This Is The Most Welcoming Town In Oregon
Ashland has been welcoming strangers since July 2, 1935, when a local teacher staged Shakespeare's Twelfth Night inside the roofless walls of an old lecture hall and charged adults 50 cents to get in. That three-night experiment grew into the Oregon Shakespeare Festival, and the southern Oregon town still embraces visitors and encourages them to join in the fun. From free shows and concerts to the family-friendly parade along Main Street, Ashland is without doubt the most welcoming town in Oregon.
A Welcome That Began With The Bard
That teacher was Angus Bowmer, who taught at Southern Oregon Normal School, now Southern Oregon University. He noticed that the walls of the town's abandoned Chautauqua building, a hall built in 1917 for the traveling lecture and music programs of the same name, looked like sketches he'd seen of Elizabethan theaters like the Globe in London: no roof, just walls around the stage.
The city advanced him a sum "not to exceed $400" to stage two plays as part of its Fourth of July celebrations, and a state relief crew built the stage. City officials were so sure the plays would lose money that they booked daytime boxing matches on the same stage to make up the difference. The plays paid their own way and covered the losses from the boxing as well.
Fast forward 91 years from that first night, and the Oregon Shakespeare Festival is now a well-established professional company (it has even won a Tony Award for outstanding regional theater). It performs from March through October in three theaters on one downtown campus: the open-air Allen Elizabethan Theatre, on the original Chautauqua site; the Angus Bowmer Theatre, opened in 1970; and the Thomas Theatre, which opened in 2002 as the New Theatre.
Shakespeare For All
The 2026 season saw 10 productions performed on the festival's stages, with A Midsummer Night's Dream, The Taming of the Shrew, and Henry IV, Part One sharing the bill with more modern shows like Come From Away, A Raisin in the Sun, and Emma.
The "most welcoming" part of it all ties in with the simple fact that nobody needs a ticket to take part. The Green Show, the festival's free outdoor program, ran Tuesday through Saturday at 6:30 pm from June to September on the Courtyard Stage, the brick courtyard in front of the Angus Bowmer Theatre (usually referred to as "the Bricks").
Acts changed nightly and have ranged from jazz guitarist Mimi Fox to students from Ashland Aerial Arts, a local aerial dance studio. Audiences bring blankets or folding chairs and sit on the lawn. The festival also runs campus tours, talks before the plays known as Prefaces, and discussions with company members, all of which make it easier for first-time visitors to get more out of the plays without breaking the bank.
A Park by Any Other Name
It's not just Shakespeare that makes this such a great town to visit. Lithia Park starts right behind the festival's downtown theaters and follows Ashland Creek uphill through 93 acres of lawns, ponds, and woodland. The park also owes its genesis to the Chautauqua group, who in 1892 bought eight acres that became the start of the park. In 1908, residents voted to write park maintenance into the city charter.
In 1914, the city hired John McLaren, the landscape designer behind Golden Gate Park in San Francisco, to plan it. The name comes from lithia water, a mineral spring water containing lithium that the city piped into the park in the hope of turning Ashland into a spa town. Today, 42 of the park's 93 acres are listed on the National Register of Historic Places, and most of the fun stuff costs nothing. Free things to do here include strolling through the Ashland Japanese Garden and taking in summer concerts at the Butler Bandshell.
The park's lower entrance faces the small downtown square, where you can join a creekside walkway called Calle Guanajuato, named after Ashland's sister city in Mexico. On weekends from mid-March to mid-November, the Lithia Artisans Market, a guild of local artists and craftspeople, sets up along the walkway from 10 am to 5 pm.
Much Ado About Parades
Ashland's welcoming nature also extends to the town's business community. The Ashland Chamber of Commerce has produced the town's Fourth of July celebration for more than 100 years. Things kick off with a pancake breakfast and 10K and 2-mile runs, followed by the parade, which leaves Triangle Park and heads to the downtown core. Post-parade events include music and fun in Lithia Park, plus a special greeting for a delegation from Guanajuato.
The holiday season starts the day after Thanksgiving with the Festival of Light, produced by the chamber and Travel Ashland, the town's tourism office. In it's 34th year in 2026, the festival's Santa Parade leads to the Plaza, where Santa switches on more than a million lights across downtown.
Other fun events where visitors will receive a warm welcome include the Ashland Sidewalk Celebration each May and September, which brings artists, musicians, and nonprofits onto the sidewalks beside the shops. The Ashland Gallery Association's First Friday Art Walks through the downtown galleries is also popular.
Oregan's Most Welcoming Town
Ashland residents have a long record of paying for things that visitors get to share. They wrote a park and a town band into the city charter, and even helped the town's mainstay, the Oregon Shakespeare Festival, get off the ground in the 1930s. The festival now describes itself as among the oldest and largest professional non-profit theatres in the nation. Add to this its parades and free music, and you're guaranteed a warm welcome in Ashland.
