What’s in a name? When it comes to Ashland, Oregon, a whole bunch of stuff: the Oregon Shakespeare Festival, great regional wine, Lithia Park, a lively pub scene, Southern Oregon University and pungent (but stunning) mineral hot springs. Located in the foothills of the Siskiyou and Cascade Mountain Ranges, late summer is the perfect time to spend a weekend exploring the Rogue Valley and dining al fresco. For the oenophiles, spend your day sipping pinots in Oregon’s latest wine belt (we like Dana Campbell Winery for the great views of Ashland, or 20 minutes up I-5 Dancin Vineyards pairs nicely with homemade wood-fire pizza). If you’re looking for something more active, grab a cup of Joe from Noble Coffee and explore stunning Lithia Park. Designed by the same landscape architect who did Golden Gate Park, Lithia’s spectacular gardens switchback across Ashland Creek through the foothills and connect to plenty of hiking and biking trails. Grab an early dinner at one of Ashland’s local cafes (you really can’t go wrong – most places proudly serve farm-to-table menus), then catch a show at the Shakespeare Festival (February – October). If the Bard isn’t your cup of tea, fret not – the OSF features plenty of modern playwrights and world premiers. After the show, grab a nightcap at one of the many pubs along the creek. With great food, awesome trails and a varied nightlife, Ashland is just the place for a weekend escape to while away the mid-summer nights!

What To Do in Ashland

Grizzly Peak: Oregon is known for environmentally conscious locals, no sales tax, and some of the most stunning and varied landscapes in the US. We count Grizzly Peak among one of the best spots. With awesome panoramic views of the valley and surrounding mountain ranges, Grizzly Peak is nothing short of jaw-dropping. And the peak is just the beginning – take the loop trail that winds through the pine forests and you’ll start to see where one forest ends and another begins. Ecology at it’s finest! Loft Brasserie: Terrace dining isn’t the exception in Ashland, it’s the norm. But Loft Brasserie is exceptional. With a menu that rotates daily, the Loft is French inspired food with a distinctly local twist. If you’re feeling adventurous, the Beef Tar Tar and Dungenese Crab Macaroni Gratin are beyond decadent, though the tried and true French Onion Soup and Lamb Shank are favorites for a reason. Ask your waitress which local wine pairs best or opt for a fresh cocktail (Mint Juleps and terraces mix well) – or have both since you’re on vacation. OSF Elizabethan Theater: Sit amongst the plebeians or gaze upon the stage with fellow patricians, either way there’s not a bad seat in the house. Modeled after outdoor theaters like the famous Globe in Renaissance London, you can’t help but feel the majesty of live theater when you’re watching a production at the Allen Elizabethan Theater. Under the stars and sans mics or elaborate sets, you’re struck by just how compelling words, some written centuries ago, can still be so relevant. As long as you dress for the weather, you’ll be mesmerized by the reverie and feel much ado about nothing. Standing Stone Brewing Co: To beer or not to beer? That is not a question - always beer. A great spot to sit on the patio and recap your day, Standing Stone Brewing Co has solidified its reputation as a classic Ashland hangout. The historic 1925 building definitely helps, but good ol’ fashioned on-site brewing and hearty local ingredients (3 cheers for Oregon Hops!) give this micro-brewery old-school street cred. The I ♥ Oregon Ale and Steel-Cut Stout pair nicely with the crisp valley air, and the kitchen is open until midnight in case you didn’t grab dinner before the show. We’ll take a late night pint and give a standing-O to this awesome brewpub.

What To Wear in Ashland

Smooth Crew: Don’t let the calendar fool you, these summer nights can get a wee bit chilly when you’re sandwiched between mountain ranges. The Smooth Crew is the perfect weekender staple. 100% organic cotton Butterknit fabric is unspeakably soft, wicks away moisture and resists wrinkles. Great on it’s own or a nice layer for crisp nights – all’s well that ends well. Tamaya Tunic: Like a Shakespearean heroine, the Tamaya tunic is a classic beauty. Our eco–friendly Samba fabric charms in any hue and print and travels like a pro – it resists wrinkles, stays super soft and keeps it’s shape all day long. The split–V neckline shows off your come-hither collarbones while the back box pleat makes for an easy, swingy fit that pairs well with leggings or shorts. You’ll look simply divine. Rosalinda Dress: When it comes to dresses, there’s no such thing as unconditional love. We want great fit, form and function – no caveats. With that in mind, we propose the Rosalinda Dress. She’s got a comfy, complementary shape, a stretchy Samba knit blend (Tencel®, organic cotton and spandex) and coffee–to–cocktails adaptability. We think you two will live happily ever after. Mojac Overshirt: Devilishly handsome, we orchestrated our Mojac to look like a jacket but feel like a shirt. Richly colored flannel is fully lined with a buttery–shirt knit (both 100% organic cotton) making it perfect accomplice to an outdoor show. Oh, and we added chest pockets, chambray lining and a relaxed, shirttail hem so you’re always the perfect degree of “dressed up”– just as you like it.