24 Hours in Ashland

by Tracy Kaler  |  Published August 6, 2023

An arty town ensconced by mountains and vineyards, Ashland is an enchanting cultural hub in Oregon’s Rogue Valley, with exceptional food, a budding wine region, and nearby natural wonders.

Ashland is situated in the Siskioyou and Cascade mountain ranges. (Photo by Tracy Kaler for Travel Mag)

Inherently Oregon, Ashland strikes all the right notes for culinary and cultural travelers. Situated in Southern Oregon in the Siskiyou and Cascade ranges about 15 miles from the California border, this enchanting mountain town has a quintessential main street studded with shops and eateries, a thriving arts community, and an idyllic Rogue Valley setting. With over 30 wineries and tasting rooms sprinkled around the outskirts, Ashland is a haven for oenophiles.

While the town offers plenty in terms of cuisine and culture, there’s no shortage of nature in and around Ashland for travelers who long to explore the great outdoors. After all, this is Oregon, one of the most active states in the US.

Although one could explore this creative city and its environs for days, read on for some recommendations on how to best spend 24 hours in Ashland, Oregon.

Charming East Main Street in Ashland (Photo by Tracy Kaler for Travel Mag)

Things to Do

Small businesses are the lifeblood of downtown Ashland, so stroll along East Main, arguably one of Oregon’s prettiest streets revealing a flurry of cafés, boutiques, and restaurants for every budget and taste. The independent Bloomsbury Books (290 E Main St) houses an impressive collection of titles; Sunday Afternoons (167 E Main St) is a must for stylish and practical hats; and for all things related to the Beaver State pop into the gift shop, Paddington Station: Inspired by Oregon (131 E Main St). Pendleton blankets, Branson’s chocolates, cards, and jewelry are just a few items to peruse. 

Bloomsbury Books on East Main Street houses an impressive collection of titles. (Photo by Tracy Kaler for Travel Mag)

Step off the main drag and discover more galleries and shops such as Noble Coffee Roasting (281 4th St) for a not-so-ordinary cup of Joe. Embodying the values of Fair Trade, the café sources green coffees from organic farms and cooperatives in Bali, Ecuador, Ethiopia, and Kenya.

The Oregon Shakespeare Festival (15 S Pioneer St) has become synonymous with Ashland, with outstanding talent on the campus’s three stages. Known as “OSF,” this performing arts organization was founded in 1935, making it one of the oldest professional nonprofit theaters in the country. Its repertory includes modern interpretations of Romeo & Juliet, Twelfth Night, the Three Musketeers, and non-Shakespeare musicals like Once on this Island and Jonathan Larson’s Rent. OSF’s season begins in April and runs through October. Be sure to purchase tickets in advance.

The Romeo & Juliet set at Oregon Shakespeare Festival (Photo by Tracy Kaler for Travel Mag)

With 50 different grape varieties across more than 4,000 acres of vineyards, wine is essential to the culture of Ashland and the surrounding region. Route 99, Interstate 5, and connecting roads lead to the wineries, and most lie within 30 minutes of downtown.

One must-visit for outstanding wines, a stunning tasting room, and sweeping views is Irvine & Roberts Vineyards (1614 Emigrant Creek Rd), five miles from downtown. While many warm-weather varieties prosper in the Rogue Valley, this winery excels at the cool-climate siblings, specifically Pinot Noir and Chardonnay. Due to the high elevation and afternoon breezes––the estate is set where the Siskiyou and Cascade mountains converge––the two varieties prosper here. 

Pinot Noir rosé, Chardonnay, and Pinot Noir at Irvine & Roberts Vineyards (Photo by Tracy Kaler for Travel Mag)

Venture three miles from downtown to Weisinger Family Winery (3150 Siskiyou Blvd), a pioneer in Rogue Valley wines that came onto the scene in 1988. The producer sources local, sustainable grapes that grow within a five-mile radius in Ashland’s Bear Creek Valley. Weisinger makes small-lot artisan wines ranging from Pinot Gris and Rosé of Grenache to Tempranillo and Cabernet Franc.

For enthusiasts interested in an entire afternoon of wine tasting, book an excursion with Wine Hopper Tours, where seasoned locals provide safe transportation and fun tidbits about wines and the region. 

