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Payson Park & Connecting Trails, Portland

Sunset at Payson Park sledding hill in Portland, Maine

It's thrilling to discover that two trail systems you've been walking for years are actually connected. This happened last week when I brought our dog Romy to a trail we visit often, Canco Woods. At the outer edge of our regular loop, there is a short path leading up to a neighborhood trailhead that I'd never explored, since we'd always turned around just before reaching it. But something inspired me to walk to the end this time...and I discovered that this trailhead led directly to Payson Park! As luck would have it, I was in the middle of writing about Payson Park and how it connects to the Back Cove Trail. Now we can add Canco Woods to this trail love triangle.

Payson is a great park to visit in the winter because of its sledding hill and ski & snowboard terrain park with rails, ramps and boxes. We have spent countless hours and winters here using equipment of all kinds.

Kids sledding at Payson Park in Portland, Maine

If you live in Portland, you already know about the Payson sledding hill, but you may not know about the skating pond...just down the hill and across from the tennis courts.

Years ago I organized regular meetups at area skating ponds for multi-generational hockey games. It was called "Skate Club" and the skate pond at Payson Park was always my top choice. For real-time updates on skating conditions at Payson and other area ponds, visit the City of Portland's website here and scroll to the bottom.

If your kids are older, and you care to drop them off for sledding or skating while you walk your dog, follow the Brook Trail past the Payson Skating Pond, Loring Little League Field, and Payson Park Playground. This trail is basically a sidewalk starting at the sledding hill and leading all the way to the Back Cove Trail.

The Back Cove Trail  trail is one of the greatest things the City of Portland has to offer. With 3.6 miles of accessible, dog-friendly (on leash), stroller- friendly, bike-friendly trails with spectacular views of the city skyline, it's unbeatable. This trail NEVER gets old for us and we use it year round. Here are pictures from this trail in all seasons.

You could choose to loop around the cove, or follow the trail until it connects with the Eastern Promenade Trail, which eventually leads to the best family-friendly, waterfront restaurant in Portland - Flat Bread Pizza.

Now I will explain how Canco Woods, today's bonus trail, also connects to Payson Park. I will not get into details on Canco Woods, but you can read a full post about it here. If you park on Canco Road and follow the lollipop loop all the way to the foot bridge at the end, then continue to the trailhead, you will find yourself at the end of Rosedale St. From here, it's just a hop, skip and a jump to Payson Park. You can actually see the Payson Park sign from the Canco Woods trailhead on Rosedale.

If your kids are sledding and you'd like to, yet again, walk that dog that always needs walking, reverse the loop I just mentioned, by starting at Payson and walking down Rosedale Street to Canco Woods. Or walk your dog down the hill towards the water and the Back Cove Trail. Or stay at Payson and enjoy some sledding with your kids. It's your adventure, do whatever fills you up. Have fun!


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