Ashland, OR


Just over five hours north by car from our cozy apartment in Berkeley lives a quaint little town called, Ashland. Situated in the midst of the gorgeous Siskiyou mountain range and nestled right along the border of California and Oregon, Ashland delivers breathtaking views from every angle. While large enough to meander about without seeing the same faces, Ashland upholds a rustic, small-town appeal embedded in its history and landscape; hipster but not egregiously so, and modern enough to not feel like you’re living a generation away from the Amish. Whether you’re looking for your next vacation destination, or are keen to explore how to blend exercise and training alongside being away from home trails, I hope this Ashland recap inspires you in the way that co-existing with the Ashlandians did for me!

Day 1.

We arrived in Ashland late Thursday evening after deciding to take the Friday before Memorial Day weekend off as well. With minimal bathroom breaks, the drive from Berkeley to Ashland covers approximately 338 miles and took us about five and a half hours. We rented two Air BnB’s for our stay, one right outside downtown Ashland and one in Hilt, CA. Our first two evenings were spent in the cutest cottage right off the I-5. As I’m currently training to run the Pine 2 Palm 100 Mile race in September, Elan and I decided to see how much of the course we could cover in three days and with only one car. After having arrived in Ashland late Thursday night, we made an executive decision to turn of all alarms and wake up leisurely. In no rush at all, I pulled my hair back into a messy top knot and we ventured out to grab our first cup of coffee at Case Coffee Roasters. With Elan being the connoisseur that he is, the small coffee boutique was perfection. Underneath the smattering of rain, light jazz music dancing around the walls and warm coffee slowly starting to rush through our bodies, the day was already off to a magnificent start.

An easy way to save a dime on vacation is to pack food and snacks so that you don’t have to buy every meal out. I stocked up at Trader Joes on almond butter, RX Bars, and quick cook oats to ensure we’d have a filling breakfast and post-run snack every day without having to go out and buy it. While we’d need to stock up on extraneous fruit for the future mornings, I also bought a couple of bananas to slice in our oats as well. While filling our bellies we mapped out the days run.

Located about an hour north of Ashland, Pine 2 Palm begins in a small town called, Williams. The first run we mapped out was the first big climb of the race, 10 miles meandering up semi-technical switchbacks on a trail named, Greyback. With a break in the rain, we laced up our shoes, filled our packs and made the drive out to the start. The run was gorgeous. Bursting with vibrant green from a fresh bucket of rain, squishy trails leaving our shoes caked in mud and crisp springtime air filling our lungs, Elan and I ran just under 9 miles directly up the single track trail and about as far as we could without being stopped by plummeting temperatures and losing the trail due to snowfall. The race begins with this treacherous 10 (ish) mile and 4500 ft climb up, wiping out the energy levels of nearly all its participants. It was vital to understand how deceptive the trail is; while completely runnable (as it was on this day) during the race it’d be crucial to preserving energy and hike with intention! There are only a few intersections in the trail that could leave a lone runner unprepared and be scurrying in the wrong direction, otherwise, it was easy to navigate, serene and beautiful. While on this day the run was not particularly challenging, by the time we reached the car on the way back, 18 miles later, I was ready to be done…mentally preparing myself that on race day, I’ll have 82 more miles left to go.

After toweling off and changing into dry(er) clothes, Elan and I headed back in the direction of Ashland. In the middle of Ashland and William lies a tiny little town called, Jacksonville. It thrives off of tourists and is abundant with friendly shopkeepers and locals. Tired, hungry and in need of a caffeine pick-me-up, we parked the car and hobbled around in search of some fuel. To my delight, we wandered into a local and organic co-op style market providing exactly the kind of fair I was hoping to find. I ordered a collard wrap with farrow, tahini, and roasted squash while Elan tucked into an egg-salad sandwich on whole wheat toast.

With full bellies and coffee in hand, we made one last stop in the local bookshop. I was pleased to find the owner and her colleague rearranging the entire shop (as you do) and more than happy to stop for a minute and talk to us about the town, how they came to open their store, and even a few suggestions on good, local reads. So, of course, Elan and I both picked out a few books written by local authors. We thanked them both and with new books in hand and set off back to our little cottage to relax before our next adventure!

Day 2.

Being more diligent around timing, we set our alarms and hoped to be on the trails by 10 o’clock at the latest. Because of the remote nature of the course, we’d have to drive about an hour to the trails each day, and with it still being our vacation we didn’t want to wake up too early…after all, that’s what we do during the week. Stumbling out of bed on a much warmer morning, we headed to a coffee shop called Re-Mix. Awake with caffeine, we filled our bellies with oats, packed our gear, water, and shoes and headed out for our longest run of the weekend.

