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Trail Tales

Where to hike near Portland, Maine

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The state of Maine has plenty of beautiful terrain to explore including mountains to hike, rivers to paddle and fish and miles of seashore and beaches to enjoy. Portland, the state’s largest city boasts an impressive variety of music, fine food and beer. Which is to say: come for the trails, stay for the entertainment.

Portland Trails is a non-profit organization dedicated to making the Greater Portland area a healthier community for people-powered transportation, conservation, and recreation. The group helps build and maintain a network of trails throughout the city that are very popular. A particular favorite is the Fore River Sanctuary, whose trail network visits a mini waterfall and brook with lots of side trails to create loop hikes.

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Baxter Woods is a popular trailed area within city limits. Photo: Portland Herald

Portland's only natural waterfall is located in the Fore River Sanctuary. Photo:

Just across the bridge from Portland, in neighboring Falmouth, there’s the Maine Audubon Society’s Laudholm Farm features hiking and skiing trails that follow the shoreline and nearby Mackworth Island, featuring a trail that encircles the island with nearly non-stop ocean views.

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Mackworth Island is definitely worth a visit.

A quick ride on the Casco Bay Lines Ferry can bring you to another world with a trip to one of the many small islands in the bay; try Long or Cliff Island for a more remote experience. Fort Williams in Cape Elizabeth isn’t a hiking destination per se, but it does feature stunning sea cliffs with waves breaking below and the iconic view of Portland Head Light.

In the winter, Riverside Municipal Golf course has miles of groomed x/c ski trails accessible to the public which can help keep the cabin fever away.

Bradbury Mountain State Park in Pownal offers a rather impressive view from its rocky summit with views of Portland and the Atlantic Ocean just a few miles away.

If you are looking for more adventure, Portland is just about a ninety minute drive from North Conway, NH and all the granite peaks and rocky trails a person could ever want.

Best of all, Portland is a wonderful place that attracts the kind of people who love to get outside—Oboz kind of people!

At the heart of everything we do are the folks who make the magic happen. A group of likeminded footwear-industry vets who left our big-brand jobs back in 2007 intent on doing business a better way. 

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