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THRILLIST — We’ll be frank: Oregon is massive. So massive, in fact, that it would take you about nine hours by car to go from the eastern Wallowa Mountains to the Pacific coastline. Along the way, you’ll find everything from active volcanos that you can ski down to unparalleled natural landscapes -- plus enough craft beer, artisan wine, and decadent cuts of beef to keep you satisfied until spring. That’s a lot to explore, so we crafted a handy guide to each of the state’s seven regions to narrow down exactly how you should explore -- and what you can’t miss.

Southern Oregon


Whether your idea of “vacation” means snowshoeing around the deepest lake in the country or hitting up foodie favorites in small cities, Southern Oregon is the place to do it. Known for stop-you-in-your-tracks-pretty attractions like Crater Lake and mountain biking trails, Southern Oregon is where you’ll satiate your craving for adventure -- and a post-adventure craft cocktail.

MUST DO: Lithia Park in Ashland sprawls over 100 acres in the city’s downtown, with plenty of hiking trails through ornamental trees that are as gorgeous in the fall as they are serene in the winter months. It also features an ice rink, open from November through February, so start working on your triple axel.

MUST EAT: MAS serves regional Cascadian cuisine (what you might call Pacific Northwestern) omakase style, meaning that you’ll leave it up to chefs Josh Dorcak and Luke VanCampen to serve up whatever they think is tastiest from farmers and suppliers in the region right now. You’re in good hands, too: Dorcak has twice won the Top Chef competition at the Ashland Culinary Festival (happening in early November so move fast if you want to attend).

MUST DRINK: The Willamette Valley isn’t the only wine region in Oregon worth traversing. Here, wineries like Troon have been operating since the ’70s, but if you prefer sampling over sweeping vistas you can taste a variety of local options at Ashland’s Alchemy, a wine bar with a cozy setting and comfort fusion dishes.

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