There are many reasons to visit Ashland and its surrounds in Southern Oregon — from its family-friendly skiing to hiking stunning trails — but it offers something really special to visitors who may find themselves in need of a quiet solo trip. Plan to be rejuvenated by its unique mix of literary arts, food and wine, with many of its charms walkable in a robust, compact downtown. Here are some highlights for an inspiring road trip to Ashland.
Food for the Mind and Body
Home to the Oregon Shakespeare Festival — which celebrated its 90th anniversary in 2025 — Ashland is home to a lively intellectual community with Southern Oregon University and a mix of small theaters and galleries throughout town. Events happen year-round in multiple venues, especially during the festival season from March through October. With three performance spaces on one campus perched on a hill overlooking Main Street, the theaters can be reached via stairs or by accessible entrances for people with disabilities. Frequent visitors often book several plays per trip, and there’s also the affordable (free) option of the Green Show, which provides entertainment in an open plaza most evenings from June through September.
The Oregon Shakespeare Festival isn’t the only game in town. Be sure to check out the seasonal comedies and musicals at the Oregon Cabaret Theatre, headquartered in a handsome former church. There’s even more theater to discover, including avant-garde performances and festivals, and art galleries galore. Several downtown bookstores offer new, used and rare titles, including a wall of screenplays for the current season at the OSF Gift Shop. Look for displays featuring mystery titles from local authors while attending a reading at independent bookseller Bloomsbury Books. Genre fans won’t want to miss the annual Ashland Mystery Festival in October.
With all the stimulating culture to experience, you may not know that the area surrounding Ashland can literally calm the nerves. Lithium-enriched spring waters lie underneath the ground here. You can experience the sulfurous spring water at Lithia Springs Resort, where rooms include deep tubs for soaking in water piped from the springs running below the property, or by sampling a taste at Ashland’s historic fountain.
For a full day of wellness, schedule a treatment at one of Waterstone Spa’s two locations, The Blue Giraffe Day Spa & Salon, or Chozu Bath & Tea Gardens, where you might relax with a cup of matcha after a sauna and soak in the communal Japanese-style bath.
A DIY forest-bathing session can happen anytime in verdant, 93-acre Lithia Park. Find yourself lost in thought as you wander on paved paths and rustic footbridges over burbling streams, and watch carp in a formal Japanese garden. Enjoy free summer concerts at the Butler Bandshell or more casual performances by talented musicians busking along the walkway.
Creative Dining Before and After Plays
Spend an enjoyable afternoon taking a formal tea service (reservations only) at Lovejoy’s Tea Room, where mismatched china and quirky antique furnishings set the tone. Sample from a tower of sandwiches, sweets and fruit as you sip. Walk-ins are welcome for a modest lunch menu, and be sure to check the website for themed events like Shakespeare plays.
With a happy hour that’s ideal for theatergoers, Bar Juillet on Ashland Plaza features soaring ceilings and an organic, farm-to-table menu with plenty of sharable, vegetable-driven small plates and sustainable seafood. Mocktails and a wine list starring Oregon producers round out the meal. For a memorable feast, spend an evening at Blue Toba, an Indonesian restaurant with classic dishes like beef rendang — a sumptuous curry with 19 spices — and vegetable-accented mie goreng noodles.
Perfect for food lovers looking to experience Ashland’s finest regional cuisine, MÄS is worth the splurge. Patrons sit at a long, narrow chef’s counter and experience an ever-changing prix-fixe menu of Cascadia-French-Japanese fusion cuisine orchestrated by three-time James Beard Award finalist chef Josh Dorcak. Dinner may include warming dashi broth or mushroom-scented desserts, available with a wine and sake pairing. Reservations here are essential, but you may find a drop-in table available for sashimi and izakaya-style nibbles at adjacent sister restaurant NAMA, or settle in a few blocks away at the team’s Good Juice Wine Shop, perfect for a natural-wine tasting flight or bubbles brunch.
With so many spots to enjoy local wine downtown, it’s hard to resist a day or more of wine tasting in the historic Rogue Valley viticultural region, or a charming subregion inside it, the Applegate Valley. Meandering along curving roads through vineyard-laden foothills, stop by family-owned tasting rooms to sample a wide range of warm-weather varietals influenced by Spanish and Italian winemaking traditions.
Relaxing Stays Downtown and Beyond
For historic luxury in the heart of downtown, book one of 70 unique rooms at the Ashland Springs Hotel, a nine-story, century-old landmark. Enter the lobby into a different world with a wraparound mezzanine, lazily stirring ceiling fans, and flora and fauna curios tucked into every nook. Higher floors have commanding views of Ashland and the surrounding hills.
For more intimate lodging, seek out one of Ashland’s many historic properties now serving as inns. In Ashland’s historic district lies the cheery yellow Craftsman-style Parkside Acoustic Bed & Breakfast, which opened in 2025. With a music theme throughout the house, the inn features three guest rooms with handmade furniture plus seating on the front porch — a wonderful way to enjoy performances at Lithia Park’s bandshell across the street.
Perfect for an impromptu weekend when smaller hotels might be booked, the Ashland Hills Hotel & Suites has 200 spacious, pet-friendly suites on a 14-acre property on the eastern outskirts of town. Guests love the seasonal outdoor pool and hot tub, complimentary loaner bikes and plenty of parking. These affordable accommodations feature hip and colorful mod decor, as well.
