Located just 4.5 hours south of Portland, Ashland, Oregon is the perfect spot for a Pacific Northwest weekend getaway. Ashland is probably most famous for its annual Shakespeare Festival. However, the town also boasts world class food, an adorable downtown, and fantastic hiking and mountain biking. See below for our Ashland Oregon weekend itinerary, including the BEST things to eat, see, and do. This itinerary is family-friendly, and covers 48 hours in and around the city. It’s the perfect itinerary for a weekend getaway to Ashland, Oregon!

This itinerary was put together in partnership with Travel Southern Oregon.

Ashland Oregon weekend itinerary: 48 hours of fun

DAY 1: Hiking, Lithia Park, and the the best date night dinner spot in Ashland

Breakfast pastries at Mix and coffee at Noble Coffee Roasters

Start your morning off with delicious pastries from MIX Bakeshop in downtown, Ashland. MIX has truly fantastic sweet and savory pastries, along with ice cream and coffee. We particularly enjoyed their bostock (a croissant loaf soaked in orange syrup, topped with orange almond cream and berries). We also got their Veggie & Gruyère Egg Pie and Brown Butter Fruit Tart (featuring a citrus brown butter filling). 

After grabbing pastries head over to Noble Coffee Roasting. I go to Nobel every time I’m in, or passing through, Ashland, and their coffee always blows me away! Their attention to their beans and brews is truly outstanding, particularly at the price point they charge. Their mochas stand out for being rich and chocolatey, without being too sweet. Additionally, there is a large indoor space that’s great for relaxing and working, as well as several outdoor patio tables.

Get a taste of the Rogue at the Rogue Valley Growers and Crafters Market

After breakfast, mosey over to Oak Street to the Saturday Rogue Valley Growers and Crafters Market! Held every Saturday from 8:30-1:00 pm, the Rogue Valley Growers and Crafters Market (RVGCM) features local farmers and artisans from the region. They have strict membership standards for their vendors, making this a truly local farmers market experience. Their Saturday market is quaint and occupies a city block in downtown. It features mostly craft artisans, and a few farmer vendors. The market runs from the beginning of May to the end of October, and they have a separate winter market.

In addition to their Saturday market, the RVGCM also has markets on Tuesday and Thursday. These markets are much larger, and include prepared food and more farmers and crafters.  

Go for a hike at Pilot Rock National Monument

Did you know that you can find a National Monument only 30 minutes from downtown Ashand? Managed by the BLM, Pilot Rock is a unique “volcanic plug” that is part of the Cascade Mountain Range. The area has diverse biology and geology, including beautiful wildflowers in summer. 

Pilot Rock Trail offers a fantastic up-close-and-personal view of the rock. The hike is 2.8 miles round trip and about 800 feet of elevation gain. It’s family friendly, except for the final segment (which we skipped), which requires a class 3-4 scramble up steep rocks. We enjoyed beautiful views of the valley, as well as lovely wildflowers!

Lunch at Pie and Vine

Located in downtown Ashland, Pie and Vine is known for their their wood-fired pizzas and wines. The indoor space is light and bright, and there is a generously sized covered patio. 

Pie and Vine’s margarita pizza had a delicious thin and crispy wood fired crust. We also got their roasted asparagus with pine nuts and mascarpone, which was fantastic. However, the highlight was their ‘mista’ salad, which included seasonal greens, sun dried tomato, red onion, roasted artichokes and pepperoncini, and a slightly sweet balsamic vinaigrette.

Spend an afternoon exploring Lithia Park

Lithia Park is the gem of Ashland, and no Ashland Oregon weekend itinerary would be complete without a trip here! Occupying over 90 acres, much of Lithia Park is listed on the historic register. Lithia Park is one of my favorite areas of Ashland, and you could easily spend a day or more exploring the park. There are a number of play areas for kids and families, and several different sections of garden you can explore. 

We did a two mile loop which takes you through a delightful wooded section of the park alongside a beautiful creek. A highlight was seeing the free Japanese Garden, which we hadn’t previously visited. It felt like a peaceful respite in the middle of the city!

Date night dinner and drinks at Bar Juillet

We’re big foodies, so I don’t say this lightly: Bar Juillet was one of the top 5 meals we’ve had in the past decade.

In true Pacific Northwest fashion, Bar Juillet offers a casual yet refined dining experience in a beautiful historic building in Ashland’s downtown plaza, making it perfect for a nice date night dinner. Bar Juillet uses super fresh, local produce, and primarily sources from within 200 miles of Ashland. They make everything in house, including their burrata (which I highly recommend), and their menu is vegetable-forward. We had the pleasure of meeting one of the owners, Corrie Reimer, and her passion for food and hospitality truly shown through. 

