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Sipayik translates to “along the edge” in the Passamaquoddy tribal language, which is a good description for the Sipayik Trail as it rolls through the Pleasant Point Reservation. The 1.9-mile paved rail-trail hugs the edge of the water along Little River, Gleason Cove, and the Western Passage. It’s also on the edge of the continent, located so far east that dawn strikes the Sipayik Trail before any other rail-trail in the United States.
The Passamaquoddy tribe built the trail in 2004 as an alternative for pedestrians and bicyclists using busy ME 190, which connects Pleasant Point with Perry on US 1. They installed the trail on the railbed left behind in 1977 when the Maine Central Railroad discontinued using a spur route that ran through the reservation between Ayers Junction and Eastport to serve that city’s sardine-canning industry.
The trail starts in the small community on Pleasant Point on Passamaquoddy Bay. This is just one of the locations where tribal members lived throughout the bay region for thousands of years before the arrival of Europeans. They spent the warmer months on the bay fishing, clamming, and hunting marine mammals. Today the tribe is split between those living in several locations in Maine and Saint Andrews in Canada.
If you’re lucky enough to be here for the second weekend in August, you’ll get to participate in the annual Sipayik Indian Days Festival. The event features the arrival of warrior canoes from Calais, a morning service at the sacred Split Rock site, concerts, and a traditional meal. For those interested in learning more about the local culture, the Waponahki Museum presents demonstrations by local artisans, dancers, chefs, and storytellers on the second Saturday of each month April–September.
As you stand at the trailhead, Canada’s Deer Island dominates the view across the bay; to the north, Saint Andrews is visible. Gazing across the bay, keep an eye open for seals, porpoises, and the occasional whales that still patrol these waters.
The trail dips out of sight of the bay for a short distance at Frost Head and then emerges in Gleason Cove. You can get down to the beach from the trail at low tide and look for critters in the tidal pools. You’ll also see seagulls and many shorebirds here; songbirds and deer populate the woods elsewhere along the trail.
The trail crosses behind another forested point of land and then comes out on the southern bank of the tidal Little River. The trail passes through a residential neighborhood before it ends on US 1, across from the post office in Perry.
A dirt track that drills into the woods across the road is a future extension of the Down East Sunrise Trail that heads to Ayers Junction on the former Maine Central Railroad right-of-way. Currently, it’s Route 82 on snowmobile maps.
Please use this form to notify us of any changes or updates that we need to make to the trail information on TrailLink for this trail. RTC staff will review your submission and contact you if there is any need for further clarification.