The second climb of the race begins at Seatle Bar Trailhead and winds up the mountain about seven miles on technical single track then plummets down into Squaw Lakes. While on a map the elevation isn’t too daunting, and the mileage “manageable,” this section kicked my ass. It was hard. Our original plan was to run 13 miles up and out to squaw lakes, fill up our bottles with water and turn around to do it again. Upon (finally) making it to Squaw, I turned to Elan and nearly begged him to come up with an alternate route. 13 miles of technical, rolling and exposed single track is no joke. After asking a few locals, we decided to make the section a loop by running out of the park and onto the highway back to our car. By the time we finished the 26 miles and 5,300 ft of elevation gain, I was left wondering which route would have been more difficult, seeing as how running on the hot asphalt wasn’t a walk in the park either. All in all, the second run of my Pine 2 Palm course recon was humbling. It was tremendous to be able to experience first hand at how rugged and challenging the trails are. You can research the course profile as much as you want, but nothing replaces physically being out there. As difficult as that section was, the views were stunning. The air was fresh, the sunshine was bright, and the smell of pine trees brought childhood memories of days spent outside in the summertime.

Grabbing coffee and provisions for the second time in Jacksonville, Elan and I headed out to our second home for the duration of our stay. Before booking our trip, Elan and I did some digging and managed to find a tiny house to rent for a few nights. While neither of us had stayed in one before, after seeing it was available we were giddy with excitement. Located in Hilt, CA, pretty much on the border of California and Oregon, our tiny house was located in what was called an “Eco-Village.” A young couple decided to buy a beautiful plot of land and invest in creating sustainable and eco-friendly (tiny) houses around their property. It was tremendous! They even had chickens roaming around the property to which the hosts graciously gave us fresh eggs in the morning.

Once we put on normal people clothes we headed into town for a lovely dinner, ice cream, and even a movie! Fun fact about Elan, when he grows old he wants to work at a movie theatre clipping tickets and it could be one of the things I love most about him.

The evening temperature was warm and a little windy, making for strolling through the streets lovely beyond compare. We ate dinner at Standing Stone Brewery; I got a chicken bowl with roasted sweet potatoes, black beans, and avocado, and Elan got a massively delicious burger with Japanese sweet potato fries! After dinner we even indulged in local ice cream that was so tasty and so creamy, I’m pretty sure we both dreamed of it that night.


Day 3.

Our last and biggest run we reserved for the one with the best views. Knowing the race has a gnarly climb up to Dutchman Peak, Elan and I decided to “save the best (and biggest) for last.” Trying to simulate running on tired legs as best as possible, it made sense to put the highest elevation run at the end to emulate race conditions. With our route uploaded and directions inputted, we set off to conquer our final adventure of the long weekend.

We started the run at a PCT and fire road junction, with absolutely stunning views of Mt. Shasta in the background. Surprisingly, our legs felt pretty fresh and unsurprisingly we were in total bliss. We were planning to do about 12 miles out on the fire road, run up Dutchman Peak and run on the PCT back in the direction of town as it goes in the race. About 11 miles in, my legs started to feel the miles and my mind went a little angry. Fatigue can play nasty tricks on your body, one of which can directly affect your mindset. I kindly asked Elan if we could loop around a little shorter and of course, he said yes. The takeaway from this run was that the course is hard. Separating the 60-odd miles we had done over three days left me tired, I could barely fathom putting them all together and covering the distance in one! But that’s what setting an audacious goal is; I know what I have to do now and though I’m intimidated I’m ready to work for it. To see the data from the run, check it out here!

After our early dinner we found a tap room that was playing the Cleveland vs. Celtics basketball game, and after one (alcoholic) kombucha and a very large glass of wine later, we could breathe easy as the king got the win and made it to the playoffs. What I love most about going on vacation (or at least vacating your normal routine) is being able to do exactly what you want to do, when you want to do it. Elan and I ate dinner at five because that’s when we were hungry….we walked around downtown and through Lithia Park as the sun was setting, then stopped back into the grocery store to pick up snacks to munch on in our Tiny House later that night. We didn’t feel pressure to squeeze every bit of sightseeing into a small and narrow bottle, instead, we marched to the beat of our own drum and found that the music was exactly what we wanted to listen to.

