By Grant Woods

Drawing a line between the cities of Bend and Ashland is a tricky task. Google Maps offers a few options, traversing mountains and crossing rivers in just over three hours. Comparing and contrasting the characteristics of the two cities, however, proves more challenging than following the directions on a GPS.

Arranged in bullet points, the commonalities are easier to identify. Both offer hiking, biking, trail running, breweries, skiing, golf, mountains, and a landscape that lures visitors from across the nation. Luckily for residents and visitors alike, however, Ashland offers even more than the marquee advertises.

“Ashland is nestled right at the convergence of the Cascade and Siskiyou Mountain ranges. Geographically, this gives it a true sense of place,” said Katharine Cato, director of Travel Ashland.

World-renowned trail running abounds in Ashland due to its location among the Cascades and Siskiyou mountain ranges.

With the Siskiyou Mountains being one of the rare east-west mountain ranges in the U.S., and the Cascades being as gnarly and majestic as any other West Coast range, Cato’s statement is valid. But more so than any panorama of natural landmarks, Cato noted the feel of the city as something that people recognize in Ashland.

Ashland has a way of being laidback and welcoming, without losing its sense of adventure. The same could be said about Bend, but considering the population alone, the scales become very different. Ashland, a city of 20,000, sees about 350,000 visitors each year. Bend’s population and visitor flow are more than quadruple that, according to Visit Bend. What people see as laidback in Bend might be seen as rush hour in Ashland.

Statistical comparisons aside, any city that attracts so many visitors annually must have something to offer. For Ashland, the list of enticing qualities and amenities is ever-growing.

In terms of recreation, Cato, who has lived in both cities, sees Ashland as virtually “untapped.” There are five wineries, a 16,000-acre watershed, beautiful Lithia Park, known for its healing mineral waters, bountiful rivers, and the perk of Mt. Ashland and its proximity to the world-renowned Pacific Crest Trail.

Where Bend is favored for its breweries, Ashland has over 70 varieties of grapes for winemaking. With both towns boasting plenty of sunshine, it’s not a matter of labeling one city as superior to the other, it’s a matter of deciding what is desirable for each unique visitor: flavors, colors, and pace.

Ashland boasts dozens of wineries that produce wines in a wide array of styles.

Geographically, both cities enjoy a wide berth from other large metropolitan areas and claim relatively small airports. Sitting on the I-5 corridor, Ashland is often viewed as a driving destination. With more direct flights out of places like Phoenix and Los Angeles landing in Medford, however, the method of visitor travel is changing.

“Ashland has a very educated visitor base,” said Cato.

Given that Ashland is home to Southern Oregon University and the world-famous Oregon Shakespeare Festival, an educated crowd shouldn’t come as a surprise. While the Shakespeare Festival accounts for nearly a third of all Ashland visitors, the remaining two-thirds are coming to play outdoors, to experience the city for its art, its culinary innovation, and the overall feel of the town.

Ask anyone who’s experienced both Bend and Ashland. They might have a personal preference, but there’s no arguing that both cities radiate unquestionable beauty in the form of friendly communities, endless amenities, and a strong sense of adventure tied to the great outdoors.

For more information about planning a trip to Ashland, visit