An Eclectic Overnight in Ashland

Overnight in Ashland_fancy cider BrickroomSure, the temperature is a few degrees warmer on the thermometer, and you’ll have to hit the road for three-plus hours to get there, but Ashland is worth it. If you haven’t already been there—and even if you have—take a romantic overnight trip south to enjoy an eclectic mix of tasty grub and fancy libations with a Shakespeare play and a walk in the park on the side. Drink with your pinky out, too. We know you want to. Hell, we want to join you.

Take a break from your 200-plus-mile drive to this southern belle of a city, and start the trip off with a full belly of beer and pizza from Kaleidoscope Pizzeria & Pub in nearby Medford. Kaleidoscope’s Thai chicken pizza was named “Best Pizza in Oregon” on Zagat’s 50 States, 50 Pizzas list in 2013. The place is also decked out in Grateful Dead memorabilia and tie-dye—which any Pacific Northwestern Deadhead can appreciate. If you really feel like celebrating an evening of Jerry, order the Garcia Bleu, a pie featuring buffalo-style chicken, bacon, blue cheese crumbles, veggies, and garlic, and take a seat next to your favorite album cover. Just don’t pull a Casey Jones and drink too much.

After you roll into Ashland, the best way to follow up your first course of pizza and beer is to drink more beer.

Keep it local and head over to Standing Stone Brewing Company on Oak Street, or Caldera Tap House on Water Street, for some seriously drinkable and delicious craft beers. Both places serve food and have excellent outdoor seating areas for you to enjoy those steamy Southern Oregon summer nights.

No visit to Ashland is complete without scoring tickets to a Shakespeare play. Just remember to practice your Old English accent before the show—no one likes it when you talk during the production.

Home to a menagerie of unique theaters and talented actors and actresses that take the various stages for the Oregon Shakespeare Festival each year, Ashland has much to offer amateur thespians and English nerds alike.

Become immersed in one of Shakespeare’s love stories with tickets to Antony & Cleopatra, which runs through Oct. 9, or Pericles, showing through Nov. 1. For a full list of plays featured in the festival lineup and ticket information, visit It’s best to order your tickets in advance.

Once you’ve had your fill of Shakespeare, head over to Brickroom Gathering House on North Main Street for some après-play fun. Brickroom features an authentic atmosphere and a fancy selection of liquor, craft brews, and ciders. Try the Sascotch, a concoction consisting of Clan MacGregor Scotch, lemon juice, and ginger beer, and order up some small plates to share with your significant other or the group of new friends you’ve met at the bar. The outdoor balcony is a great spot to people watch into the late hours of the night.

To continue on your booze cruise, wonderfully tipsy, evening out on the town, mosey over to the Black Sheep Pub on North Main Street for a nightcap. You’ll feel like you’ve been transported to the United Kingdom—just don’t cheer for the wrong soccer team. Instead, remember what you’re there for and order up a Harp Lager or Guinness Stout. If you’re feeling adventurous and a little wicked, try something fun like the Snake Bite, a mix of cider and lager. The libations menu also features Irish Car Bombs if you want to mix things up.

When you’re ready to snuggle in for the night, try resting your head at the Columbia Hotel on East Main Street. This historic, European-style hotel might cost a little bit more than a hotel room in Corvallis, but you’re close to downtown Ashland and the rooms are generously sized. Just keep in mind that “European-style” also means sharing a restroom with a few other hotel guests. It’s really not that bad—you get a break from TV screens and there’s free Wi-Fi.

In the morning, prepare to rise and shine and head over to Rogue Valley Roasting Co., also located along East Main Street, for your morning caffeine fix. While you’re there, chow down on a breakfast burrito, a muffin, or a slice of vegan-friendly pumpkin bread.

As you explore the city streets with the kind and costumed people of Ashland, stop in to browse the shelves of Bloomsbury Books. This independent bookstore has maps, cards, classic reads, and works penned by Oregon authors. There’s also good, fair trade coffee on the second level of the building at Bloomsbury Coffee House. You can even grab a sandwich for the road.

Take a stroll through Lithia Park, the “Central Park” of Ashland, and stretch your legs for a few minutes before heading back north to Corvallis. You might even find the perfect crystal, gemstone, or antique typewriter to take back home with you on the way to your car.

By Abbie Tumbleson