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June 7, 2025
Medford, OR

Caitlyn & Michael

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Things To Do

Some of our favorite restaurants, hikes, and things to do in Ashland. If you’re looking for more of an adventure off the beaten path, let us know!

Oregon Shakespeare Festival

15 South Pioneer Street, Ashland, OR 97520

For the true Ashland experience, try getting tickets to one of the shows in the Allen Elizabethan Theatre!

Lithia Park

Winburn Way, Ashland, OR 97520

Beautiful park with miles of easy trails conveniently located in downtown Ashland. Check out the Japanese Gardens!

Hobart Bluff Trailhead

Ashland, OR 97520

Easy/Moderate Hike, about 2-miles out-and-back to a stunning outlook, located in the Cascade-Siskiyou National Monument. About a 30 minute drive from Ashland.

East Applegate Ridge Trail

Jacksonville, OR 97530

Beautiful hike, very little shade (so not a good option on a hot day), but relatively easy with a beautiful view along the ridgeline the entire way. Out and back for 5 miles or as long as you want to make it. Directions: From Jacksonville Oregon, go west on Applegate St, becoming Cady Road for 1.9 miles. Turn south on Sterling Creek Road. Go approximately 4 miles, turning west on BLM Road 38-2-29.1. The trail head is approximately 1/4 of a mile at the end of the road.

Bandersnatch Trailhead

588 Glenview Drive, Ashland, OR 97520

Moderate hike in town. A really nice way to enjoy the Ashland Watershed without having to drive very far. Also intersects several other "Alice in Wonderland" themed trails in the watershed.

Green Springs Mountain Loop Trailhead

Ashland, OR 97520

About a 3 mile loop that intersects the PCT, a relatively easy hike and very beautiful.

Sushi Heaven

293 East Main Street, Ashland, OR 97520

Our go-to sushi place. Try the screaming potato roll!

Mix Bakeshop

57 North Main Street, Ashland, OR 97520

Our first date! Great place for coffee and delicious baked goods.

Blue Toba

145 East Main Street, Ashland, OR 97520

Mam’s Happy Thai Express

165 East Main Street, Ashland, OR 97520

Osteria La Briccola

18 Calle Guanajuato, Ashland, OR 97520

Skout Taphouse & Provisions

21 Winburn Way, Ashland, OR 97520

Liquid Lounge

370 East Main Street, Ashland, OR 97520

Dana Campbell Vineyards

1320 North Mountain Avenue, Ashland, OR 97520

Irvine & Roberts Vineyards

1614 Emigrant Creek Road, Ashland, OR 97520
For all the days along the way
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