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Trip List by fiveforefun

Ashland and Shakespeare with Tweens

Jun 1, 2009  Mother of three adorably annoying kids.
4.5 of 5 stars based on 1 vote

Heading to Ashland with a kid in tow? Here's some "must sees" and great places to grab a bite!

  • Explore locations featured in this Trip List: Ashland
  • Category: Recent trip
  • Traveler type: Culture, Sightseeing, Shopping, Repeat visitors, Theater
  • Appeals to: Singles, Families with small children, Families with teenagers, Students, Budget travelers, Tourists
  • Seasons: Spring, Summer, Fall
  • 1. Oregon Shakespeare Festival
    Oregon Shakespeare Festival, Ashland, Oregon

    The plays change yearly, and not all shows run all season. This was my daughter's first year seeing a play and she had a blast. We saw "The Music Man" (very light and fun with good dancing) and "The Servant of Two Masters" (hilarious, be sure to bring candy). We had a great time, the productions at OSF are always top notch.

  • 2. Shrew's House Bed and Breakfast
    Shrew's House Bed and Breakfast, Ashland, Oregon

    A bit off the beaten path, but within a 10 minute walk to the theaters. Comfortable rooms with separate entrances, beautiful gardens, and hearty breakfasts set the Shrew's a notch above everyday accommodations. Say hi to the cats - Kate and Bianca - and enjoy the warmth and friendliness of your hosts Corrin and Ronna. I wouldn't take the whole gang there, but for me and one kid it works out just right. There is a small pool on the property if you want to cool off on a hot day.

  • 3. Lithia Water Fountains

    The Lithia Water fountains are flowing again. Make sure to swing by when your kiddo is thirsty and direct them FIRST to the bubblers with white basins. After you get a photo of the their reaction to the sulphorous taste, they can take a drink of regular water from the black fountain nearby.

  • 4. Yogurt Hut

    Fro Yo! Better yet... Self Serve Fro Yo!!! Does it get any better than that?!

  • 5. Bug A Boo!

    Toys and Kidswear shop in downtown Ashland. They carry Groovy Girls (my girl was ecstatic) and a variety of wooden and other hard to find high end toys... and TIE DYE!

  • 6. Sesame Asian Kitchen
    Sesame Asian Kitchen, Ashland, Oregon

    Fairly new restaurant across from Lithia Park (in the space where the Litha Stationers used to be). Ambiance is fun, with large paper lanterns above and metallic screens giving a "bubbly" feel. I was impressed by the friendly service and very good pricing. Very little is priced over $15 and there are a lot of seafood items. We'll be back!

  • 7. Enchanted Florist

    Delicious "drinking chocolate" and sweets amongst lovely floral arrangements! Friendly staff and wonderful ambiance. Great place to make your girl feel like a princess.

  • 8. Railroad Park

    Quiet neighborhood park near "Historic Ashland" commercial area (not downtown). Very few people here so you might have the swings to yourself. Other playground equipment includes a merry-go-round and climbing structure with slides. There is a picnic shelter and bathrooms. The park is bordered on one side by the Creek to Crest bike and pedestrian route.

  • 9. Mix Sweet Shop
    Mix Sweet Shop, Ashland, Oregon

    Yummy gelato in a variety of sizes. You can get two flavors, in case you can't decide!

  • 10. Ashland Creek to Crest

    Great for novice bikers who want to ride but don't want to content with traffic This is a bike and ped trail that goes by several nice Ashland Parks.

  • 11. Garfield Park

    Nice community park with water play activities. On a hot day it gets crowded by Ashland locals looking to cool off. The park is bordered on one side by the Creek to Crest bike and pedestrian route.

  • 12. Rising Sun Farms

    In nearby Phoenix, OR there is a little farm that turns out some pretty tasty little cheese tortas. There is a tasting room where you can sample wines ($5) and try the cheese for free. We picked up an Orange-Cranberry Torta (goes great with gingersnaps) and a Mediterranean Torta to share with friends at our next gathering.

  • 13. Lithia Park
    Lithia Park, Ashland, Oregon

    If it's warm out, it might feel like everyone in Ashland is at Lithia Park. Fortunately it's big enough for everyone. But if you are looking for playground equipment, check out one of the other neighborhood parks on this list... the swings at Lithia are always packed!

  • 14. Grilla Bites

    Grilla Bites is a great place to grab something quick on the go. We just had smoothies this time and it was "just right" when we weren't quite ready for lunch but wanted something in our tummies before heading to a play. Yum!

  • 15. Greenleaf Restaurant
    Greenleaf Restaurant, Ashland, Oregon

    It's still there and it's pretty much the same. I don't understand why the service is so slow at Greenleaf but I love their chicken salad so I keep going back anyways.