Trail Running calendar near Portland 2025-2026

Join the Tortoise and the Hare Trail Races in Salisbury on April 4, 2026 for trail 10K, 5K and a fun 1 Mile Color Run. Enjoy custom tech shirts, post race music and snacks while supporting Salisbury Parks and Recreation.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Hit the trails at the Wildcat 5K Trail Run Walk Wag in Boxford on May 30, 2026, for a scenic 5K through Wildcat State Forest with pond views and separate courses for runners and walkers. Enjoy post race treats, swag, and prizes for top fini..

Take on the Chocorua Mountain Race, a rugged 14 mile trail through New Hampshire's White Mountains with steep climbs, rocky singletrack, and a summit finish. Limited to 250 runners, this scenic test rewards grit and views.

Explore scenic trails south of Sebago Lake at the inaugural Otter Pond Trail Races in Standish, Maine on June 13, 2026. Choose a timed endurance Dawn to Dusk challenge, a 10K or a kids run while supporting Bonny Eagle Athletics.

Race The Cog climbs alongside the Mount Washington Cog Railway to the summit, offering a 2.75 mile Summit Climb with cog train return or a 5.5 mile Devil's Shingle Roundtripper back on foot. Expect epic views, steep terrain and serious elev..

Cranmore UltraTrax on June 27 in North Conway NH offers scenic looped trail runs with ridgeline views of the White Mountains. Pick 7, 14, 21 or 28 miles, enjoy aid stations and a finisher shirt, and support the Conservation Lands Foundation..

Test your trail skills at the Spaulding Woods 50K, a challenging multi lap race on rocky singletrack and scenic footbridges around Northfield, New Hampshire. Well supported and community focused, the event benefits Spaulding Academy & Famil..

Take on the Summer Hill league at Ardwhallan Outdoor Pursuit Centre in West Baldwin on Sat 18 Jul 2026, a testing 4.5 km trail with 150 m of climb. Pre entry is required and junior entries welcome for a fun, competitive summer race.

Take on the famous Baldfaces in White Mountain National Forest on scenic, rugged ridgeline trails; choose a single loop 9 mile route or the double loop 17.8 mile course for a true mountain test. Part of the White Mountain Endurance Cup.

Run the Jigger Johnson Ultras in Waterville Valley, NH, across rugged White Mountain trails and exposed ridgelines for an epic mountain challenge. Multiple distances demand GPX navigation and mandatory gear for remote and night sections.

Firebird Trail Races in Windham, Maine on Aug 22, 2026 offer 50K, marathon and 13 mile courses on technical 10 mile loops through Lowell Preserve and nearby woods. Grassroots fundraiser for local trails with a wood carved medal for finisher..

Take on the Black Bear Trail Races in Waterville Valley on August 29, 2026, with distances from a rugged 50K circling 4,000 foot peaks to a family friendly 1 mile fun run. Scenic trails, big climbs, and alpine views await runners of all lev..

Run rugged trails atop Mount Megunticook in Camden Hills State Park with 10K, 20K and 50K options offering rocky singletrack, ocean views and serious climbing. Entries are limited and Indigenous runners are offered free entry.

The Mt. A Trail Challenge will take place in York Harbor on Saturday 19 September 2026. You can run 5 kilometers.

Celebrate fall trails at the TARC Stone Cat Trail Festival in Willowdale State Forest in November with distances from a fun Cider Donut Mile to a 100K. Run rugged single track on scenic loops while supporting local conservation groups.