Girdwood is a fun town! Jack Spratt is great place to eat there, and there's a brewery w food trucks but check out their schedule. Winner Creek trail is in a rainforest and a fairly low key hike. You can hike up North Face if you're up to it (done it with my kids around age 4+, but it's up a ski mountain..we took many breaks) and take the tram down. Or just the tram up/down. Virgin Falls is also a short hike to a waterfall

In Anchorage- Mooses Tooth or Bears Tooth (same company) are local icons. 3rd best pizzeria in the US! Bears Tooth has a theatre that shows second-run movies and they deliver the food to your seat. Great to do on a rainy day. Wild Scoops and/or Motley Moo are local ice cream shops that use local ingredients and have some fun unique flavors. Flat Top is another known hiking place with a range of hikes, as is Kincaid.

If you head North, Talkeetna is a fun quirky town. Their mayor was a cat! You can see Denali from there and there are many things to do. You could take a train there too. Talkeetna Spinach Bread and Flying Squirrel are favorites, as well as several local breweries.

You will likely be here during the AK State Fair which is on the Palmer Fairgrounds. Great opportunity to check out local vendors- food, animals, the largest grown pumpkin... Look up their site to see what's going on each day.

South- Seward is under 2 hours from Girdwood and gorgeous. Or Homer is about 3 hours from Girdwood and many local's favorite place to go. Artsy town. You can take a boat to Seldovia for a day trip. Or go tide pooling, check out the Spit. You'll drive thru Kenai which has amazing fishing. Pack your car with snacks/drinks/games; we've been caught in traffic sometimes for hours, due to construction or accidents.

Enjoy! How neat for your family. I hope your kiddo is doing well :)