Reservations are recommended, and dishes are best enjoyed family style. Highlights of our included:

• House made burrata with fennel, cherries, and fresh focaccia
• Little gems salad with herbed lemon cream, purple radish, avocado, sunflower seeds
• Mushroom Tartine featuring black truffle, morels, maitake, shiitake, snap peas, and crème fraîche
• Tagliatelle with egg yolk, pea tendril, prosciutto crunch, and grana padano
• Non-alcoholic seasonal shrub 

See an Oregon Shakespeare Festival performance

Founded in 1935, the Oregon Shakespeare Festival is a local institution and offers a world-class theater experience in the heart of downtown. In fact, they are among the oldest and largest professional non-profit theaters in the nation! In summer and fall they offer a forward-looking and modern interpretation of Shakespear’s classics, along with other performances. They have a classic outdoor theater (like what you can experience at Shakespeare’s Globe in London!), as well as indoor performances. 

We saw one of the evening performances, which was the perfect way to unwind after a long day of exploring Ashland!  We were actually supposed to see Much Ado About Nothing in their famous outdoor theater, but accidentally saw Macbeth instead. I have no complaints: the show was FANTASTIC! The actors on stage all did a wonderful job. The set was minimalist but highly effective. I appreciated that the performance was a relatively traditional take on Shakespeare, but with some modern nods (including a more diverse cast than is typical in these productions).  If you’re not familiar with “Shakespeare speak” (I know I don’t remember all my high school Shakespeare lessons!) it might be good to review the plot of the play beforehand so you can better follow along. 

DAY 2: Mountain biking, delicious Filipino food, and exploring downtown

Coffee and pastries at Case Coffee Roasters

Like Noble, Case Coffee Roasters also offers delicious coffee with a strong emphasis on quality beans and roasts. We last visited in 2021 on our honeymoon, so it was nice to go back! They have several locations in town, but we went to their downtown location, which is light, bright, and full of plants. Their mochas are slightly sweeter than Noble’s, and are also fantastic! They also offer fun seasonal drinks — I ordered a seasonal cold brew special with coffee cream on top, which had delightful fruity notes. 

Mountain Biking or Hiking on Mt. Ashland

Mt. Ashland is one of my favorite places to hike, especially in summer. We visited in June just at the start of wildflower season, but in late July and August the entire mountain is often covered in wildflowers. I love the hiking segments along the PCT (Pacific Crest Trail). 

If you’re up for more of an adventure I recommend Mountain Biking down the mountain! Ashland Mountain Adventures offers a convenient shuttle service that runs several times a day and brings you to the top of Mt. Ashland. You can rent their bikes or bring your own. I would describe the routes as moderate. We’re new to mountain biking so we mostly stuck to the fire roads, but we enjoyed testing our skills on the “Toothpick” trail!

Lunch at Sammich

A local institution with several locations throughout Oregon, Sammich is a queer-owned dining spot with excellent sandwiches. Their sandwiches pack a fabulous flavor punch, and their Ashland location has abundant outdoor seating.

Explore downtown Ashland 

After lunch, spend an afternoon exploring downtown Ashland! There are an abundance of shops and boutiques, and you can also take another stroll through Lithia Park or along the creek in downtown.

Enjoy a delicious Filipino dinner at Harana Cafe 

Ashland punches above its weight when it comes to food, and Harana Cafe is no exception. If you can only eat at two places in town, Bar Juillet and Harana Cafe should be where you go!

Relatively new to the Ashland restaurant scene, Harana is the brainchild of chef Chris, who is a master of mixing savory, sweet, and tart flavors. They offer truly outstanding contemporary Filipino food in a casual but elevated setting that is light and bright. We enjoyed the green mango salad to start, as well as the sisig tofu and squash and coconut stew. Their calamansi lemonade and iced tea (sweetened with local honey) are also a must-try! 

For dessert we had their Halo-Halo (which I recommend ordering with their ube ice cream!), and a fantastic gooey cassava cake with a coconut caramel sauce.

Where to stay in Ashland, Oregon: romantic B&B in downtown

If you want to be right in the heart of downtown while also feeling like you’ve been transported to the Italian countryside then the Ashland Creek Inn is where you should stay! Located along Ashland Creek, this ten-suite luxury inn offers a unique lodging experience.

Upon check-in you’ll find freshly baked cookies in your room, and cookies will magically appear on subsequent days, as well. The suites are all unique (we stayed in their “Marrakech” suite, which was Moroccan-themed), impeccably clean, and the owners also offer complimentary breakfast for lodgers. Although our schedule didn’t permit us to dine-in, all of the online reviews rave about the food. This spot is just steps from the Shakespeare Festival and all the dining locations we shared, which makes it the perfect base camp for Ashland adventures. 

Final thoughts

Ashland is a must-see gem of the Pacific Northwest, and I hope you find this Ashland Oregon weekend itinerary helpful! You can find more Pacific Northwest travel guides here.