You can just feel the whimsy in the air on this cute trail inspired by the classic Winnie The Pooh novel by A. A. Milne. The song will dance in your head as you adventure through the Winnie the Pooh trail:
♫ Winnie the Pooh, Winnie the Pooh, Tubby little cubby all stuffed with fluff
♫ He’s Winnie the Pooh, Winnie the Pooh, Willy nilly silly old bear
Winnie the Pooh Trail at the Goodwill Conservation Area
The Winnie the Pooh Trail is a small section within the Goodwill Conservation Area trails. If you are really into hiking, you could totally get your fellow hiking friends together for a day: Have littles walk the Winnie the Pooh section then throw them into hiking carriers for a hike nap while you have grown up conversations!
At the trailhead take a picture of the trail map! A few signs here and there seemed to be missing and I consulted the map at Pooh’s house to confirm that was the end. I don’t like to miss things so it was very nice to confidently know all the stops we were supposed to hit.
Access to and from the trailhead parking lot requires walking over a bridge; game of Pooh Sticks anyone?
This is not a stroller friendly trail at all, wear the babies and let the toddlers toddle it out. The trail is less than a mile out but don’t underestimate the fun – I was in that forest for over TWO HOURS! I was practically dragging them out. The youngest in our crew for this hike was 2 years old.
The Winnie the Pooh Crew’s Houses
The Winnie the Pooh whimsy starts right away with Christopher Robins door. A few on my crew were genuinely nervous to knock because they were scared who was going to come out!?!
Along this engaging trail are the homes of all the book’s characters. I thought Rabbit’s house was the most clever. It was made out of a cool piece of wood it looked like a great hidey-hole.
There are other fun features along the way like quotes from the book, a Heffalump trap, a bell to ring at Owl’s house and a very cool rock to climb at Pooh’s.
A Beautiful Trail
The forest itself is beautiful with lots of rocks to climb on, nature to discover and tree roots to examine. The start of the trail is at water level and follows along the pond a bit. Then the trail works its way up for a good but easy elevation gain. In the right season you are treated to an amazing view from the top.
Pooh and Eeyore’s houses are the end of the experience. It is possible to loop around back to the parking lot by following the Goodwill Trail. We chose to walk back along the same way and visit all the stops again. For us, it was about 1.5 hours to walk out and 30 mins to double back to the car.
Quick Facts
| Parking | Off the road trailhead parking |
| Bathroom | No bathroom |
| Trail | Less than a mile one way then you can turn around or make a loop with the Goodwill Trail. |
| Stroller Friendly? | NOT stroller friendly |
| Sun Exposure | Shady forest trail |
| Special Considerations | All of the illustrations on the trail are from the classic novel, not the modern day version. Read the novel (or parts of it) before you go! |
| Resources | Market Basket within 10 minutes |
| Playground | Barrington Public Library and Barrington Community Playground (with picnic tables) are a 2 minute drive up the road |
| Address | 245-263 Franklin Pierce Hwy, Barrington, NH |
