Activities
Crater Lake National Park
About a 2–2.5 hour drive, and absolutely worth it if you’ve never been. The deepest lake in the U.S., unreal blue water, scenic overlooks, and plenty of short walks if you’re not up for a big hike. June can still have snow, so plan for that.
Rafting the Rogue River
A classic southern Oregon experience! This river is fun, splashy, and scenic. Options range from mellow floats to more adventurous whitewater. Recommended outfitters: Indigo Creek Outfitters Noah's Rafting
Rogue River Basin
Easy access viewpoints, short trails, and dramatic lava-formed river features. This is a great stop without a long hike.
Umpqua Highway for Hot Springs and Waterfalls
A beautiful drive north with plenty of pull-offs for waterfalls, soaking, and forest views. Toketee Falls and Umpqua Hot Springs are highlights. It's the perfect slow, scenic day.
Pilot Rock (Kira's favorite hike)
A steady climb with one of the best panoramic views in the region. On a clear day, you can see multiple mountain ranges. This is a steep hike with a scramble at the top, so not the most accessible, but definitely GORGEOUS!
Acid Castles (Jeffrey's favorite hike)
A lesser-known gem with wild rock formations and a slightly surreal feel. Adventurous, unique, and very “off the beaten path.”
Lithia Park, Ashland
A must-do if you’re in Ashland. An awesome park right in town with access to easy trails, a Japanese Garden, and pickleball! The park leads into the watershed trail system if you're looking for a longer hike. Our favorite is the Snark / Bandersnatch Loop (moderate)
Oregon Shakespeare Festival
World-class theater in a charming downtown. Even if Shakespeare isn’t your thing, the productions are excellent and the town itself is fun to explore before or after a show.
Jacksonville
A historic gold-rush town with brick buildings, cute shops, wine tasting rooms. Easy, walkable, and full of character. Our favorite coffee here is Cerberus!
The Oregon Cheese Cave
Not actually a cave, but the shop owner is the best sassy french woman. Build your own charcuterie! A quick stop for cheese lovers and a fun, quirky Oregon experience. Good place to stop on your way out to get amazing cheese, or spend an hour or so sitting and enjoying a build your own charcuterie.
Vinny's Italian Kitchen
One of our favorites in the valley. Italian comfort food, generous portions, and a longtime local favorite. Great for a sit-down meal!
Osteria La Briccola
One of our favorite places! Intimate, delicious Italian food in cute Ashland. Great option for a sit down dinner.
The Great American Pizza Company
Jeffrey and Kira's go-to pizza place! Sourdough crust, good bang for your buck, and kind of the staple pizza place of Ashland. This is the spot Kira would hit after every outdoor weekend trip with friends.
Clyde's Corner
Another favorite if you want a more seasonal menu, artisanal pizza spot. This place is fantastic and has great outdoor seating.
Red Lily Vineyards
Beautiful riverfront setting and relaxed atmosphere. May have live music. They are known for their Tempranillo and their rose is very good.
Eliana Wines
Jeffrey's sister's favorite winery by far! "Best kept secret. Beautiful view of the valley and Mt. Ashland. Outdoor seating only. Super sweet and unique experience!"
Our Early Days: Zoey's Cafe & Artisan Ice Cream
Where we had our first date! We got ice cream at Zoeys and took a walk in Lithia park.
Our Early Days: Noble Coffee Roasting
Where we had our second date! A noble mocha is one of our favorite weekend rituals.
Our Early Days: Mt. Ashland Ski Area
We went here for one of our first dates. Jeffrey showed off his photography skills! This is an awesome place for a view and hiking if you want! Check out the back road to drive to the top if the gates are open.
Our Early Days: Emigrant Lake
A great place to stargaze without going too far out of town. We did this on one of our first dates and it was where we shared our first kiss! You can also go for swimming or water sports if the water levels are okay. The higher elevation lakes are usually a better bet.