Have a kid who hates to hike? Does your child complain and whine the whole time? And yet you want to get out in nature with them and maybe enjoy yourself as well? Want your kids climbs to climb, explore and smile? Maybe even stay longer outside than necessary? Then I have the trail for you!
I am a member of a Facebook group dedicated to "hiking with kids" and that's how I learned about the "Winnie the Pooh" trail in Barrington. It also happens that my younger daughter participated in a Winnie the Pooh play this summer and was super excited to explore all of the places mentioned in the script. I worried that my older daughter (10) would be bored by this hike and would find it "babyish," but she also really enjoyed herself! There are fun signs to read along the way and surprises to explore. Plus there are lots of natural structures to climb on.
The trail itself isn't long - just a 1.5 mile loop - and pretty flat. You don't need to dedicate the whole day to this activity (we spent about two hours, including our picnic lunch), yet you'll have fun and get your steps in! I want to also add that we brought our small dog (under 10 pounds) and it was perfect for him. He can't do the big 4000 footers but still enjoys getting outside and sniffing to his heart's content.
PS You probably already know this tip, but All Trails is my favorite site for hiking suggestions and reviews. You can download the app on your phone and get all of the information you need, such as length, difficulty and parking address (which can sometimes be oddly hard to find). Really recommend!