Trail Running calendar near Canterbury 2025-2026

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

Run scenic singletrack loops around ponds and woodlands at Hale Education in Westwood, with a 6 hour endurance option or a 3.5 mile loop. Bring your own bottle for this cupless event and enjoy a laid back aid station at the start.

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.

Scenic 10 mile out and back trail run along the Merrimack River on April 11, 2026, part of the North Shore Trail Series. Post race bagels, snacks and prizes await and all net proceeds support Merrimack River Trail maintenance.

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

Run the TARC Spring Classic at Jericho Town Forest on April 26, 2025, choosing distances from 10K to 50K plus a free youth fun run. Enjoy a smooth, relatively flat looped trail with one aid station offering vegan friendly options.

TARC Wapack and Back is a rugged trail race along the Wapack Trail in Ashburnham offering 21.5, 43 and 50 mile options. Expect technical rocky singletrack, big climbs and limited entries so register early for a backcountry challenge.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

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

Take on the Drummer Hill Trail Races in Keene NH on May 23, with a 12.5k loop you can repeat for 12.5K, 25K, 37.5K or 50K. Expect technical single track, rocks, roots and stream crossings, aid stops and DHTR drumstick awards.

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.

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

Race the Cirque Series at Cannon Mountain on June 13, 2026, a rugged 6.9 mile climb to the 4,031 foot summit with 3,080 feet of gain. Expect rocky, steep trails and sweeping views on this demanding mountain course.

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.

Explore rugged singletrack and an old railroad bed on a tough 5 mile loop at the Flat Rock Trail Race in Dunstable MA. Proceeds benefit the Humane Society for Greater Nashua and runners can repeat loops for up to six hours.

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..

Tackle 8.2 miles and 3,010 ft of climbing at the Cirque Series Killington on June 27, 2026, a steep, technical loop that visits three resort peaks and finishes at the K1 Lodge. Expect rocky, grassy trails and a brutal Needle's Eye climb.

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..