Ashland is surrounded by vineyards. (Photo by Tracy Kaler for Travel Mag)

With mountains, lakes, rivers, and waterfalls close by, hiking, swimming, fishing, and more adventures are a car ride away, proving that the Ashland area is a West Coast destination for outdoor recreation. But urban green space is abundant, too. For nature in the heart of town, wander through Lithia Park (Winburn Way). Ashland Creek flows through the bucolic 93-acre green space, a reprieve from busy East Main Street. Lithia Park’s manicured lawn is excellent for reading and relaxing, but the plot also offers pickleball courts, a Japanese garden, and the Butler Bandshell for concerts. Trek to the wild and untouched southern end of the park and dive deeper into nature.

For nature in the heart of town, wander through Lithia Park. (Photo by Tracy Kaler for Travel Mag)

Where to Stay

On the National Register of Historic Places, Peerless Hotel (243 4th St) has been an Ashland landmark since 1900. This boutique property is furnished with 18th and 19th-century antiques and features complimentary Prosecco and truffle chocolates, plus a fully-stocked beverage bar. Also loaded with character, the 21-room Winchester Inn (35 S 2nd St)is set in a Victorian mansion and promises a luxurious experience. All accommodations come with plush robes, Antica Farmacista toiletries and honor bars, and some quarters have fireplaces and private balconies. Beyond guest rooms and suites, the property offers cottages for larger groups and families.

Consider Ashland Springs Hotel (212 E Main St) for a classic stay on East Main Street. Initially the Lithia Springs Hotel when it opened in 1925, the historical building has seen several iterations over the years and even closed twice before its resurgence in the late 1990s. Today, the hotel houses 70 guest rooms featuring traditional décor with European flair and modern conveniences. Amenities include Frette bed linens, complimentary breakfast, off-street parking, and an on-site spa. 

Expect classic decor at Ashland Springs Hotel. (Photo by Tracy Kaler for Travel Mag)

 Where to Eat

Providing a large interior and a sidewalk café, Larks Home Kitchen Cuisine (212 E Main St) is on the ground floor of Ashland Springs Hotel. A lively bar scene makes this French-inspired, New American restaurant an excellent option for cocktails as well as a meal. Chef Franco Console spotlights Oregon’s bounty, plating seasonal comfort food and inventive takes on traditional dishes. The menu highlights are white wine and Pernod-steamed clams, a Caesar salad with lemon breadcrumb gremolata, and fried chicken with bacon pan gravy. Save space for the warm butter cake alongside strawberry rhubarb compote and salted honey basil ice cream.

Larks in Ashland Springs Hotel features a sidewalk cafe.

Chef Josh Dorcak pushes the envelope with “Cascadian cuisine” at MÄS (141 Will Dodge Way), an upscale yet approachable spot serving a multi-course tasting menu. A 2023 James Beard Best Chef finalist, Dorcak keeps the menu evolving, but one aspect is consistent: the ingredients hail from Southern Oregon. The Omakase-like tasting rotates ingredients but may feature caviar, halibut, oyster, and eel, leading the way for wagyu before the dessert course. Sake and wine pairings complete the experience.

Head to Brothers’ Restaurant (95 N Main St)for all-day breakfast and lunch. Serving Ashland since 1976, the eatery prides itself on sourcing sustainably farmed meat and produce so guests can expect quality ingredients. More than 20 omelets, fluffy pancakes, bagels and lox, burgers, salads, and deli sandwiches round out the offerings. Also responsibly sourcing ingredients, Pink Pangea (272 E Main St) is a lunch and dinner café specializing in gluten-free, vegan, and vegetarian fare. Choose from soups, salads, wraps, and grilled panini layered with tempeh and veggies like roasted red peppers, sun-dried tomatoes, and caramelized onions.

Located in The Winchester Inn, the acclaimed Alchemy Restaurant & Bar (35 S 2nd St)provides a formal dining experience in the restaurant and more casual meals in the bar, even though the menu is the same on both sides. Don’t fear overindulging here, as the dishes are worth the calories. Start with the decadent “mushroom mushroom,” a medley of porcini flan, porcini consommé, and sauteed local mushrooms. Follow this starter with the succulent crispy duck leg confit with forest mushroom duxelles, house fettuccine pasta, a 63-degree egg, and roasted chicken demi-glace. Room for dessert? Chocolate fondant–-made with Scharffenberger chocolate–-awaits. Ask the friendly and knowledgeable staff for a wine pairing from the Wine Spectator-awarded list or an expertly-crafted cocktail––the bar was named one of the Great Bourbon Bars in America. 

At Alchemy Restaurant & Bar, the duck confit is worth the calories. (Photo by Tracy Kaler for Travel Mag)