Trail Running calendar near Greenwood 2025-2026

Light up the trails at Cranmore Resort in North Conway with 5K and 10K night runs over ski trails and access roads. Trails are marked with reflective flags and LED lanterns, headlamps are required, and pizza and apres follow the finish.

Join the Holistic Hustle 5K and 10K at Emmons Preserve on Nov 1 for scenic runs and a kids fun run. Earn a wood burned finisher medal, enjoy music, games and treats, and enter a raffle supporting School Around Us.

CircumBurke trail race on November 1 at Victory Hill in Victory VT offers an 18 mile loop of rugged singletrack with about 1,800 ft of climbing. All proceeds support trail maintenance, with snacks and a taco truck onsite.

Celebrate the season with the Jackson 5k Turkey Trot and kids 1k on scenic trails in Jackson, New Hampshire. This family friendly event brings the community together while raising funds for Jackson Grammar School and Girls on the Run.

The TruStrength "Uphill Will" 24 Hr skimo will take place in Greenwood on Saturday 14 March 2026.

Riverlands 100 & Relay is a trail ultramarathon held in Turner, Maine, on May 2–3, 2026. The event centers on a 100‑mile race with a relay option, inviting solo runners and teams to tackle the course over two days. The race information page..

Run laps on a scenic 2 mile single track loop around White Lake in Tamworth, NH with 6, 12 or 24 hour timed options and a beach start and aid station. Costumes encouraged and bring your own hydration.

Chocorua Mountain Race is a rugged 23K loop in the White Mountains that climbs Mount Chocorua and packs about 4,500 feet of ascent into technical trails and alpine views. Limited to 250 runners, it rewards strong trail skills and grit.

Hit the trails in Standish, Maine on June 13, 2026 for the Otter Pond Trail Races, featuring a scenic 10K, a lively Kids Fun Run, and a Dawn to Dusk challenge. Perfect for runners and families seeking a day of outdoor fun.

Take on the Cirque Series at Cannon Mountain on June 13, 2026: a rugged 6.9 mile mountain run with 3,080 feet of climb to a 4,031 foot summit in Franconia Notch. Expect steep, rocky terrain, epic views, and fierce competition across Sport,..

Race the Cog on June 27, 2026 at Mount Washington for a classic alpine challenge alongside the historic Cog Railway, finishing on the summit. Choose a 2.75 mile summit climb or a 5.5 mile roundtrip and earn 3,500 feet of gain with stunning..

Test your limits at the Back Cove Backyard Ultra in Portland, ME, where runners complete a 4.16 mile loop every hour around Back Cove Park until one remains. Enjoy a flat scenic course, basic aid stations, and a friendly volunteer crew.

Take on Loon Mountain's Upper Walking Boss on July 12 in Lincoln, New Hampshire, a roughly one kilometer black diamond climb that will test every runner. Men, women and U20 categories plus a $1,500 challenge purse raise the stakes.

Take on the rugged Baldface Scramble in Chatham NH July 25, 2026, with a challenging 29K or shorter 14K loop over the iconic Baldfaces with big climbs and alpine views. Technical, cupless trail racing for experienced mountain runners.

Tackle rugged, high climbing trail ultras in the White Mountain National Forest with 20, 50 and 100 mile options. Expect technical trails, huge elevation, cupless aid and camping options for an epic mountain challenge.

Firebird Trail Races in Windham Falmouth Maine feature 50K, marathon and 13M races on technical single track through Lowell Preserve. Tackle rocky, root strewn trails with friendly aid stations and earn a carved wood Firebird medal.

Run the Black Bear Trail Races in Waterville Valley NH with options from a family friendly 1 mile fun run to a rugged 50K across White Mountain peaks. Scenic singletrack, big climbs and aid stations offer a memorable mountain challenge.

Test your limits at the Last Man Standing Ultramarathon on September 5, 2026 at Pineland Farms in New Gloucester, Maine. Run repeating 4.2 mile wooded loops until a single finisher remains in this backyard ultra classic.

Run the Megunticook Trail Festival in Camden Hills State Park on Sep 12, 2026, with 50K, 20K and 10K options across rocky summits, ocean views and classic Maine woodland trails. Entries are limited so register early.

Take on the Kilkenny Ridge Race in the White Mountain National Forest, a remote, rugged traverse of peaks including Mount Cabot and Mount Waumbek. Choose 50 Miler, 25 Miler or 25K and come prepared with navigation and mandatory gear.