If you are driving between Seattle and San Francisco and want an overnight stop that feels like part of the trip, one night in Ashland, Oregon is my recommendation: close to I-5, compact enough to enjoy in one evening, and full of historic architecture, creekside patios, and dog-friendly places to stay.
I recently returned from a road trip with my dog Pepper from San Francisco to Seattle and back. The perfect overnight stop to break up the long drive along I-5 is Ashland. As an architect, I love a walkable downtown with historic buildings, art, and gorgeous natural scenery. Ashland checks all the boxes and is also incredibly dog-friendly. If you love artsy small towns in the West, you will love spending one night in Ashland, Oregon.
Ashland is the Perfect Location for an Overnight Stop
If you do long road trips, you know how much of a difference a good overnight stop can make. Ashland is about halfway between San Francisco and Seattle and close to I-5, so it breaks up the drive perfectly. As you drive along I-5, you drop down into a valley surrounded by rolling hills and pine trees in Southern Oregon. Take a short detour off Highway 99, and you’ve arrived in Ashland. The historic downtown is adorable and feels like a town you want to stay in longer, so it feels more like part of a vacation rather than just an overnight stop at a chain hotel along a freeway.
Related Post: Solo Female Travel With a Dog
Save My Free Ashland Map
Save my free Ashland map before your trip so you can quickly find downtown stops, dog-friendly places, and dinner ideas mentioned in this guide for your one night in Ashland, Oregon.
Where to Stay in Ashland, Oregon
I stayed at a couple different hotels in Ashland, and my favorite was the Ashland Springs Hotel. It is a historic hotel right in the center of downtown Ashland, and they even allow dogs. I stayed in a corner king room with a view over Main Street and watched the sunset over the hills in the distance. The bed was incredibly comfortable, which made it a perfect stop for a good rest on my road trip.
Ashland Springs Hotel is a hybrid of gothic and beaux arts architecture, and is the tallest building in Ashland. Even if you don’t stay here, make sure to admire the original stained-glass windows at the entry and check out the historic lobby.
Things to Do in Ashland for One Night
You could easily spend more time in Ashland, but if you are just staying one night on a road trip like me, here are some things to check out on your visit.
Walk the Downtown Historic District in Ashland
Downtown Ashland is listed on the National Register of Historic Places, and the historic core is compact enough to explore on foot. Wander down Main Street and make sure to peek into shops, galleries, and bookstores. Many of the commercial buildings in downtown Ashland are from the late 1800s and early 1900s and make Ashland incredibly charming.
One of the most notable buildings along this stretch is the historic Ashland Springs Hotel. If you aren’t staying here, you can still peek into the lobby or enjoy dinner at their restaurant, Larks.
Shakespeare Theater and Free Shows at the Green Show
Ashland is known for its summer Oregon Shakespeare Festival. One thing I didn’t realize until I arrived is the festival also hosts free outdoor performances at The Green Show. Check out the schedule before your trip to see if there is a show during your visit.
I stumbled upon a concert while I was out walking my dog. The Green Show is an open area that is just off the street, free, and was full of families and dogs just enjoying the free concert on a summer evening.
Visit Lithia Park (or Ashland Dog Park)
Every list I saw of Ashland recommends Lithia Park, but unfortunately, dogs are not allowed. If you are dog-free, make sure to take a stroll through the park. You can enter Lithia Park from downtown just off Main Street. If you are traveling with a dog, you can still enjoy the downtown edge of Lithia Park, and wander along Ashland Creek on the trails in Calle Guanajuato Park.
For a good park for dogs, I recommend the Ashland Dog Park. It is a short drive from downtown and closer to the freeway. On both of my visits, I took Pepper to the Ashland Dog Park when we first arrived to let her get her energy out after a long car ride. The dog park is a large fenced-in grassy area. There is another gate you can go through that has access to a creek where my water dog loved cooling down!
Outdoor Dining Along Ashland Creek
Make sure to walk along the pedestrian street Calle Guanajuato. It runs along Ashland Creek and is lined with outdoor dining for bars, restaurants, and cafes. Many of the patios are dog-friendly, so it was the perfect location for dinner after a long drive, and I appreciated being able to bring Pepper with me.
Even if you decide to have dinner elsewhere, grab a beer at Skout and enjoy a relaxing drink at one of the picnic tables along Ashland Creek.
Gear I Actually Used on This Road Trip
Vapur Collapsible Water Bottle – I love to use these as ice packs in a cooler on driving days and then I have cold water when they melt
Packing Cubes – I used the small and slim sized cubes for various organization
Osprey Daypack – Perfect size for day outings, my new favorite small daypack
Travel Towel – Always in my car for Pepper, came in handy after the creek at the Ashland Dog Park
Collapsible Dog Bowl – I always keep one in my car for Pepper
Related Post: How to Pack for a Road Trip With a Dog
Sample Itinerary for a One Night Road Trip Stop in Ashland
4:00 pm – Arrive in Ashland and give your dog a break at the Ashland Dog Park.
5:00 pm – Check into Ashland Springs Hotel.
5:30 pm – Walk downtown along historic Main Street. Check out historic buildings and shops. Make sure to check if there is a free show at the Green Show at the Shakespeare Theater.
6:30pm – Have dinner along Ashland Creek on Calle Guanajuato.
Evening – Wander back to your hotel and enjoy a slow night downtown.
Morning – Take a downtown walk or wander Lithia Park if you are not traveling with a dog. Grab coffee and breakfast in Ashland before getting back on the road.
Enjoy the Perfect Overnight Road Trip Stop in Ashland!
Ashland ended up being exactly what I wanted from a road trip stop: easy to reach, easy to walk, and interesting enough that one night felt like a tiny vacation. If you are planning the drive between Seattle and San Francisco, it is worth building in time for dinner downtown, a little architecture wandering, and a slower start before getting back on I-5. I hope you enjoy at least one night in Ashland, Oregon!
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