Stripping out of our “fancy clothes” and back into cotton t-shirts and target active-wear shorts, we chowed down on artisanal kettle corn, carrots and hummus and organic peppermint chocolate. It was a perfect end to a perfect day!

The prospect of running 100 miles still terrifies me. Even on much shorter training runs, I experience nausea, fatigue and complete muscle soreness that makes me question why I even have the audacity to sign up for something five times in length. But if my partner (Elan) has taught me anything, it’s that turning your back to the unknown is what paralyzes us with fear. Not knowing is scary…whether that be not knowing the outcome of a race, not knowing where you are on a map or not knowing what each day brings, if we stopped doing things because we were afraid, we would amount to nothing. So I’m terrified and I’m excited at the same time because I know it’s going to be difficult, but it has always been worth it. Until I find my shoes on the line, I’ll know I’ve left a little piece of my heart in Ashland.

The last morning + Drive Home.

Come Monday morning as the sun came crashing through our tiny house windows, Elan rolled over and gave me a soft kiss on the cheek. I think we both woke up knowing that running today just wasn’t in the cards, instead, we wanted to wake up slowly and enjoy our last morning away without having to get smelly. Brewing up some coffee and packing up our bags, we got dressed and headed into town for breakfast and one last walk around the park before the long drive home. The breakfast we got wasn’t that great, although the vegan savory waffle with cilantro pesto did redeem itself. Luckily the coffee from Hither just next door may have just about won me over to a lighter roast. With more caffeine surging through our bodies, we took a stroll through the park and back up to Rogue Valley Runners to chat with some of the employees and of course buy a t-shirt to rep in the bay!

With snacks purchased for the drive home and audiobooks downloaded (we listened to Fahrenheit 451) google maps said five hours and off we went. Just as we were about to pull out of town, we passed a little shop called, the Falafel Republic. Elan had been eyeing it since we arrived in town but for some reason the timing of our meals never aligned. With hunger ques just about to knock on the walls of our tummies, we went inside and were blown away. Despite not having ordered my own falafel and pita (huge mistake on my end) Elan and I both agreed that it was one of the best falafels we’ve ever had. The hummus and zataar spices were profoundly delicious, and the man who owned the shop had clearly been to Israel (says Elan) because the recipe tasted perfect. From tearing off the opening of the pita, dousing it in olive oil and spice blend to munch on while they make the rest of your pita, it’s the details of such authenticity that made Elan proud of his Israeli roots. The food was marvelous and a perfect end to a perfect trip.

Here are some tips for making running accessible in a new place.

1. Tell someone. Give a text or a call to a friend or family member (doesn’t really matter who) to tell them where you’re going, how far you’re expecting to be going, and how long you anticipate it will take. This way, someone with assured cell service will know to keep you in the back of their mind.

2. Do your homework! I’m lucky enough to wear a SUUNTO Spartan mega watch that allows me to plan a route on Strava, map out the exact distance and location, and upload it to my watch so that I can follow a very specific route while I’m running. Should I take a wrong turn, my watch will buzz and alert me that I’m going in the wrong direction. These watches are very expensive, so if you don’t have one, I would suggest making it a priority to stop in the local run shop and ask for the 4-1-1 on local trails and routes to follow that are safe and easy to navigate before heading out in the wilderness on your own. If you do have a watch capable of multi-GPS functions, make a route on strava, download the GPX fileand then upload it to the Suunto MyMoves Count app. It’s easy and worth the few minutes…plus it’s fun to create a route!

3. Bring more water than you need. While Elan and I carefully mapped out each of our runs for the day, ensuring there was a source to refill our bottles, we always carried more than we needed just to be safe. Running on new mountains is a privilege that needs to be enjoyed safely. While the extra weight didn’t make our times any faster, we were never worried we would run out of the water, and ultimately that peace of mind was supremely worth it.

A quick list of places to eat and things to do.


  • Sauce Cafe
  • Standing Stone Brewery
  • The Falafel Republic
  • Market of Choice
  • Jefferson Farm Kitchen
  • The Growler Guys

Coffee Shops:

  • Noble Coffee Roasters
  • Case Coffee Roasters
  • Remix Coffee
  • Mix Coffee
  • Extras!

Other things!

  • Rebel Heart Book Shop
  • Rogue Valley Running Company
  • Shakespeare Outdoor Theatre
  • Lithia Park

About the author

Gabi Maudiere enjoys eating rice cakes (smothered in crunchy peanut butter) despite popular criticisms and adheres strictly to the notion of reading before bed, even if it's just half a page before falling asleep.