithia Springs Hotel has been giving travelers a good night’s sleep since 1925. Today, the 3-star hotel features original chandeliers and elegant rooms that still evoke the charm of a bygone century. Look for the original stained glass bearing the “LH” (Lithia Hotel) crest over the front entrance.

The McCall House
This boutique bed and breakfast operates out of a Victorian Italianate mansion built in 1883 for John McCall — a gold prospector, former Ashland mayor, and founder of the Ashland Woolen Mill, Ashland Library, and Bank of Ashland. The historic house has been an inn since 1981 with guests applauding its hospitality, quaint-but-updated beauty, and personal touches.

The Bard’s Inn Hotel
It takes 7 minutes to walk from this charming hotel at the north end of downtown Ashland to the Oregon Shakespeare Festival. The property includes an outdoor pool and four separate buildings, each bearing names like “Sonnet” and “Juliet,” with a variety of unique rooms and suites to fit guests’ needs. Look for the mural of Shakespeare on the northwest wall of the Verona building.

Wait a minute, Portlanders. Before you head out the door, find the cheapest places to fill up your gas tank and stock up on road trip snacks from New Seasons Market. Also, bookmark this map so you have no trouble finding all of our recommendations while visiting Ashland.