By Shannon Gomes
I have a handful of favorite small towns in the U.S. and Ashland, Oregon is on that list.
Right of the Interstate-5 near the border of California, Ashland is a delightful small town that the entire family can enjoy. Featuring the world-class theater company, Oregon Shakespeare Festival, delicious local food & drink plus great outdoor activities, Ashland is a gem. Just a 6 hour drive north from the SF Bay Area, if you are looking for a relaxing, peaceful and inspiring getaway to Southern Oregon for a few days – add Ashland to your must-visit list.
🚗 The best way to travel to/from Ashland is via car. Only a 6 hour drive from the SF Bay Area and a 4.5 hour drive from Portland, OR, Ashland is right off the I-5.
✈️ If you prefer to fly, the closest airport is in Medford, OR. Be sure to rent a car so you can explore the surrounding Ashland area.
🗓️ How long should you stay in Ashland? I recommend 2-3 days to truly experience the charming town.
☀️ Best time of year to visit? Late Spring – Early Fall. Ashland is truly bustling in the summertime with outdoor theater performances, local festivals and nearby opportunities to go white water rafting and more. If you prefer a quieter but just as lovely scene, I suggest visiting in the Spring or Fall.
🏨 The best hotel to stay at in Ashland is the historic Ashland Springs Hotel. Based right in the center of town, everything is town is walkable from the hotel. Plus, it is both family and dog-friendly.
Prefer a quaint Bed & Breakfast experience instead? You are in luck! Ashland offers tons of charming B&Bs, which is best for couples or a getaway with friends. My favorite B&B in Ashland is The Morical House Garden Inn.
🎭 You can’t visit Ashland without seeing a play at the Oregon Shakespeare Festival. Not a Shakespeare fan? No problem! This world-class theater company also offers contemporary plays and musicals throughout the year. Be sure to check their calendar and book tickets well in advance (yes, it’s that popular). Some of the best actors in the U.S. perform at OSF…I guarantee that the talent will blow you away! 🔥
🌿 Don’t miss spending time in beautiful Lithia Park. Consisting of 93 acres of lush canyon land around Ashland Creek from the downtown plaza towards the headwaters near Mt. Ashland, you won’t want to miss taking a long walk or enjoying a picnic in the park.
🛍️ Don’t forget to visit all of the local boutiques shops while in Ashland. From home decor to gourmet food to clothing and more, Ashland offers it all and the local shopkeepers are so friendly! One of my favorite shops that I always visit is Prize Shoppe, which is right on the Main Street near the Ashland Springs Hotel.
Let’s talk food!
☕️ Looking for the best cup of coffee and a pastry to start you day in Ashland? Look no further than Mix Bakeshop in the downtown Plaza area. Another great spot for your morning coffee fix is Noble Coffee Roasting. If you are looking for a sit-down, old school diner experience for breakfast, look no further than Breadboard.
🧀 Cheese! A visit to Southern Oregon isn’t complete without enjoying some scrumptious local cheeses. Be sure to visit both Ashland Food Co-op and Market of Choice to purchase some incredible cheeses. Also highly recommend taking the short drive out of Ashland to visit the fabulous Rogue Creamery. Their famous blue cheeses will knock your socks off!
🥪 Where to go for lunch? I recommend eating lunch creekside at Greenleaf or experience a peaceful Moroccan vibe at Dobra Tea.
🍫 Have a sweet tooth? You are in luck – there are so many delicious chocolate companies in the area. It’s always a must to visit the Rocky Mountain Chocolate Factory, Inc. in downtown Ashland and then be sure to visit Scharffen Berger Chocolate Maker, a chef-favorite chocolate. And if you are really into chocolate, Ashland hosts the annual Oregon Chocolate Festival in March.
🍺 Thirsty for a refreshing beer? Ashland has you covered! Be sure not to miss Caldera Brewing Company and The Growler Guys. Caldera is also a great spot for a casual lunch or dinner.
🍽️ Ready for dinner? Ashland restaurants offer a wide variety of cuisines from Indian to Thai to Mexican to Italian, and everything in between. A few favorites include:
💦 In Ashland in the summertime? Need to cool off from the hot Oregon heat? I highly recommend a day rafting down the beautiful Rogue River! Book a half-day or full-day trip with Noah’s River Adventures at their kiosk in downtown Ashland next to Mix Bakeshop. A van will pick you up and drop you off in downtown Ashland. Guaranteed to be a day to remember!
🚙 Looking for a quick day trip from Ashland? I recommend taking a 30 minute drive from Ashland to the historic town of Jacksonville, OR. Not only it is a beautiful drive to Jacksonville, once you arrive – you’ll feel like you’ve been transported back to the old Western Days. Jacksonville is best known for its annual Britt Festival that takes place every summer and features some incredible artists. Be sure to check the calendar and find a show you’d like to see and book your trip to Ashland around it!
Enjoy your escape to this laid-back yet inspiring slice of the West in charming Ashland, OR!
